Natural products that cleave DNA

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The antitumor agent bleomycin is believed to mediate its thera- peutic effects at the level of DNA strand scission; this process requires oxygen and an appropriate metal ion and proceeds via oxidative damage to the carbohydrate moiety of DNA. Metallobleamycins participate catalytically in DNA cleavage, apparently via the intermediacy of high valent metal-oxo complexes, which delivers a reactive form of oxygen to a DNA sugar subsequent to binding of the metallobleomycin to the DNA duplex. Also investigated were two structural series of natural products that have been shown for the first time to cleave DNA. One series, exemplified by (-)-epicatechin and procyanidin B2, was identified initially as constituents of Celastrus pringli Rose. Also studied was a series of 5-alkylresorcinols isolated from Hakea trifurcata. In common with blecmycin, DNA strand scission by both types of agents required a metal ion and O2. However, for both the flavanoids and 5-alkylresorcinols, DNA cleavage did not require any reductant and was actually diminished in the presence of thiols.

Original languageEnglish (US)
Pages (from-to)577-580
Number of pages4
JournalPure and Applied Chemistry
Volume61
Issue number3
DOIs
StatePublished - Jan 1 1989
Externally publishedYes

Fingerprint

Biological Products
DNA
Metal ions
Oxygen
Catechin
Reducing Agents
Bleomycin
Carbohydrates
Sulfhydryl Compounds
Sugars
Antineoplastic Agents
Metals

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Natural products that cleave DNA. / Hecht, Sidney.

In: Pure and Applied Chemistry, Vol. 61, No. 3, 01.01.1989, p. 577-580.

Research output: Contribution to journalArticle

@article{64b544e23a2c4fb5be97f67f09972aa6,
title = "Natural products that cleave DNA",
abstract = "The antitumor agent bleomycin is believed to mediate its thera- peutic effects at the level of DNA strand scission; this process requires oxygen and an appropriate metal ion and proceeds via oxidative damage to the carbohydrate moiety of DNA. Metallobleamycins participate catalytically in DNA cleavage, apparently via the intermediacy of high valent metal-oxo complexes, which delivers a reactive form of oxygen to a DNA sugar subsequent to binding of the metallobleomycin to the DNA duplex. Also investigated were two structural series of natural products that have been shown for the first time to cleave DNA. One series, exemplified by (-)-epicatechin and procyanidin B2, was identified initially as constituents of Celastrus pringli Rose. Also studied was a series of 5-alkylresorcinols isolated from Hakea trifurcata. In common with blecmycin, DNA strand scission by both types of agents required a metal ion and O2. However, for both the flavanoids and 5-alkylresorcinols, DNA cleavage did not require any reductant and was actually diminished in the presence of thiols.",
author = "Sidney Hecht",
year = "1989",
month = "1",
day = "1",
doi = "10.1351/pac198961030577",
language = "English (US)",
volume = "61",
pages = "577--580",
journal = "Pure and Applied Chemistry",
issn = "0033-4545",
publisher = "IUPAC Secretariat",
number = "3",

}

TY - JOUR

T1 - Natural products that cleave DNA

AU - Hecht, Sidney

PY - 1989/1/1

Y1 - 1989/1/1

N2 - The antitumor agent bleomycin is believed to mediate its thera- peutic effects at the level of DNA strand scission; this process requires oxygen and an appropriate metal ion and proceeds via oxidative damage to the carbohydrate moiety of DNA. Metallobleamycins participate catalytically in DNA cleavage, apparently via the intermediacy of high valent metal-oxo complexes, which delivers a reactive form of oxygen to a DNA sugar subsequent to binding of the metallobleomycin to the DNA duplex. Also investigated were two structural series of natural products that have been shown for the first time to cleave DNA. One series, exemplified by (-)-epicatechin and procyanidin B2, was identified initially as constituents of Celastrus pringli Rose. Also studied was a series of 5-alkylresorcinols isolated from Hakea trifurcata. In common with blecmycin, DNA strand scission by both types of agents required a metal ion and O2. However, for both the flavanoids and 5-alkylresorcinols, DNA cleavage did not require any reductant and was actually diminished in the presence of thiols.

AB - The antitumor agent bleomycin is believed to mediate its thera- peutic effects at the level of DNA strand scission; this process requires oxygen and an appropriate metal ion and proceeds via oxidative damage to the carbohydrate moiety of DNA. Metallobleamycins participate catalytically in DNA cleavage, apparently via the intermediacy of high valent metal-oxo complexes, which delivers a reactive form of oxygen to a DNA sugar subsequent to binding of the metallobleomycin to the DNA duplex. Also investigated were two structural series of natural products that have been shown for the first time to cleave DNA. One series, exemplified by (-)-epicatechin and procyanidin B2, was identified initially as constituents of Celastrus pringli Rose. Also studied was a series of 5-alkylresorcinols isolated from Hakea trifurcata. In common with blecmycin, DNA strand scission by both types of agents required a metal ion and O2. However, for both the flavanoids and 5-alkylresorcinols, DNA cleavage did not require any reductant and was actually diminished in the presence of thiols.

UR - http://www.scopus.com/inward/record.url?scp=0000804433&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000804433&partnerID=8YFLogxK

U2 - 10.1351/pac198961030577

DO - 10.1351/pac198961030577

M3 - Article

VL - 61

SP - 577

EP - 580

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

SN - 0033-4545

IS - 3

ER -