Increasing the aqueous solubility of the anesthetic propofol through wormlike micelle formation.

Propofol, a phenol derivative, is commonly employed as an intravenous anesthetic during clinical procedures, formulated as an oil/water emulsion due to its poor solubility in water. The stability limitations associated with emulsions have prompted research efforts towards developing aqueous formulations of propofol. In this work, we investigate the solubility enhancement of propofol in anionic and cationic surfactants. Our findings reveal that the solubility of propofol can increase significantly, up to 100-fold, depending on the nature of the micellar aggregate, as observed for alkylammonium halogenates CnTAB (for n = 12, 14 and 16), contrasting with the lower solubility with SDS. Interestingly, C14TAB and C16TAB demonstrate significantly higher solubility than C12TAB. This was attributed to the formation of wormlike micelles, in which the propofol molecules are positioned between the cationic heads of the surfactant molecules, changing the micellar curvature and the morphology of the aggregate. Therefore, the aromatic molecules in the micellar environment can be partitioned into the micellar cores and their palisades. Regarding C12TAB, the alkyl chain is too short to form wormlike micelles, thus, concentrating propofol molecules mainly into the micellar core, and consequently, leading to their aggregation. Solubility diagrams of propofol were constructed in conjunction with different surfactants. The systems exhibiting viscoelastic behavior, indicative of wormlike micelle formation, were further investigated using rheology. Additionally, the fluorescent properties of propofol enabled the examination of the anesthetic molecule within diverse micellar environments.

Effective targeting of proton transfer at ground and excited states of ortho-(2'-imidazolyl)naphthol constitutional isomers.

Steady-state and time-resolved spectroscopy and quantum chemical computational studies were employed to investigate ground and excited state proton transfer of a novel series of ortho-(1H-imidazol-2-yl)naphthol constitutional isomers: 1-(1H-imidazol-2-yl)naphthalen-2-ol (1NI2OH), 2-(1H-imidazol-2-yl)naphthalen-1-ol (2NI1OH) and 3-(1H-imidazol-2-yl)naphthalen-2-ol (3NI2OH). Proper Near Attack Conformations (NACs) involving a strong intramolecular hydrogen bond between the naphthol moiety and the ortho-imidazole group account for the highest ground state acidity of 2NI1OH compared with 1NI2OH and 3NI2OH. Moreover, ESIPT for 2NI1OH and 3NI2OH is further associated with planar chelate H-ring formation whereas 1NI2OH shows the highest ESIPT barrier and a noncoplanar imidazole group. In addition to energetic and structural requirements, the final state also depends on electronic configuration of the ESIPT product with the neutral 3NI2OH showing an ICT effect that correlates with the excited state pKa of the cationic species.