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Journal articles on the topic 'Acridinique'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Maas, Gerhard, and Berndt Singer. "Dikationether, 6 [1] Spektroskopische Vergleiche von 9,9′-Oxy-bis(acridinium)- und 9,9′-Thio-bis(acridinium)-Salzen mit anderen 9-substituierten Acridinium-Ionen / Dication Ethers, 6 [1] Spectroscopic Comparisons of 9,9′-Oxy-bis(acridinium)- and 9,9′-Thio-bis(acridinium) Salts with Other 9-Substituted Acridinium Ions." Zeitschrift für Naturforschung B 40, no. 1 (January 1, 1985): 90–99. http://dx.doi.org/10.1515/znb-1985-0118.

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9,9′-Oxy-bis(acridinium) salts 2a and 2b as well as the 9,9′-thio-bis(acridinium) salt 2c have been compared with other 9-substituted acridinium salts by 1H NMR, 13C NMR, and UV/VIS spectra. The data show that the bond state of the acridine rings in 2a-c is quite similar to that in 9-(pseudo)halide-substituted acridinium ions, i.e., the aromatic conjugation throughout the heterocyclic system is not disturbed

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2

Natrajan, Anand, and David Wen. "A comparison of chemiluminescent acridinium dimethylphenyl ester labels with different conjugation sites." Organic & Biomolecular Chemistry 13, no. 9 (2015): 2622–33. http://dx.doi.org/10.1039/c4ob02528h.

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3

Katoh, Makoto, Susumu Chishima, Nobukazu Kiuchi, Tomihiro Ikeo, and yasuhiko Sasaki. "A New Method for the Assay of Exposed Platelet Fibrinogen Receptor Using a Chemiluminescent Label." Thrombosis and Haemostasis 74, no. 06 (1995): 1546–50. http://dx.doi.org/10.1055/s-0038-1649980.

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SummaryAssay of the platelet fibrinogen-binding receptor glycoprotein (GP) IIb/IIIa is widely performed using 125I-labeled fibrinogen (125I-fibrinogen). We successfully devised a receptor binding assay system with high selectivity and sensitivity using a stable chemiluminescent acridinium derivative I-labeled fibrinogen (acridinium-fibrinogen).Human fibrinogen in saline was labeled with equimolar acridinium dissolved in dimethylformamide, and allowed to react with gel-filtered human platelets in the presence of ADP. Acridinium-fibrinogen binding to GPIIb/IIIa was assayed by measuring chemiluminescence emitted on addition of 0.1 N NaOH containing 0.06% H202 in a luminometer. Non-specific binding was measured in the presence of 10 mM EDTA. Acridinium-fibrinogen binding to human platelets was rapid and reversible, specific and saturable, and dependent on ADP concentrations. Scatchard plot analysis revealed one class of binding sites with a Kd of 326 nM and Bmax of 7.8 pmol/108 platelets. These values were comparable to the data obtained by using 125I-fibrinogen. Unlabeled fibrinogen, RGDS, and HHLGGAKQAGDV (fibrinogen γ-chain 400-411) displaced acridinium-fibrinogen from its binding site with Ki values of 322 nM, 9.2 μM and 31.3μM, respectively. Thus, this binding assay system may be useful in measuring the binding between platelet GPIIb/IIIa and fibrinogen without using a radioisotop.

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4

Shaameri, Zurina, Ning Shan, and William Jones. "Acridinium isophthalate." Acta Crystallographica Section E Structure Reports Online 57, no. 10 (September 20, 2001): o945—o946. http://dx.doi.org/10.1107/s1600536801013927.

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5

White, Alexander, Leifeng Wang, and David Nicewicz. "Synthesis and Characterization of Acridinium Dyes for Photoredox Catalysis." Synlett 30, no. 07 (March 12, 2019): 827–32. http://dx.doi.org/10.1055/s-0037-1611744.

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Photoredox catalysis is a rapidly evolving platform for synthetic methods development. The prominent use of acridinium salts as a sustainable option for photoredox catalysts has driven the development of more robust and synthetically useful versions based on this scaffold. However, more complicated syntheses, increased cost, and limited commercial availability have hindered the adoption of these catalysts by the greater synthetic community. By utilizing the direct conversion of a xanthylium salt into the corresponding acridinium as the key transformation, we present an efficient and scalable preparation of the most synthetically useful acridinium reported to date. This divergent strategy also enabled the preparation of a suite of novel acridinium dyes, allowing for a systematic investigation of substitution effects on their photophysical properties.

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6

Eshtiagh-Hosseini, Hossein, Azam Hassanpoor, Masoud Mirzaei, and Ali R. Salimi. "Acridinium 2-hydroxybenzoate." Acta Crystallographica Section E Structure Reports Online 66, no. 11 (October 31, 2010): o2996. http://dx.doi.org/10.1107/s160053681004345x.

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7

Zilate, Bouthayna, Christian Fischer, Lukas Schneider, and Christof Sparr. "Scalable Synthesis of Acridinium Catalysts for Photoredox Deuterations." Synthesis 51, no. 23 (October 21, 2019): 4359–65. http://dx.doi.org/10.1055/s-0039-1690694.

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The continuous development of photocatalytic methods incentivizes the design of organic catalysts to complement the frequently used and precious polypyridyl transition metal systems. Herein, a scalable synthesis of suitable acridinium dyes and their application in photoredox deuterations are described. The acridinium catalysts, prepared on multi-gram scale, allowed the deuteration of a pharmaceutically relevant scaffold in high yield and selectivity under mild conditions.

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8

Derikvand, Zohreh, Hossein Aghabozorg, and Jafar Attar Gharamaleki. "Acridinium 3,5-dicarboxybenzoate monohydrate." Acta Crystallographica Section E Structure Reports Online 65, no. 5 (April 30, 2009): o1173. http://dx.doi.org/10.1107/s1600536809015529.

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9

Zadykowicz, Beata, Damian Trzybiński, Artur Sikorski, and Jerzy Błażejowski. "9-(Methylsulfanyl)acridinium trifluoromethanesulfonate." Acta Crystallographica Section E Structure Reports Online 65, no. 3 (February 21, 2009): o566—o567. http://dx.doi.org/10.1107/s1600536809004978.

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10

Natrajan, Anand, David Wen, and David Sharpe. "Synthesis and properties of chemiluminescent acridinium ester labels with fluorous tags." Org. Biomol. Chem. 12, no. 23 (2014): 3887–901. http://dx.doi.org/10.1039/c4ob00456f.

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11

Gosset, A., Z. Xu, F. Maurel, L. M. Chamoreau, S. Nowak, G. Vives, C. Perruchot, V. Heitz, and H. P. Jacquot de Rouville. "A chemically-responsive bis-acridinium receptor." New Journal of Chemistry 42, no. 6 (2018): 4728–34. http://dx.doi.org/10.1039/c7nj03712k.

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12

Meyer, Andreas Uwe, Anna Lucia Berger, and Burkhard König. "Metal-free C–H sulfonamidation of pyrroles by visible light photoredox catalysis." Chemical Communications 52, no. 72 (2016): 10918–21. http://dx.doi.org/10.1039/c6cc06111g.

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13

Jacquot de Rouville, Henri-Pierre, Nathalie Zorn, Emmanuelle Leize-Wagner, and Valérie Heitz. "Entwined dimer formation from self-complementary bis-acridiniums." Chemical Communications 54, no. 78 (2018): 10966–69. http://dx.doi.org/10.1039/c8cc05958f.

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14

Wen, Min, Chen Li, Mengyuan Zhang, Yan Sun, Fengming Liu, Xiaoyan Cui, and Yongkui Shan. "Acridinium benzoates for ratiometric fluorescence imaging of cellular viscosity." Analyst 146, no. 5 (2021): 1538–42. http://dx.doi.org/10.1039/d0an02321c.

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15

Adamczyk, Maciej, Phillip G. Mattingly, Jeffrey A. Moore, You Pan, Kevin Shreder, and Zhiguang Yu. "Design of Acridinium-9-carboxamides and Anti-acridinium Antibodies for Chemiluminescent Signal Enhancement." Bioconjugate Chemistry 12, no. 3 (May 2001): 329–31. http://dx.doi.org/10.1021/bc000152j.

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16

Kronenburg, M. J., K. Goubitz, C. A. Reiss, and D. Heijdenrijk. "Crystal studies of acridinium dyes. III. 10-Methyl-9-(2-methylphenyl)acridinium perchlorate." Acta Crystallographica Section C Crystal Structure Communications 45, no. 9 (September 15, 1989): 1352–53. http://dx.doi.org/10.1107/s0108270189002313.

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17

Stam, C. H. "Crystal studies of acridinium dyes. XII. 9-(4-Dimethylaminophenyl)-10-methyl-acridinium chloride." Acta Crystallographica Section C Crystal Structure Communications 46, no. 6 (June 15, 1990): 1079–81. http://dx.doi.org/10.1107/s0108270189010322.

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18

Uygur, Mustafa, Tobias Danelzik, and Olga García Mancheño. "Metal-free desilylative C–C bond formation by visible-light photoredox catalysis." Chemical Communications 55, no. 20 (2019): 2980–83. http://dx.doi.org/10.1039/c8cc10239b.

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19

Verhoeven, Jan W., Hendrik J. van Ramesdonk, Hong Zhang, Michiel M. Groeneveld, Andrew C. Benniston, and Anthony Harriman. "Long-lived Charge-Transfer States in 9-Aryl-Acridinium Ions; A Critical Reinvestigation." International Journal of Photoenergy 7, no. 2 (2005): 103–8. http://dx.doi.org/10.1155/s1110662x05000152.

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In the recent literature a simple 9-aryl-acridinium ion was claimed to undergo an intramolecular, photoinduced charge shift to produce an extremely long-lived and very high energy charge-transfer state. The possible consequences of this observation are discussed and the tenability of the claims made is investigated via time resolved spectroscopy of a closely related system with spectroscopic characteristics allowing more solid identification of the actual photophysical events taking place. From the results obtained it appears likely that the long-lived species observed earlier in solution cannot be charge transfer in nature but must instead be identified as the lowest triplet state of the acridinium chromophore.

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20

Lawson, Connor A., Andrew P. Dominey, Glynn D. Williams, and John A. Murphy. "Visible light-mediated Smiles rearrangements and annulations of non-activated aromatics." Chemical Communications 56, no. 77 (2020): 11445–48. http://dx.doi.org/10.1039/d0cc04666c.

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21

Natrajan, Anand, and David Wen. "Effect of branching in remote substituents on light emission and stability of chemiluminescent acridinium esters." RSC Adv. 4, no. 42 (2014): 21852–63. http://dx.doi.org/10.1039/c4ra02516d.

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22

Yoshida, Yuma, Tetsuya Shimada, Tamao Ishida, and Shinsuke Takagi. "Thermodynamic study of the adsorption of acridinium derivatives on the clay surface." RSC Advances 10, no. 36 (2020): 21360–68. http://dx.doi.org/10.1039/d0ra03158e.

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23

Sparr, Christof, and Christian Fischer. "Configurationally Stable Atropisomeric Acridinium Fluorophores." Synlett 29, no. 16 (August 3, 2018): 2176–80. http://dx.doi.org/10.1055/s-0037-1610233.

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Arylated heterocyclic fluorophores are particularly useful scaffolds for numerous applications, such as bioimaging or synthetic photochemistry. While variation of the substitution pattern at the heterocycle and aryl groups allows dye modulation, the bond rotational barriers are also strongly affected. Unsymmetrically substituted ring systems of rotationally restricted arylated heterocycles therefore lead to configurationally stable atropisomeric fluorophores. Herein, we describe these characteristics by determining the properties and configurational stability of atropisomeric, tri-ortho-substituted naphthyl-acridinium fluorophores. A significant barrier to rotation of >120 kJ mol–1 was measured, which renders these dyes and related compounds distinct atropisomers with stereoisomer-specific properties over a broad temperature range.

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24

Trzybiński, Damian, Beata Zadykowicz, Karol Krzymiński, Artur Sikorski, and Jerzy Błażejowski. "9-Phenyl-10H-acridinium trifluoromethanesulfonate." Acta Crystallographica Section E Structure Reports Online 66, no. 11 (October 20, 2010): o2845—o2846. http://dx.doi.org/10.1107/s1600536810040900.

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25

Attar Gharamaleki, Jafar, Zohreh Derikvand, and Helen Stoeckli-Evans. "Acridinium 3-carboxypyrazine-2-carboxylate." Acta Crystallographica Section E Structure Reports Online 66, no. 9 (August 11, 2010): o2231. http://dx.doi.org/10.1107/s1600536810030588.

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26

Best, Quinn A., Richard A. Haack, Kerry M. Swift, Brian M. Bax, Sergey Y. Tetin, and Stefan J. Hershberger. "A rainbow of acridinium chemiluminescence." Luminescence 36, no. 4 (March 9, 2021): 1097–106. http://dx.doi.org/10.1002/bio.4038.

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27

Hartmann, Horst. "A Simple Route to Benz[a]acridinium Salts." Zeitschrift für Naturforschung B 66, no. 7 (July 1, 2011): 711–14. http://dx.doi.org/10.1515/znb-2011-0711.

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28

Fuse, Hiromu, Hiroyasu Nakao, Yutaka Saga, Arisa Fukatsu, Mio Kondo, Shigeyuki Masaoka, Harunobu Mitsunuma, and Motomu Kanai. "Photocatalytic redox-neutral hydroxyalkylation of N-heteroaromatics with aldehydes." Chemical Science 11, no. 44 (2020): 12206–11. http://dx.doi.org/10.1039/d0sc04114a.

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29

Wang, Bin, Pinhua Li, Tao Miao, Long Zou, and Lei Wang. "Visible-light induced decarboxylative C2-alkylation of benzothiazoles with carboxylic acids under metal-free conditions." Organic & Biomolecular Chemistry 17, no. 1 (2019): 115–21. http://dx.doi.org/10.1039/c8ob02476f.

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30

Wang, Kuai, Ling-Guo Meng, Qi Zhang, and Lei Wang. "Direct construction of 4-aryl tetralones via visible-light-induced cyclization of styrenes with molecular oxygen." Green Chemistry 18, no. 9 (2016): 2864–70. http://dx.doi.org/10.1039/c5gc02550h.

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31

Wang, Shenliang, and Anand Natrajan. "Synthesis and properties of chemiluminescent acridinium esters with different N-alkyl groups." RSC Advances 5, no. 26 (2015): 19989–20002. http://dx.doi.org/10.1039/c5ra00334b.

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Acridinium esters containingN-alkyl groups with charge-neutral sulfobetaine zwitterions when compared toN-sulfopropyl groups exhibit faster light emission, improved chemiluminescence stability and lower non-specific binding.

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32

Deng, Yongming, Jason Zhang, Bradley Bankhead, Jonathan P. Markham, and Matthias Zeller. "Photoinduced oxidative cyclopropanation of ene-ynamides: synthesis of 3-aza[n.1.0]bicycles via vinyl radicals." Chemical Communications 57, no. 43 (2021): 5254–57. http://dx.doi.org/10.1039/d1cc02016a.

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33

Zadykowicz, Beata, Justyna Czechowska, Agnieszka Ożóg, Anton Renkevich, and Karol Krzymiński. "Effective chemiluminogenic systems based on acridinium esters bearing substituents of various electronic and steric properties." Organic & Biomolecular Chemistry 14, no. 2 (2016): 652–68. http://dx.doi.org/10.1039/c5ob01798j.

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A series of new acridinium esters, variously substituted in the benzene ring, have been investigated for the mechanism of light generation and ability to show chemiluminescence in various environments.

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34

Chelli, Riccardo, Giangaetano Pietraperzia, Andrea Bencini, Claudia Giorgi, Vito Lippolis, Pier Remigio Salvi, and Cristina Gellini. "A fluorescent receptor for halide recognition: clues for the design of anion chemosensors." Physical Chemistry Chemical Physics 17, no. 16 (2015): 10813–22. http://dx.doi.org/10.1039/c5cp00131e.

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The chemosensing properties for halide ions of a polyammine ligand containing acridine are investigated by fluorescence spectroscopy. The emission is due to acridinium species formed after photoinduced proton transfer.

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35

Ruberto, Michael A., and Mary Lynn Grayeski. "Acridinium chemiluminescence detection with capillary electrophoresis." Analytical Chemistry 64, no. 22 (November 15, 1992): 2758–62. http://dx.doi.org/10.1021/ac00046a018.

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36

Derikvand, Zohreh, Marilyn M. Olmstead, and Jafar Attar Gharamaleki. "Acridinium 6-carboxypyridine-2-carboxylate monohydrate." Acta Crystallographica Section E Structure Reports Online 67, no. 2 (January 15, 2011): o416. http://dx.doi.org/10.1107/s1600536810053791.

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37

Wen, Min, Xijing Wang, Ting Wang, Yan Sun, Mengting Fan, Min Li, Junru Zhu, Dazhi Zhang, Xiaoyan Cui, and Yongkui Shan. "Acridinium Benzoates for Ratiometric Fluorescence Imaging." Chemistry – A European Journal 26, no. 15 (March 12, 2020): 3247–51. http://dx.doi.org/10.1002/chem.201905810.

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38

Septak, M. "Acridinium ester-labelled DNA oligonucleotide probes." Journal of Bioluminescence and Chemiluminescence 4, no. 1 (July 1989): 351–56. http://dx.doi.org/10.1002/bio.1170040148.

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39

Adamczyk, M. "O-(Acridinium)hydroxylamine (AHA): a reagent for the preparation of chemiluminescent acridinium oxime (AO)-steroid conjugates." Steroids 65, no. 7 (July 2000): 387–94. http://dx.doi.org/10.1016/s0039-128x(00)00095-7.

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40

Mandal, Susanta, Karan Chhetri, Samuzal Bhuyan, and Biswajit G. Roy. "Efficient iron catalyzed ligand-free access to acridines and acridinium ions." Green Chemistry 22, no. 10 (2020): 3178–85. http://dx.doi.org/10.1039/d0gc00617c.

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A general synthesis of both acridines and acridinium ions is descried from inexpensive and commercially available aliphatic starting materials using iron as catalyst and aerobic oxygen as oxidant in alcoholic solvent to produce water as only by product.

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41

Goubitz, K., C. A. Reiss, and D. Heijdenrijk. "Crystal studies of acridinium dyes. XIII. The structures of 10-methyl-9-(4-methylphenyl)acridinium perchlorate (A) and 10-methyl-9-(4-methoxyphenyl)acridinium perchlorate (B)." Acta Crystallographica Section C Crystal Structure Communications 46, no. 6 (June 15, 1990): 1081–84. http://dx.doi.org/10.1107/s0108270189010334.

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42

Bian, Zi-Long, Xin-Xin Lv, Ya-Lan Li, Wen-Wu Sun, Ji-Kai Liu, and Bin Wu. "Acid-promoted synthesis and photophysical properties of substituted acridine derivatives." Organic & Biomolecular Chemistry 18, no. 40 (2020): 8141–46. http://dx.doi.org/10.1039/d0ob01824d.

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A simple and efficient synthetic protocol for the preparation of acridinium esters and amides through the cyclization and esterification or amidation of isatins with alcohols or amines as nucleophiles in the presence of CF₃SO₃H is established.

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43

Sato, Kazuaki, Eiji Matsuda, Keiichi Kamisango, Hiroaki Iwasaki, Shuzo Matsubara, and Yasuko Matsunaga. "Development of a Hypersensitive Detection Method for Human Parvovirus B19 DNA." Journal of Clinical Microbiology 38, no. 3 (2000): 1241–43. http://dx.doi.org/10.1128/jcm.38.3.1241-1243.2000.

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A new detection method for human parvovirus B19 DNA was established using PCR coupled with a hybridization protection assay. The amplified product was detected using acridinium ester-labeled DNA probes. By this method, a few copies of B19 DNA were detected in human serum albumin.

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44

Zomer, Gijsbert, Rijk H. van den Berg, and Eugène H. J. M. Jansen. "Optimal labelling of proteins with acridinium ester." Analytica Chimica Acta 205 (1988): 267–71. http://dx.doi.org/10.1016/s0003-2670(00)82338-7.

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45

Linden, A., J. Guspanová, J. Bernát, and P. Kristian. "9-Propylidenehydrazino-10-acridinium Thiocyanate at 173K." Acta Crystallographica Section C Crystal Structure Communications 53, no. 6 (June 15, 1997): 732–34. http://dx.doi.org/10.1107/s010827019700108x.

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46

Razavi, Zia, and Frank McCapra. "Stable and versatile active acridinium esters I." Luminescence 15, no. 4 (2000): 239–44. http://dx.doi.org/10.1002/1522-7243(200007/08)15:4<239::aid-bio587>3.0.co;2-w.

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47

Razavi, Zia, and Frank McCapra. "Stable and versatile active acridinium esters II." Luminescence 15, no. 4 (2000): 245–49. http://dx.doi.org/10.1002/1522-7243(200007/08)15:4<245::aid-bio588>3.0.co;2-3.

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48

Sikorski, Artur, Agnieszka Niziołek, Karol Krzymiński, Tadeusz Lis, and Jerzy Błażejowski. "10-Methyl-9-(2-nitrophenoxycarbonyl)acridinium trifluoromethanesulfonate." Acta Crystallographica Section E Structure Reports Online 64, no. 2 (January 4, 2008): o372—o373. http://dx.doi.org/10.1107/s1600536807068109.

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49

Sikorski, Artur, Karol Krzymiński, Agata Białońska, Tadeusz Lis, and Jerzy Błażejowski. "10-Methyl-9-(2-methylphenoxycarbonyl)acridinium trifluoromethanesulfonate." Acta Crystallographica Section E Structure Reports Online 62, no. 2 (January 27, 2006): o822—o824. http://dx.doi.org/10.1107/s1600536806002340.

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50

Goubitz, K., C. A. Reiss, and D. Heijdenrijk. "Crystal studies of acridinium dyes. V. 10-Methyl-9-[4-(1,4,7,10-tetraoxa-13-aza-13-cyclopentadecyl)phenyl]acridinium perchlorate." Acta Crystallographica Section C Crystal Structure Communications 45, no. 9 (September 15, 1989): 1356–58. http://dx.doi.org/10.1107/s0108270189002337.

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