title: Synthesis of novel lipoamino acid conjugates of sapienic acid and evaluation of their cytotoxicity activities.
abstract: Novel lipoamino acids were prepared with the coupling of sapienic acid [(Z)-6-hexadecenoic acid] with α - amino group of amino acids and the resulting N-sapienoyl amino acids were tested for their cytotoxicity activities against four cancer based cell lines. Initially, sapienic acid was synthesized by the Wittig coupling of triphenylphosphonium bromide salt of 6-bromohexanoic acid and decanal with a Z specific reagent. The prepared sapienic acid was subsequently converted to its acid chloride which was further coupled with amino acids by the Schotten-Baumann reaction to form N-sapienoyl amino acid conjugates. Structural characterization of the prepared N-sapienoyl amino acid derivatives was done by spectral data (IR, mass spectra and NMR). These lipoamino acid derivatives were screened for in vitro cytotoxicity evaluation. Cytotoxicity evaluation against four cancer cell lines showed that N-sapienoyl isoleucine was active against three cell lines whereas other derivatives either showed activity against only one or two cell lines with very moderate activity and two derivatives were observed to be inactive against the tested cell lines.
authors.affiliation: Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology.
authors.forename: Sanganamoni Chinna
authors.initials: SC
authors.lastname: Gopal
authors.forename: Shiva Shanker
authors.initials: SS
authors.lastname: Kaki
authors.forename: Bhamidipati V S K
authors.initials: BV
authors.lastname: Rao
authors.forename: Yedla
authors.initials: Y
authors.lastname: Poornachandra
authors.forename: Chityal Ganesh
authors.initials: CG
authors.lastname: Kumar
authors.forename: Rachapudi Badari
authors.initials: RB
authors.lastname: Narayana Prasad
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D045744:Cell Line, Tumor; D003358:Cosmetics; D006801:Humans; D007532:Isoleucine / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D007930:Leucine; D008055:Lipids / Q000737:chemistry; D009369:Neoplasms / Q000473:pathology; D010169:Palmitic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D013473:Sunscreening Agents; D014466:Ultraviolet Rays
chemical_list: D000596:Amino Acids; D003358:Cosmetics; D008055:Lipids; D010169:Palmitic Acids; D013473:Sunscreening Agents; C090151:delta(6)-hexadecenoic acid; D007532:Isoleucine; D007930:Leucine