Physico-chemical investigation of asymmetrical peptidolipidyl-cyclodextrins

Journal of Colloid and Interface Science
Angelina AngelovaLaurent Mauclaire

Abstract

A new class of amphiphilic peptidolipidyl-cyclodextrins is reported. The derivatives are chiral due to the presence of an L-leucine in the spacer arm that links a saccharide moiety and a grafted, saturated hydrocarbon chain. Self-assembly properties of the peptidolipidyl-cyclodextrins are characterized by quasi-elastic light scattering, turbidity and UV-visible absorption measurements. NMR experiments give insight into the intermolecular dipolar interactions as a function of temperature and concentration. N-dodecyl-N alpha-(6 I-amidosuccinyl-6 1-deoxy-cyclomaltoheptaose)-L-leucine (1) is poorly soluble in aqueous media. N-dodecyl-N(alpha)-(6 I-amidosuccinyl-6 I-deoxy-2 I,3 I-di-O-methyl-hexakis-(2 II-VII,3 II-VII,6 II-VII-tri-O-methyl)-cyclomaltoheptaose)-L-leucine (2) is found to be more soluble and self-assembles into stable supramolecular colloidal aggregates with nanometric dimensions above a critical aggregation concentration (CAC). It has a propensity for solubilization of hydrophobic species revealing a micellar-like behavior, which is compared to that of the non-ionic detergent octyl glucoside. On the contrary, compound 1 precipitates in a crystalline phase beyond its water solubility limit, and it does not display any ...Continue Reading

References

Nov 10, 1996·Journal of Colloid and Interface Science·& a r i n g ; WaltermoI Johansson
Mar 27, 1999·Journal of Colloid and Interface Science·A AngelovaA Baszkin
Mar 27, 1999·Journal of Colloid and Interface Science·A AngelovaA Baszkin
Aug 10, 2000·Chemistry and Physics of Lipids·S LesieurD Wouessidjewe
May 7, 2005·Langmuir : the ACS Journal of Surfaces and Colloids·Caroline SultanemBruno Perly

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Citations

Jun 18, 2009·The Journal of Organic Chemistry·Yongbin HanFrederick A Villamena
Jul 20, 2010·Journal of Colloid and Interface Science·Mary Cano-SarabiaJaume Veciana
Jun 4, 2015·Drug Discovery Today·Véronique BonnetCatherine Sarazin
Sep 29, 2011·Biochimie·Cédric GervaiseFlorence Djedaïni-Pilard
Dec 17, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Ewelina WajsAlex Fragoso
Feb 16, 2013·Langmuir : the ACS Journal of Surfaces and Colloids·Michel RouxFlorence Djedaíni-Pilard
Sep 21, 2017·Chemical Society Reviews·Wing-Fu LaiWing-Tak Wong
Jan 1, 2015·Beilstein Journal of Organic Chemistry·Florian HamonFlorence Djedaini-Pilard
Mar 19, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Gabriel Guerrero-LunaJesús Sandoval-Ramírez
Nov 20, 2016·International Journal of Pharmaceutics·Dominique Duchêne, Amélie Bochot
Oct 23, 2019·Langmuir : the ACS Journal of Surfaces and Colloids·Yawen LiAihua Zou
Oct 1, 2019·Langmuir : the ACS Journal of Surfaces and Colloids·Michel RouxFlorence Djedaini-Pilard

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