title: Nicotine-based surface active ionic liquids: Synthesis, self-assembly and cytotoxicity studies.
abstract: New ester-functionalized surface active ionic liquids (SAILs) based on nicotine, [CnENic][Br] (n=8, 10 and 12), with bromide counterions have been synthesized, characterized and investigated for their self-assembly behavior in aqueous medium. Conductivity measurements in aqueous solutions of the investigated SAILs have provided information about their critical micelle concentration (cmc), and degree of counterion binding (β), where cmc was found to be 2-3-fold lower than homologous SAILs or conventional cationic surfactants. The inherent fluorescence of SAILs in the absence of any external fluorescent probe have shed light on cmc as well as interactions prevailing between the monomers in micelle at molecular level. The thermodynamic parameters related to micellization have been deduced from isothermal titration calorimetry (ITC) and conductivity measurements.1H NMR, spin-lattice (T1) relaxation time and 2D1H-IH ROESY measurements have been exploited to get detailed account of internal structure of micelle. The size and shape of the micelles have been explored using dynamic light scattering (DLS) and transmission electron microscopy (TEM) measurements. The synthesized SAILs have been found to be non-cytotoxic towards C6-Glioma cell line, which adds to the possible utility of these SAILs for diverse biological applications.
authors.affiliation: Department of Chemistry, UGC-centre for Advance Studies - II, Guru Nanak Dev University, Amritsar 143005, India.
authors.forename: Gurbir
authors.initials: G
authors.lastname: Singh
authors.affiliation: Department of Chemistry, DAV College, Chandigarh 160011, India.
authors.forename: Raman
authors.initials: R
authors.lastname: Kamboj
authors.affiliation: Department of Chemistry, UGC-centre for Advance Studies - II, Guru Nanak Dev University, Amritsar 143005, India.
authors.forename: Venus
authors.initials: V
authors.lastname: Singh Mithu
authors.affiliation: Department of Chemistry and Chemical Engineering, Applied Surface Chemistry Kemivagen 10, Chalmers University of Technology, Göteborg SE-412 96, Sweden.
authors.forename: Vinay
authors.initials: V
authors.lastname: Chauhan
authors.affiliation: Department of Biotechnology, Guru Nanak Dev University, Amritsar 143005, India.
authors.forename: Taranjeet
authors.initials: T
authors.lastname: Kaur
authors.affiliation: Department of Biotechnology, Guru Nanak Dev University, Amritsar 143005, India.
authors.forename: Gurcharan
authors.initials: G
authors.lastname: Kaur
authors.affiliation: Department of Chemistry, UGC-centre for Advance Studies - II, Guru Nanak Dev University, Amritsar 143005, India. Electronic address: sukhprit@gmail.com.
authors.forename: Sukhprit
authors.initials: S
authors.lastname: Singh
authors.affiliation: Department of Chemistry, UGC-centre for Advance Studies - II, Guru Nanak Dev University, Amritsar 143005, India. Electronic address: tejwantsinghkang@gmail.com.
authors.forename: Tejwant
authors.initials: T
authors.lastname: Singh Kang
mesh_terms: D001965:Bromides / Q000737:chemistry*; D002151:Calorimetry; D045744:Cell Line, Tumor; D000067493:Dynamic Light Scattering; D004553:Electric Conductivity; D004952:Esters / Q000737:chemistry; D006801:Humans; D052578:Ionic Liquids / Q000032:analysis / Q000138:chemical synthesis* / Q000633:toxicity; D008027:Light; D008823:Micelles; D046529:Microscopy, Electron, Transmission; D009538:Nicotine / Q000737:chemistry*; D010316:Particle Size; D013499:Surface Properties; D013501:Surface-Active Agents / Q000032:analysis / Q000138:chemical synthesis* / Q000633:toxicity; D013816:Thermodynamics; D014867:Water
chemical_list: D001965:Bromides; D004952:Esters; D052578:Ionic Liquids; D008823:Micelles; D013501:Surface-Active Agents; D014867:Water; D009538:Nicotine
keywords: Cytotoxicity; Nicotine; Self-assembly; Surface active ionic liquids; Surfactants