Synthesis, cytotoxic and antimicrobial screening of a proline-rich cyclopolypeptide.
Present study describes the first total synthesis of a cyclic heptapeptide, stylisin 1 (8) via coupling of tetrapeptide Boc-L-tyrosinyl-L-prolyl-L-leucyl-L-proline-OH and tripeptide L-phenylalanyl-L-isoleucyl-L-proline-OMe followed by cyclization of linear heptapeptide segment. Structure elucidation of synthesized cyclopeptide was done on basis of detailed spectral as well as elemental analysis. From the results of pharmacological screening, it was concluded that cyclopeptide 8 possessed moderate cytotoxicity against Dalton's lymphoma ascites (DLA) and Ehrlich's ascites carcinoma (EAC) cell lines with IC(50) (inhibitory concentration, 50%) values of 10.6 and 14.6 microM. Furthermore, cyclopeptide 8 exhibited moderate to good antimicrobial activity against Gram -ve (negative) bacteria Klebsiella pneumoniae and Pseudomonas aeruginosa, dermatophytes and Candida albicans with minimum inhibitory concentration (MIC) of 6 microg/ml.
Dahiya
Rajiv
R
Department of Pharmaceutical Chemistry, NRI Institute of Pharmacy, Bhopal, Madhya Pradesh, India. rajivdahiya77@rediffmail.com
Kumar
Akhilesh
A
Gupta
Rajul
R
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D045744:Cell Line, Tumor; D003500:Cyclization; D004354:Drug Screening Assays, Antitumor; D005658:Fungi / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D010455:Peptides / Q000138:chemical synthesis* / Q000494:pharmacology*; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D011392:Proline / Q000737:chemistry*
D000890:Anti-Infective Agents; D000903:Antibiotics, Antineoplastic; D000970:Antineoplastic Agents; D010455:Peptides; D010456:Peptides, Cyclic; D011392:Proline