PMID: 2125476Oct 2, 1990Paper

Sequence preferences of DNA interstrand cross-linking agents: dG-to-dG cross-linking at 5'-CG by structurally simplified analogues of mitomycin C

Biochemistry
M F WeidnerP B Hopkins

Abstract

The nucleotide sequence preferences of the DNA interstrand cross-linking agents dehydroretronecine diacetate (DHRA), 2,3-bis(acetoxymethyl)-1-methylpyrrole (BAMP), dehydromonocrotaline, and dehydroretrorsine were studied by using synthetic DNA duplex fragments and polyacrylamide gel electrophoresis (PAGE). These agents have structural features in common with the reductively activated aziridinomitosene of mitomycin C (MC). Like MC, they preferentially cross-linked DNA duplexes containing the duplex sequence 5'-CG. For DHRA and BAMP interstrand cross-linked DNA duplexes, PAGE analysis of iron(II)-EDTA fragmentation reactions revealed the interstrand cross-links to be deoxyguanosine to deoxyguanosine (dG-to-dG), again analogous to DNA cross-links caused by MC. Unlike MC, DHRA could be shown to dG-to-dG cross-link a 5'-GC sequence. Furthermore, the impact of flanking sequence on the efficiency of interstrand cross-linking at 5'-CG was reduced for BAMP, with 5'-TCGA and 5'-GCGC being equally efficiently cross-linked. Possible origins of the 5'-CG sequence recognition common to all of the agents are discussed. A model is presented in which the transition state for the conversion of monoadducts to cross-links more closely resembles gr...Continue Reading

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Citations

Nov 1, 1995·European Journal of Cancer : Official Journal for European Organization for Research and Treatment of Cancer (EORTC) [and] European Association for Cancer Research (EACR)·J CummingsJ F Smyth
Nov 3, 2004·Journal of the American Society for Mass Spectrometry·Yuesong WangYinsheng Wang
Sep 9, 1999·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·H Y KimR A Coulombe
May 17, 2001·Bioorganic & Medicinal Chemistry·V S LiH Kohn
Apr 20, 2007·Chemical Research in Toxicology·Keith P RomanoJulie T Millard
Dec 25, 2009·Chemical Research in Toxicology·Brian A WaduguJulie T Millard
Jan 15, 2013·European Journal of Medicinal Chemistry·Maria I L SoaresTeresa M V D Pinho e Melo
Apr 6, 2004·Environmental and Molecular Mutagenesis·Rocío OrtizEdith Cortés
Jan 30, 2010·Journal of Applied Toxicology : JAT·Tao ChenPeter P Fu
Jun 11, 2002·Biochemical and Biophysical Research Communications·Atsuhiro JoguchiDai Ayusawa
Dec 18, 2013·Bioorganic & Medicinal Chemistry·Amany Belal, Bahaa El-Dien M El-Gendy
Nov 30, 1993·Biochemistry·J T Millard, T M Beachy
Dec 31, 2009·Critical Reviews in Biochemistry and Molecular Biology·Parameswary A MuniandyMichael M Seidman
May 31, 2003·The Journal of Biological Chemistry·Laura J NiedernhoferLawrence J Marnett
Apr 4, 2017·Chemical Communications : Chem Comm·Fan LiaoAiwen Lei
Apr 25, 2019·Cell Reports·Ana Mendanha FalcãoGonçalo Castelo-Branco
May 19, 2021·Archives of Toxicology·Yisheng HeGe Lin
Feb 19, 2002·Chemical Reviews·Scott R. Rajski, Robert M. Williams
Jan 8, 2003·Journal of the American Chemical Society·Ivan D KozekovThomas M Harris
Oct 5, 2001·Journal of Medicinal Chemistry·Y NaH Kohn

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