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Self-assembled cation transporters made from lipophilic 8-phenyl-2'-deoxyguanosine derivatives

Martin-Hidalgo, M., Camacho-Soto, K., Gubala, V., Rivera, J.M. (2010) Self-assembled cation transporters made from lipophilic 8-phenyl-2'-deoxyguanosine derivatives. Supramolecular Chemistry, 22 (11-12). pp. 862-869. ISSN 1061-0278. (doi:10.1080/10610278.2010.510263)


We have previously reported that 8-phenyl-2'-deoxyguanosine derivatives (8PhGs) are able to extract metal cations from an aqueous phase into an organic phase. Herein, we report on the ability of 8PhGs to transport metal cations across a bulk lipophilic liquid membrane. The experiments were performed using lithium, sodium, potassium and strontium picrate salts with the parent lipophilic Gi, two isomeric 8PhG derivatives, cis-dicyclohexano-18-crown-6 (DC18C6) and [222] cryptand as reference compounds. The relative amounts of the picrate salts were measured by UV spectroscopy in both the source phase and the receiving phase over a period of 24h. The results show that the transport efficiency of the self-assembled ionophores formed by 8PhGs is either similar or superior to that of DC18C6, and in all but one case higher than the parent compound Gi. The varying efficiencies between the derivatives can be attributed to the stability (kinetic and thermodynamic) and the different molecularities of the supramolecules formed by these 8PhGs. The ease of the synthesis of 8PhGs, their anion-independent assembly and the fact that the transport efficiency can be modulated as a function of the structure of the 8PhGs bode well for the use of such compounds in the development of novel antimicrobial agents and cation-sensing devices. © 2010 Taylor & Francis.

Item Type: Article
DOI/Identification number: 10.1080/10610278.2010.510263
Additional information: Unmapped bibliographic data: LA - English [Field not mapped to EPrints] J2 - Supramol. Chem. [Field not mapped to EPrints] AD - Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, Rio Piedras, San Juan, 00931, Puerto Rico [Field not mapped to EPrints] DB - Scopus [Field not mapped to EPrints]
Uncontrolled keywords: cation recognition, ion transport, self-assembly
Divisions: Faculties > Sciences > Medway School of Pharmacy
Depositing User: Vladimir Gubala
Date Deposited: 14 Dec 2017 21:00 UTC
Last Modified: 29 May 2019 13:41 UTC
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