Literature DB >> 21088763

Few constraints limit the design of quinone methide-oligonucleotide self-adducts for directing DNA alkylation.

Clifford S Rossiter1, Emilia Modica, Dalip Kumar, Steven E Rokita.   

Abstract

Nucleotide sequences minimally containing adenosine, cytosine or guanosine are sufficient to form intrastrand oligonucleotide quinone methide self-adducts reversibly for subsequent alkylation of complementary DNA. The general lack of sequence restrictions should now allow for alkylation of most any target of interest although reaction is most efficient when the self-adducts contain guanine residues and do not form hairpin structures.

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Year:  2010        PMID: 21088763      PMCID: PMC3895935          DOI: 10.1039/c0cc03317k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  17 in total

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Authors:  T Antony; T Thomas; L H Sigal; A Shirahata; T J Thomas
Journal:  Biochemistry       Date:  2001-08-07       Impact factor: 3.162

2.  Dynamic cross-linking is retained in duplex DNA after multiple exchange of strands.

Authors:  Huan Wang; Steven E Rokita
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-09       Impact factor: 15.336

3.  Immortalizing a transient electrophile for DNA cross-linking.

Authors:  Huan Wang; Manvinder S Wahi; Steven E Rokita
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-quinone methide.

Authors:  Lee M Bishop; Michael Winkler; Kendall N Houk; Robert G Bergman; Dirk Trauner
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

5.  Molecular beacons: probes that fluoresce upon hybridization.

Authors:  S Tyagi; F R Kramer
Journal:  Nat Biotechnol       Date:  1996-03       Impact factor: 54.908

6.  Sequence-specific delivery of a quinone methide intermediate to the major groove of DNA.

Authors:  Q Zhou; P Pande; A E Johnson; S E Rokita
Journal:  Bioorg Med Chem       Date:  2001-09       Impact factor: 3.641

7.  Modeling H-bonding and solvent effects in the alkylation of pyrimidine bases by a prototype quinone methide: a DFT study.

Authors:  Mauro Freccero; Cristiana Di Valentin; Mirko Sarzi-Amadè
Journal:  J Am Chem Soc       Date:  2003-03-26       Impact factor: 15.419

8.  Quenching of quercetin quinone/quinone methides by different thiolate scavengers: stability and reversibility of conjugate formation.

Authors:  Hanem M Awad; Marelle G Boersma; Sjef Boeren; Peter J Van Bladeren; Jacques Vervoort; Ivonne M C M Rietjens
Journal:  Chem Res Toxicol       Date:  2003-07       Impact factor: 3.739

9.  BINOL-amino acid conjugates as triggerable carriers of DNA-targeted potent photocytotoxic agents.

Authors:  Filippo Doria; Sara N Richter; Matteo Nadai; Stefano Colloredo-Mels; Mariella Mella; Manlio Palumbo; Mauro Freccero
Journal:  J Med Chem       Date:  2007-11-30       Impact factor: 7.446

10.  A transient product of DNA alkylation can be stabilized by binding localization.

Authors:  Willem F Veldhuyzen; Praveen Pande; Steven E Rokita
Journal:  J Am Chem Soc       Date:  2003-11-19       Impact factor: 15.419

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  6 in total

1.  Inducible alkylation of DNA by a quinone methide-peptide nucleic acid conjugate.

Authors:  Yang Liu; Steven E Rokita
Journal:  Biochemistry       Date:  2012-01-24       Impact factor: 3.162

2.  Unraveling Reversible DNA Cross-Links with a Biological Machine.

Authors:  Shane R Byrne; Steven E Rokita
Journal:  Chem Res Toxicol       Date:  2020-11-05       Impact factor: 3.739

3.  Directing Quinone Methide-Dependent Alkylation and Cross-Linking of Nucleic Acids with Quaternary Amines.

Authors:  Mark A Hutchinson; Blessing D Deeyaa; Shane R Byrne; Sierra J Williams; Steven E Rokita
Journal:  Bioconjug Chem       Date:  2020-04-23       Impact factor: 4.774

4.  Targeting duplex DNA with the reversible reactivity of quinone methides.

Authors:  Chengyun Huang; Yang Liu; Steven E Rokita
Journal:  Signal Transduct Target Ther       Date:  2016-06-24

5.  Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity.

Authors:  Matija Sambol; Patricia Benčić; Antonija Erben; Marija Matković; Branka Mihaljević; Ivo Piantanida; Marijeta Kralj; Nikola Basarić
Journal:  Molecules       Date:  2021-06-02       Impact factor: 4.411

6.  Crosslinking reactions of 4-amino-6-oxo-2-vinylpyrimidine with guanine derivatives and structural analysis of the adducts.

Authors:  Shuhei Kusano; Shogo Ishiyama; Sik Lok Lam; Tsukasa Mashima; Masato Katahira; Kengo Miyamoto; Misako Aida; Fumi Nagatsugi
Journal:  Nucleic Acids Res       Date:  2015-08-05       Impact factor: 16.971

  6 in total

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