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Nucleic Acids Research, 1989, Vol. 17, No. 11 4177-4187
© 1989

CHEMISTRY

Modelling basic features of specificity in the binding of a dicationic steroid diamine to double-stranded oligonucleotides

Xiaowen Hui*, Nohad Gresh and Bernard Pullman

Institut de Biologie Physico-Chimique, Laboratoire de Biochimie Théorique Associé au CNRS 13 rue Pierre et Mane Curie, 75005 Paris, France

Received April 14, 1989. Accepted May 9, 1989.

An investigation of the intrinsically preferred binding modes of a steroid diamine, dipyrandium, to the double-stranded hexanucleotides d(TATATA)2, d(ATATAT)2, and d(CGCGCG)2 is carried out by the energy minimization procedure JUMNA. Several alternative binding modes are compared : groove binding in which the conformation of the oligonucleotide remains close to that of B-DNA, intercalation between base-pairs and interaction with variously kinked structures in which base pairs of dinucleoside steps open towards the groove in which the binding occurs.

The favored binding configuration occurs at the d(TpA) step of the AT kinked nucleotides in which the kink opens the base pairs towards the minor groove. Thus, for the d(T1A2T3A4T5A6)2 sequences the preferred complexation involves the kink at the T3A4 step facing the cyclohexane rings A, B, and C of the ligand. For the d(A1T2A3T4A5T6)2 sequence, the kink occurs at the T2A3 step facing the cationic pyrrolidine ring linked to ring A.

The binding of dipyrandium to d(CGCGCG)2 is found to be considerably less favourable than for either of the two (AT) sequences.

*Permanent address: University of Shenyang, China


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