title: D-glucose derived novel gemini surfactants: synthesis and study of their surface properties, interaction with DNA, and cytotoxicity.
abstract: Four new D-glucose derived m-s-m type gemini surfactants with variable spacer and tail length have been synthesized by a simple and efficient synthetic methodology utilizing the free C-3 hydroxy group of diisopropylidene glucose. The synthetic route to these gemini surfactants with a quaternary ammonium group as polar head group involves a sequence of simple reactions including alkylation, imine formation, quaternization of amine etc. The surface properties of the new geminis were evaluated by surface tension and conductivity measurements. These gemini surfactants showed low cytotoxicity by MTT assay on HeLa cell line. The DNA binding capabilities of these surfactants were determined by agarose gel electrophoresis, fluorescence titration, and DLS experiments. The preliminary studies by agarose gel electrophoresis indicated chain length dependent DNA binding abilities, further supported by ethidium bromide exclusion experiments. Two of the D-glucose derived gemini surfactants showed effective binding with pET-28a plasmid DNA (pDNA) at relatively low N/P ratio (i.e., cationic nitrogen/DNA phosphate molar ratio).
authors.affiliation: Department of Chemistry, Birla Institute of Technology and Science, Pilani-K.K. Birla, Goa Campus, Goa 403 726, India. Electronic address: kumarniper@gmail.com.
authors.forename: Vikash
authors.initials: V
authors.lastname: Kumar
authors.affiliation: Department of Chemistry, Birla Institute of Technology and Science, Pilani-K.K. Birla, Goa Campus, Goa 403 726, India. Electronic address: amrita@goa.bits-pilani.ac.in.
authors.forename: Amrita
authors.initials: A
authors.lastname: Chatterjee
authors.affiliation: Department of Biological Sciences, Birla Institute of Technology and Science, Pilani-K.K. Birla, Goa Campus, Goa 403 726, India. Electronic address: nupurk89@gmail.com.
authors.forename: Nupur
authors.initials: N
authors.lastname: Kumar
authors.affiliation: Department of Biological Sciences, Birla Institute of Technology and Science, Pilani-K.K. Birla, Goa Campus, Goa 403 726, India. Electronic address: ganguly@goa.bits-pilani.ac.in.
authors.forename: Anasuya
authors.initials: A
authors.lastname: Ganguly
authors.affiliation: Department of Chemistry, St. Xavier's College, Kolkata 700 016, India. Electronic address: pcindranil@yahoo.co.in.
authors.forename: Indranil
authors.initials: I
authors.lastname: Chakraborty
authors.affiliation: Department of Chemistry, Birla Institute of Technology and Science, Pilani-K.K. Birla, Goa Campus, Goa 403 726, India. Electronic address: mainak@goa.bits-pilani.ac.in.
authors.forename: Mainak
authors.initials: M
authors.lastname: Banerjee
mesh_terms: D002117:Calcitriol / Q000031:analogs & derivatives / Q000737:chemistry; D002470:Cell Survival / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D004247:DNA / Q000378:metabolism*; D004587:Electrophoresis, Agar Gel; D005947:Glucose; D006367:HeLa Cells / Q000187:drug effects; D006801:Humans; D008823:Micelles; D010316:Particle Size; D013329:Structure-Activity Relationship; D013499:Surface Properties; D013500:Surface Tension; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism* / Q000494:pharmacology*
chemical_list: C411462:1,25-dihydroxy-21-(3-hydroxy-3-methylbutyl)vitamin D(3); D008823:Micelles; D013501:Surface-Active Agents; D004247:DNA; D002117:Calcitriol; D005947:Glucose
keywords: Critical micelle concentration; Cytotoxicity; DNA binding; Worm-like micelle; d-Glucose derived gemini surfactants