Cytosine substituted calix[4]pyrroles: neutral receptors for 5'-guanosine monophosphate

Proceedings of the National Academy of Sciences of the United States of America
Jonathan L SesslerPhilip A Gale

Abstract

The synthesis and characterization of two cytosine-substituted calix[4]pyrrole conjugates, bearing the appended cytosine attached at either a beta- or meso-pyrrolic position, is described. These systems were tested as nucleotide-selective carriers and as active components of nucleotide-sensing ion-selective electrodes at pH 6.6. Studies of carrier selectivity were made using a Pressman-type model membrane system consisting of an initial pH 6.0 aqueous phase, an intervening dichloromethane barrier containing the calix[4]pyrrole conjugate, and a receiving basic aqueous phase. Good selectivity for the Watson-Crick complementary nucleotide, 5'-guanosine monophosphate (5'-GMP), was seen in the case of the meso-linked conjugate with the relative rates of through-membrane transport being 7.7:4.1:1 for 5'-GMP, 5'-AMP, and 5'-CMP, respectively. By contrast, the beta-substituted conjugate, while showing a selectivity for 5'-GMP that was enhanced relative to unsubstituted calix[4]pyrrole, was found to transport 5'-CMP roughly 4.5 times more quickly than 5'-GMP. Higher selectivities were also found for 5'-CMP when both the beta- and meso-substituted conjugates were incorporated into polyvinyl chloride membranes and tested as ion selective ...Continue Reading

Citations

Sep 14, 2011·Chemical Reviews·Amanda E HargroveEric V Anslyn
Nov 13, 2010·Journal of the American Chemical Society·Shang-U KimFrederick A Villamena
Dec 16, 2005·Organic Letters·Prakash P NeelakandanDanaboyina Ramaiah
Apr 19, 2005·Chemical Communications : Chem Comm·Jonathan L Sessler, Janarthanan Jayawickramarajah
Nov 7, 2006·Chemistry : a European Journal·J Ramón BlasModesto Orozco
Apr 9, 2005·Angewandte Chemie·Kavitha ChellappanKwang S Kim
Dec 17, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Yang LiuChunying Duan
Apr 9, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Carolina MendozaRamón Vilar
May 21, 2010·Organic & Biomolecular Chemistry·Alejandra Sornosa-TenIvo Piantanida
Jul 24, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Yang LiuChunying Duan
Apr 7, 2010·Physical Review Letters·Tobias Galla
Jan 7, 2011·Organic & Biomolecular Chemistry·Prakash P NeelakandanDanaboyina Ramaiah
Apr 6, 2004·Organic & Biomolecular Chemistry·Vladimír KrálChristopher T Brown
Apr 11, 2008·Chemical Communications : Chem Comm·Chang-Hee LeeJonathan L Sessler
Jan 8, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Wei-Ming SunZhi-Ru Li
Feb 23, 2008·The Journal of Organic Chemistry·Behzad KhaliliMohammed M Hashemi
Dec 9, 2004·Journal of the American Chemical Society·Piotr PiatekJonathan L Sessler

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