Five-member thio-heterocyclic fused naphthalimides with aminoalkyl side chains: intercalation and photocleavage to DNA

Yufang Xu; Baoyuan Qu; Xuhong Qian; Yonggang Li

doi:10.1016/j.bmcl.2004.12.011

Five-member thio-heterocyclic fused naphthalimides with aminoalkyl side chains: intercalation and photocleavage to DNA

Bioorg Med Chem Lett. 2005 Feb 15;15(4):1139-42. doi: 10.1016/j.bmcl.2004.12.011.

Authors

Yufang Xu¹, Baoyuan Qu, Xuhong Qian, Yonggang Li

Affiliation

¹ Shanghai Key Lab. Chem. Biology, East China University of Science and Technology, Shanghai 200237, China.

PMID: 15686929
DOI: 10.1016/j.bmcl.2004.12.011

Abstract

Novel five-member thio-heterocyclic fused naphthalimides with aminoalkyl side chains were designed, synthesized and evaluated. These compounds have high Scatchard binding constants. They could damage DNA (supercoiled pBR322) from form I (closed) to II (nicked) at a concentration as low as 10 microM and from form I to form III at a concentration of 50 microM. The results implied that the influence of intercalating ability of chromophores on photocleaving ability of photocleavers depended on the mechanism of photocleavage.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

DNA Damage / drug effects*
DNA Damage / radiation effects
DNA, Superhelical / drug effects
Dose-Response Relationship, Drug
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / pharmacology
Imides / chemical synthesis*
Imides / pharmacology
Intercalating Agents / chemical synthesis*
Intercalating Agents / pharmacology
Naphthalenes / chemical synthesis
Naphthalenes / pharmacology
Photolysis
Structure-Activity Relationship
Sulfides / chemical synthesis
Sulfides / pharmacology

Substances

DNA, Superhelical
Heterocyclic Compounds, 4 or More Rings
Imides
Intercalating Agents
Naphthalenes
Sulfides