Journal of
Cancer Research and Experimental Oncology

  • Abbreviation: J. Cancer Res. Exp. Oncol.
  • Language: English
  • ISSN: 2141-2243
  • DOI: 10.5897/JCREO
  • Start Year: 2009
  • Published Articles: 52

Full Length Research Paper

Solid-phase total synthesis of cyclic pentapeptide Longicalycinin A, by using 2-chlorotrityl chloride resin

Waqar Ahmad
  • Waqar Ahmad
  • State Key Laboratory of Chemical Resource Engineering, Institute of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. China.
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Farzana Shaheen
  • Farzana Shaheen
  • International Center for Chemical and Biological Sciences, University of Karachi, 75270, Pakistan.
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Yunshan Zhou
  • Yunshan Zhou
  • State Key Laboratory of Chemical Resource Engineering, Institute of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. China.
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Lijuan Zhang
  • Lijuan Zhang
  • State Key Laboratory of Chemical Resource Engineering, Institute of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. China.
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  •  Accepted: 03 October 2013
  •  Published: 30 November 2013

Abstract

Naturally isolated cyclic pentapeptide Longicalycinin A, which showed cytotoxicity to Hep G2 cancer cell line with an IC50 value 13.52 μg/mL, has been successfully synthesized by solid-phase methodology with Fmoc/t-Bu protecting schemes via solution-phase macrocyclization. 2-chlorotrityl chloride resin was used as solid support. Solution phase macrocyclization of linear pentapeptide precursor was carried out by two different routes with mild and severe acidic conditions correspondingly and found that percentage yield of Longicalycinin A under mild acidic condition (33%) was better than severe acidic conditions (13.7%). In addition, the cytotoxicity against Dalton’s lymphoma ascites (DLA) and Ehrlich’s ascites carcinoma (EAC) cell lines with CTC50 values were found to be 2.62 and 6.17 µM respectively.

 

Key words: Longicalycinin A, solid phase synthesis, 2-chlorotrityl chloride, solution-phase macrocyclization, cytotoxicity.