title: Syntheses of [12]aneN₃-oligopeptide conjugates as effective DNA condensation agents.
abstract: With the aim to develop effective and low toxicity DNA condensation agents, a series of oligopeptide derived macrocyclic polyamine [12]aneN(3) conjugates 7a-h·3HCl have been designed and synthesized through multi-step amidation reactions. Structure-property study through gel electrophoresis proved that the conjugates containing high hydrophobic ending amino acids exhibited effective condensation ability at concentration of 150-250 μM, which was further confirmed by dynamic light scattering and atomic force microscopy experiments. EB displacement assay, ionic salt effect, and structure-property relationship in gel electrophoresis indicated that DNA condensation resulted from both the electrostatic interaction of [12]aneN(3) unit and hydrogen-bonding/hydrophobic multi-interaction of oligopeptide moiety in the conjugates with DNA. The reversible condensation process and their low cytotoxicity suggest that the new condensing agents are potential for the development of non-viral vectors.
authors.affiliation: College of Chemistry, Beijing Normal University, Beijing 100875, China.
authors.forename: Zhi-Fen
authors.initials: ZF
authors.lastname: Li
authors.forename: Zhi-Fo
authors.initials: ZF
authors.lastname: Guo
authors.forename: Hao
authors.initials: H
authors.lastname: Yan
authors.forename: Zhong-Lin
authors.initials: ZL
authors.lastname: Lu
authors.forename: Da-Yong
authors.initials: DY
authors.lastname: Wu
mesh_terms: D002470:Cell Survival / Q000187:drug effects; D004247:DNA / Q000378:metabolism*; D004587:Electrophoresis, Agar Gel; D056945:Hep G2 Cells; D006801:Humans; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D018625:Microscopy, Atomic Force; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D011073:Polyamines / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D009842:Oligopeptides; D011073:Polyamines; D004247:DNA