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Journal articles on the topic 'Structural analogs'

Author: Grafiati

Published: 4 June 2021

Last updated: 14 February 2022

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1

Gao, Wenli, Annie Pei-Chun Chen, Chung-Hang Leung, Elizabeth A. Gullen, Alois Fürstner, Qian Shi, Linyi Wei, Kuo-Hsiung Lee, and Yung-Chi Cheng. "Structural analogs of tylophora alkaloids may not be functional analogs." Bioorganic & Medicinal Chemistry Letters 18, no. 2 (January 2008): 704–9. http://dx.doi.org/10.1016/j.bmcl.2007.11.054.

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Babkin, I. Yu, G. V. Nazarov, S. E. Galan, O. P. Yudina, A. Yu Lamanov, M. V. Gutsalyuk, and A. V. Aksenov. "Synthesis of structural analogs of epibatidine." Russian Chemical Bulletin 64, no. 2 (February 2015): 466–69. http://dx.doi.org/10.1007/s11172-015-0888-4.

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3

Jankowitsch, Frank, Julia Schwarz, Valentino Konjik, Carmen Schneider, and Matthias Mack. "Antivitamine oder Trojanische Pferde in der Mikrobiologie." BIOspektrum 27, no. 3 (May 2021): 240–45. http://dx.doi.org/10.1007/s12268-021-1573-9.

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AbstractVitamin analogs can be potent antibiotics. We exemplarily study the structural riboflavin (vitamin B2) analog roseoflavin synthesized by Streptomyces davaonensis to pave the way for the structured analysis of other vitamin analogs yet to be discovered. We investigate the biosynthesis of roseoflavin, its mechanism of action, and the resistance mechanism of the producer. As riboflavin is the most important organic cofactor roseoflavin has a broad impact on the soil microbiome.

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Kim, Minseon, Jinyoung Son, and Yongae Kim. "Structural and Mechanismic Studies of Lactophoricin Analog, Novel Antibacterial Peptide." International Journal of Molecular Sciences 22, no. 7 (April 2, 2021): 3734. http://dx.doi.org/10.3390/ijms22073734.

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Naturally derived antibacterial peptides exhibit excellent pharmacological action without the risk of resistance, suggesting a potential role as biologicals. Lactophoricin-I (LPcin-I), found in the proteose peptone component-3 (PP3; lactophorin) of bovine milk, is known to exhibit antibiotic activity against Gram-positive and Gram-negative bacteria. Accordingly, we derived a new antibacterial peptide and investigated its structure–function relationship. This study was initiated by designing antibacterial peptide analogs with better antibacterial activity, less cytotoxicity, and shorter amino acid sequences based on LPcin-I. The structural properties of antibacterial peptide analogs were investigated via spectroscopic analysis, and the antibacterial activity was confirmed by measurement of the minimal inhibitory concentration (MIC). The structure and mechanism of the antibacterial peptide analog in the cell membrane were also studied via solution-state nuclear magnetic resonance (NMR) and solid-state NMR spectroscopy. Through 15N one-dimensional and two-dimensional NMR experiments and 31P NMR experiments, we suggest the 3D morphology and antibacterial mechanism in the phospholipid bilayer of the LPcin analog. This study is expected to establish a system for the development of novel antibacterial peptides and to establish a theoretical basis for research into antibiotic substitutes.

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Sessler, Jonathan L., Rebecca S. Zimmerman, Christophe Bucher, Vladimír Král, and Bruno Andrioletti. "Calixphyrins. Hybrid macrocycles at the structural crossroads between porphyrins and calixpyrroles." Pure and Applied Chemistry 73, no. 7 (July 1, 2001): 1041–57. http://dx.doi.org/10.1351/pac200173071041.

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Calixphyrins are a class of hybrid molecules that lie at the structural crossroads between porphyrins and calixpyrroles. Porphyrins, long known for their versatile metal cation coordination chemistry, are macrocycles that contain only sp2-hybridized bridging meso carbon atoms within their framework. Calix[n]pyrroles, on the other hand, are porphyrin analogs that contain pyrroles bridged exclusively by sp3 meso carbon centers, and in recent years have been shown to display remarkable anion-binding properties. Calix[n]phyrins bear analogy to both the porphyrins and calixpyrroles and are macrocyclic analogs that contain a mixture of sp2- and sp3-hybridized meso carbon bridges. This leads to partial interruptions in the conjugation pathway of the molecule, introduces novel structural features, and leads to interesting anion and cation recognition properties. It also allows for modular syntheses. In the present paper, the chemistry of calix[n]phyrins, still at an early stage of exploration, is reviewed.

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6

Shvachkin, Yu P., A. A. Shishkina, and L. A. Kolomeitseva. "Synthesis of new structural analogs of tetragastrin." Chemistry of Natural Compounds 23, no. 1 (1987): 134–35. http://dx.doi.org/10.1007/bf00602490.

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7

Falck, J. R., U. Murali Krishna, Y. Krishna Reddy, P. Srinagesh Kumar, K. Malla Reddy, Sarah B. Hittner, Christine Deeter, Kamalesh K. Sharma, Kathryn M. Gauthier, and William B. Campbell. "Comparison of vasodilatory properties of 14,15-EET analogs: structural requirements for dilation." American Journal of Physiology-Heart and Circulatory Physiology 284, no. 1 (January 1, 2003): H337—H349. http://dx.doi.org/10.1152/ajpheart.00831.2001.

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Epoxyeicosatrienoic acids (EETs) are endothelium-derived eicosanoids that activate potassium channels, hyperpolarize the membrane, and cause relaxation. We tested 19 analogs of 14,15-EET on vascular tone to determine the structural features required for activity. 14,15-EET relaxed bovine coronary arterial rings in a concentration-related manner (ED50 = 10−6 M). Changing the carboxyl to an alcohol eliminated dilator activity, whereas 14,15-EET-methyl ester and 14,15-EET-methylsulfonimide retained full activity. Shortening the distance between the carboxyl and epoxy groups reduced the agonist potency and activity. Removal of all three double bonds decreased potency. An analog with a Δ8 double bond had full activity and potency. However, the analogs with only a Δ5 or Δ11 double bond had reduced potency. Conversion of the epoxy oxygen to a sulfur or nitrogen resulted in loss of activity. 14( S),15( R)-EET was more potent than 14( R),15( S)-EET, and 14,15-( cis)-EET was more potent than 14,15-( trans)-EET. These studies indicate that the structural features of 14,15-EET required for relaxation of the bovine coronary artery include a carbon-1 acidic group, a Δ8 double bond, and a 14( S),15( R)-( cis)-epoxy group.

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8

Shustova, Ekaterina A. "HETEROCYCLIZATION REACTIONS OF NITROACETONITRILES AND THEIR STRUCTURAL ANALOGS." NATURAL SCIENCES 59, no. 2 (2017): 110–32. http://dx.doi.org/10.21672/1818-507x-2017-59-2-110-132.

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9

Dadiboyena, Sureshbabu, and Ashton T. Hamme II. "Synthesis of Celecoxib and Structural Analogs- A Review." Current Organic Chemistry 16, no. 11 (May 1, 2012): 1390–407. http://dx.doi.org/10.2174/138527212800672664.

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10

Jung, Byunghyuck, Jungkyu K. Lee, Jungnam Kim, Eunhye K. Kang, Sang Yeong Han, Hee‐Yoon Lee, and Insung S. Choi. "Synthetic Strategies for (−)‐Cannabidiol and Its Structural Analogs." Chemistry – An Asian Journal 14, no. 21 (October 8, 2019): 3749–62. http://dx.doi.org/10.1002/asia.201901179.

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11

Dadiboyena, Sureshbabu, and Ashton T. II Hamme. "ChemInform Abstract: Synthesis of Celecoxib and Structural Analogs." ChemInform 43, no. 38 (August 23, 2012): no. http://dx.doi.org/10.1002/chin.201238246.

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12

Guerler, Aysam, and Ernst-Walter Knapp. "Novel protein folds and their nonsequential structural analogs." Protein Science 17, no. 8 (August 2008): 1374–82. http://dx.doi.org/10.1110/ps.035469.108.

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13

Akhundov, R. A., V. A. Zagorevskii, and T. A. Voronina. "Nootropic activity of nicotinamide and its structural analogs." Bulletin of Experimental Biology and Medicine 110, no. 4 (October 1990): 1365–68. http://dx.doi.org/10.1007/bf00842287.

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14

Reddy, G. Venkateswar, T. Vijaya Kumar, B. Siva, K. Suresh Babu, P. V. Srinivas, Irum Sehar, A. K. Saxena, and J. Madhusudana Rao. "Novel malyngamide structural analogs: synthesis and biological evaluation." Medicinal Chemistry Research 22, no. 10 (January 13, 2013): 4581–91. http://dx.doi.org/10.1007/s00044-013-0466-y.

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15

Jeong, Ji-Ho, Ji-Sun Kim, Sung-Sub Choi, and Yongae Kim. "NMR Structural Studies of Antimicrobial Peptides: LPcin Analogs." Biophysical Journal 110, no. 2 (January 2016): 423–30. http://dx.doi.org/10.1016/j.bpj.2015.12.006.

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16

Ghielmetti, Mascia, Anca Reschner, Marianne Zwicker, and Elisabetta Padovan. "Synthetic bacterial lipopeptide analogs: structural requirements for adjuvanticity." Immunobiology 210, no. 2-4 (August 2005): 211–15. http://dx.doi.org/10.1016/j.imbio.2005.05.015.

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17

Freeman, Stephanie A., and Gary T. Rochelle. "Thermal degradation of piperazine and its structural analogs." Energy Procedia 4 (2011): 43–50. http://dx.doi.org/10.1016/j.egypro.2011.01.021.

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18

Mello, Francisco V. C., Alcione S. Carvalho, Mônica M. Bastos, Nubia Boechat, Claudia A. F. Aiub, and Israel Felzenszwalb. "Evaluation of Genotoxic Effects of New Molecules with Possible Trypanocidal Activity for Chagas Disease Treatment." Scientific World Journal 2013 (2013): 1–8. http://dx.doi.org/10.1155/2013/287319.

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Chagas disease is responsible for a large number of human infections and many are also at risk of infection. There is no effective drug for Chagas disease treatment. The Institute of Pharmaceutical Technology at Fiocruz, Brazil, has designed three nitro analogs of the nitroimidazole-thiadiazole, megazol: two triazole analogs PTAL 05-02 and PAMT 09 and a pyrazole analog PTAL 04-09. A set ofSalmonella entericaserovar Typhimurium strains were used in the bacterial reverse mutation test (Ames test) to determine the mutagenicity and cytotoxicity of megazol and its nitro analogs. Megazol presented positive mutagenic activity at very low concentration, either with or without metabolic activation S9 mix. The mutagenic response of the analogs was detected at higher concentration than the lowest megazol concentration to yield mutagenic activity showing that new advances can be made to develop new analogs. The micronucleus test with rat macrophage cells was used in the genotoxic evaluation. The analogs were capable of inducing micronucleus formation and showed cytotoxic effects. PTAL 04-09 structural modifications might be better suitable for the design of promising new drugs candidate for Chagas’ disease treatment.

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19

Buckner, Frederick S., Maria Terezinha Bahia, Praveen Kumar Suryadevara, Karen L. White, David M. Shackleford, Naveen Kumar Chennamaneni, Matthew A. Hulverson, et al. "Pharmacological Characterization, Structural Studies, andIn VivoActivities of Anti-Chagas Disease Lead Compounds Derived from Tipifarnib." Antimicrobial Agents and Chemotherapy 56, no. 9 (July 9, 2012): 4914–21. http://dx.doi.org/10.1128/aac.06244-11.

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ABSTRACTChagas disease, caused by the protozoan pathogenTrypanosoma cruzi, remains a challenging infection due to the unavailability of safe and efficacious drugs. Inhibitors of the trypanosome sterol 14α-demethylase enzyme (CYP51), including azole antifungal drugs, are promising candidates for development as anti-Chagas disease drugs. Posaconazole is under clinical investigation for Chagas disease, although the high cost of this drug may limit its widespread use. We have previously reported that the human protein farnesyltransferase (PFT) inhibitor tipifarnib has potent anti-T. cruziactivity by inhibiting the CYP51 enzyme. Furthermore, we have developed analogs that minimize the PFT-inhibitory activity and enhance the CYP51 inhibition. In this paper, we describe the efficacy of the lead tipifarnib analog compared to that of posaconazole in a murine model ofT. cruziinfection. The plasma exposure profiles for each compound following a single oral dose in mice and estimated exposure parameters after repeated twice-daily dosing for 20 days are also presented. The lead tipifarnib analog had potent suppressive activity on parasitemia in mice but was unsuccessful at curing mice, whereas posaconazole as well as benznidazole cured 3 of 5 and 4 of 6 mice, respectively. The efficacy results are consistent with posaconazole having substantially higher predicted exposure than that of the tipifarnib analog after repeat twice-daily administration. Further changes to the tipifarnib analogs to reduce plasma clearance are therefore likely to be important. A crystal structure of a trypanosomal CYP51 bound to a tipifarnib analog is reported here and provides new insights to guide structure-based drug design for further optimized compounds.

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20

Strokov, I. I., K. S. Lebedev, and B. G. Derendyaev. "Structural data representation and search for structural analogs in molecular spectroscopy databases." Journal of Structural Chemistry 37, no. 6 (November 1996): 954–62. http://dx.doi.org/10.1007/bf02439081.

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21

Knecht, Kirsten M., Olga Buzovetsky, Constanze Schneider, Dominique Thomas, Vishok Srikanth, Lars Kaderali, Florentina Tofoleanu, et al. "The structural basis for cancer drug interactions with the catalytic and allosteric sites of SAMHD1." Proceedings of the National Academy of Sciences 115, no. 43 (October 10, 2018): E10022—E10031. http://dx.doi.org/10.1073/pnas.1805593115.

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SAMHD1 is a deoxynucleoside triphosphate triphosphohydrolase (dNTPase) that depletes cellular dNTPs in noncycling cells to promote genome stability and to inhibit retroviral and herpes viral replication. In addition to being substrates, cellular nucleotides also allosterically regulate SAMHD1 activity. Recently, it was shown that high expression levels of SAMHD1 are also correlated with significantly worse patient responses to nucleotide analog drugs important for treating a variety of cancers, including acute myeloid leukemia (AML). In this study, we used biochemical, structural, and cellular methods to examine the interactions of various cancer drugs with SAMHD1. We found that both the catalytic and the allosteric sites of SAMHD1 are sensitive to sugar modifications of the nucleotide analogs, with the allosteric site being significantly more restrictive. We crystallized cladribine-TP, clofarabine-TP, fludarabine-TP, vidarabine-TP, cytarabine-TP, and gemcitabine-TP in the catalytic pocket of SAMHD1. We found that all of these drugs are substrates of SAMHD1 and that the efficacy of most of these drugs is affected by SAMHD1 activity. Of the nucleotide analogs tested, only cladribine-TP with a deoxyribose sugar efficiently induced the catalytically active SAMHD1 tetramer. Together, these results establish a detailed framework for understanding the substrate specificity and allosteric activation of SAMHD1 with regard to nucleotide analogs, which can be used to improve current cancer and antiviral therapies.

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22

Bayrak, Nilüfer, Mahmut Yıldız, Hatice Yıldırım, Emel Mataracı-Kara, and Amaç Fatih Tuyun. "Novel plastoquinone analogs containing benzocaine and its analogs: structure‐based design, synthesis, and structural characterization." Research on Chemical Intermediates 47, no. 5 (February 3, 2021): 2125–41. http://dx.doi.org/10.1007/s11164-020-04384-5.

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23

Jamil, Muhammad, Boubacar A. Kountche, Imran Haider, Xiujie Guo, Valentine O. Ntui, Kun-Peng Jia, Shawkat Ali, et al. "Methyl phenlactonoates are efficient strigolactone analogs with simple structure." Journal of Experimental Botany 69, no. 9 (December 28, 2017): 2319–31. http://dx.doi.org/10.1093/jxb/erx438.

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abstract Strigolactones (SLs) are a new class of phytohormones that also act as germination stimulants for root parasitic plants, such as Striga spp., and as branching factors for symbiotic arbuscular mycorrhizal fungi. Sources for natural SLs are very limited. Hence, efficient and simple SL analogs are needed for elucidating SL-related biological processes as well as for agricultural applications. Based on the structure of the non-canonical SL methyl carlactonoate, we developed a new, easy to synthesize series of analogs, termed methyl phenlactonoates (MPs), evaluated their efficacy in exerting different SL functions, and determined their affinity for SL receptors from rice and Striga hermonthica. Most of the MPs showed considerable activity in regulating plant architecture, triggering leaf senescence, and inducing parasitic seed germination. Moreover, some MPs outperformed GR24, a widely used SL analog with a complex structure, in exerting particular SL functions, such as modulating Arabidopsis roots architecture and inhibiting rice tillering. Thus, MPs will help in elucidating the functions of SLs and are promising candidates for agricultural applications. Moreover, MPs demonstrate that slight structural modifications clearly impact the efficiency in exerting particular SL functions, indicating that structural diversity of natural SLs may mirror a functional specificity.

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Balch, Alan L., Lechoslaw Latos-Grazynski, Bruce C. Noll, Marilyn M. Olmstead, Ludmila Szterenberg, and Nasser Safari. "Structural characterization of verdoheme analogs. Iron complexes of octaethyloxoporphyrin." Journal of the American Chemical Society 115, no. 4 (February 1993): 1422–29. http://dx.doi.org/10.1021/ja00057a027.

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Bayrak, Nilüfer, Mahmut Yıldız, Hatice Yıldırım, Emel Mataracı Kara, Berna Ozbek Celik, and Amaç Fatih Tuyun. "Brominated plastoquinone analogs: Synthesis, structural characterization, and biological evaluation." Journal of Molecular Structure 1219 (November 2020): 128560. http://dx.doi.org/10.1016/j.molstruc.2020.128560.

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26

Orthaber, Doris, and Otto Glatter. "Synthetic phospholipid analogs: a structural investigation with scattering methods." Chemistry and Physics of Lipids 107, no. 2 (October 2000): 179–89. http://dx.doi.org/10.1016/s0009-3084(00)00171-7.

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27

Sakamoto, Miho, Jin Suzuki, Yuri Saito, Seiko Shimizu, Kazue Kobayashi, Machiko Nagashima, Takako Moriyasu, Haruhiko Fukaya, and Koichi Saito. "Structural characterization of dimethyldithiodenafil and dimethylthiocarbodenafil, analogs of sildenafil." Journal of Pharmaceutical and Biomedical Analysis 148 (January 2018): 136–41. http://dx.doi.org/10.1016/j.jpba.2017.09.025.

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28

Bhattacharjee, Apurba K., Dennis E. Kyle, and Jonathan L. Vennerstrom. "Structural Analysis of Chloroquine Resistance Reversal by Imipramine Analogs." Antimicrobial Agents and Chemotherapy 45, no. 9 (September 1, 2001): 2655–57. http://dx.doi.org/10.1128/aac.45.9.2655-2657.2001.

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ABSTRACT For imipramine, desipramine, and eight analogs of these well-known drugs, an N-5-aminoalkyl substitution was a minimum but insufficient structural feature associated with chloroquine resistance reversal. Although a second distal aliphatic nitrogen atom was unnecessary for resistance reversal, the direction of the dipole moment vector was critical.

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29

Jarosz, Slawomir, Mateusz Mach, and Jadwiga Frelek. "Synthesis and Structural Analysis of Higher Analogs of Sucrose." Journal of Carbohydrate Chemistry 19, no. 6 (January 2000): 693–715. http://dx.doi.org/10.1080/07328300008544111.

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30

Tokumura, A., H. Homma, and D. J. Hanahan. "Structural analogs of alkylacetylglycerophosphocholine inhibitory behavior on platelet activation." Journal of Biological Chemistry 260, no. 23 (October 1985): 12710–14. http://dx.doi.org/10.1016/s0021-9258(17)38932-9.

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31

Xiao, Hao, Ronald R. Marquardt, Andrew A. Frohlich, and Yang Z. Ling. "Synthesis and structural elucidation of analogs of ochratoxin A." Journal of Agricultural and Food Chemistry 43, no. 2 (February 1995): 524–30. http://dx.doi.org/10.1021/jf00050a050.

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32

Adelfinskaya, Olga, Weidong Wu, V. Jo Davisson, and Donald E. Bergstrom. "Synthesis and Structural Analysis of Oxadiazole Carboxamide Deoxyribonucleoside Analogs." Nucleosides, Nucleotides & Nucleic Acids 24, no. 10-12 (September 1, 2005): 1919–45. http://dx.doi.org/10.1080/15257770500269267.

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33

Schwartz, Arthur G., and Laura L. Pashko. "Cancer prevention with dehydroepiandrosterone and non-androgenic structural analogs." Journal of Cellular Biochemistry 59, S22 (1995): 210–17. http://dx.doi.org/10.1002/jcb.240590826.

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34

Egli, Martin. "Structural Aspects of Nucleic Acid Analogs and Antisense Oligonucleotides." Angewandte Chemie International Edition in English 35, no. 17 (September 20, 1996): 1894–909. http://dx.doi.org/10.1002/anie.199618941.

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35

Gmeiner, William H., Shuyuan Yu, Richard T. Pon, Philippe Pourquier, and Yves Pommier. "Structural Basis for Topoisomerase I Inhibition by Nucleoside Analogs." Nucleosides, Nucleotides and Nucleic Acids 22, no. 5-8 (October 2003): 653–58. http://dx.doi.org/10.1081/ncn-120022604.

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36

Schwartz, Arthur G., and Laura L. Pashko. "Analysis: Potential Therapeutic Use of Dehydroepiandrosterone and Structural Analogs." Diabetes Technology & Therapeutics 3, no. 2 (June 2001): 221–24. http://dx.doi.org/10.1089/152091501300209589.

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37

Bourgault, Steve, David Vaudry, Laure Guilhaudis, Émilie Raoult, Alain Couvineau, Marc Laburthe, Isabelle Ségalas-Milazzo, Hubert Vaudry, and Alain Fournier. "Biological and Structural Analysis of Truncated Analogs of PACAP27." Journal of Molecular Neuroscience 36, no. 1-3 (May 13, 2008): 260–69. http://dx.doi.org/10.1007/s12031-008-9081-7.

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38

Doroshenko, A. O., V. N. Baumer, A. V. Kirichenko, V. M. Shershukov, and A. V. Tolmachev. "Molecular structural features of unsymmetrical ortho analogs of POPOP." Chemistry of Heterocyclic Compounds 33, no. 11 (November 1997): 1341–49. http://dx.doi.org/10.1007/bf02320339.

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Islyaikin, M. K., and E. A. Danilova. "Structural analogs of tetrapyrrole macrocycles and their biological properties." Russian Chemical Bulletin 56, no. 4 (April 2007): 689–706. http://dx.doi.org/10.1007/s11172-007-0107-z.

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40

Heavner, George A., Tapan Audhya, Daniel Kroon, and Gideon Goldstein. "Structural requirements for the biological activity of thymopentin analogs." Archives of Biochemistry and Biophysics 242, no. 1 (October 1985): 248–55. http://dx.doi.org/10.1016/0003-9861(85)90499-0.

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41

Liu, Yun, Yang Liu, Shihui Wang, Shengzhao Dong, Ping Chang, and Zhaofeng Jiang. "Structural characteristics of (−)-epigallocatechin-3-gallate inhibiting amyloid Aβ42 aggregation and remodeling amyloid fibers." RSC Advances 5, no. 77 (2015): 62402–13. http://dx.doi.org/10.1039/c5ra09608a.

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To elucidate the structural requirements of EGCG analogs inhibiting Aβ42 protein aggregation and remodeling amyloid fibers, the interactions mechanism between Aβ42 and four EGCG analogs, EGCG, GCG, ECG and EGC, were investigated in this work.

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Hu, Ye, Bijun Zhang, Martin Vogt, and Jürgen Bajorath. "AnalogExplorer2 – Stereochemistry sensitive graphical analysis of large analog series." F1000Research 4 (October 9, 2015): 1031. http://dx.doi.org/10.12688/f1000research.7146.1.

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AnalogExplorer is a computational methodology for the extraction and organization of series of structural analogs from compound data sets and their graphical analysis. The method is suitable for the analysis of large analog series originating from lead optimization programs. Herein we report AnalogExplorer2 designed to explicitly take stereochemical information during graphical analysis into account and describe a freely available deposition of the original AnalogExplorer program, AnalogExplorer2, and exemplary compound sets to illustrate their use.

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Grob, Nathalie M., Roger Schibli, Martin Béhé, and Thomas L. Mindt. "Improved Tumor-Targeting with Peptidomimetic Analogs of Minigastrin 177Lu-PP-F11N." Cancers 13, no. 11 (May 27, 2021): 2629. http://dx.doi.org/10.3390/cancers13112629.

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The cholecystokinin-2 receptor (CCK2R) is an attractive target in nuclear medicine due to its overexpression by different tumors. Several radiolabeled peptidic ligands targeting the CCK2R have been investigated in the past; however, their low stability against proteases can limit their uptake in tumors and metastases. Substitution of single or multiple amide bonds with metabolically stable 1,4-disubstituted 1,2,3-triazoles as amide bond bioisosteres proved a promising strategy for improving the tumor-targeting properties of a truncated analog of minigastrin. In this study, we applied the previously studied structural modifications to improve the pharmacokinetic and pharmacodynamic properties of PP-F11N, a minigastrin analog currently in clinical trials. Novel minigastrins (NMGs) as analogs of PP-F11N with one or two amide bonds substituted by 1,2,3-triazoles were synthesized, radiolabeled with 177Lu3+, and subjected to full evaluation in vitro (cell internalization, receptor affinity, stability in blood plasma) and in vivo (stability, biodistribution, SPECT/CT imaging). NMGs with triazoles inserted between the amino acids DGlu10-Ala11 and/or Tyr12-Gly13 showed a significantly increased cellular uptake and affinity toward the CCK2R in vitro. Resistance against the metabolic degradation of the NMGs was comparable to those of the clinical candidate PP-F11N. Imaging by SPECT/CT and biodistribution studies demonstrated a higher uptake in CCK2R-positive tumors but also in the CCK2R-positive stomach. The peptidomimetic compounds showed a slow tumor washout and high tumor-to-kidney ratios. The structural modifications led to the identification of analogs with promising properties for progression to clinical applications in the diagnosis and therapy of CCK2R-positive neoplasms.

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44

Hinrichs, Thomas, and Kenneth D. Forbus. "Transfer Learning through Analogy in Games." AI Magazine 32, no. 1 (March 16, 2011): 70. http://dx.doi.org/10.1609/aimag.v32i1.2332.

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We report on a series of transfer learning experiments in game domains, in which we use structural analogy from one learned game to speed learning of another related game. We find that a major benefit of analogy is that it reduces the extent to which the source domain must be generalized before transfer. We describe two techniques in particular, minimal ascension and metamapping, that enable analogies to be drawn even when comparing descriptions using different relational vocabularies. Evidence for the effectiveness of these techniques is provided by a large-scale external evaluation, involving a substantial number of novel distant analogs.

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Smith, Kathryn A., Stephen D. Merrigan, and Kamisha L. Johnson-Davis. "Selecting a Structural Analog as an Internal Standard for the Quantification of 6-Methylmercaptopurine by LC-MS/MS." Journal of Applied Laboratory Medicine 3, no. 3 (November 1, 2018): 384–96. http://dx.doi.org/10.1373/jalm.2018.026187.

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Abstract Background When choosing an analog internal standard (IS) in a quantitative LC-MS/MS assay, careful selection and thorough verification are important for developing an accurate quantitative assay. The IS is a critical component in quantitative mass spectrometry because it is used to normalize results by compensating for variations in sample preparation and instrument performance. Here we present the results of our investigation in the selection process for a structural analog IS (SA-IS) to be used in the quantification of 6-methylmercaptopurine (6-MMP) in cytolysed red blood cell (RBC). Methods A cocktail solution of 9 SA-ISs including the isotopically labeled structural isomer and the 6-MMP stable isotope-labeled IS (SIL-IS) was spiked into cytolysed RBC controls and patient samples. Linearity, accuracy, sensitivity, precision, run stability, method comparison, and reinjection reproducibility experiments were performed. Ion suppression was also assessed by T-infusing the cocktail solution. Results All analogs were linear from 100 to 1200 ng/mL 6-MMP with acceptable precision and sensitivity by use of a spiked blank lysate. Method comparison plots of 6-MMP concentrations in patient samples had excellent agreement for 2 of the SA-ISs (i.e., the isotopically labeled structural isomer and an SA-IS with an added methyl group) when compared to the SIL-IS. Halogen-substituted analogs (i.e., Cl and Br) also met the criteria as an acceptable IS. However, 2 of the selected SA-ISs having substituted amine moieties showed unacceptable performance, with ≥15% bias when compared to the SIL-IS. Conclusion There are many parameters to consider when determining if an analog will be a good IS choice, and the approaches highlighted in this article can be applied to the selection of SA-IS in the development of other LC-MS/MS assays.

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Kondrin, Mikhail V., Yulia B. Lebed, and Vadim V. Brazhkin. "Structure and topology of three-dimensional hydrocarbon polymers." Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 72, no. 4 (August 1, 2016): 634–41. http://dx.doi.org/10.1107/s2052520616007253.

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A new family of three-dimensional hydrocarbon polymers which are more energetically favorable than benzene is proposed. Although structurally these polymers are closely related to well known diamond and lonsdaleite carbon structures, using topological arguments we demonstrate that they have no known structural analogs. Topological considerations also give some indication of possible methods of synthesis. Taking into account their exceptional optical, structural and mechanical properties these polymers might have interesting applications.

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Ishii, Satoshi, Atsumi Taguchi, Nozomu Okino, Makoto Ito, and Hiroki Maruyama. "Determination of globotriaosylceramide analogs in the organs of a mouse model of Fabry disease." Journal of Biological Chemistry 295, no. 17 (March 16, 2020): 5577–87. http://dx.doi.org/10.1074/jbc.ra120.012665.

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Fabry disease is a heritable lipid disorder caused by the low activity of α-galactosidase A and characterized by the systemic accumulation of globotriaosylceramide (Gb3). Recent studies have reported a structural heterogeneity of Gb3 in Fabry disease, including Gb3 isoforms with different fatty acids and Gb3 analogs with modifications on the sphingosine moiety. However, Gb3 assays are often performed only on the selected Gb3 isoforms. To precisely determine the total Gb3 concentration, here we established two methods for determining both Gb3 isoforms and analogs. One was the deacylation method, involving Gb3 treatment with sphingolipid ceramide N-deacylase, followed by an assay of the deacylated products, globotriaosylsphingosine (lyso-Gb3) and its analogs, by ultra-performance LC coupled to tandem MS (UPLC-MS/MS). The other method was a direct assay established in the present study for 37 Gb3 isoforms and analogs/isoforms by UPLC-MS/MS. Gb3s from the organs of symptomatic animals of a Fabry disease mouse model were mainly Gb3 isoforms and two Gb3 analogs, such as Gb3(+18) containing the lyso-Gb3(+18) moiety and Gb3(−2) containing the lyso-Gb3(−2) moiety. The total concentrations and Gb3 analog distributions determined by the two methods were comparable. Gb3(+18) levels were high in the kidneys (24% of total Gb3) and the liver (13%), and we observed Gb3(−2) in the heart (10%) and the kidneys (5%). These results indicate organ-specific expression of Gb3 analogs, insights that may lead to a deeper understanding of the pathophysiology of Fabry disease.

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Beg, Mohd A., and Ishfaq A. Sheikh. "Endocrine disruption: Molecular interactions of environmental bisphenol contaminants with thyroid hormone receptor and thyroxine-binding globulin." Toxicology and Industrial Health 36, no. 5 (May 2020): 322–35. http://dx.doi.org/10.1177/0748233720928165.

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Many bisphenol A (BPA) analogs have been commercially used recently, such as 2,2-bis(4-hydroxyphenyl)butane (BPB), 4,4′-ethylidenebisphenol, 4,4′-methylenediphenol (BPF), 4,4′-(1,4-phenylenediisopropylidene)bisphenol (BPP), 4,4′-dihydroxydiphenyl sulfone (BPS), 4,4′-cyclohexylidenebisphenol (BPZ), 4,4′-(hexafluoroisopropylidene)diphenol (BPAF), 4,4′-(1-phenylethylidene)bisphenol (BPAP), and 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane (TMBPA), to circumvent adverse effects of BPA. However, their increasing use is also contaminating the environment, which is a potential cause of concern for human health. Thyroid hormone transport and signaling are potential targets for endocrine-disrupting activity of BPA analogs. Thyroxine-binding globulin (TBG) is the major carrier protein for thyroxine (T4) and triiodothyronine (T3) in blood. Thyroid hormones exert their action through thyroid hormone receptors (TRα and TRβ). This report presents the thyroid-disrupting potential of indicated nine BPA analogs from structure-based studies with TBG and TRα. Each BPA analog formed important polar and hydrophobic interactions with a number of residues of TBG and TRα. Majority of TBG residues (77–100%) and TRα residues (70–91%) interacting with BPA analogs were common with those of native ligands T4 and T3, respectively. Majority of BPA analogs interacted with TBG forming a salt bridge interaction at Lys-270. The hydrogen-bonding interaction of T3 with TRα at His-381 was also shared by majority of analogs. The binding energy for BPP, BPB, BPZ, BPAP, and TMBPA with both proteins was closer to binding energy of respective native ligands. The similarity in structural binding characteristics suggested potential disrupting activity of thyroid hormone signaling and transport.

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Fehér, Evelin, István Szatmári, Tamás Dudás, Anna Zalatnai, Tamás Farkas, Bálint Lőrinczi, Ferenc Fülöp, László Vécsei, and József Toldi. "Structural Evaluation and Electrophysiological Effects of Some Kynurenic Acid Analogs." Molecules 24, no. 19 (September 26, 2019): 3502. http://dx.doi.org/10.3390/molecules24193502.

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Kynurenic acid (KYNA), a metabolite of tryptophan, as an excitatory amino acid receptor antagonist is an effective neuroprotective agent in case of excitotoxicity, which is the hallmark of brain ischemia and several neurodegenerative processes. Therefore, kynurenine pathway, KYNA itself, and its derivatives came into the focus of research. During the past fifteen years, our research group has developed several neuroactive KYNA derivatives, some of which proved to be neuroprotective in preclinical studies. In this study, the synthesis of these KYNA derivatives and their evaluation with divergent molecular characteristics are presented together with their most typical effects on the monosynaptic transmission in CA1 region of the hippocampus of the rat. Their effects on the basic neuronal activity (on the field excitatory postsynaptic potentials: fEPSP) were studied in in vitro hippocampal slices in 1 and 200 μM concentrations. KYNA and its derivative 4 in both 1 and 200 μM concentrations proved to be inhibitory, while derivative 8 only in 200 μM decreased the amplitudes of fEPSPs. Derivative 5 facilitated the fEPSPs in 200 μM concentration. This is the first comparative study which evaluates the structural and functional differences of formerly and newly developed KYNA analogs. Considerations on possible relations between molecular structures and their physiological effects are presented.

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Quiñones, Winston, Gustavo Escobar, Fernando Echeverri, Fernando Torres, Yoni Rosero, Victor Arango, Gloria Cardona, and Adriana Gallego. "Synthesis and Antifungal Activity of Musa Phytoalexins and Structural Analogs." Molecules 5, no. 12 (July 26, 2000): 974–80. http://dx.doi.org/10.3390/50700974.

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