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CC-1065 CBI analogs: an example of enhancement of DNA alkylation efficiency through introduction of stabilizing electrostatic interactions.

Abstract：

:The three trimethylammonium salts 3-5 proved to be 100 times more efficient at alkylating DNA than 2 and exhibited DNA alkylation efficiencies identical to that of (+)-CC-1065 (1). In addition, the agents 3 and 4 exhibited DNA alkylation selectivities identical to that of 2. This may be attributed to spatially well-defined stabilizing electrostatic interactions between the positively charged trimethylammonium salt lying on the peripheral face of the agents and the bracketing, negatively charged phosphates located in the DNA backbone that enhance the DNA noncovalent binding affinity without affecting DNA binding or alkylation selectivity. The agent 5 exhibited an altered and more discriminating AT-rich adenine N3 alkylation selectivity than 2-4 that may be attributed to the groove placement of the large trimethylammonium salt.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Boger DL,Yun W,Han N,Johnson DS

doi

10.1016/0968-0896(95)00048-l

subject

Has Abstract

pub_date

1995-06-01 00:00:00

pages

611-21

issue

6

eissn

0968-0896

issn

1464-3391

pii

0968-0896(95)00048-L

journal_volume

3

pub_type

杂志文章

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