DOI: https://doi.org/10.18524/2304-0947.2020.1(73).198316

6- ТА 7-АМІНОМЕТИЛ-11H-ІНДЕНО[1,2-b]ХІНОКСАЛІН-11-ОНИ – СИНТЕЗ, АФІНІТЕТ ДО ДНК ТА ТОКСИЧНІСТЬ

H. I. Duma, K. D. Sazonov, L. S. Liakhov, S. V. Toporov, S. A. Liakhov

Анотація


Синтезовані нові похідні інденохіноксаліну – 6-амінометил-11H-індено[1,2-b]хіноксалін-11-они та 7-амінометил-11H-індено[1,2-b]хіноксалін-11-они, показано, що вони є інтеркаляторами ДНК з афінітетом на рівні противірусного агенту та індуктору інтерферону аміксину та в цілому менш токсичні за нього, що зумовлює доцільність їх подальшого дослідження як потенційних противірусних агентів.

Ключові слова


амінометил-11H-індено[1,2-b]хіноксалін-11-они; синтез; інтеркаляція; афінітет; токсичність

Повний текст:

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Посилання


Lerman L.S. Structural considerations in the interaction of DNA and acridines. J. Mol. Biol, 1961, vol. 3, no 1, pp. 18-30. https://doi.org/10.1016/s0022-2836(61)80004-1

Douthart R.J., Burnett J.P., Beasley F.W., Frank B.H. Binding of ethidium bromide to double-stranded ribonucleic acid. Biochemistry, 1973, vol. 12, no 2, pp. 214-220. https://doi.org/10.1021/bi00726a006

Berman H.M., Young P.R. The Interaction of Intercalating Drugs with Nucleic Acids. Annu. Rev. Biophys. Bioeng, 1981, vol. 10, no 1, pp. 87-114. https://doi.org/10.1146/annurev.bb.10.060181.000511

Piestrzeniewicz M., Studzian K., Wilmanska D., Plucienniczak G., Gniazdowski M. Effect of DNA-interacting drugs on phage T7 RNA polymerase. Acta Biochim.Pol, 1998, vol. 45, no 1, pp. 127-132. https://www.ncbi.nlm.nih.gov/pubmed/9701505

Acheson R.M., Taylor G.N., Waring M.J., Haylock S., Abel G. The intercalative DNA binding and antitumor activity of some bis-acridines related to nitracrine. Chem. Biol. Interact, 1985, vol. 53, pp. 371-375. https://doi.org/10.1016/s0009-2797(85)80111-3

Drake J.W. The distribution of rates of spontaneous mutation over viruses, prokaryotes, and eukaryotes. Ann. N. Y. Acad. Sci, 1999, vol. 870, pp. 100-107. https://doi.org/10.1111/j.1749-6632.1999.tb08870.x

Mucsi I., Molnar J., Tanaka M., Santelli-Rouvier C., Patelis A.M., Galy J.P., Barbe J. Effect of acridine derivatives on the multiplication of herpes simplex virus. Anticancer Res, 1998, vol. 18, no 4C, pp. 3011-3015.

Loddo R., Francesconi vol., Laurini E., Boccardo S., Aulic S., Fermeglia M., Pricl S., Tonelli M. 9-Aminoacridine-based agents impair the bovine viral diarrhea virus (BVDV) replication targeting the RNA-dependent RNA polymerase (RdRp). Bioorg. Med. Chem, 2018, vol. 26, no 4, pp. 855-868. https://doi.org/10.1016/j.bmc.2018.01.001

Andrews E.R., Fleming R.W., Grisar J.M., Kihm J.C., Wenstrup D.L., Mayer G.D. Bis-basic-substituted polycyclic aromatic compounds. A new class of antiviral agents. 2. Tilorone and related bis-basic ethers of fluorenone, fluorenol, and fluorene. J. Med. Chem, 1974, vol. 17, no 8, pp. 882-886. https://doi.org/10.1021/jm00254a020

Garcia-Gancedo A., Gil C., Roldan C.M., Perez S., Vilas P. Antiviral action of benzo[de]isoquinoline-1,3-diones: 5-nitro-2-(2-dimethyl-aminoethyl) and 5-nitro-2-[2-(1-pyrrolidine)-ethyl] derivatives. Chemotherapy,1979, vol. 25, no 2, pp. 83-90.

Harmenberg J., Wahren B., Bergman J., Akerfeldt S., Lundblad L. Antiherpesvirus activity and mechanism of action of indolo[2,3-b]quinoxaline and analogs. Antimicrob.Agents Chemother, 1988, vol. 32, no 11, pp. 1720- 1724. https://doi.org/10.1128/aac.32.11.1720

Shibinskaya M.O., Lyakhov S.A., Mazepa A.vol., Andronati S.A., Turov A.vol., Zholobak N.M., Spivak N.Y. Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminoethyl)-6Hindolo[2,3-b]quinoxalines. Eur. J. Med. Chem, 2010, vol. 45, no 3, pp. 1237-1243. https://doi.org/10.1016/j.ejmech.2009.12.014

Tseng C.H., Chen Y.R., Tzeng C.C., Liu W., Chou C.K., Chiu C.C., Chen Y.L. Discovery of indeno[1,2-b]quinoxaline derivatives as potential anticancer agents. Eur.J.Med.Chem, 2016, vol. 108, no , pp. 258-273.https://doi.org/10.1016/j.ejmech.2015.11.031

Deady L.W., Desneves J., Ross A.C. Synthesis of some 11H-indeno[1,2-b]quinoxalin-11-ones. Tetrahedron,1993, vol. 49, no 43, pp 9823-9828. https://doi.org/10.1016/S0040-4020(01)80184-8

Solis P.N., Wright C.W., Anderson M.M., Gupta M.P., Phillipson J.D. A microwell cytotoxicity assay using Artemia salina (brine shrimp). Planta Med, 1993, vol. 59, no 3, pp 250-252. https://doi.org/10.1055/s-2006-959661

Antonini I., Polucci P., Kelland L.R., Menta E., Pescalli N., Martelli S. 2,3-Dihydro-1H,7H-pyrimido[5,6,1-de]acridine-1,3,7-trione Derivatives, a Class of Cytotoxic Agents Active on Multidrug-Resistant Cell Lines:Synthesis, Biological Evaluation, and Structure-Activity Relationships. J. Med. Chem, 1999, vol. 42, no 14, pp. 2535-2541. https://doi.org/10.1021/jm9805586


Пристатейна бібліографія ГОСТ


1. Lerman L.S. Structural considerations in the interaction of DNA and acridines // J. Mol. Biol. – 1961. – Vol. 3,N 1. – P. 18 – 30. https://doi.org/10.1016/s0022-2836(61)80004-1

2. Douthart R.J., Burnett J.P., Beasley F.W., Frank B.H. Binding of ethidium bromide to double-stranded ribonucleic acid // Biochemistry. – 1973. – Vol. 12, N 2. – P. 214 – 220. https://doi.org/10.1021/bi00726a006

3. Berman H.M., Young P.R. The Interaction of Intercalating Drugs with Nucleic Acids // Annu. Rev. Biophys. Bioeng. – 1981. – Vol. 10, N 1. – P. 87 – 114. https://doi.org/10.1146/annurev.bb.10.060181.000511

4. Piestrzeniewicz M., Studzian K., Wilmanska D., Plucienniczak G., Gniazdowski M. Effect of DNA-interacting drugs on phage T7 RNA polymerase // Acta Biochim.Pol. – 1998. – Vol. 45, N 1. – P. 127 – 132. https://www.ncbi.nlm.nih.gov/pubmed/9701505

5. Acheson R.M., Taylor G.N., Waring M.J., Haylock S., Abel G. The intercalative DNA binding and antitumor activity of some bis-acridines related to nitracrine // Chem. Biol. Interact. – 1985. – Vol. 53, – P. 371 – 375. https://doi.org/10.1016/s0009-2797(85)80111-3

6. Drake J.W. The distribution of rates of spontaneous mutation over viruses, prokaryotes, and eukaryotes // Ann. N. Y. Acad. Sci. – 1999. – Vol. 870. – P. 100 – 107. https://doi.org/10.1111/j.1749-6632.1999.tb08870.x

7. Mucsi I., Molnar J., Tanaka M., Santelli-Rouvier C., Patelis A.M., Galy J.P., Barbe J. Effect of acridine derivatives on the multiplication of herpes simplex virus // Anticancer Res. – 1998. – Vol. 18, N 4C. – P. 3011 – 3015.

8. Loddo R., Francesconi Vol., Laurini E., Boccardo S., Aulic S., Fermeglia M., Pricl S., Tonelli M. 9-Aminoacridinebased agents impair the bovine viral diarrhea virus (BVDV) replication targeting the RNA-dependent RNA polymerase (RdRp) // Bioorg. Med. Chem. – 2018. – Vol. 26, N 4. – P. 855 – 868. https://doi.org/10.1016/j.bmc.2018.01.001

9. Andrews E.R., Fleming R.W., Grisar J.M., Kihm J.C., Wenstrup D.L., Mayer G.D. Bis-basic-substituted polycyclic aromatic compounds. A new class of antiviral agents. 2. Tilorone and related bis-basic ethers of fluorenone, fluorenol, and fluorene // J. Med. Chem. – 1974. – Vol. 17, N 8. – P. 882 – 886. https://doi.org/10.1021/jm00254a020

10. Garcia-Gancedo A., Gil C., Roldan C.M., Perez S., Vilas P. Antiviral action of benzo[de]isoquinoline-1,3-diones: 5-nitro-2-(2-dimethyl-aminoethyl) and 5-nitro-2-[2-(1-pyrrolidine)-ethyl] derivatives // Chemotherapy. – 1979. – Vol. 25, N 2. – P. 83 – 90.

11. Harmenberg J., Wahren B., Bergman J., Akerfeldt S., Lundblad L. Antiherpesvirus activity and mechanism of action of indolo[1,2-b]quinoxaline and analogs // Antimicrob.Agents Chemother. – 1988. – Vol. 32, N 11. – P. 1720 – 1724. https://doi.org/10.1128/aac.32.11.1720

12. Shibinskaya M.O., Lyakhov S.A., Mazepa A.Vol., Andronati S.A., Turov A.Vol., Zholobak N.M., Spivak N.Y. Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminoethyl)-6H-indolo[1,2-b] quinoxalines // Eur. J. Med. Chem. – 2010. – Vol. 45, N 3. – P. 1237 – 1243. https://doi.org/10.1016/j.ejmech.2009.12.014

13. Tseng C.H., Chen Y.R., Tzeng C.C., Liu W., Chou C.K., Chiu C.C., Chen Y.L. Discovery of indeno[1,2-b]quinoxaline derivatives as potential anticancer agents // Eur.J.Med.Chem. – 2016. – Vol. 108, N . – P. 258 – 273. https://doi.org/10.1016/j.ejmech.2015.11.031

14. Deady L.W., Desneves J., Ross A.C. Synthesis of some 11H-indeno[1,2-b]quinoxalin-11-ones // Tetrahedron. – 1993. – Vol. 49, N 43. – P. 9823 – 9828. https://doi.org/10.1016/S0040-4020(01)80184-8

15. Solis P.N., Wright C.W., Anderson M.M., Gupta M.P., Phillipson J.D. A microwell cytotoxicity assay using Artemia salina (brine shrimp) // Planta Med. – 1993. – Vol. 59, N 3. – P. 250 – 252. https://doi.org/10.1055/s-2006-959661

16. Antonini I., Polucci P., Kelland L.R., Menta E., Pescalli N., Martelli S. 2,3-Dihydro-1H,7H-pyrimido[5,6,1-de]acridine-1,3,7-trione Derivatives, a Class of Cytotoxic Agents Active on Multidrug-Resistant Cell Lines:Synthesis, Biological Evaluation, and Structure-Activity Relationships // J. Med. Chem. – 1999. – Vol. 42,N 14. – P. 2535 – 2541. https://doi.org/10.1021/jm9805586

 





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