A few atoms make the difference: synthetic, CD, NMR and computational studies on antiviral and antibacterial activities of glycopeptide antibiotic aglycon derivatives

European Journal of Medicinal Chemistry
Ilona BereczkiPál Herczegh

Abstract

Despite the close structural similarity between the heptapeptide cores of the glycopeptide antibiotics teicoplanin and ristocetin, synthetically modified derivatives of their aglycons show significantly different antibacterial and antiviral properties. The teicoplanin aglycon derivatives with one exception proved to be potent antibacterials but they did not exhibit anti-influenza virus activity. In contrast, the aglycoristocetin derivatives generally showed high anti-influenza virus activity and possessed moderate antibacterial activity. A systematic structure-activity relationship study has been carried out on ristocetin and teicoplanin aglycon derivatives, to explore which structural differences are responsible for these markedly different biological activities. According to electronic circular dichroism and in silico conformational studies, it was found that the differences in anti-influenza virus activity are mainly determined by the conformation of the heptapeptide core of the antibiotics controlled by the presence or absence of chloro substituents. Knowledge of the bioactive conformation will help to design new analogs with improved anti-influenza virus activity. For the teicoplanin derivatives, it was shown that derivati...Continue Reading

References

Jul 15, 1998·Blood Coagulation & Fibrinolysis : an International Journal in Haemostasis and Thrombosis·B BardsleyT P Baglin
Sep 20, 2001·Current Medicinal Chemistry·A Malabarba, R Ciabatti
Oct 18, 2001·Journal of Chemical Information and Computer Sciences·I V TetkoA E Villa
Oct 16, 2002·Journal of Chemical Information and Computer Sciences·Igor V Tetko, Vsevolod Yu Tanchuk
Jun 13, 2003·Journal of Medicinal Chemistry·Jan BalzariniMaria N Preobrazhenskaya
Jan 1, 1960·Archives of Internal Medicine·E J GANGAROSAH S RAMOS
Nov 19, 2003·Bioorganic & Medicinal Chemistry Letters·J Kevin Judice, John L Pace
Apr 30, 2004·Journal of Computational Chemistry·Junmei WangDavid A Case
Feb 7, 2006·Journal of Molecular Graphics & Modelling·Junmei WangDavid A Case
Apr 13, 2010·Bioorganic & Medicinal Chemistry Letters·Gábor PintérPál Herczegh
Jun 29, 2012·Journal of Virology·Evelien VanderlindenLieve Naesens
Nov 15, 2012·European Journal of Medicinal Chemistry·Attila SiposPál Herczegh

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antivirals (ASM)

Antivirals are medications that are used specifically for treating viral infections. Discover the latest research on antivirals here.

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antivirals

Antivirals are medications that are used specifically for treating viral infections. Discover the latest research on antivirals here.