التفاصيل البيبلوغرافية
| العنوان: |
Total synthesis and modification of proline-rich cyclopeptides Phakellistatins 17 and 18 isolated from marine sponge. |
| المؤلفون: |
Wu, Ming-hao1, Li, Yu-lei1, Chang, Qi1, Zhao, Xia1 zhaoxia@ouc.edu.cn, Chen, Qing1 |
| المصدر: |
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Nov2018, Vol. 59 Issue 45, p4011-4014. 4p. |
| مصطلحات موضوعية: |
*CYCLIC peptides synthesis, *CYCLIC peptides, *PROLINE, *SPONGES (Invertebrates), *SULFONYL group, *FLUORIDES, *ARGININE, *SUBSTITUTION reactions |
| مستخلص: |
Graphical abstract Highlights • Two proline-rich cyclopeptides from marine sponge were totally synthesized. • Two analogues containing sulfonyl fluoride group and arginine substituted were synthesized. • All peptides were identified by means of HR-QTOF-MS, 1H NMR and 13C NMR. • Analogue P18-1 with sulfonyl fluoride group exhibited significantly enhanced cytotoxicity. Abstract The Phakellistatins 17 and 18, two naturally occurring cyclic proline-rich peptides from marine sponge, were synthesized by utilizing a two-step solid-phase/solution synthesis strategy for the first time. Phakellistatin 18 exhibited a weak inhibitory activity against human lung carcinoma cell (A549) and human hepatoma (BEL-7042). In order to improve the activity of Phakellistatin 18, two of its analogues which contain sulfonyl fluoride group (P18-1) and arginine substituted derivative (P18-2) were also synthesized respectively. The spectral data of Phakellistatins 17 and 18 were identical to that reported for the natural products. Analogues P18-1 and P18-2 were identified by means of HR-QTOF-MS, 1H NMR and 13C NMR. More importantly, analogue P18-1 exhibited significantly enhanced cytotoxicity against BEL-7042 cancer cells compared with Phakellistatin 18, suggesting that the sulfonyl fluoride group in the parent peptide may contribute to the improvement of antitumor activity. This strategy provides a reference method for improving the activity of natural peptides. reserved. [ABSTRACT FROM AUTHOR] |
| قاعدة البيانات: |
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