title: Synthesis, molecular docking and anticancer studies of peptides and iso-peptides.
abstract: Chiral peptides and iso-peptides were synthesized in excellent yield by using benzotriazole mediated solution phase synthesis. Benzotriazole acted both as activating and leaving group, eliminating frequent use of protection and subsequent deprotection. The procedure was based on the hypothesis that epimerization should be suppressed in solution due to a faster coupling rate than SPPS. All the synthesized peptides complied with Lipinski's Ro5 except for the rotatable bonds. Inhibition of cell proliferation of cancer cell lines is one of the most commonly used methods to study the effectiveness of any anticancer agents. Synthesized peptides and iso-peptides were tested against three cancer cell lines (MCF-7, MDA-MB 231) to determine their anti-proliferative potential. NFkB was also determined. Molecular docking studies were also carried out to complement the experimental results.
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA; Department of Chemistry, Quaid-i-Azam University, Islamabad 44000, Pakistan.
authors.forename: Farukh
authors.initials: F
authors.lastname: Jabeen
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA. Electronic address: sspanda12@gmail.com.
authors.forename: Siva S
authors.initials: SS
authors.lastname: Panda
authors.affiliation: College of Pharmacy, University of Hawii at Hilo, Hilo, HI, USA.
authors.forename: Tamara P
authors.initials: TP
authors.lastname: Kondratyuk
authors.affiliation: College of Pharmacy, University of Hawii at Hilo, Hilo, HI, USA.
authors.forename: Eun-Jung
authors.initials: EJ
authors.lastname: Park
authors.affiliation: College of Pharmacy, University of Hawii at Hilo, Hilo, HI, USA.
authors.forename: John M
authors.initials: JM
authors.lastname: Pezzuto
authors.affiliation: Department of Pharmacy, Quaid-i-Azam University, Islamabad 44000, Pakistan.
authors.lastname: Ihsan-ul-Haq
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
authors.forename: C Dennis
authors.initials: CD
authors.lastname: Hall
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA; Chemistry Department, King Abdulaziz University, Jeddah 21589, Saudi Arabia.
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000188:drug therapy / Q000378:metabolism; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D061986:MCF-7 Cells; D062105:Molecular Docking Simulation; D016328:NF-kappa B / Q000037:antagonists & inhibitors / Q000378:metabolism; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014230:Triazoles / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D016328:NF-kappa B; D010455:Peptides; D014230:Triazoles; C012771:benzotriazole
keywords: Anti-cancer; Benzotriazole; Molecular docking; Peptides; iso-Peptides