Synthesis of a phenylalanine-rich peptide as potential anthelmintic and cytotoxic agent.

نویسنده

  • Rajiv Dahiya
چکیده

A natural cyclic heptapeptide segetalin D [VIII] was synthesized by coupling of tripeptide unit Boc-Pro-Gly-Leu-OMe [V] with tetrapeptide unit Boc-Ser-Phe-Ala-Phe-OMe [VI] after proper deprotection at carboxyl and amino ends followed by cyclization of linear peptide segment. Structure of VIII was confirmed by spectral and elemental analyses. The newly synthesized cyclopeptide was tested for its antibacterial, antifungal, anthelmintic and cytotoxic activities. Compound VIII showed high cytotoxicity against Dalton's lymphoma ascites (DLA) and Ehrlich's ascites carcinoma (EAC) cell lines with CTC50 values of 7.54 and 13.56 microM. Moreover, VIII exhibited potent anthelmintic activity against earthworms Eudrilus species, Megascoplex konkanensis and Pontoscotex corethruses at a dose of 2 mg/mL.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

First Total Synthesis and Pharmacological Potential of a Plant Based Hexacyclopeptide

  A new bioactive proline-rich cyclohexapeptide - diandrine C (6), previously isolated from whole plant of Drymaria diandra (Caryophyllaceae), was synthesized through coupling reactions of tetrapeptide unit Boc-Gly-l-Pro-l-Tyr-l-Trp-OH with dipeptide unit l-Pro-Gly-OMe using N,N-diisopropylcarbodiimide (DIPC) as the coupling agent, followed by cyclization of l...

متن کامل

First Total Synthesis and Pharmacological Potential of a Plant Based Hexacyclopeptide

  A new bioactive proline-rich cyclohexapeptide - diandrine C (6), previously isolated from whole plant of Drymaria diandra (Caryophyllaceae), was synthesized through coupling reactions of tetrapeptide unit Boc-Gly-l-Pro-l-Tyr-l-Trp-OH with dipeptide unit l-Pro-Gly-OMe using N,N-diisopropylcarbodiimide (DIPC) as the coupling agent, followed by cyclization of l...

متن کامل

Synthesis, Characterization, and Biological Activity Studies on Fanlizhicyclopeptide A

The synthesis of a proline-rich cyclic heptapeptide, fanlizhicyclopeptide A (8), previouslyisolated from the fruits of Annona squamosa (sugar-apples), is described via coupling oftetrapeptide l-prolyl-l-tyrosyl-l-leucyl-l-proline methyl ester with tripeptide Boc-glycyl-lvalyl-l-proline followed by cyclization of the linear fragment having seven amino acid units.Structure of the synthesized cycl...

متن کامل

Synthesis, Characterization, and Biological Activity Studies on Fanlizhicyclopeptide A

The synthesis of a proline-rich cyclic heptapeptide, fanlizhicyclopeptide A (8), previouslyisolated from the fruits of Annona squamosa (sugar-apples), is described via coupling oftetrapeptide l-prolyl-l-tyrosyl-l-leucyl-l-proline methyl ester with tripeptide Boc-glycyl-lvalyl-l-proline followed by cyclization of the linear fragment having seven amino acid units.Structure of the synthesized cycl...

متن کامل

Synthesis and Bioactivity of a Cyclopolypeptide from Caribbean Marine Sponge

Synthesis of a natural proline-rich cyclopolypeptide - rolloamide A [8] was carried out by coupling of tri- and tetrapeptide units Boc-Phe-Pro-Val-OMe and Boc-Pro-Leu-Pro-Ile-OMe after proper deprotection at carboxyl and amino terminals using carbodiimide chemistry in alkaline environment followed by cyclization of linear heptapeptide segment in the presence of base. The structure of synthesize...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:
  • Acta poloniae pharmaceutica

دوره 64 6  شماره 

صفحات  -

تاریخ انتشار 2007