Source:http://linkedlifedata.com/resource/pubmed/id/18083523
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
5
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pubmed:dateCreated |
2008-3-17
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pubmed:abstractText |
To investigate the effect of incorporation of beta-alanine in alkylating N-methylpyrrole (Py)-N-methylimidazole (Im) polyamide, seco-CBI conjugates 2-8 were synthesized by an Fmoc solid-phase method and subsequent coupling with an alkylating moiety. DNA-alkylating activities of conjugates 2-8 were evaluated by high-resolution denaturing gel electrophoresis with 202-base pair (bp) DNA fragments. Alkylation by conjugates 2 and 3, which have antiparallel pairings of beta-alanine (beta) opposite beta (beta/beta) and Py/beta, occurred mainly at the adenine (A) of the matching sequences, 5'-AGCTCCA-3' (site 1) and 5'-AGCACCA-3' (site 3). However, conjugate 4, with beta/Py, did not show any DNA-alkylating activities. Similarly, conjugate 5, which possessed a Py/Py pair, weakly alkylated the matching sites at micromolar concentrations. Conjugates 6 and 7, which possessed beta/beta and Py/beta pairs, respectively, alkylated at the A of the matching sequences, 5'-ACTACCA-3' (site 2) and 5'-ACAACCA-3' (site 4). In contrast, conjugated 8, with a Py/Py pair, showed lower activity and less alkylated DNA at sites 2 and 4 with mismatched alkylation at site 1 at a higher concentration than that of 6 and 7. These results demonstrate that incorporation of beta-alanine is required for the sequence-specific alkylation by seco-CBI Py-Im conjugates with a seven-base pair sequence.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Alanine,
http://linkedlifedata.com/resource/pubmed/chemical/DNA,
http://linkedlifedata.com/resource/pubmed/chemical/Imidazoles,
http://linkedlifedata.com/resource/pubmed/chemical/Pyrroles,
http://linkedlifedata.com/resource/pubmed/chemical/imidazole
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pubmed:status |
MEDLINE
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pubmed:month |
Mar
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pubmed:issn |
1464-3391
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pubmed:author |
pubmed-author:BandoToshikazuT,
pubmed-author:FujimotoJunJ,
pubmed-author:KashiwazakiGengoG,
pubmed-author:MinoshimaMasafumiM,
pubmed-author:MurakamiMasatakaM,
pubmed-author:NakazonoSatomiS,
pubmed-author:OhtsukiAkimichiA,
pubmed-author:SasakiShuntaS,
pubmed-author:ShinoharaKen-IchiK,
pubmed-author:SugiyamaHiroshiH
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pubmed:issnType |
Electronic
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pubmed:day |
1
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pubmed:volume |
16
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
2286-91
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pubmed:meshHeading |
pubmed-meshheading:18083523-Alanine,
pubmed-meshheading:18083523-Alkylation,
pubmed-meshheading:18083523-Base Pairing,
pubmed-meshheading:18083523-Base Sequence,
pubmed-meshheading:18083523-DNA,
pubmed-meshheading:18083523-Imidazoles,
pubmed-meshheading:18083523-Pyrroles,
pubmed-meshheading:18083523-Temperature
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pubmed:year |
2008
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pubmed:articleTitle |
Requirement of beta-alanine components in sequence-specific DNA alkylation by pyrrole-imidazole conjugates with seven-base pair recognition.
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pubmed:affiliation |
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8501, Japan.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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