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Comparative study of aclacinomycin versus adriamycin by means of resonance Raman spectroscopy
Author(s) -
aka Yasuomi,
Tsuboi Masamichi,
Nakamoto Kazuo
Publication year - 1990
Publication title -
journal of raman spectroscopy
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.748
H-Index - 110
eISSN - 1097-4555
pISSN - 0377-0486
DOI - 10.1002/jrs.1250210211
Subject(s) - raman spectroscopy , chromophore , chemistry , hydrogen bond , resonance raman spectroscopy , intramolecular force , resonance (particle physics) , photochemistry , stereochemistry , crystallography , nuclear magnetic resonance , molecule , organic chemistry , physics , particle physics , optics
Resonance Raman spectra of adriamycin and aclacinomycin A were examined in their H 2 O and D 2 O solutions. These spectra appear totally different from each other, but the differences are found to be similar to those between 1,4‐ and 1,8‐dihydroxyanthraquinone, which are considered to be model chromophores of adriamycin and aclacinomycin, respectively. Surface‐enhanced resonance Raman spectra of these two drugs were also compared by the use of silver sols. The effects of DNA binding on the resonance Raman spectra are also significantly different for these two drugs. Adriamycin was found to be intercalated in the CpG (or GpC) site of the DNA duplex, but aclacinomycin in the TpA (or ApT) site. Most of the differences in the spectra and sequence specificity are explained in terms of the molecular structures of their chromophores, i.e. in the adriamycin chromophore (1,4‐dihydroxyanthraquinone) two OH groups are hydrogen bonded to different CO groups, whereas in the aclacinomycin chromophore (1,8‐dihydroxyanthraquinone) two OH groups form hydrogen bonds with the same CO group, leaving the other CO group free from any intramolecular hydrogen bonding.