The interaction of β‐cyclodextrin with dinucleoside phosphates

Abstract

Circular dichroism studies of the interaction of β‐cyclodextrin with a series of eight dinucleoside phosphates, and with 3′‐AMP are reported. From results with ApU and ApA, it is shown that β‐cyclodextrin binding is sensitive to dinucleoside stacking in approximately the same way as optical measures of stacking. Some qualitative uses of β‐cyclodextrin binding are suggested, based on the fact that the change in the CD spectrum caused by cyclodextrin binding is unique to each of the dinucleosides studied. Hoffman and Bock have previously suggested the use of β‐cyclodextrin as a probe of nucleic acid structure. Their work indicated that only binding to adenosine and inosine would have to be considered. The present paper shows that binding to other bases cannot be neglected, and will impose serious restrictions on the use of β‐cyclodextrin as a structural probe.

Artificial Receptors for the Recognition of Phosphorylated Molecules

“…Formoso reported similar binding trends with β-CyD through the use of circular dichroism (CD) spectroscopy in a sodium phosphate buffered solution at pH 7. 775,776 Using this method, a 1:1 binding constant of 41 M- 1 was measured for the complex of β-CyD and 5′-AMP at 25°C. Studies at various temperatures allowed for the calculation of thermodynamic parameters.…”

Unusual Covalent Bond-Breaking Reactions of β-cyclodextrin Inclusion Complexes of Nucleobases/Nucleosides and Related Guest Molecules

“…1 An examination of the literature reveals that several previous studies have used a range of techniques to demonstrate that inclusion complex formation can occur between b-cyclodextrin and various nucleobases, nucleosides and nucleotides. [16][17][18][19][20][21][22] Early ultraviolet absorption difference spectroscopy studies by Hoffman and Bock showed that bcyclodextrin was only able to interact with two of the six mononucleotides tested, viz. AMP and IMP.…”

“…17 Once again, inclusion complexes containing adenine derivatives were found to have the strongest interactions. In a series of papers, 18,19 Formoso used circular dichroism to investigate the interactions of b-cyclodextrin with various nucleic acid base derivatives. In contrast to Hoffman's studies, inclusion complexes containing guanine, uracil and cytosine derivatives were observed in addition to those containing adenine.…”

Organophosphorus Supramolecular Chemistry Part 1. Receptors for Organophosphorus Compounds

“…Ability of -and -CDs to create complexes with nucleic acid monomer units as well as with dinucleoside phosphates resulted in their application as potential probes of nucleic acid structure [94][95][96]. Also the regioselective catalysis of P-O(2,3) bond cleavage in 2',3'-cyclic monophosphates of ribonucleotides by ribonuclease, could be successfully mimicked by -, -or -CDs [97,[90][91][92][93].…”

“…The interactions between nucleotides as well as nucleosides and native cyclodextrins were intensively investigated [89][90][91][92][93][94][95][96][97]. Ability of -and -CDs to create complexes with nucleic acid monomer units as well as with dinucleoside phosphates resulted in their application as potential probes of nucleic acid structure [94][95][96].…”