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Journal articles on the topic 'Tripyrrole'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

Bröring, Martin, Dirk Penno, and Robin Krüger. "MnII/O2-oxidation products of α,ω-dimethyldipyrrins." Journal of Porphyrins and Phthalocyanines 11, no. 10 (October 2007): 755–60. http://dx.doi.org/10.1142/s1088424607000874.

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A α,ω-dimethyldipyrrin with and without a meso-situated phenyl substituent has been investigated as the substrate in the oxidation reaction with the Mn II/ O 2 system. While for the meso-phenyldipyrrin, the expected, though impure and sensitive diformyl derivative is formed, the reaction of the meso unsubstituted dipyrrin leads to a novel tripyrrolic species, the α-(vinylpyrrolyl)dipyrrin, as the only isolable product. The new tripyrrole displays positive solvatochromic behavior and has been investigated with respect to this property.

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2

Blanco, Juan B., Verónica I. Dodero, M. Eugenio Vázquez, Manuel Mosquera, Luis Castedo, and José L. Mascareñas. "Sequence-Specific DNA Binding by Noncovalent Peptide–Tripyrrole Conjugates." Angewandte Chemie International Edition 45, no. 48 (December 11, 2006): 8210–14. http://dx.doi.org/10.1002/anie.200603115.

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Blanco, Juan B., Verónica I. Dodero, M. Eugenio Vázquez, Manuel Mosquera, Luis Castedo, and José L. Mascareñas. "Sequence-Specific DNA Binding by Noncovalent Peptide–Tripyrrole Conjugates." Angewandte Chemie 118, no. 48 (December 11, 2006): 8390–94. http://dx.doi.org/10.1002/ange.200603115.

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4

Fürstner, Alois, Jaroslaw Grabowski, and Christian W. Lehmann. "Total Synthesis and Structural Refinement of the Cyclic Tripyrrole Pigment Nonylprodigiosin." Journal of Organic Chemistry 64, no. 22 (October 1999): 8275–80. http://dx.doi.org/10.1021/jo991021i.

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5

Blanco, Juan B., Olalla Vázquez, José Martínez-Costas, Luis Castedo, and José L. Mascareñas. "High Affinity, Sequence Specific DNA Binding by Synthetic Tripyrrole-Peptide Conjugates." Chemistry - A European Journal 11, no. 14 (July 4, 2005): 4171–78. http://dx.doi.org/10.1002/chem.200500010.

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6

Rath, Sankar Prasad, Marilyn M. Olmstead, Lechoslaw Latos-Grażyński, and Alan L. Balch. "Formation and Isolation of an Iron-Tripyrrole Complex from Heme Degradation." Journal of the American Chemical Society 125, no. 42 (October 2003): 12678–79. http://dx.doi.org/10.1021/ja036656k.

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7

Kreher, Richard P., and Thomas Hildebrand. "Struktur und Reaktivität von isoanellierten heterocyclischen Systemen mit 4nπ- und (4n+2)π-Elektronen, XIV [1]: Tri- und tetracyclische Hetarene mit lokalisierten oder delokalisierten PyrroI-Strukturen / Structure and Reactivity of Isoannellated Heterocyclic Systems with 4nπ- and (4n+2)π-Electrons, XIV [1]: Tri- and Tetracyclic Hetarenes with Localized or Delocalized Pyrrole Units." Zeitschrift für Naturforschung B 43, no. 1 (January 1, 1988): 125–31. http://dx.doi.org/10.1515/znb-1988-0122.

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Abstract 2,7-Di-tert-butyl-2,7-dihydro-benzo[ 1,2-c:3,4-c′]dipyrrole (2b) and 2,5,8-Tri-tert-butyl-5.8-di-hydro-2H-benzo[1,2-c:3,4-c′:5,6-c″]tripyrrole (3b) have been prepared by acetolysis of the cor-responding tri-and tetracyclic N-oxides, isolated in crystallinic form and characterized by spectroscopic data. The scope of the N-oxide route is documented and the existence of benzoannellated pyrroles is proofed. The stabilizing effect of the tert-butyl group is presumably sup-ported by the vicinal annellated heterocycles.

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8

Subramanian, Mahesh, Ramesh Chander, and Subrata Chattopadhyay. "A novel naturally occurring tripyrrole with potential nuclease and anti-tumour properties." Bioorganic & Medicinal Chemistry 14, no. 8 (April 2006): 2480–86. http://dx.doi.org/10.1016/j.bmc.2005.11.062.

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9

Bérubé, Christian D., Mohammad Yazdanbakhsh, Sandro Gambarotta, and Glenn P. A. Yap. "Serendipitous Isolation of the First Example of a Mixed-Valence Samarium Tripyrrole Complex." Organometallics 22, no. 18 (September 2003): 3742–47. http://dx.doi.org/10.1021/om030155q.

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10

Fuerstner, Alois, Jaroslaw Grabowski, and Christian W. Lehmann. "ChemInform Abstract: Total Synthesis and Structural Refinement of the Cyclic Tripyrrole Pigment Nonylprodigiosin." ChemInform 31, no. 7 (June 10, 2010): no. http://dx.doi.org/10.1002/chin.200007185.

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11

Han, Ning, Tingting Ran, Xiangdi Lou, Yanyan Gao, Jianhua He, Lin Tang, Dongqing Xu, and Weiwu Wang. "Expression, crystallization and preliminary crystallographic data analysis of PigI, a putativeL-prolyl-AMP ligase from the prodigiosin synthetic pathway inSerratia." Acta Crystallographica Section F Structural Biology Communications 70, no. 5 (April 17, 2014): 624–27. http://dx.doi.org/10.1107/s2053230x14005780.

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Prodigiosin, a member of the prodiginines, is a tripyrrole red pigment synthesized bySerratiaand some other microbes. A bifurcated biosynthesis pathway of prodigiosin has been proposed inSerratiain which MBC (4-methoxy-2,2′-bipyrrole-5-carbaldehyde) and MAP (2-methyl-3-N-amyl-pyrrole) are synthesized separately and then condensed by PigC to form prodigiosin. The first step for the synthesis of MBC is the activation of L-proline by PigI, but its catalytic mechanism has remained elusive. To elucidate its mechanism, recombinant PigI was purified and crystallized. Crystals obtained by the sitting-drop method belonged to space groupP1 and diffracted to 2.0 Å resolution, with unit-cell parametersa= 51.2,b= 62.8,c= 91.3 Å, α = 105.1, β = 90.1, γ = 92.2°. Matthews coefficient analysis suggested two molecules in the asymmetric unit, with aVMof 2.6 Å3 Da−1and a solvent content of 52.69%.

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12

Dodero, Verónica I., Manuel Mosquera, Juan B. Blanco, Luis Castedo, and José L. Mascareñas. "Modulating the Rate of a Native Ligation Coupling between Tripyrrole Derivatives by Using Specific dsDNA Sequences." Organic Letters 8, no. 20 (September 2006): 4433–36. http://dx.doi.org/10.1021/ol061551i.

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13

Horng, Yu-Tze, Kai-Chih Chang, Yen-Ni Liu, Hsin-Chih Lai, and Po-Chi Soo. "The RssB/RssA two-component system regulates biosynthesis of the tripyrrole antibiotic, prodigiosin, in Serratia marcescens." International Journal of Medical Microbiology 300, no. 5 (June 2010): 304–12. http://dx.doi.org/10.1016/j.ijmm.2010.01.003.

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14

Fineran, Peter C., Lee Everson, Holly Slater, and George P. C. Salmond. "A GntR family transcriptional regulator (PigT) controls gluconate-mediated repression and defines a new, independent pathway for regulation of the tripyrrole antibiotic, prodigiosin, in Serratia." Microbiology 151, no. 12 (December 1, 2005): 3833–45. http://dx.doi.org/10.1099/mic.0.28251-0.

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Biosynthesis of the red, tripyrrole antibiotic prodigiosin (Pig) by Serratia sp. ATCC 39006 (39006) is controlled by a complex regulatory network involving an N-acyl homoserine lactone (N-AHL) quorum-sensing system, at least two separate two-component signal transduction systems and a multitude of other regulators. In this study, a new transcriptional activator, PigT, and a physiological cue (gluconate), which are involved in an independent pathway controlling Pig biosynthesis, have been characterized. PigT, a GntR homologue, activates transcription of the pigA–O biosynthetic operon in the absence of gluconate. However, addition of gluconate to the growth medium of 39006 repressed transcription of pigA–O, via a PigT-dependent mechanism, resulting in a decrease in Pig production. Finally, expression of the pigT transcript was shown to be maximal in exponential phase, preceding the onset of Pig production. This work expands our understanding of both the physiological and genetic factors that impinge on the biosynthesis of the secondary metabolite Pig in 39006.

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15

Setsune, Jun-ichiro, and Keigo Watanabe. "Synthesis and structure of expanded pyriporphyrins containing a dipyrrylpyridine unit." Journal of Porphyrins and Phthalocyanines 16, no. 05n06 (May 2012): 508–17. http://dx.doi.org/10.1142/s1088424612500502.

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Expanded pyriporphyrins with five and ten nitrogens were prepared in 67% and 6.5% yield, respectively, by the reactions of bis(azafulvene) and dipyrrylpyridine. The minimum 17-membered non-aromatic macrocycle made of four pyrroles and one pyridine is highly non-planar in comparison with orangarin that contains a tripyrrole unit instead of a dipyrrylpyridine unit. This highly non-planar ring structure is basically unchanged in the complex with trifluoroacetic acid (TFA) where carboxylate anions are bound on both sides of the macrocyle plane by multiple hydrogen bondings. This monopyridine-tetrapyrrole hybrid macrocycle was able to act as a dianionic ligand for various metal ions including lanthanide ions. In contrast to the reported figure eight type X-ray structure of turcasarin that is a double sized macrocycle of orangarin, the pyridine-containing macrocycle analog of the same 34-membered ring size isolated in this study was found not to take a figure eight type conformation as evidenced by X-ray crystallography of the tetracation with TFA anions.

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16

Satz, Alexander L., and Thomas C. Bruice. "Recognition of Nine Base Pairs in the Minor Groove of DNA by a Tripyrrole Peptide−Hoechst Conjugate." Journal of the American Chemical Society 123, no. 11 (March 2001): 2469–77. http://dx.doi.org/10.1021/ja003095d.

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17

Subramanian, Mahesh, Ramesh Chander, Malini Krishna, and Subrata Chattopadhyay. "Involvement of cytoplasmic membrane damage in the copper (II)-dependent cytotoxicity of a novel naturally occurring tripyrrole." Biochimica et Biophysica Acta (BBA) - General Subjects 1770, no. 1 (January 2007): 143–49. http://dx.doi.org/10.1016/j.bbagen.2006.10.009.

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18

Chen, Jihua, Yuji Li, Fuqiang Liu, De-Xing Hou, Jingjing Xu, Xinying Zhao, Fei Yang, and Xiangling Feng. "Prodigiosin Promotes Nrf2 Activation to Inhibit Oxidative Stress Induced by Microcystin-LR in HepG2 Cells." Toxins 11, no. 7 (July 12, 2019): 403. http://dx.doi.org/10.3390/toxins11070403.

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Microcystin-LR (MC-LR), a cyanotoxin produced by cyanobacteria, induces oxidative stress in various types of cells. Prodigiosin, a red linear tripyrrole pigment, has been recently reported to have antimicrobial, antioxidative, and anticancer properties. How prodigiosin reacts to reactive oxygen species (ROS) induced by MC-LR is still undetermined. This study aimed to examine the effect of prodigiosin against oxidative stress induced by MC-LR in HepG2 cells. Ros was generated after cells were treated with MC-LR and was significantly inhibited with treatment of prodigiosin. In prodigiosin-treated cells, the levels of nuclear factor erythroid 2-related factor 2 (Nrf2) and Nrf2-related phase II enzyme heme oxygenase-1 (HO-1) were increased. Besides, prodigiosin contributed to enhance nuclear Nrf2 level and repressed ubiquitination. Furthermore, prodigiosin promoted Nrf2 protein level and inhibited ROS in Nrf2 knocked down HepG2 cells. Results indicated that prodigiosin reduced ROS induced by MC-LR by enhancing Nrf2 translocation into the nucleus in HepG2 cells. The finding presents new clues for the potential clinical applications of prodigiosin for inhibiting MC-LR-induced oxidative injury in the future.

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19

Wetzler, Diana E., Maria J. Comin, Krzysztof Krajewski, and Mariana Gallo. "New Human Papilloma Virus E2 Transcription Factor Mimics: A Tripyrrole-Peptide Conjugate with Tight and Specific DNA-Recognition." PLoS ONE 6, no. 7 (July 25, 2011): e22409. http://dx.doi.org/10.1371/journal.pone.0022409.

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20

Chauhan, Ritika, Aniket Choudhuri, and Jayanthi Abraham. "EVALUATION OF ANTIMICROBIAL, CYTOTOXICITY, AND DYEING PROPERTIES OF PRODIGIOSIN PRODUCED BY SERRATIA MARCESCENS STRAIN JAR8." Asian Journal of Pharmaceutical and Clinical Research 10, no. 8 (August 1, 2017): 279. http://dx.doi.org/10.22159/ajpcr.2017.v10i8.18173.

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Objective: Prodigiosin is a red tripyrrole pigment which is synthesized as a secondary metabolite by biotypes A1, A2, and A6 of Serretia marcescens. This study was aimed to optimize production parameters for prodigiosin pigment produced by S. marcescens strain JAR8 and to determine its antimicrobial, cytotoxicity, and dyeing properties.Methods: The effect of various media components, process parameters (temperature, pH, incubation period), and other supplements was investigated, and the maximum production of prodigiosin was found to be at temperature 28°C, pH 7.0, incubation period of 5 day with peptone in the media. Antibacterial, cytotoxicity, and dyeing properties of prodigiosin were studied in depth.Results: The antimicrobial study of prodigiosin revealed that it is a potent inhibitor of Gram-positive bacteria as well as Gram-negative bacteria. The prodigiosin exhibited commendable dose-dependent cytotoxicity effect against human bone cancer cells with the IC50 of 108 μg/ml. Prodigiosin produced by strain JAR8 resisted the action of acid, alkali and detergent when applied to textile cloth.Conclusion: The deep red pigment prodigiosin produced by strain JAR8 is economically effective and can be categorized as microbial natural product for further pharmaceutical applications.

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21

Bley-Escrich, Jordi, Serguei Prikhodovski, Carsten D. Brandt, Martin Bröring, and Jean-Paul Gisselbrecht. "Electrochemical investigations of tripyrrin complexes." Journal of Porphyrins and Phthalocyanines 07, no. 04 (April 2003): 220–26. http://dx.doi.org/10.1142/s1088424603000306.

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Electrochemical investigations on divalent transition metal complexes with a conjugated linear tripyrrole ligand, namely 3,4,8,9,13,14-hexaethyl-2,15-dimethyltripyrrin (HTrpy) are reported. This tripyrrin ligand behaves as a tridentate monoanionic ligand and forms a series of neutral metal complexes of the type TrpyMX, where M = Zn ( II ), Cu ( II ), Ni ( II ) Co ( II ) or Pd ( II ) and X is a chloride anion ( Cl -). The studied nickel, cobalt and zinc complexes undergo respectively three and two ligand-centered reversible one-electron reductions and a reversible ligand-centered one-electron oxidation. Only irreversible electron transfers are observed for TrpyPdCl , due to the instability of the reduced complex. TrpyCoCl does not undergo any metal-centered electron transfer which is unexpected compared to related complexes. The copper(II) complex shows an additional reduction step occurring on the metal, generating a stable copper(I) complex. A comparison of the redox behavior of tripyrrin complexes with porphyrins and linear tetrapyrrolic complexes, namely bidipyrrins, clearly indicates that the observed redox behavior of tripyrrin complexes is mainly metal dependent. The observed HOMO-LUMO gap in the studied series of tripyrrins is rather small (about 1.70 V) compared to porphyrins (2.25 V), but it is close to bidipyrrins (1.60 V).

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22

Bruice, T. C., H. Y. Mei, G. X. He, and V. Lopez. "Rational design of substituted tripyrrole peptides that complex with DNA by both selective minor-groove binding and electrostatic interaction with the phosphate backbone." Proceedings of the National Academy of Sciences 89, no. 5 (March 1, 1992): 1700–1704. http://dx.doi.org/10.1073/pnas.89.5.1700.

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23

Ouellet, Yannick H., Cheikh Tidiane Ndiaye, Stéphane M. Gagné, Anne Sebilo, Michael D. L. Suits, Éric Jubinville, Zongchao Jia, Anabella Ivancich, and Manon Couture. "An alternative reaction for heme degradation catalyzed by the Escherichia coli O157:H7 ChuS protein: Release of hematinic acid, tripyrrole and Fe(III)." Journal of Inorganic Biochemistry 154 (January 2016): 103–13. http://dx.doi.org/10.1016/j.jinorgbio.2015.11.002.

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24

Mancini, Joshua A., Molly Sheehan, Goutham Kodali, Brian Y. Chow, Donald A. Bryant, P. Leslie Dutton, and Christopher C. Moser. "De novo synthetic biliprotein design, assembly and excitation energy transfer." Journal of The Royal Society Interface 15, no. 141 (April 2018): 20180021. http://dx.doi.org/10.1098/rsif.2018.0021.

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Bilins are linear tetrapyrrole chromophores with a wide range of visible and near-visible light absorption and emission properties. These properties are tuned upon binding to natural proteins and exploited in photosynthetic light-harvesting and non-photosynthetic light-sensitive signalling. These pigmented proteins are now being manipulated to develop fluorescent experimental tools. To engineer the optical properties of bound bilins for specific applications more flexibly, we have used first principles of protein folding to design novel, stable and highly adaptable bilin-binding four-α-helix bundle protein frames, called maquettes, and explored the minimal requirements underlying covalent bilin ligation and conformational restriction responsible for the strong and variable absorption, fluorescence and excitation energy transfer of these proteins. Biliverdin, phycocyanobilin and phycoerythrobilin bind covalently to maquette Cys in vitro . A blue-shifted tripyrrole formed from maquette-bound phycocyanobilin displays a quantum yield of 26%. Although unrelated in fold and sequence to natural phycobiliproteins, bilin lyases nevertheless interact with maquettes during co-expression in Escherichia coli to improve the efficiency of bilin binding and influence bilin structure. Bilins bind in vitro and in vivo to Cys residues placed in loops, towards the amino end or in the middle of helices but bind poorly at the carboxyl end of helices. Bilin-binding efficiency and fluorescence yield are improved by Arg and Asp residues adjacent to the ligating Cys on the same helix and by His residues on adjacent helices.

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25

He, Gong-Xin, Kenneth A. Browne, Andrei Blasko, and Thomas C. Bruice. "Microgonotropens and Their Interactions with DNA. 4. Synthesis of the Tripyrrole Peptides Tren-Microgonotropen-a and -b and Characterization of Their Interactions with dsDNA." Journal of the American Chemical Society 116, no. 9 (May 1994): 3716–25. http://dx.doi.org/10.1021/ja00088a007.

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26

Williamson, N. R., H. T. Simonsen, A. K. P. Harris, F. J. Leeper, and George P. C. Salmond. "Disruption of the copper efflux pump (CopA) of Serratia marcescens ATCC 274 pleiotropically affects copper sensitivity and production of the tripyrrole secondary metabolite, prodigiosin." Journal of Industrial Microbiology & Biotechnology 33, no. 2 (September 27, 2005): 151–58. http://dx.doi.org/10.1007/s10295-005-0040-9.

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27

Hunt, Alison C., Luis Servín-González, Gabriella H. Kelemen, and Mark J. Buttner. "The bldC Developmental Locus of Streptomyces coelicolor Encodes a Member of a Family of Small DNA-Binding Proteins Related to the DNA-Binding Domains of the MerR Family." Journal of Bacteriology 187, no. 2 (January 15, 2005): 716–28. http://dx.doi.org/10.1128/jb.187.2.716-728.2005.

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ABSTRACT The bldC locus, required for formation of aerial hyphae in Streptomyces coelicolor, was localized by map-based cloning to the overlap between cosmids D17 and D25 of a minimal ordered library. Subcloning and sequencing showed that bldC encodes a member of a previously unrecognized family of small (58- to 78-residue) DNA-binding proteins, related to the DNA-binding domains of the MerR family of transcriptional activators. BldC family members are found in a wide range of gram-positive and gram-negative bacteria. Constructed ΔbldC mutants were defective in differentiation and antibiotic production. They failed to form an aerial mycelium on minimal medium and showed severe delays in aerial mycelium formation on rich medium. In addition, they failed to produce the polyketide antibiotic actinorhodin, and bldC was shown to be required for normal and sustained transcription of the pathway-specific activator gene actII-orf4. Although ΔbldC mutants produced the tripyrrole antibiotic undecylprodigiosin, transcripts of the pathway-specific activator gene (redD) were reduced to almost undetectable levels after 48 h in the bldC mutant, in contrast to the bldC + parent strain in which redD transcription continued during aerial mycelium formation and sporulation. This suggests that bldC may be required for maintenance of redD transcription during differentiation. bldC is expressed from a single promoter. S1 nuclease protection assays and immunoblotting showed that bldC is constitutively expressed and that transcription of bldC does not depend on any of the other known bld genes. The bldC18 mutation that originally defined the locus causes a Y49C substitution that results in instability of the protein.

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28

Tiberghien, Arnaud C., David A. Evans, Konstantinos Kiakos, Christopher R. H. Martin, John A. Hartley, David E. Thurston, and Philip W. Howard. "An asymmetric C8/C8′-tripyrrole-linked sequence-selective pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimer DNA interstrand cross-linking agent spanning 11 DNA base pairs." Bioorganic & Medicinal Chemistry Letters 18, no. 6 (March 2008): 2073–77. http://dx.doi.org/10.1016/j.bmcl.2008.01.096.

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29

Li, Dan, Jun Liu, Xin Wang, Di Kong, Wei Du, Hongbo Li, Chung-Yun Hse, Todd Shupe, Dongpo Zhou, and Kai Zhao. "Biological Potential and Mechanism of Prodigiosin from Serratia marcescens Subsp. lawsoniana in Human Choriocarcinoma and Prostate Cancer Cell Lines." International Journal of Molecular Sciences 19, no. 11 (November 4, 2018): 3465. http://dx.doi.org/10.3390/ijms19113465.

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Tripyrrole molecules have received renewed attention due to reports of numerous biological activities, including antifungal, antibacterial, antiprotozoal, antimalarial, immunosuppressive, and anticancer activities. In a screen of bacterial strains with known toxicities to termites, a red pigment-producing strain, HDZK-BYSB107, was isolated from Chamaecyparis lawsoniana, which grows in Oregon, USA. Strain HDZK-BYSB107 was identified as Serratia marcescens subsp. lawsoniana. The red pigment was identified as prodigiosin using ultraviolet absorption, LC-MS, and 1H-NMR spectroscopy. The bacterial prodigiosin had an inhibitory effect on both Gram-negative and Gram-positive bacteria. The main objective of this study was to explore the anticancer activities and mechanism of strain HDZK-BYSB107 prodigiosin by using human choriocarcinoma (JEG3) and prostate cancer cell lines (PC3) in vitro and JEG3 and PC3 tumor-bearing nude mice in vivo. In vitro anticancer activities showed that the bacterial prodigiosin induced apoptosis in JEG3 cells. In vivo anticancer activities indicated that the prodigiosin significantly inhibited the growth of JEG3 and PC3 cells, and the inhibitory activity was dose and time dependent. The anticancer efficacy of the bacterial prodigiosin on JEG3 and PC3 cells, JEG3 and PC3 tumor exhibited a correlation with the down regulation of the inhibitor of IAP family, including XIAP, cIAP-1 and cIAP-2, and the activation of caspase-9 and caspase-3 accompanied by proteolytic degradation of poly (ADP-ribose)-polymerase. The expressions of P53 and Bax/Bcl-2 in JEG3 and PC3 cells were significantly higher than in untreated groups. Our results indicated that the bacterial prodigiosin extracted from C. lawsoniana is a promising molecule due to its potential for therapeutic applications.

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30

Nikiforov, Grigory B., Patrick Crewdson, Sandro Gambarotta, Ilia Korobkov, and Peter H. M. Budzelaar. "Reduction of Titanium Supported by aσ-/π-Bonded Tripyrrole Ligand: Ligand C−N Bond Cleavage and Coordination of Olefin and Arene with an Inverse Sandwich Structure." Organometallics 26, no. 1 (January 2007): 48–55. http://dx.doi.org/10.1021/om060908j.

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31

Uno, Hidemitsu, Yumiko Fumoto, Kentarou Inoue, and Noboru Ono. "NMR and X-ray analyses of triethyl 3,7,11-triphenylcyclonona[1,2-b;4,5-b′;7,8-b″]tripyrrole-2,6,10-tricarboxylate: reinvestigation of crown vs saddle conformation of cyclononatripyrroles." Tetrahedron 59, no. 5 (January 2003): 601–5. http://dx.doi.org/10.1016/s0040-4020(02)01589-2.

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32

Fineran, Peter C., Holly Slater, Lee Everson, Katie Hughes, and George P. C. Salmond. "Biosynthesis of tripyrrole and β-lactam secondary metabolites inSerratia: integration of quorum sensing with multiple new regulatory components in the control of prodigiosin and carbapenem antibiotic production." Molecular Microbiology 56, no. 6 (May 9, 2005): 1495–517. http://dx.doi.org/10.1111/j.1365-2958.2005.04660.x.

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33

Blanco, Juan B., M. Eugenio Vázquez, Luis Castedo, and José L. Mascareñas. "Sequence-Specific DNA Recognition by Monomeric bZIP Basic Regions Equipped with a Tripyrrole Unit on the N-Terminal Side. Towards the Development of Synthetic Mimics of Skn-1." ChemBioChem 6, no. 12 (October 17, 2005): 2173–76. http://dx.doi.org/10.1002/cbic.200500294.

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34

HE, G. X., K. A. BROWNE, J. C. GROPPE, A. BLASKO, H. Y. MEI, and T. C. BRUICE. "ChemInform Abstract: Microgonotropens and Their Interactions with DNA. Part 1. Synthesis of the Tripyrrole Peptides Dien-Microgonotropen-a, -b, and -c and Characterization of Their Interactions with dsDNA." ChemInform 24, no. 49 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199349254.

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35

Yip, Chee-Hoo, Sobina Mahalingam, Kiew-Lian Wan, and Sheila Nathan. "Prodigiosin inhibits bacterial growth and virulence factors as a potential physiological response to interspecies competition." PLOS ONE 16, no. 6 (June 23, 2021): e0253445. http://dx.doi.org/10.1371/journal.pone.0253445.

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Prodigiosin, a red linear tripyrrole pigment, has long been recognised for its antimicrobial property. However, the physiological contribution of prodigiosin to the survival of its producing hosts still remains undefined. Hence, the aim of this study was to investigate the biological role of prodigiosin from Serratia marcescens, particularly in microbial competition through its antimicrobial activity, towards the growth and secreted virulence factors of four clinical pathogenic bacteria (methicillin-resistant Staphylococcus aureus (MRSA), Enterococcus faecalis, Salmonella enterica serovar Typhimurium and Pseudomonas aeruginosa) as well as Staphylococcus aureus and Escherichia coli. Prodigiosin was first extracted from S. marcescens and its purity confirmed by absorption spectrum, high performance liquid chromatography (HPLC) and liquid chromatography-tandem mass spectrophotometry (LC-MS/MS). The extracted prodigiosin was antagonistic towards all the tested bacteria. A disc-diffusion assay showed that prodigiosin is more selective towards Gram-positive bacteria and inhibited the growth of MRSA, S. aureus and E. faecalis and Gram-negative E. coli. A minimum inhibitory concentration of 10 μg/μL of prodigiosin was required to inhibit the growth of S. aureus, E. coli and E. faecalis whereas > 10 μg/μL was required to inhibit MRSA growth. We further assessed the effect of prodigiosin towards bacterial virulence factors such as haemolysin and production of protease as well as on biofilm formation. Prodigiosin did not inhibit haemolysis activity of clinically associated bacteria but was able to reduce protease activity for MRSA, E. coli and E. faecalis as well as decrease E. faecalis, Salmonella Typhimurium and E. coli biofilm formation. Results of this study show that in addition to its role in inhibiting bacterial growth, prodigiosin also inhibits the bacterial virulence factor protease production and biofilm formation, two strategies employed by bacteria in response to microbial competition. As clinical pathogens were more resistant to prodigiosin, we propose that prodigiosin is physiologically important for S. marcescens to compete against other bacteria in its natural soil and surface water environments.

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36

He, Gong Xin, Kenneth A. Browne, Jay C. Groppe, Andrei Blasko, Houng Yau Mei, and Thomas C. Bruice. "Chemistry of phosphodiesters, DNA and models. 3. Microgonotropens and their interactions with DNA. 1. Synthesis of the tripyrrole peptides dien-microgonotropen-a, -b, and -c and characterization of their interactions with dsDNA." Journal of the American Chemical Society 115, no. 16 (August 1993): 7061–71. http://dx.doi.org/10.1021/ja00069a002.

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37

Blanco, Juan B., M. Eugenio Vázquez, Luis Castedo, and José L. Mascareñas. "Cover Picture: Sequence-Specific DNA Recognition by Monomeric bZIP Basic Regions Equipped with a Tripyrrole Unit on the N-Terminal Side. Towards the Development of Synthetic Mimics of Skn-1 (ChemBioChem 12/2005)." ChemBioChem 6, no. 12 (November 30, 2005): 2113. http://dx.doi.org/10.1002/cbic.200590039.

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38

Zhang, Tao, Alfonso Davila, Mark L. McLaughlin, Steven F. Watkins, and Frank R. Fronczek. "1,3,5-Trichloro-2,4,6-tripyrrol-1-ylbenzene." Acta Crystallographica Section E Structure Reports Online 63, no. 2 (January 12, 2007): o604—o605. http://dx.doi.org/10.1107/s1600536806056376.

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39

Manzila, Ifa, Tri P. Priyatno, Rahminovita Herlis, Iman Rusmana, I. Made Samudra, and Yadi Suryadi. "Pengaruh Media terhadap Produksi Prodigiosin Isolat Bakteri Entomopatogen Serratia marcescens Asal Wereng Batang Cokelat." Jurnal AgroBiogen 10, no. 2 (August 23, 2016): 77. http://dx.doi.org/10.21082/jbio.v10n2.2014.p77-84.

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<p>Prodigiosin, the red pigment produced<br />by the bacterium Serratia marcescens, is a secondary<br />metabolite of the family tripyrrole that has been widely used<br />as an antibiotic in the multifunction treatment of<br />antibacterial as well as antifungal. This study was aimed to<br />study the effect of Luria-Bertani (LB) broth and nutrient<br />broth (NB) media suplemented with several concentrations<br />of FeSO4 and CaCO3 on the production and characteristic of<br />prodigiosin derived from S. marcescens. The study was<br />arranged in a completely randomized factorial design with<br />four replications. The LB and NB media were supplemented<br />with 0, 2.5, 5, and 10 mM CaCO3 and 0, 0.25, 0.5, and 1 mM<br />FeSO4. Results showed a red pigment produced by S.<br />marcescens when cultured on both LB and NB media. Redlike<br />pigmentation was varied when supplemented with<br />different concentration of Fe2+ and Ca2+. The higher the<br />concentration of Fe2+, the more intense the red color,<br />conversely, the higher the concentration of Ca2+, the lighter<br />the red color. The interaction was found between the media<br />and concentrations of CaCO3 and FeSO4 on the production<br />of prodigiosin. The highest prodigiosin production was<br />obtained on NB media supplemented with FeSO4.<br />Meanwhile, the addition of CaCO3 did not affect the<br />prodigiosin production. An addition of 1 mM FeSO4 to LB<br />and NB media produced crude prodigiosin of 486.0 mg/ml<br />and 489.0 mg/ml, respectively. Based on purification by<br />column chromatography using silica gel, the prodigiosin<br />production on LB and NB media was 378 mg/ml and 450<br />mg/ml, with the purity level of 77.8% and 92%, respectively.<br />Detection of prodigiosin by thin-layer chromatography using<br />silica gel showed the red pigment had Rf value of 0.83 and<br />bioautography assay showed there was an antibacterial<br />activity against Xanthomanas oryzae pv. oryzae.</p>

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40

Lee, D. H., S. G. Lee, D. I. Jung, and J. T. Hahn. "Synthesis of Heteroaromatic Derivatives with Nitrogen Atoms: Tripyrrolyl Pyrimidine and Tripyrrolyl[1,3,5]triazine." Asian Journal of Chemistry 25, no. 1 (2013): 501–4. http://dx.doi.org/10.14233/ajchem.2013.13307.

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41

Tomat, Elisa. "Coordination Chemistry of Linear Tripyrroles: Promises and Perils." Comments on Inorganic Chemistry 36, no. 6 (May 16, 2016): 327–42. http://dx.doi.org/10.1080/02603594.2016.1180291.

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42

Greening, Sarah M., Katherine N. Robertson, and Alison Thompson. "Synthesis and characterization of pyrrolyldipyrrin F-BODIPYs." Photochemical & Photobiological Sciences 17, no. 1 (2018): 89–98. http://dx.doi.org/10.1039/c7pp00341b.

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43

Sathish Kumar, B., Narendra N. Pati, K. V. Jovan Jose, and Pradeepta K. Panda. "Synthetic access to calix[3]pyrroles via meso-expansion: hosts with diverse guest chemistry." Chemical Communications 56, no. 42 (2020): 5637–40. http://dx.doi.org/10.1039/d0cc01447h.

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44

Slugovc, Christian, Karl Kirchner, and Kurt Mereiter. "Chloro(dimethylformamide-κO)(hydridotripyrazolylborato)(tripyrrol-1-ylphosphine-κP)ruthenium(II)." Acta Crystallographica Section E Structure Reports Online 62, no. 6 (May 24, 2006): m1356—m1358. http://dx.doi.org/10.1107/s1600536806018277.

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45

Jolicoeur, Benoit, and William D. Lubell. "Prodigiosin synthesis with electron rich 2,2′-bipyrroles." Canadian Journal of Chemistry 86, no. 3 (March 1, 2008): 213–18. http://dx.doi.org/10.1139/v07-150.

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The prodigiosins possess a linear tripyrrolic scaffold with the A and B pyrrolic rings connected directly in a bipyrrole unit, and the B and C rings joined in a dipyrrin. These red streptomycete metabolites exhibit among other activities, antitumor, antimicrobial, and immunomodulating properties. A new prodigiosin synthesis has been developed that employs electron rich 2,2′-bipyrroles. In particular, undecylprodigiosin and PNU-156804 were synthesized by condensations of 4-methoxy and 4-benzyloxy 2,2′-bipyrroles, 20a and 20b, respectively, with 5-undecylpyrrole-2-carboxaldehyde in 75% and 83% yields. The 4-alkoxy-2,2′-bipyrroles were synthesized from 4-alkoxypyrrolyl butenyl ketones (15a and 15b), which were made by a novel one-pot process from 2-acyl-N-(PhF)pyrrolidin-4-one (13) [PhF = 9-(9-phenylfluorenyl)] using PhFNa in the presence of alkyl halide. A sequence of alkoxy pyrrole 15a and 15b protection, olefin oxidation, Paal–Knorr condensation, and deprotection gave the requisite 4-alkoxy-2,2′-bipyrroles (20). This route offers utility for making 4-alkoxybipyrroles as well as prodigiosins with diversity at the 6-position of the linear tripyrrolic skeleton.Key words: prodigiosin, pyrrole, bipyrrole, PNU-156804, undecylprodigiosin.

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Sessler, Jonathan L., Andreas Gebauer, Vladimír Král, and Vincent Lynch. "Synthesis and Characterization of a Tripyrrane−Copper(II) Complex." Inorganic Chemistry 35, no. 23 (January 1996): 6636–37. http://dx.doi.org/10.1021/ic9606789.

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47

Marchal, Estelle, Md Imam Uddin, Cassandra L. A. Hawco, and Alison Thompson. "Synthesis of prodigiosene–estrogen conjugates: optimization of protecting group strategies and anticancer properties." Canadian Journal of Chemistry 93, no. 5 (May 2015): 526–35. http://dx.doi.org/10.1139/cjc-2014-0516.

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The tripyrrolic prodigiosene skeleton was conjugated to several estrogen ligands. The conjugation was achieved via an ester linker that proved to be unusually sensitive to hydrolysis during synthesis. This work describes the determination of an appropriate protecting group for the hydroxy groups of the estrogen linker. The anticancer properties of the target prodigiosene–estrogen conjugates were evaluated against breast cancer cells and some show selectivity for ER+ breast cancer cell lines.

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48

Liu, Peng Peng, Ya Qing Feng, Cheng Zhi Gu, Cheng Jie Li, Shu Xian Meng, and Bao Zhang. "A Meso-Substituted Tripyrrin Metal Complex as the Candidate for Fluorescent Material." Advanced Materials Research 557-559 (July 2012): 665–68. http://dx.doi.org/10.4028/www.scientific.net/amr.557-559.665.

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We herein report the synthesis of bis-(5,10-diphenyltripyrrin)nickel(II), which is the first meso-substituted tripyrrin metal complex. The use of tripyrrane as the starting material provides a new synthetic route to tripyrrins. The functionalization on the meso positions endows this type of compound a brighter perspective in synthetic chemistry. Meanwhile, the fluorescent property of the compound has been detected, indicating that this type of compound a strong candidate for fluorescent materials.

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49

Mori, Hirotaka, and Atsuhiro Osuka. "meso–meso Directly-linked trimeric and pentameric electron-deficient porphyrin–hexaphyrin hybrid arrays." Journal of Porphyrins and Phthalocyanines 20, no. 01n04 (January 2016): 245–53. http://dx.doi.org/10.1142/s1088424616500024.

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meso–meso Directly-linked trimeric and pentameric porphyrin–hexaphyrin hybrid arrays 5 and 6 comprising of electron-deficient porphyrin units were prepared by cross-condensation of monomeric and dimeric electron-deficient meso-formyl porphyrins with a tripyrrane. The solid-state structures of 5 and 6 have been determined by single crystal X-ray diffraction analysis. The latter is the largest crystal structure of meso–meso linked multiporphyrinic array analogues reported to date.

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50

Boudif, Arezki, Sandrine Gimenez, Bernard Loock, and Michel Momenteau. "vic-Diacrylic ester porphyrins as starting materials for monobenzoporphyrin and opp-dibenzoporphyrin syntheses." Canadian Journal of Chemistry 76, no. 8 (August 1, 1998): 1215–19. http://dx.doi.org/10.1139/v98-137.

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Synthesis of a bis(vic-diacrylic ester) porphyrin using the "3+1" methodology is described. A two-step procedure is used to convert the vic-diacrylic ester porphyrin and the bis(vic-diacrylic ester) porphyrin to the monobenzoporphyrin and the opp-dibenzoporphyrin, respectively. Characterization of the compounds by 1H NMR and UV-visible spectroscopies is also discussed.Key words: tripyrrane, diformylpyrrole, vic-diacrylic ester porphyrin, "3+1" synthesis methodology, monobenzoporphyrin, opp-dibenzoporphyrin, photosensitizer.

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