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. 2006;32(4):303–322. doi: 10.1134/S1068162006040017

Structure-activity relationships in a series of semisynthetic polycyclic glycopeptide antibiotics

E N Olsuf’eva 1,✉, M N Preobrazhenskaya 1
PMCID: PMC7089445  PMID: 32214779

Abstract

The main achievements in the development of methods for the design of semisynthetic antibiotics of a new generation belonging to the group of polycyclic glycopeptides directed against infections caused by multidrug-resistant bacteria and dangerous human and animal viruses are reviewed. The review is focused on the results obtained at the Gauze Institute in the area of chemical modification of natural antibiotics (eremomycin, vancomycin, teicoplanin, etc.) directed toward modification of their antibacterial and/or antiviral activity. A special emphasis is placed on the study of the mechanisms of action of these antibiotics, which could be the basis of a rational approach to their chemical modification involving the transformation of the inner binding pocket and the peripheral regions of the molecules that participate in the formation of their complexes with targets. The recently discovered antiviral activity of modified glycopeptides antibiotics is also discussed. A possibility of obtaining new highly active anti-HIV-1 and anti-HIV-2 preparations on the basis of hydrophobic derivatives of the aglycones of glycopeptide antibiotics was demonstrated. New semisynthetic derivatives of antibiotics that exhibit a high antibacterial activity in vivo, have good pharmacological characteristics, and are promising for practical use are described.

Key words: antibacterial and antiviral activity, eremomycin, glycopeptide-resistant bacteria, semisynthetic polycyclic glycopeptides, teicoplanin, vancomycin

Abbreviations

AR

amino acid residue

DPPA

diphenylphosphoryl azide

EC50

the concentration of antibiotic necessary for the protection of 50% human T lymphocytes from HIV-1 and HIV-2 viruses μM)

EDC

ethyldimethylaminopropyl carbodiimide

GISA

staphylococci with an intermediate resistance to glycopeptides

GINA

Gause Institute of New Antibiotics

GSE and GRE

glycopeptidesensitive and glycopeptide-resistant enterococci

HBTU

(benzotriazol-1-yl)-1,1,3,3-bistetramethyleneuronium hexafluoro-phosphate; Lac, lactic acid

MIC

minimal inhibitory concentration of antibiotic (μg/ml)

Mur

muramic acid

IC50

the concentration of antibiotic that inhibits the activity of enzymes responsible for the synthesis of peptidoglycan by 50% (μM)

PyBOP

(benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate

TBTU

(benzotriazol-1-yl)-1,1,3,3-bistetramethyleneuronium tetrafluoroborate

Footnotes

Original Russian Text © E.N. Olsuf’eva, M.N. Preobrazhenskaya, 2006, published in Bioorganicheskaya Khimiya, 2006, Vol. 32, No. 4, pp. 339–359.

References

  • 1.Walsh C. Antibiotics: Actions, Origins, Resistance. Washington, DC: ASM; 2003. [Google Scholar]
  • 2.Preobrazhenskaya M.N., Olsufyeva E.N. Expert Opinion on Therapeutic, Patents. 2004;14:141–173. doi: 10.1517/13543776.14.2.141. [DOI] [PubMed] [Google Scholar]
  • 3.Trenin A.S., Olsuf’eva E.N. Bioorg. Khim. 1997;23:851–867. [PubMed] [Google Scholar]
  • 4.Pavlov A.Yu., Preobrazhenskaya M.N. Bioorg. Khim. 1998;24:644–662. [PubMed] [Google Scholar]
  • 5.Printsevskaya S.S., Olsuf’eva E.N., Lazhko E.I., Preobrazhenskaya M.N. Bioorg. Khim. 2002;28:79–88. [PubMed] [Google Scholar]
  • 6.Pavlov A.Yu., Olsuf’eva E.N., Miroshnikova O.V., Reznikova M.I., Lazhko E.I., Malabarba A., Chabatti R., Preobrazhenskaya M.N. Bioorg. Khim. 1997;23:410–421. [PubMed] [Google Scholar]
  • 7.Printsevskaya S.S., Pavlov A.Y., Olsufyeva E.N., Mirchink E.P., Isakova E.B., Reznikova M.I., Goldman R.C., Brandstrom A.A., Baizman E.R., Longley C.B., Sztaricskai F., Batta G., Preobrazhenskaya M.N. J. Med. Chem. 2002;45:1340–1345. doi: 10.1021/jm010460i. [DOI] [PubMed] [Google Scholar]
  • 8.Printsevskaya S.S., Solovieva S.E., Olsufyeva E.N., Mirchink E.P., Isakova E.B., De Clercq E., Balzarini J., Preobrazhenskaya M.N. J. Med. Chem. 2005;45:3885–3889. doi: 10.1021/jm0500774. [DOI] [PubMed] [Google Scholar]
  • 9.Malabarba A., Ciabatti R., Maggini M., Ferrari P., Colombo L., Denaro M. J. Org. Chem. 1996;61:2151–2157. doi: 10.1021/jo9506746. [DOI] [Google Scholar]
  • 10.Berdnikova T.F., Lomakina N.N., Olsuf’eva E.N., Aleksandrova L.G., Malkova I.V. Antibiot. Khimioter. 1991;36:28–31. [PubMed] [Google Scholar]
  • 11.Olsufyeva E.N., Berdnikova T.F., Miroshnikova O.V., Reznikova M.I., Preobrazhenskaya M.N. J. Antibiot. 1999;52:319–324. doi: 10.7164/antibiotics.52.319. [DOI] [PubMed] [Google Scholar]
  • 12.Pavlov A.Y., Lazhko E.I., Preobrazhenskaya M.N. J. Antibiot. 1996;50:509–513. doi: 10.7164/antibiotics.50.509. [DOI] [PubMed] [Google Scholar]
  • 13.Printsevskaya S.S., Pavlov A.Y., Olsufyeva E.N., Mirchink E.P., Preobrazhenskaya M.N. J. Med. Chem. 2003;46:1204–1209. doi: 10.1021/jm020320o. [DOI] [PubMed] [Google Scholar]
  • 14.Pavlov, A.Y., Preobrazhenskaya, M.N., Malabarba, A., and Ciabatti, R., Abstracts of Papers, 1st Intern. Conference on Chemistry of Antibiotics and Related Microbial Products, Bologna (Italy), 1998, p. 13.
  • 15.Goldman R.C., Baizman E.R., Longley C.B., Branstrom A. FEMS Microlett. 2000;183:209–214. doi: 10.1111/j.1574-6968.2000.tb08959.x. [DOI] [PubMed] [Google Scholar]
  • 16.Pavlov A.Y., Miroshnikova O.V., Printsevskaya S.S., Olsufyeva E.N., Preobrazhenskaya M.N., Goldman R.C., Branstrom A.A., Baizman E.R., Longley C.B. J. Antibiot. 2001;54:455–459. doi: 10.7164/antibiotics.54.455. [DOI] [PubMed] [Google Scholar]
  • 17.Preobrazhenskaya, M.N., Olsufyeva, E.N., Miroshnikova, O.V., Printsevskaya, S.S., Plattner, J.J., and Chu, D., Abstracts of Papers, 45 Intern. Conference on Antimicrobial Agents and Chemotherapy, Washington, DC, 2005, F-1227, p. 190.
  • 18.Olsuf’eva E.N., Berdnikova T.F., Dokshina N.Yu., Lomakina N.N., Orlova G.I., Malkova I.V., Prozorova I.N. Antibiot. Khimioter. 1989;34:352–358. [PubMed] [Google Scholar]
  • 19.Cooper R.D.G., Snyder N.J., Zweifel M.J., Staszak M.A., Rodrigues M.J., Huff B.E., Thomphson R.C. J. Antibiot. 1996;49:575–581. doi: 10.7164/antibiotics.49.575. [DOI] [PubMed] [Google Scholar]
  • 20.Pavlov A.Yu., Olsuf’eva E.N., Berdnikova T.F., Aleksandrova L.G., Preobrazhenskaya M.N., Malkova I.V. Bioorg. Khim. 1991;17:857–861. [PubMed] [Google Scholar]
  • 21.Pavlov A.Y., Berdnikova T.F., Olsufyeva E.N., Malkova I.V., Preobrazhenskaya M.N., Risbridger G.D. J. Antibiot. 1994;47:225–232. doi: 10.7164/antibiotics.47.225. [DOI] [PubMed] [Google Scholar]
  • 22.Pavlov A.Y., Berdnikova T.F., Olsufyeva E.N., Miroshnikova O.V., Filipposyanz S.T., Preobrazhenskaya M.N., Sottani C., Colombo L., Goldstein B.P. J. Antibiot. 1996;49:194–198. doi: 10.7164/antibiotics.49.194. [DOI] [PubMed] [Google Scholar]
  • 23.Miroshnikova O.V., Printsevskaya S.S., Olsufyeva E.N., Pavlov A.Y., Nilius A., Hensey-Rudloff D., Preobrazhenskaya M.N. J. Antibiot. 2001;54:455–459. doi: 10.7164/antibiotics.53.286. [DOI] [PubMed] [Google Scholar]
  • 24.Maples, K., Plattner, J.J., Chu, D., Preobrazhenskaya, M.N., Olsufyeva, E.N., Printsevskaya, S.S., Solovyeva, S.E., Lovchik, J., and Lyons, R., Abstracts of Papers, 45 Intern. Conference on Antimicrobial Agents and Chemotherapy, Washington, DC, 2005, F-2073, p. 230.
  • 25.Pavlov A.Y., Berdnikova T.F., Olsufyeva E.N., Lazhko E.I., Malkova I.V., Preobrazhenskaya M.N., Tesla R.T., Petersen P.J. J. Antibiot. 1993;46:1731–1739. doi: 10.7164/antibiotics.46.1731. [DOI] [PubMed] [Google Scholar]
  • 26.Sharman, G.J. and Williams, D.H., Chem. Commun., 1997, pp. 723–724.
  • 27.Allen N.E., Nicas T. FEBS Microbiol. Rev. 2003;26:511–532. doi: 10.1111/j.1574-6976.2003.tb00628.x. [DOI] [PubMed] [Google Scholar]
  • 28.Olsufyeva, E.N., Joergensen, P., Mirgorodskaya, O.A., Pavlov, A.Y., Miroshnikova, O.V., and Preobrazhenskaya, M.N., Abstracts of Papers, 1st Intern. Conference on Chemistry of Antibiotics and Related Microbial Products. Bologna (Italy), 1998, Abstr. PC12.
  • 29.Mirgorodskaya O.A., Olsuf’eva E.N., Kolume D.E., Iorgensen E.D.D., Roepstorf P., Pavlov A.Yu., Miroshnikova O.V., Preobrazhenskaya M.N. Bioorg. Khim. 2000;26:630–639. [PubMed] [Google Scholar]
  • 30.Batta, G., Sztaricskai, F., Makarova, M.O., Gladkikh, E.G., Rogozheva, V.V., and Berdnikova, T.F., Chem. Commun., 2001, pp. 501–502.
  • 31.Kim J.S., Cegelsky L., Preobrazhenskaya M., Schaefer J. Biochemistry. 2006;45:5235–5250. doi: 10.1021/bi052660s. [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 32.Chen Z., Onishi H.R., Kohler J., Silver L.L., Kerns R., Fukuzawa S., Thompson C., Kahne D. Science. 1999;284:507–511. doi: 10.1126/science.284.5423.2174. [DOI] [PubMed] [Google Scholar]
  • 33.Leimkuhler C., Chen L., Barrett D., Panzone G., Sun B., Falcone B., Oberthur M., Donadio S., Walker S., Kahne D. J. Am. Chem. Soc. 2005;127:3250–3251. doi: 10.1021/ja043849e. [DOI] [PubMed] [Google Scholar]
  • 34.Balzarini J., Pannecouque C., De Clercq E., Pavlov A.Y., Printsevskaya S.S., Miroshnikova O.V., Reznikova M.I., Preobrazhenskaya M.N. J. Med. Chem. 2003;46:2755–2764. doi: 10.1021/jm0300882. [DOI] [PubMed] [Google Scholar]
  • 35.Printsevskaya S.S., Solovieva S.E., Olsufyeva E.N., Mirchink E.P., Isakova E.B., De Clercq E., Balzarini J., Preobrazhenskaya M.N. J. Med. Chem. 2005;48:3885–3890. doi: 10.1021/jm0500774. [DOI] [PubMed] [Google Scholar]
  • 36.Preobrazhenskaya, M.N., Printsevskaya, S.S., Olsufyeva, E.N., Solovyeva, S.E., De Clercq, E., and Balzarini, J., Drug of the Future 2004, vol. 29,Suppl. A, Prous. J.R., Ed., Prous Science Barcelona-Philadelphia, XVIII Int. Symp. on Medicinal Chemistry, 2004, Sweden, Poster 267, p. 375.
  • 37.De Clercq E. J. Med. Chem. 2005;48:1297–1313. doi: 10.1021/jm040158k. [DOI] [PubMed] [Google Scholar]
  • 38.Matsuzak K., Ikeda H., Ogino T., Matsumoto A., Woodruff H.B., Tanaka H., Omura S. J. Antibiot. 1994;47:1173–1174. doi: 10.7164/antibiotics.47.1173. [DOI] [PubMed] [Google Scholar]
  • 39.Naruse N., Tenmyo O., Kobaru S., Hatori M., Tomita K., Hamigishi Y., Oki T. J. Antibiot. 1993;46:1804–1811. doi: 10.7164/antibiotics.46.1804. [DOI] [PubMed] [Google Scholar]
  • 40.Singh S.B., Jayasuriya H., Salituro G.M., Zink D.L., Shafiee A., Heimbuch B., Silverman K.C., Lingham R.B., Genniloud O., Teran A., Vilella D., Felock P., Hazuda D. J. Nat. Prod. 2001;64:874–882. doi: 10.1021/np000632z. [DOI] [PubMed] [Google Scholar]

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