title: Supramolecular complexation of biological phosphates with an acyclic triazolium-linked anthracenyl-1,3-diconjugate of calix[4]arene: synthesis, characterization, spectroscopy, microscopy, and computational studies.
abstract: A triazolium-anthracenyl calix[4]arene conjugate (L) was synthesized by methylating the precursor triazole derivative and then characterized. The potential of the cationic L to differentiate nucleoside triphosphates (NTPs) from their mono- and diphosphates was demonstrated. Due to its unique combination of arms with the calix-platform, a fluorescence enhancement was observed for L with all the NTPs, whereas there is no report with such enhancement being exhibited in case of all the NTPs. This has been supported by the aggregation of L observed from microscopy. Selectivity of L towards NTPs over other phosphates was a result of specific weak interactions, namely, ion-ion, hydrogen bonding and π⋅⋅⋅π, present in the 1:2 complex of L and NTPs (based on ESI MS), which were absent in their congener-phosphates as delineated by NMR and computational studies. Thus, L stands as a unique receptor for NTPs.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Powai, Mumbai-400076 (India), Fax: (+91) 22-2576-7152.
authors.forename: V V
authors.initials: VV
authors.lastname: Sreenivasu Mummidivarapu
authors.forename: Vijaya
authors.initials: V
authors.lastname: Kumar Hinge
authors.forename: Kushal
authors.initials: K
authors.lastname: Samanta
authors.forename: Deepthi S
authors.initials: DS
authors.lastname: Yarramala
authors.forename: Chebrolu
authors.initials: C
authors.lastname: Pulla Rao
mesh_terms: D047250:Calixarenes / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010755:Organophosphates / Q000138:chemical synthesis / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D010755:Organophosphates; D014230:Triazoles; D047250:Calixarenes
keywords: NMR spectroscopy; calixarenes; host-guest systems; molecular modeling; nucleosides; phosphates