PMID: 9162901Apr 15, 1997Paper

Structure of a bis-amidinium derivative of hoechst 33258 complexed to dodecanucleotide d(CGCGAATTCGCG)2: the role of hydrogen bonding in minor groove drug-DNA recognition

Nucleic Acids Research
G R ClarkS Neidle

Abstract

The crystal structure is reported of a complex between the dodecanucleotide sequence d(CGCGAATTCGCG)2and an analogue of the DNA binding drug Hoechst 33258, in which the piperazine ring has been replaced by an amidinium group and the phenol ring by a phenylamidinium group. The structure has been refined to an R factor of 19.5% at 2.2 A resolution. The drug is held in the minor groove by five strong hydrogen bonds, together with bridging water molecules at both ends. There are few other contacts with the floor of the groove, indicating a lack of isohelicity with the groove and suggesting (i) that the observed high DNA affinity of this drug is primarily due to the array of hydrogen bonds and (ii) that these more than compensate for its poor isohelicity.

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Citations

Oct 13, 2001·Bioorganic & Medicinal Chemistry·Y H JiW Leupin
Sep 19, 2008·Accounts of Chemical Research·Binh NguyenW David Wilson
Mar 11, 1998·Natural Product Reports·S Neidle, C M Nunn
May 28, 2005·Journal of Biomolecular Structure & Dynamics·Rita KakkarRajni Grover
Feb 22, 2003·Nucleic Acids Research·Christian BaillyStephen Neidle
Mar 26, 2009·The Journal of Chemical Physics·Sudipta SamantaDhananjay Bhattacharyya
Apr 25, 2007·Chemistry, an Asian Journal·Santanu Bhattacharya, Padmaparna Chaudhuri
Apr 16, 2016·The Journal of Physical Chemistry. B·Subhas C BeraPadmaja P Mishra
May 24, 2014·Molecular BioSystems·Christos DeligkarisAlan Jonathan Quentin Greene
Dec 2, 1999·Pharmacology & Therapeutics·B S ReddyJ W Lown
Apr 7, 2021·Chemistry : a European Journal·Danielle van der WesthuizenDaniela I Bezuidenhout
Sep 19, 2002·Bioconjugate Chemistry·Jakob BunkenborgJens Peter Jacobsen

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