Synthetic analogues of netropsin and distamycin. I. Pyridine-containing analogues of distamycin--a molecular modelling study

K Bielawski; D Bartulewicz; A Rózański

Synthetic analogues of netropsin and distamycin. I. Pyridine-containing analogues of distamycin--a molecular modelling study

Rocz Akad Med Bialymst. 1995;40(2):352-63.

Authors

K Bielawski¹, D Bartulewicz, A Rózański

Affiliation

¹ Department of Organic Chemistry, Medical Academy of Białystok.

PMID: 8834619

Abstract

We have investigated new series of pyridine-containing analogues III-XXII of distamycin A. Molecular mechanics technique revealed evident structural similarities between III-VI and pyridine-2-carboxamide-netropsin, suggesting possible interactions of compounds III-VI with DNA. Molecular modelling to the B-DNA d(CGCAGCTTTGCG) duplex shows that III fits tightly into the minor groove. The pattern of hydrogen bonds in the computed complex covers C6.G19, T7.A18, T8.A17, and T9.A16. The most striking feature of III.DNA (1:1) complex is the recognition of the guanine amino group (G19) by the pyridine nitrogen of III.

MeSH terms

Antiviral Agents / chemistry*
Base Sequence
Binding Sites
Computer Simulation
DNA / chemistry
Distamycins / chemistry*
Drug Design
Guanine / chemistry
Models, Molecular*
Molecular Conformation
Molecular Sequence Data
Netropsin / analogs & derivatives*
Pyridines / chemistry

Substances

Antiviral Agents
Distamycins
Pyridines
Guanine
Netropsin
stallimycin
DNA
pyridine