CaltechAUTHORS
  A Caltech Library Service

Molecular recognition of DNA by Hoechst benzimidazoles: Exploring beyond the pyrrole-imidazole-hydroxypyrrole polyamide-pairing code

Minehan, Thomas G. and Gottwald, Konstanze and Dervan, Peter B. (2000) Molecular recognition of DNA by Hoechst benzimidazoles: Exploring beyond the pyrrole-imidazole-hydroxypyrrole polyamide-pairing code. Helvetica Chimica Acta, 83 (9). pp. 2197-2213. ISSN 0018-019X. https://resolver.caltech.edu/CaltechAUTHORS:20160510-083823240

Full text is not posted in this repository. Consult Related URLs below.

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20160510-083823240

Abstract

A series of three-ring analogs of the minor-groove-binding molecule Hoechst 33258 (1), consisting of benzimidazole (B), imidazopyridine (P), and hydroxybenzimidazole (H) monomers, have been synthesized in order to investigate both their sequence specificity and binding modes. MPE⋅FeII Footprinting has revealed the preference of both PBB and BBB ligands for 5′-WGWWW-3′ and 5′-WCWWW-3′ tracts, as well as A⋅T-rich sequences. Affinity-cleavage titrations show no evidence for a 2 : 1 binding mode of these Hoechst analogs. Importantly, all derivatives are oriented in one direction at each of their binding sites. The implications of these results for the design of minor-groove-binding small molecules is discussed.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/1522-2675(20000906)83:9<2197::AID-HLCA2197>3.0.CO;2-N DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/1522-2675(20000906)83:9%3C2197::AID-HLCA2197%3E3.0.CO;2-N/abstractPublisherArticle
ORCID:
AuthorORCID
Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 2000 Neue Schweizerische Chemische Gesellschaft, Switzerland. Received May 22, 2000. Article first published online: 25 SEP 2000. We are grateful for financial support from the National Institutes of Health, the Beckman Institute, BASF, and Studienstifung des deutschen Volkes for a postdoctoral fellowship to K. G., and the American Cancer Society for a postdoctoral fellowship to T G. M. We also wish to thank Victor Rucker for performing gas-phase minimizations on distamycin, ImPyPy, PBB, and BBB.
Funders:
Funding AgencyGrant Number
NIHUNSPECIFIED
Caltech Beckman InstituteUNSPECIFIED
BASFUNSPECIFIED
Studienstifung des deutschen VolkesUNSPECIFIED
American Cancer SocietyUNSPECIFIED
Issue or Number:9
Record Number:CaltechAUTHORS:20160510-083823240
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160510-083823240
Official Citation:Minehan, Thomas G., Gottwald, K. and Dervan, Peter B. (2000), Molecular Recognition of DNA by Hoechst Benzimidazoles: Exploring Beyond the Pyrrole-Imidazole-Hydroxypyrrole Polyamide-Pairing Code. HCA, 83: 2197–2213. doi: 10.1002/1522-2675(20000906)83:9<2197::AID-HLCA2197>3.0.CO;2-N
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66834
Collection:CaltechAUTHORS
Deposited By: Victoria Brennan
Deposited On:10 May 2016 16:39
Last Modified:26 Nov 2019 11:15

Repository Staff Only: item control page