Synthesis of DNA-Interactive Pyrrolo[2,1-c][1,4]benzodiazepines (PBDs)

Antonow, D. and Thurston, D.E. (2011) Synthesis of DNA-Interactive Pyrrolo[2,1-c][1,4]benzodiazepines (PBDs). Chemical Reviews, 111 (4). pp. 2815-2864. 10.1021/cr100120f.

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DOI: 10.1021/cr100120f

Abstract

Pyrrolobenzodiazepines (PBD) are an important class of sequence-selective DNA-interactive agents that bind covalently to guanine bases within the minor groove of DNA. The PBD monomers are remarkable in possessing a 3-dimensional shape that allows them to fit perfectly within the minor groove of DNA, partly due to the longitudinal twist created by the chiral center at their C11a-position. A PBD produced synthetically, semisynthetically, or isolated from natural sources can exist as a mixture of two or even three forms or can exist predominantly as just one. Various biochemical and structural studies on PBD-DNA adducts have suggested that the molecules locate themselves with their N10-position pointing toward the floor of the minor groove. A further important feature of the PBDs is that they interact selectively with specific DNA sequences. A significant effort has also been made to increase the base-pair span and sequence-selectivity of PBD molecules so that they might be used as gene-targeting agents in biological experiments and possibly as therapeutic agents.

Item Type:Article
Departments, units and centres:Department of Pharmaceutical and Biological Chemistry > Department of Pharmaceutical and Biological Chemistry
ID Code:2884
Journal or Publication Title:Chemical Reviews
Deposited By:Library Staff
Deposited On:01 Mar 2012 10:45
Last Modified:01 Mar 2012 10:45

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