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Study of cavity size and nature of bridging units on recognition of nucleotides by cyclophanes

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dc.contributor.author Prakash, P N
dc.contributor.author Nandajan, P C
dc.contributor.author Baby Subymol
dc.contributor.author Ramaiah, D
dc.date.accessioned 2013-11-20T08:47:38Z
dc.date.available 2013-11-20T08:47:38Z
dc.date.issued 2011
dc.identifier.citation Organic & Biomolecular Chemistry 9(4):1021-1029;18 Oct 2011 en_US
dc.identifier.issn 1477-0520
dc.identifier.uri http://ir.niist.res.in:8080/jspui/handle/123456789/773
dc.description.abstract We synthesized a few novel cyclophanes CP-1 to CP-4 containing anthracene units linked together through different bridging and spacer groups and have investigated their interactions with various nucleosides and nucleotides. Of these systems, CP-1 and CP-3 showed selectivity for 5'-GTP and 5'-ATP as compared to other nucleotides and nucleosides, whereas negligible selectivity was observed with CP-2 and CP-4. Interestingly, CP-1, CP-2 and CP-3 exhibited significant binding interactions with the fluorescent indicator, 8-hydroxy-1,3,6-pyrene trisulfonate (HPTS), resulting in the formation of non-fluorescent complexes. Titration of these complexes with nucleosides and nucleotides resulted in the displacement of HPTS, leading to the revival of its fluorescence intensity. It was observed that 5'-GTP induced the maximum displacement of HPTS from the complex [CP-1 center dot HPTS] with an overall fluorescence enhancement of ca. 150-fold, while 5'-ATP induced ca. 45-fold. Although the displacement of HPTS from the complexes [CP-2 center dot HPTS] and [CP-3 center dot HPTS] was found to be similar to that of [CP-1 center dot HPTS], these complexes showed lesser selectivity and sensitivity. In contrast, negligible displacement of HPTS was observed from the complex [CP-4 center dot HPTS] under similar conditions. These results indicate that CP-1, having a well-defined cavity and good electron acceptor (viologen), is capable of forming selective and stable complexes. Though CP-2 and CP-3 retain the good electron acceptor (viologen), their reduced aromatic surface and larger cavity, respectively, resulted in lesser sensitivity. In contrast, CP-4 having a large cavity and a poor acceptor (1,2-bis(pyridin-4-yl) ethene) showed negligible selectivity, thereby indicating the importance of cavity size, bridging unit and aromatic surface on biomolecular recognition properties of cyclophanes. en_US
dc.language.iso en en_US
dc.publisher Royal Society of Chemistry en_US
dc.subject Aqueous-solution en_US
dc.subject Macrocyclic bisacridine en_US
dc.subject Selective recognition en_US
dc.subject Molecular recognition en_US
dc.subject Electron-transfer en_US
dc.subject Single-strand dna en_US
dc.subject Host-guest complexes en_US
dc.subject Dna-binding properties en_US
dc.subject Viologen-linked acridines en_US
dc.subject Isothermal titration calorimetry en_US
dc.title Study of cavity size and nature of bridging units on recognition of nucleotides by cyclophanes en_US
dc.type Article en_US


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