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Effect of side chains on the groove‐binding specificity of anthraquinone intercalators
Author(s) -
Hui Xiaowen,
Gresh Nohad,
Pullman Bernard
Publication year - 1991
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560400721
Subject(s) - intercalation (chemistry) , side chain , anthraquinone , groove (engineering) , dna , threading (protein sequence) , chemistry , anthraquinones , stereochemistry , crystallography , materials science , biochemistry , polymer , biology , protein structure , organic chemistry , botany , metallurgy
Anthraquinone intercalators possessing two side chains offer potentially the three possibilities of having these chains located (1) both in the major groove, (2) both in the minor groove, and (3) one in the major and the other in the minor groove (“threading” mode of intercalation). Computations carried out on two related doubly substituted anthraquinones, mitoxantrone ( I ) and bis‐glycylglycylanthraquinone ( II ), indicate that while I should intercalate with its two side chains located both in the major groove, II should adopt the threading arrangement. This result is interpreted in terms of the importance of ligand–DNA mutual adaptation. The results of the computations are in agreement with very recent experimental findings of Palumbo and Gatto at the University of Padova in Italy.