Synthetic analogues of netropsin and distamycin. I. Pyridine-containing analogues of distamycin--a molecular modelling study.
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.
Bielawski
K
K
Department of Organic Chemistry, Medical Academy of Białystok.
Bartulewicz
D
D
Rózański
A
A
D000998:Antiviral Agents / Q000737:chemistry*; D001483:Base Sequence; D001665:Binding Sites; D003198:Computer Simulation; D004247:DNA / Q000737:chemistry; D004214:Distamycins / Q000737:chemistry*; D015195:Drug Design; D006147:Guanine / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D009429:Netropsin / Q000031:analogs & derivatives*; D011725:Pyridines / Q000737:chemistry
D000998:Antiviral Agents; D004214:Distamycins; D011725:Pyridines; D006147:Guanine; D009429:Netropsin; C030000:stallimycin; D004247:DNA; C023666:pyridine