2026-04-28T12:58:35Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/47432022-04-29T12:02:46Zcom_10259_3924com_10259_5086com_10259_2604col_10259_3925

QSAR analysis of substituent effects on tambjamine anion transporters Knight, Nicola J. . Hernando Santa Cruz, Elsa Haynes, Cally J. E. . Busschaert, Nathalie Clarke, Harriet J. . Takimoto, Koji García Valverde, María Frey, Jeremy G. . Quesada Pato, Roberto Gale, Philip A. . Chemistry, Organic Química orgánica The transmembrane anion transport activity of 43 synthetic molecules based on the structure of marine alkaloid tambjamine were assessed in model phospholipid (POPC) liposomes. The anionophoric activity of these molecules showed a parabolic dependence with lipophilicity, with an optimum range for transport efficiency. Using a quantitative structure–transport activity (QSAR) approach it was possible to rationalize these results and to quantify the contribution of lipophilicity to the transport activity of these derivatives. While the optimal value of log P and the curvature of the parabolic dependence is a property of the membrane (and so similar for the different series of substituents) we found that for relatively simple substituents in certain locations on the tambjamine core, hydrophobic interactions clearly dominate, but for others, more specific interactions are present that change the position of the membrane hydrophobicity parabolic envelope. RQ acknowledges funding from Consejer´ıa de Educaci´on de la Junta de Castilla y Le´on (Project BU340U13) and Fundaci´o la Marat´o de TV3 (20132730). PAG thanks the EPSRC for funding (EP/J009687/1 and EP/K039466/1). COST CM1005 Supramolecular Chemistry in Water for a STSM (EH). JGF thanks the EPSRC (GR/R67729 & EP/ K003569) for funding 2018-03-07T10:33:46Z 2018-03-07T10:33:46Z 2016-02 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion 2041-6520 http://hdl.handle.net/10259/4743 10.1039/c5sc03932k eng Chemical Science. 2016, V. 7, n. 2, p. 1600-1608 https://doi.org/10.1039/c5sc03932k info:eu-repo/grantAgreement/JCyL/BU340U13 info:eu-repo/grantAgreement/Fundació la Marató de TV3/20132730 info:eu-repo/grantAgreement/EPSRC/EP-J009687-1 info:eu-repo/grantAgreement/EPSRC/EP-K039466-1 info:eu-repo/grantAgreement/EPSRC/GR-R67729 info:eu-repo/grantAgreement/EPSRC/EP- K003569 Attribution 3.0 Unported http://creativecommons.org/licenses/by/3.0/ info:eu-repo/semantics/openAccess application/pdf Royal Society of Chemistry