96107-96-9Relevant articles and documents
P-Sulfocalix[6]arene as Nanocarrier for Controlled Delivery of Doxorubicin
Ostos, Francisco J.,Lebrón, José A.,Moyá, Maria L.,López-López, Manuel,Sánchez, Antonio,Clavero, Amparo,García-Calderón, Clara B.,Rosado, Iván V.,López-Cornejo, Pilar
, p. 679 - 689 (2017/03/22)
Given the high toxicity of the anthracycline antibiotic doxorubicin (DOX), it is relevant to search for nanocarriers that decrease the side effects of the drug and are able to transport it towards a therapeutic target Here, the encapsulation of DOX by p-sulfocalix[6]arene (calix) has been studied. The interaction of DOX with the macrocycle, as well as with DNA, has been investigated and the equilibrium constant for each binding process estimated. The results showed that the binding constant of DOX to DNA, KDNA, is three orders of magnitude higher than that to calix, Kcalix. The ability of calixarenes to encapsulate DOX molecules, as well as the capability of the DOX molecules included into the inner cavity of the macrocycle to bind with DNA have been examined. Cytotoxicity measurements were done in different cancer and normal cell lines to probe the decrease in the toxicity of the encapsulated DOX. The low toxicity of calixarenes has also been demonstrated for different cell lines.
Hexasulfonated Calixarene Derivatives: A New Class of Catalysts, Surfactants, and Host Molecules
Shinkai, Seiji,Mori, Seiichi,Koreishi, Hiroshi,Tsubaki, Takayuki,Manabe, Osamu
, p. 2409 - 2416 (2007/10/02)
Water-soluble hexasulfonated calixarenes with various substituens (1-R) have been sythesized for the first time and applied as host molecules in an aqueous system.Dynamic 1H NMR studies established that calixarene-p-hexasulfonate (1-H) adopts a "winged" or "hinged" conformation in D2O-Me2SO-d6 (2:1 v/v) owing to hydrogen bonding among the OH groups, while 5,11,17,23,29,35-hexasulfonato-37,38,39,40,41,42-hexakis(hexyloxy)calixarene (1-C) adopts a similar conformation in D2O owing to hydrophobic bonding among the hexyl groups.The aggregation behavior in water was examined about 1-C6 and 1-C12.Physical (light-scattering, surface tension, and conductance) and spectral (fluorescence and absorption spectroscopies) studies established that 1-C6 has a cmc at ca. 6E-4 M, as does sodium dodecyl sulfate (SDS), while 1-C12 has no detectable cmc and rather acts as a "unimolecular" micelle.In fact, 1-C6 associated with small molecules (pyrene, 2-anilinonaphtalene, and Orange OT) according to the micelle-like biphasic concentration dependence, while 1-C12 formed host-guest-type 1:1 complexes with these molecules.It was found that these calixarene derivatives efficiently accelerate acid-catalysed hydration of 1-benzyl-1,4-dihydronicotinamide and the reaction proceeds according to the Michaelis-Menten kinetics.In particular, the rate constans for 1-H and 1-CH2COOH, which both have acidic protons to catalyze the reaction and anionic sulfonates to stabilize the cationic intermediate at the two edges of the cavity, were greater by 426-1220-fold than those for noncyclic analogues.These findings indicate that hexasulfonated calixarenes serve as a new class of catalysts, surfactants, and host molecules.This is the first example for the host-guest-type behavior of calixarenes observed in an aqueous system.
