Self-assembled structures built from amphiphilic molecules find application in different fields. a The synthetic versatility of calixarene macrocycles, whose skeleton can be differently functionalized with a variety of hydrophilic and hydrophobic moieties, allows the development of amphiphilic derivatives able to aggregate in different higher order supramolecular architectures. b, c Here we describe the capability of an amphiphilic calix[4]arene derivative, bearing four carboxylic acid groups at the calixarene upper rim and four dodecyl chains at the lower rim, to form discrete and stable multilamellar vesicles in aqueous medium by using an emulsion/solvent evaporation method. Dynamic Light Scattering (DLS) measurements, Field Emission Scanning Electron Microscopy (FE-SEM) and Transmission Electron Microscopy (TEM) images provided information about size, size distribution and morphology of the nanostructured assemblies. The vesicular nature was confirmed by entrapment of a hydrophilic dye such as rodhamine B in aqueous lumen. A preliminary study showed that the self-assembled structures of the carboxy-calix[4]arene can entrap also a hydrophobic drug such as curcumin. The amphiphilic carboxy-calix[4]arene represents the first example of calix[4]arene derivative assembling in very stable multilamellar vesicles in aqueous medium with a narrow polydispersity. Suitable nanometer-size, very size narrow distribution, well-defined spherical shape, negatively charged hydrophilic multilamellar wall, high size stability (more than two years), and guest encapsulation ability make the vesicles of the carboxy-calix[4]arene derivative appealing in the research of drug delivery systems. Acknowledgment: Research funded by PON R&C 02_00355_2964193 (MIUR, Rome). References: a) Hill, J. P.; Shrestha, L. K.; Ishihara, S.; Ji, Q.; Ariga, K. Molecules 2014, 19, 8589-8609. b) Helttunen, K.; Shahgaldian, P. New J. Chem. 2010, 34, 2704-2714. c) Consoli, G. M. L.; Granata, G.; Lo Nigro, R.; Malandrino, G.; Geraci, C. Langmuir 2008, 24, 6194-6200.
ASSEMBLY OF A SUCCINYL-CALIX[4]ARENE DERIVATIVE IN MULTILAMELLAR VESICLES
Granata G;Consoli G M L;Geraci C;Lo Nigro R;
2015
Abstract
Self-assembled structures built from amphiphilic molecules find application in different fields. a The synthetic versatility of calixarene macrocycles, whose skeleton can be differently functionalized with a variety of hydrophilic and hydrophobic moieties, allows the development of amphiphilic derivatives able to aggregate in different higher order supramolecular architectures. b, c Here we describe the capability of an amphiphilic calix[4]arene derivative, bearing four carboxylic acid groups at the calixarene upper rim and four dodecyl chains at the lower rim, to form discrete and stable multilamellar vesicles in aqueous medium by using an emulsion/solvent evaporation method. Dynamic Light Scattering (DLS) measurements, Field Emission Scanning Electron Microscopy (FE-SEM) and Transmission Electron Microscopy (TEM) images provided information about size, size distribution and morphology of the nanostructured assemblies. The vesicular nature was confirmed by entrapment of a hydrophilic dye such as rodhamine B in aqueous lumen. A preliminary study showed that the self-assembled structures of the carboxy-calix[4]arene can entrap also a hydrophobic drug such as curcumin. The amphiphilic carboxy-calix[4]arene represents the first example of calix[4]arene derivative assembling in very stable multilamellar vesicles in aqueous medium with a narrow polydispersity. Suitable nanometer-size, very size narrow distribution, well-defined spherical shape, negatively charged hydrophilic multilamellar wall, high size stability (more than two years), and guest encapsulation ability make the vesicles of the carboxy-calix[4]arene derivative appealing in the research of drug delivery systems. Acknowledgment: Research funded by PON R&C 02_00355_2964193 (MIUR, Rome). References: a) Hill, J. P.; Shrestha, L. K.; Ishihara, S.; Ji, Q.; Ariga, K. Molecules 2014, 19, 8589-8609. b) Helttunen, K.; Shahgaldian, P. New J. Chem. 2010, 34, 2704-2714. c) Consoli, G. M. L.; Granata, G.; Lo Nigro, R.; Malandrino, G.; Geraci, C. Langmuir 2008, 24, 6194-6200.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
