Solid-phase total synthesis of cyclic peptide brachystemin A and its immunomodulating activity

Zafar Ali Shah, Almas Jabeen, Samreen Soomro, Osman Mesaik Mohammed Ahmed Hassan, M. Iqbal Choudhary, Farzana Shaheen

Research output: Contribution to journalArticle

Abstract

Brachystemin A (1) is a biologically active peptide from a Chinese traditional plant Brachystemma calycinum D. Don. (Caryophyllaceae). The current study describes the complete solid-phase total synthesis of peptide 1 by using Kenner's sulfonamide safety-catch linker strategy. It was identified by QTOF/MS data and NMR studies. Synthetic peptide 1 was tested for its immunomodulatory effect on different in ammatory parameters, including production of in ammatory cytokines, interleukin 2 (IL-2), tumor necrosis factor-α (TNF-α) , and interleukin-1fi (IL-1fi) , and generation of nitric oxide (NO:) . The synthetic peptide 1 showed a moderate to low level of inhibition on the production of IL-2 (35.2%), TNF-α (19.3%), and IL-1fi (7.5%) at a concentration of 25 M. The effect of the compound on viability of cells was also evaluated, and it was found to be nontoxic on 3T3 cells.

Original languageEnglish
Pages (from-to)930-938
Number of pages9
JournalTurkish Journal of Chemistry
Volume39
Issue number5
DOIs
Publication statusPublished - 2015

Fingerprint

Cyclic Peptides
Peptides
Interleukins
Interleukin-2
Tumor Necrosis Factor-alpha
Sulfonamides
Nitric Oxide
Cells
Nuclear magnetic resonance
Cytokines

Keywords

  • Brachystemin A
  • Brachystemma calycinum
  • Cyclic peptide
  • Cytokines
  • Immunomodulatory effect
  • Safety-catch linker

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Solid-phase total synthesis of cyclic peptide brachystemin A and its immunomodulating activity. / Shah, Zafar Ali; Jabeen, Almas; Soomro, Samreen; Mohammed Ahmed Hassan, Osman Mesaik; Choudhary, M. Iqbal; Shaheen, Farzana.

In: Turkish Journal of Chemistry, Vol. 39, No. 5, 2015, p. 930-938.

Research output: Contribution to journalArticle

Shah, Zafar Ali ; Jabeen, Almas ; Soomro, Samreen ; Mohammed Ahmed Hassan, Osman Mesaik ; Choudhary, M. Iqbal ; Shaheen, Farzana. / Solid-phase total synthesis of cyclic peptide brachystemin A and its immunomodulating activity. In: Turkish Journal of Chemistry. 2015 ; Vol. 39, No. 5. pp. 930-938.
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AU - Choudhary, M. Iqbal

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