PMID: 7542784Jul 18, 1995Paper

Binding studies of cationic thymidyl deoxyribonucleic guanidine to RNA homopolynucleotides

Proceedings of the National Academy of Sciences of the United States of America
K A BrowneT C Bruice

Abstract

Deoxyribonucleic guanidine is a potential antisense agent that is generated via the replacement of the negative phosphodiester linkages of DNA [--O--(PO2-)--O--] with positively-charged guanidinium (g) linkages [--NH--C(==NH2+)--NH--]. A pentameric thymidyl deoxyribonucleic guanidine molecule [d(Tg)4T-azido] has been shown to base pair specifically to poly(rA) with an unprecedented affinity. Both double and triple strands consisting of one and two equivalents of d(Tg)4T-azido paired with one equivalent of poly(rA) are indicated by thermal denaturation experiments. At an ionic strength of 0.22, the five bases of d(Tg)4T-azido are estimated to dissociate from a double helix with poly(rA) at > 100 degrees C! The effect of ionic strength on thermal denaturation is very pronounced, with stability greatest at low ionic strengths. The method of continuous variation indicates that there is an equilibrium complex with a molar ratio of d(Tg) to r(Ap) or d(Ap) of 2:1. Based on this evidence, models of the structures of d(Tg)9T-azido bound to r(Ap)9A are proposed.

References

Jan 1, 1992·Annual Review of Pharmacology and Toxicology·S T Crooke
Jun 20, 1995·Proceedings of the National Academy of Sciences of the United States of America·R O DempcyT C Bruice
Aug 16, 1994·Proceedings of the National Academy of Sciences of the United States of America·R O DempcyT C Bruice
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Jan 19, 1993·Biochemistry·G RaghunathanV Sasisekharan
Jul 1, 1958·Biochimica Et Biophysica Acta·G FELSENFELD

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Citations

Jun 7, 2005·Bioorganic & Medicinal Chemistry Letters·Myunji Park, Thomas C Bruice
Apr 30, 1996·Proceedings of the National Academy of Sciences of the United States of America·R O DempcyT C Bruice
Mar 31, 2011·Future Medicinal Chemistry·Tsuyoshi YamamotoSatoshi Obika
Jul 7, 2018·Beilstein Journal of Organic Chemistry·Melissa Meng, Christian Ducho
Apr 16, 2014·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Hiroyuki Isobe, Tomoko Fujino
Dec 13, 2001·Chemical Reviews·D J HillJ S Moore
Aug 31, 2021·RSC Chemical Biology·Guillaume ClavéMichael Smietana

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