Diastereoselective DNA cleavage recognition by Ni(II) x Gly-Gly-His-derived metallopeptides

Journal of the American Chemical Society
Ya-Yin FangEric C Long

Abstract

Site-selective DNA cleavage by diastereoisomers of Ni(II) x Gly-Gly-His-derived metallopeptides was investigated through high-resolution gel analyses and molecular dynamics simulations. Ni(II) x L-Arg-Gly-His and Ni(II) x D-Arg-Gly-His (and their respective Lys analogues) targeted A/T-rich regions; however, the L-isomers consistently modified a subset of available nucleotides within a given minor groove site, while the D-isomers differed in both their sites of preference and their ability to target individual nucleotides within some sites. In comparison, Ni(II) x L-Pro-Gly-His and Ni(II) x D-Pro-Gly-His were unable to exhibit a similar diastereoselectivity. Simulations of the above systems, along with Ni(II) x Gly-Gly-His, indicated that the stereochemistry of the amino-terminal amino acid produces either an isohelical metallopeptide that associates stably at individual DNA sites (L-Arg or L-Lys) or, with D-Arg and D-Lys, a noncomplementary metallopeptide structure that cannot fully employ its side chain nor amino-terminal amine as positional stabilizing moieties. In contrast, amino-terminal Pro-containing metallopeptides of either stereochemistry, lacking an extended side chain directed toward the minor groove, did not exhibit...Continue Reading

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Citations

Feb 22, 2013·Environmental Science & Technology·Maoyong SongGuibin Jiang
Sep 14, 2011·Chemical Communications : Chem Comm·Alexander N Zaykov, Zachary T Ball
Oct 26, 2011·Future Medicinal Chemistry·Béla Gyurcsik, Anikó Czene
Dec 9, 2014·Biochemical and Biophysical Research Communications·M Daben J LibardoAlfredo M Angeles-Boza
Aug 31, 2016·Communicative & Integrative Biology·Reina Inokuchi, Tomonori Kawano
Jul 17, 2018·Metallomics : Integrated Biometal Science·Agnieszka Belczyk-CiesielskaWojciech Bal
May 7, 2014·ChemMedChem·Rodrigo Galindo-Murillo, Thomas E Cheatham
Jan 24, 2008·Chemistry : a European Journal·Stefan StadlbauerBurkhard König
Feb 5, 2019·Chemistry : a European Journal·Biplab K MaitiJosé J G Moura
Oct 8, 2016·Metallomics : Integrated Biometal Science·Caleb Mawuli AgbaleOctávio Luiz Franco

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