TY - JOUR
T1 - Synthesis and reactions with DNA of a family of DNA-DNA afinity cross-linking agents
AU - Sigurdsson, Snorri Th
AU - Hopkins, Paul B.
PY - 1994
Y1 - 1994
N2 - A family of DNA-DNA cross-linking agents has been synthesized, in which 2,3-bis-(hydroxymethyl)-pyrrole is linked to the oligopeptide distamycin. These substances were efficient, sequence selective, DNA-DNA interstrand and intrastrand cross-linking agents. Substance 1a formed interstand and intrastrand cross-links at the sequences 5′ d(CGAATT) and 5′ d(GGAATT), respectively. The lesions from hydrolysis of the phosphodiester backbones of inter- and intrastrand cross-linked DNA were identical, and possessed the structure 20. Substance 1a was 1000-fold more active as a cross-linking agent than 2,3-bis-(hydroxymethyl)-1-methylpyrrole (19). The cytotoxicity of 2a was comparable to cis-DDP.
AB - A family of DNA-DNA cross-linking agents has been synthesized, in which 2,3-bis-(hydroxymethyl)-pyrrole is linked to the oligopeptide distamycin. These substances were efficient, sequence selective, DNA-DNA interstrand and intrastrand cross-linking agents. Substance 1a formed interstand and intrastrand cross-links at the sequences 5′ d(CGAATT) and 5′ d(GGAATT), respectively. The lesions from hydrolysis of the phosphodiester backbones of inter- and intrastrand cross-linked DNA were identical, and possessed the structure 20. Substance 1a was 1000-fold more active as a cross-linking agent than 2,3-bis-(hydroxymethyl)-1-methylpyrrole (19). The cytotoxicity of 2a was comparable to cis-DDP.
UR - https://www.scopus.com/pages/publications/0027941701
U2 - 10.1016/S0040-4020(01)89560-0
DO - 10.1016/S0040-4020(01)89560-0
M3 - Article
SN - 0040-4020
VL - 50
SP - 12065
EP - 12084
JO - Tetrahedron
JF - Tetrahedron
IS - 42
ER -