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

被引:31
作者
Rossiter, Clifford S. [1 ]
Modica, Emilia [1 ]
Kumar, Dalip [1 ]
Rokita, Steven E. [1 ]
机构
[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA
关键词
STABILITY;
D O I
10.1039/c0cc03317k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:1476 / 1478
页数:3
相关论文
共 20 条
  • [1] A molecular beacon strategy for the thermodynamic characterization of triplex DNA: Triplex formation at the promoter region of cyclin D1
    Antony, T
    Thomas, T
    Sigal, LH
    Shirahata, A
    Thomas, TJ
    [J]. BIOCHEMISTRY, 2001, 40 (31) : 9387 - 9395
  • [2] Quenching of quercetin quinone/quinone methides by different thiolate scavengers: Stability and reversibility of conjugate formation
    Awad, HM
    Boersma, MG
    Boeren, S
    van Bladeren, PJ
    Vervoort, J
    Rietjens, IMCM
    [J]. CHEMICAL RESEARCH IN TOXICOLOGY, 2003, 16 (07) : 822 - 831
  • [3] Mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-quinone methide
    Bishop, Lee M.
    Winkler, Michael
    Houk, Kendall N.
    Bergman, Robert G.
    Trauner, Dirk
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (18) : 5405 - 5408
  • [4] Photogenerated quinone methides as useful intermediates in the synthesis of chiral BINOL ligands
    Colloredo-Mels, S
    Doria, F
    Verga, D
    Freccero, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (10) : 3889 - 3895
  • [5] o-Quinone methide as alkylating agent of nitrogen, oxygen, and sulfur nucleophiles.: The role of H-bonding and solvent effects on the reactivity through a DFT computational study
    Di Valentin, C
    Freccero, M
    Zanaletti, R
    Sarzi-Amadè, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) : 8366 - 8377
  • [6] BINOL-amino acid conjugates as triggerable carriers of DNA-targeted potent photocytotoxic agents
    Doria, Filippo
    Richter, Sara N.
    Nadai, Matteo
    Colloredo-Mels, Stefano
    Mella, Mariella
    Palumbo, Manlio
    Freccero, Mauro
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (26) : 6570 - 6579
  • [7] Modeling H-bonding and solvent effects in the alkylation of pyrimidine bases by a prototype quinone methide:: A DFT study
    Freccero, M
    Di Valentin, C
    Sarzi-Amadè, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) : 3544 - 3553
  • [8] Phototriggered drug release from functionalized oligonucleotides by a molecular beacon strategy
    Okamoto, A
    Tanabe, K
    Inasaki, T
    Saito, I
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (22) : 2502 - 2504
  • [9] Alkylation of nucleic acids by a model quinone methide
    Pande, P
    Shearer, J
    Yang, JH
    Greenberg, WA
    Rokita, SE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) : 6773 - 6779
  • [10] Rokita SE., 2009, Quinone Methides, V9, P297