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Volumn 119, Issue 26, 1997, Pages 5999-6005

DNA-DNA interstrand cross-linking by FR66979: Intermediates in the activation cascade

Author keywords

[No Author keywords available]

Indexed keywords

1 ACETYL 8ALPHA (CARBAMOYLOXYMETHYL) 3,9 EPOXY 5 FORMYL 1,1A,2,8,9,9A OCTAHYDROAZIRINO[2,3 C][1]BENZAZOCINE 7,9 DIOL ACETATE; 4 FORMYL 6,9 DIHYDROXY 14 OXA 1,11 DIAZATETRACYCLO[7.4.1.0 2,7 0 10,12]TETRADECA 2,4,6 TRIEN 8 YLMETHYLCARBAMATE; ANTINEOPLASTIC ANTIBIOTIC; BENZOXAZINE DERIVATIVE; FR 66979; MITOMYCIN C; UNCLASSIFIED DRUG;

EID: 0030848358     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970350u     Document Type: Article
Times cited : (53)

References (35)
  • 27
    • 16944362497 scopus 로고    scopus 로고
    • note
    • For example, equally compatible with the UV and mass spectral data are the two diastereoisomers resulting from monohydrolysis of the scissile bond of the aziridine moiety of 9.
  • 28
    • 16944366677 scopus 로고    scopus 로고
    • note
    • This situation is complicated by the chance occurrence that the new substance (11) and the same retention time on HPLC as the major diastereoisomer of the initial products (13).
  • 29
    • 16944366623 scopus 로고    scopus 로고
    • note
    • The presence of iron(II) was critical: FR66979 is essentially inert to treatment with sodium borohydride alone, as evidenced by the fact that this is one method of preparing FR66979 from FR900482.
  • 30
    • 16944367306 scopus 로고    scopus 로고
    • note
    • This was confirmed by exposing freshly collected "13" from the HPLC to excess sodium borohydride, with the result that no 11 was produced.
  • 31
    • 16944362425 scopus 로고    scopus 로고
    • note
    • This rate constant is probably the least reliable of those we have measured, because in the course of the incubation the pH rose from 8.9 to roughly 9.5.
  • 32
    • 16944366540 scopus 로고    scopus 로고
    • note
    • A variant of this experiment provided support for the hypothesis that the hydrolysis of the relatively long-lived intermediate was accelerated by exposure to the packing material of an HPLC column. The reductively activated sample was aged in the presence of some C-18 silica gel from a used HPLC column, resulting in roughly a doubling of the rate at which the intermediate was diverted to materials incapable of being converted to dihydroindole 11 during subsequent treatment with sodium borohydride.
  • 33
    • 16944361929 scopus 로고    scopus 로고
    • note
    • -1 at pH 7.5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.