OJSTA  Vol.3 No.3 , July 2014
Quinolinium Structure as Labeled Biomarkers
ABSTRACT
In this study the compatible chemical and biological investigations of several N-phenylquinolinium derivatives have been carried out in order to find the most perspective quinolinium structures for the nuclear-chemical synthesis of tritium labeled biomarkers.

Cite this paper
Shchepina, N. , Avrorin, V. , Badun, G. , Alexandrova, G. , Agafonova, I. and Popova, N. (2014) Quinolinium Structure as Labeled Biomarkers. Open Journal of Synthesis Theory and Applications, 3, 21-26. doi: 10.4236/ojsta.2014.33004.
References
[1]   Pozharskii, A.F., Soldatenkov, A.T. and Katritzky, A.R. (1997) Heterocycles in Life and Society. John Wiley & Sons Ltd., New York.

[2]   Carey, J.S., Laffan, D., Thomson, C. and Williams, M.T. (2006) Analysis of the Reactions Used for the Preparation of Drug Candidate Molecules. Organic and Biomolecular Chemistry, 4, 2337-2347.
http://dx.doi.org/10.1039/b602413k

[3]   Zhao, T. and Sun, G. (2008) Hydrophobicity and Antimicrobial Activities of Quaternary Pyridinium Salts. Journal of Applied Microbiology, 104, 824-830.
http://dx.doi.org/10.1111/j.1365-2672.2007.03616.x

[4]   Laufer, R., Bathori, M., Csermery, T., Petroiani, G., Kuca, K., Toth, N. and Kalasz, H. (2007) LC Determination of Hydrophilicity Parameter of Some Pyridinium Aldoximes. Journal of Liquid Chromatography and Related Technologies, 30, 2337-2344.
http://dx.doi.org/10.1080/10826070701451738

[5]   Kumar, V. and Malhotra, S.V. (2010) Ionic Liquids as Pharmaceutical Salts: A Historical Perspective. ACS Symposium Series, 1038, 1-12.

[6]   Docherty, K. and Kulpa, C.F. (2005) Toxicity and Antimicrobial Activity of Imidazolium and Pyridinium Ionic Liquids. Green Chemistry, 7, 185-189.
http://dx.doi.org/10.1039/b419172b

[7]   Zhao, T. and Sun, G. (2006) Synthesis and Characterization of Antimicrobial Cationic Surfactants: Aminopyridinium Salts. Journal of Surfactants and Detergents, 9, 325-330.
http://dx.doi.org/10.1007/s11743-006-5010-3

[8]   Musilek, K., Kusa, K., Jun, D., Dohnal, V. and Dolezal, M. (2005) Synthesis of a Novel Series of Bispyridinium Compounds Bearing a Xylene Linker and Evaluation of Their Reactivation Activity Against Chlorpyyrifos-Inhibited Acetylcholinnesterase. Journal of Enzyme Inhibition and Medicinal Chemistry, 20, 409-415.
http://dx.doi.org/10.1080/14756360500179762

[9]   Gutsulyak, B.M. (1972) Biological Activity of Quinolinium Salts. Russian Chemical Reviews, 41, 187-202.
http://dx.doi.org/10.1070/RC1972v041n02ABEH002038

[10]   Sidorchuk, I.I., Stadniichuk, R.F., Tishchenko, E.I. and Bordyakovskaya, L.T. (1978) Antimicrobial Activity of Quaternary Quinolinium Salts. Pharmaceutical Chemistry Journal, 12, 893-895. http://dx.doi.org/10.1007/BF00777632

[11]   Voznyak, V.I., Savitskaya, L.G. and Neporadnyi, D.D. (1984) Antimicrobial Activity of Quaternary 4-(P-Dimethylaminostyryl)Quinolinium Salts. Pharmaceutical Chemistry Journal, 18, 561-563.

[12]   Cox, O., Jackson, H., Vargas, A., Báez, A., Colón, J.I., González, B.C. and de León, M. (1982) Synthesis and Biological Activity of Benzothiazoloand Benzoxazolo[3, 2-a]Quinolinium Salts. Journal of Medicinal Chemistry, 25, 13781381.
http://dx.doi.org/10.1021/jm00353a020

[13]   Hernández, H.J. (1982) Synthesis and Biological Activity of Some Benzoheterazolo (3, 2-a) Quinolinium Salts. Universidad de Puerto Rico, 208.

[14]   Joaquin, C.R., Galanakis, D., Piergentili, A., Bhandari, K., Ganellin, C.R., Dunn, P.M. and Jenkinson, D.H. (2000) Synthesis, Molecular Modeling, and Pharmacological Testing of Bis-Quinolinium Cyclophanes: Potent, Non-Peptidic Blockers of the Apamin-Sensitive Ca2+-Activated K+ Channel. Journal of Medicinal Chemistry, 43, 420-431.
http://dx.doi.org/10.1021/jm9902537

[15]   Campos, J.M., Nú-ez, M.C., Sánchez, R.M., Gómez-Vidal, J.A., Rodríguez-González, A., Bá-ez, M., Gallo, M.A., Lacal, J.C. and Espinosa, A. (2002) Quantitative Structure-Activity Relationships for a Series of Symmetrical Bisquaternary Anticancer Compounds. Bioorganic & Medicinal Chemistry, 10, 2215-2231.
http://dx.doi.org/10.1016/S0968-0896(02)00054-8

[16]   Barchéchath, S.D., Tawatao, R.I., Corr, M., Carson, D.A. and Cottam, H.B. (2005) Quinolinium Salt as a Potent Inhibitor of Lymphocyte Apoptosis. Bioorganic & Medicinal Chemistry Letters, 15, 1785-1788.
http://dx.doi.org/10.1016/j.bmcl.2005.02.047

[17]   Srivani, P. and Sastry, G.N. (2009) Potential Choline Kinase Inhibitors: A Molecular Modeling Study of Bis-Quinolinium Compounds. Journal of Molecular Graphics & Modelling, 27, 676-688.
http://dx.doi.org/10.1016/j.jmgm.2008.10.010

[18]   Zayas, B. and Cox, O. (2012) Method for Producing Benzazoloquinolium (BQs) Salts, Using the Composition as Cellular Markers, and Using the Biological Activity of the Composition. US Patent No. 20120129882.

[19]   Vélez, C., Cox, O., Rosado-Berrios, C.A., Molina, D., Arroyo, L., Carro, S., Filikov, A., Kumar, V., Malhotra, S.V., Cordero, M. and Zayas, B. (2013) Novel Nitrobenzazolo [3, 2-a] Quinolinium Salts Induce Cell Death through a Mechanism Involving DNA Damage, Cell Cycle Changes, and Mitochondrial Permeabilization. Open Journal of Apoptosis, 2, 13-22.
http://dx.doi.org/10.4236/ojapo.2013.22002

[20]   Bringmanna, G., Thomale, K., Bischof, S., Schneider, C., Schultheis, M., Schwarz, T., Mollb, H. and Schurigtb, U. (2013) A Novel Leishmania major Amastigote Assay in 96-Well Format for Rapid Drug Screening and Its Use for Discovery and Evaluation of a New Class of Leishmanicidal Quinolinium Salts. Antimicrobial Agents and Chemotherapy, 57, 3003-3011.
http://dx.doi.org/10.1128/AAC.02201-12

[21]   Pausacker, K.H. (1958) Arylation of Aromatic Compounds. VI. Benzoyl Peroxide with Pyridine and Quinoline. Australian Journal of Chemistry, 11, 200-210.
http://dx.doi.org/10.1071/CH9580200

[22]   Brody, F. and Ruby, P.R. (1960) Pyridine and Its Derivatives. Part I, In Klingsberg, Ed., Interscience Publishers, Inc., New York.

[23]   Shchepina, N.E., Avrorin, V.V., Badun, G.A., Lewis, S.B., Fedoseev, V.M. and Ukhanov, S.E. (2009) The Reaction of Direct Phenylation by Nucleogenic Cations as a Method of Synthesis of Unknown or Complicated Tritium Labeled Compounds. Moscow University Chemistry Bulletin, 64, 244-248.
http://dx.doi.org/10.3103/S0027131409050034

[24]   Shchepina, N.E., Avrorin, V.V., Badun, G.A., Alexandrova, G.A., Ukhanov, S.E., Fedoseev, V.M. and Boiko, I.I. (2009) Preparation of N-Phenyl-Substituted Quinolinium Derivatives Labeled with Tritium by Chemonuclear Synthesis. Chemistry of Heterocyclic Compounds, 45, 796-801.
http://dx.doi.org/10.1007/s10593-009-0359-7

[25]   Shchepina, N.E., Avrorin, V.V., Badun, G.A., Fedoseev, V.M. and Lewis, S.B. (2010) New Method for the Synthesis of Difficultly Available Sterically Hindered Tritium-Labeled Pyridinium Derivatives. Chemistry of Heterocyclic Compounds, 46, 547-552.
http://dx.doi.org/10.1007/s10593-010-0544-8

[26]   Shchepina, N.E., Avrorin, V.V., Badun, G.A., Bumagin, N.A., Lewis, S.B. and Shurov S.N. (2012) Pathways of Ionmolecular Interactions of Nucleogenic Phenyl Cations with the Nucleophilic Centers of Picolines. Organic and Medicinal Chemistry Letters, 2, 14.
http://dx.doi.org/10.1186/2191-2858-2-14

[27]   Shchepina, N.E., Avrorin, V.V., Alexandrova, G.A., Badun, G.A., Boiko, I.I. and Shurov, S.N. (2013) Investigation of the Phenylation of Methyl-Quinolines Using Tritium-Labeled Nucleogenic Phenyl Cations. Chemistry of Heterocyclic Compounds, 49, 428-434.
http://dx.doi.org/10.1007/s10593-013-1264-7

[28]   Pilyugin, G.T. and Gutsulyak, B.M. (1963) Advances in the Preparation, Investigation, and Use of Quinolinium Compounds. Russian Chemical Reviews, 32, 167-188.
http://dx.doi.org/10.1070/RC1963v032n04ABEH001327

[29]   Pilyugin, G.T. and Krainer, Z.Y. (1951) Phenylsubstituted Quinocyanines. Doklady Akademii Nauk, 8, 609-612.

[30]   Chernyuk, I.N., Pilyugin, G.T. and Zlochevskaya, A.V. (1970) Studies in the Field of Synthetic Dyes. Chemistry of Heterocyclic Compounds, 4, 236-237.
http://dx.doi.org/10.1007/BF00601137

[31]   Pilyugin, G.T. and Gutsulyak, B.M. (1959) Studies of Synthetic Dyes: Synthesis of n-Phenyllepidine Perchlorate and Some of Its Transformation. XIV. Zhurnal Obshchei Khimii, 29, 3076-3079.

[32]   Pilyugin, G.T. and Opanasenko, E.P. (1952) Synthesis of β-Naphtoquinaldine Iodinephenilate and Its Transformations. Ukrainskii Khimicheskii Zhurnal (Russian Edition), 18, 625-630.

[33]   Shchepina, N.E., Boiko, I.I. and Aleksandrova, G.A. (2011) Synthesis and Antimicrobial Activity of Quaternary N-Aryl-5, 6-benzoquinaldinium Derivatives. Pharmaceutical Chemistry Journal, 45, 159-161.
http://dx.doi.org/10.1007/s11094-011-0583-1

[34]   Pilyugin, G.T. and Opanasenko, E.P. (1957) Cyandyes. VII. Cyclization of Secondary Aromatic Amines with Vinyl Ethers and Arylquinaldinium Derivatives Formation. Zhurnal Obshchei Khimii, 27, 1015-1018.

[35]   Pilyugin, G.T., Gorichok, Ya.O., Gutsulyak, B.M. and Gorichok, S.I. (1965) Researches on Synthetic Dyes. Chemistry of Heterocyclic Compounds, 1, 603-608.
http://dx.doi.org/10.1007/BF00472701

[36]   Shchepina, N.E., Avrorin, V.V., Badun, G.A., Lewis, S.B. and Ukhanov, S.E. (2012) Preparation of Fused N-Phenylsubstituted Pyridinium Derivatives by Direct Phenylation with Nucleogenic Phenyl Cations. Chemistry of Heterocyclic Compounds, 48, 301-308.
http://dx.doi.org/10.1007/s10593-012-0990-6

[37]   Pershin, G.N. (1971) Methods of Experimental Chemotherapy. Medgiz, Moscow.

 
 
Top