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Synthesis and Molecular Modeling Studies of Fullerene−5,6,7‐Trimethoxyindole−Oligonucleotide Conjugates as Possible Probes for Study of Photochemical Reactions in DNA Triple Helices
Author(s) -
Ros Tatiana Da,
Bergamin Massimo,
Vázquez Ester,
Spalluto Giampiero,
Baiti Benedetta,
Moro Stefano,
Boutorine Alexandre,
Prato Maurizio
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(20022)2002:3<405::aid-ejoc405>3.0.co;2-2
Subject(s) - chemistry , triple helix , oligonucleotide , supramolecular chemistry , fullerene , dna , molecular model , conjugate , combinatorial chemistry , sequence (biology) , stereochemistry , molecule , organic chemistry , biochemistry , mathematical analysis , mathematics
The synthesis of novel functionalized fullerene derivatives containing DNA minor groove binders is reported. In order to construct sequence‐specific probes for DNA photomodification, the compounds were attached to a triple helix forming oligonucleotide, and the formation of triplexes was monitored. The triplex formation was demonstrated, but the presence of fullerene moieties gives rise to a high degree of instability. Molecular modeling studies on these supramolecular structures provided useful information for the current study and for future developments.