DNA alkylation by leinamycin can be triggered by cyanide and phosphines

Authors
Zang, H Breydo, L Mitra, K Dannaldson, J Gates, KS
Citation
H. Zang et al., DNA alkylation by leinamycin can be triggered by cyanide and phosphines, BIOORG MED, 11(12), 2001, pp. 1511-1515
Citations number
17
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
11
Issue
12
Year of publication
2001
Pages
1511 - 1515
Database
ISI
SICI code
0960-894X(20010618)11:12<1511:DABLCB>2.0.ZU;2-F
Abstract
Previous work has shown that alkylation of DNA by the antitumor agent leina mycin (1) is potentiated by reaction of the antibiotic with thiols. Here, i t is shown that other soft nucleophiles such as cyanide and phosphines can also trigger DNA alkylation by leinamycin. Overall, the results suggest tha t reactions of cyanide and phosphines with leinamycin produce the oxathiola none intermediate (2), which is known to undergo rearrangement to the DNA-a lkylating episulfonium ion 4. (C) 2001 Elsevier Science Ltd. All rights res erved.