Design of Novel Carboxamides of Eremomycin and Vancomycin with 4- or 3-Amino Methyl Phenyl Boric Acid and Their Investigation
Abstract
Amidation of the end carboxyl group of eremomycin and vancomycin by pinacolinic 4- or 3-amino methyl phenyl boron acids esters in the presence of the condensing reagent PyBOP resulted in formation of novel carboxamides of the antibiotics (IIIa-VIa). After elimination of the pinacolinic group under mild hydrolysis in weak acid aqueous medium there formed the respective derivatives with a residue of the nonprotected boric acid (III-VI). It was shown that the activity of the 4-substituted derivatives of the borole-containing eremomycin and vancomycin practically was the same as that of the initial antibiotics, while higher than that of the respective 3-substituted derivatives of the borole-containing derivatives against 8 strains of grampositive bacteria.
About the Authors
E. N. Bychkova
G.F. Gause Institute of New Antibiotics
Russian Federation
Russian Federation
A. M. Korolev
G.F. Gause Institute of New Antibiotics
Russian Federation
Russian Federation
E. N. Olsufyeva
G.F. Gause Institute of New Antibiotics
Russian Federation
Russian Federation
E. P. Mirchink
G.F. Gause Institute of New Antibiotics
Russian Federation
Russian Federation
E. B. Isakova
G.F. Gause Institute of New Antibiotics
Russian Federation
Russian Federation
References
1. Berdy J. Thoughts and facts about antibiotics: where we are now and where we are heading. Antibiotics 2012; 65: 385-395.
2. Faier R.J., Tor Y. Antibiotics and bacterial resistance in the 21st century. Perspectives in Medicinal Chemistry. 2014; 6: 25-64.
3. Ashford P.A., Bew S.P. Recent advances in the synthesis of new glycopeptide antibiotics. Chem Soc Rev 2012; 41: 957-978.
4. Hattangady D.S., Singh A.K., Muthaiyan A. et al. Genomic, transcriptomic and metabolomic studies of two well-characterized, laboratory-derived vancomycin-intermediate Staphylococcus aureus strains derived from the same parent strain. Antibiotics 2015; 4: 76-112.
5. Олсуфьева E.H., Преображенская М.Н. Изучение связи структура-активность в ряду полусинтетических антибиотиков группы полициклических гликопептидов. Биоорг хим 2006; 32: 4: 1-21
6. Preobrazhenskaya M.N., Olsufyeva E.N. Patents on glycopeptides of the vancomycin family and their derivatives as antimicrobials: January 1999 - June 2003. Ex Opin Ther Pat 2004; 14: 2: 1-33.
7. Butler M.S., Blaskovich M.A., Cooper M.A. Antibiotics in the clinical pipeline in 2013. Antibiotics 2013; 66: 571-591.
8. Van Bambeke F. Glycopeptides and glycodepsipeptides in clinical development: a comparative review of their antibacterial spectrum, pharmacokinetics and clinical efficacy. Curr Opin Invest Drugs 2006; 7: 8: 740-749.
9. Тевяшова A.H., Олсуфьева E.H., Преображенская М.Н. Создание антибиотиков двойного действия как путь поиска новых перспективных лекарственных препаратов. Успехи химии 2015; 84: 1: 61-97
10. Liu C.T., Tomsho J.W., Benkovic S.J. The unique chemistry of benzoxaboroles: current and emerging applications in biotechnology and therapeutic treatments. Bioorgan Med Chem. 2014; 22: 4462-4473.
11. Adams J., Kauffman M. Development of the Proteasome Inhibitor Velcade (Bortezomib). Cancer Invest 2004; 22: 2: 304-311.
12. Putty S., Rai A., Jamindar D. et al. Characterization of d-boroAla as a novel broad-spectrum antibacterial agent targeting d-Ala-d-Ala ligase. Chem Biol Drug Design 2011; 78: 5: 11: 757-763.
13. Printsevskaya S.S., Reznikova M.I., Korolev A.M. et al. Synthesis and study of antibacterial activities of antibacterial glycopeptide antibiotics conjugated with benzoxaboroles. Future Med Chem 2013; 5: 6: 641-652.
14. Tevyashova A.N., Printsevskaya S.S., Olsufyeva E.N. et al. The use of ben-zoxaboroles for constructing of dual-acting antibiotics on the basis of glycopeptides and amphotericin B. Abstr. 14 International Conference on the Chemistry of Antibiotics and other Bioactive Compounds, ICCA-2015, 2015; October 13- 16: Galveston: Texas: USA: P 20.
15. Lapa G.B., Korolev A.M., Luzikov Y.N. et al. Two approaches to the use of bezo[c][1,2]oxaboroles as active fragments for synthetic transformation of clarithromycin. Abstr. XV Inernational Conference «Heterocycles in Bioorganic Chemistry» Riga. Latvia. 2013; May 27- 30: PO 135: 192.
16. Определение чувствительности микроорганизмов к антибактериальным препаратам (Методические указания МУК 4.2.1890-04). Утверждены и введены в действие Главным государственным санитарным врачом Российской Федерации Г.Г. Онищенко 04.03.2004 г.
17. Руководством по проведению доклинических исследований лекарственных средств / часть первая. Издание ФГБУ «НЦЭСМП» Минздравсоцразвития России, 2012
18. Рекомендациями Национального Комитета Клинических Лабораторных Стандартов США (NCCLS), [NCCLS Reference Method for Broth Dilution Antibacterial Susceptibility Testing, USA 2000]
19. Printsevskaya S.S., Pavlov A.Y., Olsufyeva E.N. et al. Synthesis and mode of action of hydrophobic derivatives of glycopeptide antibiotic eremomycin and des-(N-methyl-D-leucyl) eremomycin against glycopeptide-sensitive and - resiatant bacteria. J Med Chem 2002; 45: 1340-1345
Review
For citations:
Bychkova E.N., Korolev A.M., Olsufyeva E.N., Mirchink E.P., Isakova E.B. Design of Novel Carboxamides of Eremomycin and Vancomycin with 4- or 3-Amino Methyl Phenyl Boric Acid and Their Investigation. Antibiot Khimioter = Antibiotics and Chemotherapy. 2015;60(9-10):7-11. (In Russ.)
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