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• W2085804569 abstract "The pyrrolobenzodiazepines (PBDs) are covalent DNA minor-groove binding agents with a reported preference for binding to 5′-Pu-G-Pu sequences with their A rings oriented toward the 3′-end of the covalently modified DNA strand. Using HPLC/MS methodology and a range of designed hairpin-forming 17-mer oligonucleotides, the kinetics of reaction of a bis-pyrrole PBD conjugate (GWL-78, 2) has been evaluated with eight isomeric oligonucleotides, each containing a single PBD binding site in one of two locations. The PBD-binding base pair triplets were designed to include every possible combination of A and T bases adjacent to the covalently reacting guanine. Contrary to expectations, 2 reacted most rapidly with TGT and TGA sequences, and adducts were observed to form in both the 3′- and the 5′-directions. Molecular modeling studies revealed that for 3′-oriented adducts, this preference could be explained by formation of a hydrogen bond between the N10-H of the PBD and the oxygen of the C2-carbonyl of a thymine base on the 3′-side of the covalently bound guanine. For 5′-adducts, an analogous PBD N10-H hydrogen bond may form instead to the N3 of an equivalent adenine on the opposite strand." @default.
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• W2085804569 date "2010-08-13" @default.
• W2085804569 modified "2023-10-11" @default.
• W2085804569 title "DNA Sequence Preference and Adduct Orientation of Pyrrolo[2,1-<i>c</i>][1,4]benzodiazepine Antitumor Agents" @default.
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• W2085804569 doi "https://doi.org/10.1021/ml100131b" @default.
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