title: First Total Synthesis and Biological Screening of a Proline-Rich Cyclopeptide from a Caribbean Marine Sponge.
abstract: A natural heptacyclopeptide, stylissamide G (7), previously isolated from the Bahamian marine spongeStylissa caribicafrom the Caribbean Sea, was synthesized via coupling of the tetrapeptide l-phenylalanyl-l-prolyl-l-phenylalanyl-l-proline methyl ester with the tripeptide Boc-l-leucyl-l-isoleucyl-l-proline, followed by cyclization of the linear heptapeptide fragment. The structure of the synthesized cyclooligopeptide was confirmed using quantitative elemental analysis, FT-IR, ¹H NMR,13C NMR and mass spectrometry. Results of pharmacological activity studies indicated that the newly synthesized cycloheptapeptide displayed good anthelmintic potential againstMegascoplex konkanensis,Pontoscotex corethrusesandEudrilus eugenieaat 2 mg/mL and in addition, potent antifungal activity against pathogenicCandida albicansand dermatophytesTrichophyton mentagrophytesandMicrosporum audouiniiat a concentration of 6 μg/mL.
authors.affiliation: Laboratory of Peptide Research and Development, School of Pharmacy, Faculty of Medical Sciences, The University of the West Indies, St. Augustine, Trinidad and Tobago. Rajiv.Dahiya@sta.uwi.edu.
authors.forename: Rajiv
authors.initials: R
authors.lastname: Dahiya
authors.affiliation: Department of Pharmacy, Mewar University, Gangrar, Chittorgarh, Rajasthan 312901, India. drrajivdahiya@gmail.com.
authors.forename: Sunil
authors.initials: S
authors.lastname: Singh
authors.affiliation: Department of Pharmacy, College of Health Sciences, Mizan-Tepi University, Mizan Teferi 5140, Ethiopia. ajaysharmapharma1979@gmail.com.
authors.forename: Ajay
authors.initials: A
authors.lastname: Sharma
authors.affiliation: Department of Pharmacy, College of Medical and Health Sciences, Wollega University, P.O. Box 395 Nekemte, Ethiopia. sureshchennupati@rediffmail.com.
authors.forename: Suresh V
authors.initials: SV
authors.lastname: Chennupati
authors.affiliation: Laboratory of Peptide Research and Development, School of Pharmacy, Faculty of Medical Sciences, The University of the West Indies, St. Augustine, Trinidad and Tobago. Sandeep.Maharaj@sta.uwi.edu.
authors.forename: Sandeep
authors.initials: S
authors.lastname: Maharaj
mesh_terms: D000818:Animals; D000871:Anthelmintics / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D017691:Caribbean Region; D003500:Cyclization; D004151:Dipeptides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008826:Microbial Sensitivity Tests / Q000379:methods; D010456:Peptides, Cyclic / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods
chemical_list: D000871:Anthelmintics; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D004151:Dipeptides; D010456:Peptides, Cyclic; C492946:leucyl-isoleucyl; D011392:Proline
keywords: Stylissa caribica; cycloheptapeptide; macrocyclization; marine sponge; peptide synthesis; pharmacological activity; stylissamide G