Abstract
Amphiphilic substances, surfactants, are in common use to enhance the aqueous solubility of organic compounds. Solubilization of 3-{3,5-bis (trifluoromethyl)phenyl}quinoline was investigated by employing spectrophotometry, light scattering and tensiometry in micellar solutions of nonionic surfactants {dimethyldodecylamine-N-oxide, DDAO; polyoxyethylene(23)lauryl ether, Brij35; and polyoxyethylene(04)lauryl ether, Brij30}, a cationic surfactant (dodecyltrimethyl-ammonium bromide, DTAB), anionic surfactants (sodium dodecylbenzenesulfonate, SDBS; sodium dodecyl sulfate, SDS), and a zwitterionic surfactant (N-dodecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate, DDAPS). It is noted that the solubility of the title compound 3-{3,5-bis (trifluoromethyl)phenyl}quinoline increased linearly with the increase in surfactant concentration irrespective of the type of surfactant. This is due to association of the title compound with surfactants. The molar solubilization ratio (MSR), micelle–water partition coefficient (KM), and the Gibbs energy of solubilization (\( \Delta G_{\text{S}}^{\text{o}} \)) of the title compound in the micelles were determined and correlated with each other. The nonionic surfactant DDAO showed the highest solubilization capacity. The order of degree of solubility among nonionic, cationic, and anionic surfactants for 3-{3,5-bis (trifluoromethyl)phenyl}quinoline is DDAO > DDAPS > SDBS > DTAB > SDS > Brij35 > Brij30. This comparative study can be used to select an appropriate medium for the title compound’s solubilization, where the nonionic surfactants DDAO, Brij35 and Brij30 would be more beneficial due to their minimal protein binding and retention of their micellar form even after large dilution in blood owing to their very low critical micellar concentration values. The light scattering study indicated that the hydrodynamic radius of the blank and drug-loaded surfactants remained the same within experimental error.
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