About: On the solubility and lipophilicity of metallacarborane pharmacophores

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Metallacarborane moieties have been identified as promising pharmacophores. The pharmaceutical use of such compounds is, however, complicated by their low solubility and tendency to self-assemble in aqueous solution. In this work, we estimated the solubilities of a vast series of metallacarboranes [cobalt bis(dicarbollide) derivatives] in pure water, saline, and saline with human serum albumin as a model of blood plasma. In addition, we determined the octanol-water partition coefficients (P-ow) as a lipophilicity descriptor. P-ow correlates with the water solubility of metallacarboranes, whereas the ability of HSA to increase the solubility of metallacarboranes correlates well with their P-ow values. Because metallacarboranes are known inhibitors of HIV protease, the possible correlation between P-ow and the ability to inhibit HIV protease was investigated. Results from this study indicate that interaction of metallacarborane inhibitors with HIV protease is driven by specific binding rather than by promiscuous lipophilic interactions. The most promising candidates for further drug development were identified by ligand lipophilicity efficiency analysis. Metallacarborane moieties have been identified as promising pharmacophores. The pharmaceutical use of such compounds is, however, complicated by their low solubility and tendency to self-assemble in aqueous solution. In this work, we estimated the solubilities of a vast series of metallacarboranes [cobalt bis(dicarbollide) derivatives] in pure water, saline, and saline with human serum albumin as a model of blood plasma. In addition, we determined the octanol-water partition coefficients (P-ow) as a lipophilicity descriptor. P-ow correlates with the water solubility of metallacarboranes, whereas the ability of HSA to increase the solubility of metallacarboranes correlates well with their P-ow values. Because metallacarboranes are known inhibitors of HIV protease, the possible correlation between P-ow and the ability to inhibit HIV protease was investigated. Results from this study indicate that interaction of metallacarborane inhibitors with HIV protease is driven by specific binding rather than by promiscuous lipophilic interactions. The most promising candidates for further drug development were identified by ligand lipophilicity efficiency analysis. (en)
Title	On the solubility and lipophilicity of metallacarborane pharmacophores On the solubility and lipophilicity of metallacarborane pharmacophores (en)
skos:prefLabel	On the solubility and lipophilicity of metallacarborane pharmacophores On the solubility and lipophilicity of metallacarborane pharmacophores (en)
skos:notation	RIV/60461373:22340/13:43895056!RIV14-TA0-22340___
http://linked.open...avai/riv/aktivita	I P Z
http://linked.open...avai/riv/aktivity	I, P(GAP303/11/1291), P(IAAX00320901), P(LH11027), P(TE01020028), Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika	5
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Dejlová, Barbora Lampová, Hana Kaplánek, Robert Král, Vladimír Rak, Jakub
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Fakulta chemicko-inženýrská
http://linked.open...dnocenehoVysledku	93964
http://linked.open...ai/riv/idVysledku	RIV/60461373:22340/13:43895056
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	solubility; P-ow; lipophilicity; inhibitor; HIV protease; serum albumin; cobalt bis(dicarbollide); metallacarborane (en)
http://linked.open.../riv/klicoveSlovo	metallacarborane HIV protease serum albumin lipophilicity inhibitor P-ow cobalt bis(dicarbollide) solubility
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[4667AC3EB41D]
http://linked.open...i/riv/nazevZdroje	Molecular Pharmaceutics
http://linked.open...in/vavai/riv/obor	FR
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	7 (xsd:int)
http://linked.open...vavai/riv/projekt	Biocompatibilization and Targeting of Nanoparticles for Diagnostic and Therapeutic Applications Functionalized boron clusters as viral enzyme inhihitors New types of ligands interfering with cancer cell communication as a new therapeutic strategy Center for Development of Original Drugs
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	10
http://linked.open...iv/tvurceVysledku	Cígler, Petr Kaplánek, Robert Král, Vladimír Matějíček, Pavel Rak, Jakub Dejlová, Barbora Lampová, Hana
http://linked.open...ain/vavai/riv/wos	000318669600024
http://linked.open...n/vavai/riv/zamer	Nové molekulární systémy pro pokročilé aplikace prospěšné pro zdraví a šetrné k životnímu prostředí
issn	1543-8384
number of pages	9 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/mp300565z
http://localhost/t...ganizacniJednotka	22340

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