Synthesis, characterization and comparative evaluation of phenoxy ring containing long chain gemini imidazolium and pyridinium amphiphiles

• Published in: Journal of colloid and interface science Vol. 361; no. 1; pp. 33 - 41
• Main Authors: Bhadani, Avinash, Kataria, Hardeep, Singh, Sukhprit
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Inc 01.09.2011; Elsevier
• Subjects: agarose; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Binding; Bonding; Bromides; Cationic; Cell Line, Tumor; Cell Survival - drug effects; Chains; Chemistry; cmc; Colloidal state and disperse state; Cytotoxicity; Deoxyribonucleic acid; DNA; DNA - metabolism; DNA interaction; ethidium; Exact sciences and technology; gel electrophoresis; Gemini imidazolium amphiphile; Gemini pyridinium amphiphile; General and physical chemistry; Humans; Imidazoles - chemical synthesis; Imidazoles - chemistry; Imidazoles - pharmacology; Micelles; Micelles. Thin films; Neoplasms - drug therapy; oils; Phenols - chemical synthesis; Phenols - chemistry; Phenols - pharmacology; Pyridines - chemical synthesis; Pyridines - chemistry; Pyridines - pharmacology; Spacers; Surface-Active Agents - chemical synthesis; Surface-Active Agents - chemistry; Surface-Active Agents - pharmacology; Transmission electron microscopy; Gemini pyridinium amphiphile; cmc; Cytotoxicity; Gemini imidazolium amphiphile; DNA interaction; Binding; Conductivity; Characterization; Assay; Micellar critical concentration; Oil; Transmission electron microscopy; Synthesis; DNA; Bromides; Electrophoresis; Physicochemical properties; Comparative study
• ISSN: 0021-9797; 1095-7103
• DOI: 10.1016/j.jcis.2011.05.023

Phenoxy ring containing long chain gemini imidazolium amphiphite synthesized from renewable cardanol oil and its interaction with pDNA to form lipoplexes. [Display omitted] . ► Eight gemini imidazolium and pyridinium amphiphiles have been synthesized. ► Phenoxy ring containing long chain gemini amphiphiles have lower cmc values compared to other cationic gemini surfactants. ► Gemini amphiphiles demonstrate high DNA binding affinity. ► Amphiphiles form stable lipoplex with DNA. ► Display low cytotoxicity on C6 Glioma cell. Two series of phenoxy ring containing long chain imidazolium and pyridinium based gemini amphiphiles have been synthesized from renewable cardanol oil having different spacers (i. e. S(CH2)nS, where n is 2, 3, 4 & 6). Critical micelle concentration (cmc) of these new gemini amphiphiles has been determined by conductivity method. Further, these new cationic amphiphiles have been evaluated for their DNA binding capability by agarose gel electrophoresis, ethidium bromide exclusion experiments and transmission electron microscopy (TEM). The cytotoxicity of these new amphiphiles have been evaluated by MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Comparative studies of these phenoxy ring containing long chain gemini imidazolium amphiphiles and their pyridinium analogues depicted low cmc values of the later but greater DNA interaction capability and low cytotoxicity of the former series of amphiphiles.