Improved transport of nucleotide monophosphates by lipophilic phosphonium–nucleobase conjugates

Jung, Yong-Gyu; Yeo, Woon‐Seok; Lee, Sang Bok; Hong, Jong‐In

doi:10.1039/a700527j

Cited by 10 publications

(6 citation statements)

References 15 publications

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“…First, we confirmed that lipophilic G 1 and C 2 catalyse transport of their complementary Watson-Crick partner, confirming earlier findings on transport of nucleosides across liquid membranes (16,17). When the organic phase did not contain G 1, we observed no diffusion of rC 3 or dC 4 across the liquid membrane, even after 24 h. As shown in Figure 1(A), G 1 catalysed transmembrane transport of dC 4 in a concentration-dependent manner.…”

Section: Supramolecular Chemistry 287supporting

confidence: 92%

“…Furuta et al (16) nucleoside derivatives function as selective transporters of their complementary hydrogen-bonding partner. In this approach, the lipophilic transporter forms stable WatsonCrick base pairs with its hydrophilic complementary target, enabling selective extraction of the nucleoside from water into the organic phase (16,17). Later, Kral et al (18) showed that attachment of a cationic group to the lipophilic nucleoside yielded a compound that catalysed transmembrane transport of complementary nucleotides.…”

Section: Introduction: Transmembrane Nucleoside Transport and Main Fomentioning

confidence: 98%

“…In reviewing nucleoside transport studies, we were drawn to these lipophilic nucleoside carriers (16)(17)(18). This interest stemmed, in part, from our research on the structure and transport properties of self-assembled Gquartets formed from lipophilic guanosines (19).…”

Section: Introduction: Transmembrane Nucleoside Transport and Main Fomentioning

confidence: 99%

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Controlling the transmembrane transport of nucleosides

Peters

Davis

2014

Supramolecular Chemistry

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Nucleoside analogues are used as drugs. Due to their hydrophilicity, nucleosides are poorly permeable to membranes and transporter proteins are required for efficient uptake. One approach towards improving membrane permeability of nucleosides is to use synthetic transporters. We describe ways to control transport of nucleosides across a liquid membrane. Hexanoylguanosine 1 selectively extracts and transports cytidines across a CHCl 3 membrane. Transport catalysed by G 1 was influenced by the nucleoside's sugar, with a selectivity of dC 4 . rC 3 . araC 5. Selective transport could be modulated by adding compounds to the aqueous source phase or to the organic phase. Addition of K þ 2,6-DNP -8 to CHCl 3 containing G 1 switched off transport of rC 3 and dC 4 due to formation of a G-quartet assembly. A lipophilic G 1·C 2 base pair could not transport dC 4, but did catalyse transport of dG 7 across the CHCl 3 barrier. We propose that transport occurs because of formation of a base triple G 1·C 2·dG 7. Addition of Na 2 B 4 O 7 9 to a source phase containing rC 3, dC 4 and araC 5 shuts down transport of rC 3 by G 1, due to formation of borate esters. These results indicate that one can control the selective transport of nucleosides.

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Section: Supramolecular Chemistry 287supporting

confidence: 92%

Section: Introduction: Transmembrane Nucleoside Transport and Main Fomentioning

confidence: 98%

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Controlling the transmembrane transport of nucleosides

Peters

Davis

2014

Supramolecular Chemistry

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“…These systems were found to extract and transport GMP and AMP effectively through a chloroform membrane. 326 Concentration-dependent extraction studies provided support for the conclusion that 1:1 host:guest complexes were found at pH 5.0 and 2:1 host:guest complexes at pH 7.0. In accord with design expectations, better transport rates were observed with these combined receptors than was observed with either the phosphonium or nucleobase component alone or when the individual components were both contained separately within the organic phase.…”

Section: Major Phosphate-binding Functionalitiesmentioning

confidence: 82%

Artificial Receptors for the Recognition of Phosphorylated Molecules

et al. 2011

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“…Phosphates play a crucial role in a wide range of biological processes. Numerous efforts have been devoted to molecular recognition, − transport, and catalytic hydrolysis of phosphates. Further understanding of the structure and dynamics of phosphates in biological systems requires the development of nondestructive and real-time optical sensing techniques .…”

mentioning

confidence: 99%