1993
DOI: 10.1021/bi00055a010 View full text |Buy / Rent full text
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Abstract: Duocarmycin A, a novel antitumor antibiotic, has a reactive cyclopropane ring, which has been reported to alkylate adenine at the 3' end of sequences of three or more consecutive A or T in DNA [Boger, D. L., et al. (1990) J. Am. Chem. Soc. 112, 8961-8971]. In order to study the DNA recognition, the reaction of DNA with duocarmycin A was performed in the presence of DNA ligands. Distamycin A, berenil, Hoechst 33258, and 4',6-diamidino-2-phenylindole (DAPI), which are minor-groove binders with affinity to A.T-ri… Show more

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“…A series of DNA oligonucleotide hairpins whose stems contain the preferred target sequence as deduced (27) have been synthesized on an automated DNA synthesizer. The alkylation of DNA oligonucleotides was carried out according to the following procedure.…”
Section: Methodsmentioning
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rupbmjkragerfmgwileyiopcupepmcmbcthiemesagefrontiersapsiucrarxivemeralduhksmucshluniversity-of-gavle
“…A series of DNA oligonucleotide hairpins whose stems contain the preferred target sequence as deduced (27) have been synthesized on an automated DNA synthesizer. The alkylation of DNA oligonucleotides was carried out according to the following procedure.…”
Section: Methodsmentioning
“…1C), markedly modulates the site of alkylation by Duo in longer DNA fragments where the major alkylation occurs at G residues in GϩC-rich sequences, although the molecular mechanism for the G-alkylation has not been established (27). To understand the molecular basis of how this highly efficient G-N3 alkylation is achieved through the cooperative binding of the heterodimer between Duo and Dist to the minor groove of DNA, we analyzed the detailed results from the alkylation reactions between Duo and a series of DNA oligonucleotides in the absence and presence of Dist.…”
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“…34) [91]. It was shown that the addition of distamycin causes duocarmycins to switch their site of DNA alkylation to N3 of guanine [92], and further that a synthetic pyrrole/imidazole polyamide can be substituted for distamycin to direct the site of DNA alkylation [93]. Hybrids 61 were unreactive with DNA in the absence of distamycin; in its presence they readily alkylated guanine of a nucleotide sequence designed to match the specific hybrid.…”
Section: Bifunctional Alkylating Agentsmentioning
“…The event, sequence selectivity, quantitation, reversibility, and structure determination of the predominant DNA alkylation reaction by 1-3 have been defined (42)(43)(44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54)(55)(56)(57)(58)(59). The alkylation site identification and the assessment of relative selectivity were derived through thermally induced depurination and strand cleavage of labeled DNA after exposure to the agents (Scheme I).…”
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“…The quantitation of the adenine-N3 alkylation, confirmation of its structure through isolation and characterization of the thermally released adducts, and the search for unde- tPercentage composition within the DNA examined. (50), within oligodeoxynucleotides lacking a high-affinity adenine-N3 alkylation site (51), or when the adenine alkylation sites within AT-rich regions of DNA were protected from alkylation with high-6, Duocarmycin B1: X = Br 7, Duocarmycin Ci: X= Cl affinity AT-rich minor groove binding agents (52). In contrast, duocarmycin SA (3) showed no evidence of guanine-N3 alkylation when subjected to similar or more forcing conditions (43 consequence of the diastereomeric relationship of the adducts and the reversed binding orientation in the minor groove with respect to the alkylation site is required to permit adenine-N3 addition to the least substituted carbon of the electrophilic cyclopropane.…”
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