PMID: 11920770Mar 29, 2002Paper

Interactions of cyclosporines with lipid membranes as studied by solid-state nuclear magnetic resonance spectroscopy and high-sensitivity titration calorimetry

Journal of Pharmaceutical Sciences
Uwe SchoteJoachim Seelig

Abstract

Cyclosporin A (CyA) interacts with lipid membranes. Binding reaction and membrane location of CyA and analogs were examined with 2H-NMR, high-sensitivity isothermal titration calorimetry (ITC), and CD spectroscopy. Effects of CyA and charged analogs on the phosphocholine head group and on the membrane interior were investigated using selectively deuterated phospholipids. Incorporation of cyclosporin generated small disordering of the lipid acyl chains. Binding of CyA and neutral and positively charged analogs to lipid membranes showed endothermic heats of reaction between + 5.9 and + 11.3 kcal/mol, whereas enthalpy of binding was close to zero for the negatively charged derivative. Binding constants of cyclosporines to liposomal membranes were in the range of K(P) = 1650-5560 M(- 1) depending on the cholesterol content. (2)H-NMR provides evidence that CyA is essentially located in the interior of the bilayer membrane. For the charged analogs an additional interaction occurs at the head group level, placing the polar groups of these CyA analogs in the vicinity of the phosphocholine dipoles. The association of CyA and its analogs is accompanied by a positive enthalpy change, which is overcompensated by positive entropy changes. B...Continue Reading

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Citations

Apr 23, 2010·Pharmaceutical Research·Gert FrickerChristel Müller-Goymann
Oct 15, 2013·Journal of Pharmaceutical and Biomedical Analysis·Piotr DraczkowskiKrzysztof Jozwiak
Jun 23, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Slim AzouziKarim El Kirat
Jan 22, 2013·Drug Delivery and Translational Research·Aparna DagarHayat Onyuksel
Aug 9, 2007·Expert Opinion on Drug Delivery·Alfred Fahr, Xiangli Liu
Jun 24, 2004·Chemistry and Physics of Lipids·Maria Polikandritou Lambros, Yueh Erh Rahman
Nov 3, 2004·Biochimica Et Biophysica Acta·Joachim Seelig
Aug 23, 2005·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Alfred FahrMathew L S Leigh
Nov 14, 2008·Cellular & Molecular Biology Letters·Aleksander Czogalla
Feb 6, 2007·Journal of Colloid and Interface Science·Dima LibsterNissim Garti
Jan 21, 2004·Journal of Molecular Recognition : JMR·Matthew J Cliff, John E Ladbury
Dec 18, 2020·Nature Communications·Philipp A M SchmidpeterCrina M Nimigean
Aug 25, 2009·Langmuir : the ACS Journal of Surfaces and Colloids·Slim AzouziSandrine Morandat
Apr 30, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Małgorzata JurakSantiago Martín
Jun 17, 2006·Biochimica Et Biophysica Acta·Kaoru Nomura, Gerardo Corzo
Dec 24, 2008·Journal of Natural Products·Marek KuzmaVladimír Havlícek
Feb 6, 2018·The Journal of Physical Chemistry. B·Conan K WangDavid J Craik
Oct 22, 2008·Colloids and Surfaces. B, Biointerfaces·Bizhan Malaekeh-NikoueiAfshin Samiei
Oct 5, 2010·Journal of Controlled Release : Official Journal of the Controlled Release Society·Hossam HefeshaAlfred Fahr

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