Photo-induced synthesis, structure and in vitro bioactivity of a natural cyclic peptide Yunnanin A analog

作者: Shitian Jiang , Lishuang Zhao , Jingwan Wu , Yujun Bao , Zhiqiang Wang

DOI: 10.1039/C9RA09163G

关键词:

摘要: A cyclic analog of natural peptide Yunnanin was synthesized via photoinduced single electron transfer reaction (SET) in the paper. The resulting compound exhibited potent bioactivity (with IC50 values 29.25 μg mL−1 against HepG-2 cell lines and 65.01 HeLa lines), but almost have no toxicity to normal cells 203.25 L929 which may be served as a potential antitumor drug for medical treatment. spatial structure examined by experimental electronic circular dichroism (ECD) quantum chemistry calculations. Moreover, theoretical study suggested that special intramolecular hydrogen bonds γ, β-turn secondary structures possible sources affecting peptide's bioactivity.

参考文章(28)
N. Barton, F.E. Blaney, S. Garland, B. Tehan, I. Wall, Seven Transmembrane G Protein-Coupled Receptors: Insights for Drug Design from Structure and Modeling Comprehensive Medicinal Chemistry II. ,vol. 4, pp. 669- 701 ,(2007) , 10.1016/B0-08-045044-X/00270-4
Hiroshi Morita, Akira Shishido, Takashi Kayashita, Masako Shimomura, Koichi Takeya, Hideji Itokawa, Two Novel Cyclic Peptides, Yunnanins A and B from Stellaria yunnanensis Chemistry Letters. ,vol. 1994, pp. 2415- 2418 ,(1994) , 10.1246/CL.1994.2415
Abba J. Kastin, Handbook of biologically active peptides Elsevier, Academic Press. ,(2006)
Hans-Dieter Jakubke, Norbert Sewald, Peptides: Chemistry and Biology ,(2002)
Assunta Napolitano, Manuela Rodriquez, Ines Bruno, Stefania Marzocco, Giuseppina Autore, Raffaele Riccio, Luigi Gomez-Paloma, Synthesis, structural aspects and cytotoxicity of the natural cyclopeptides yunnanins A, C and phakellistatins 1, 10 Tetrahedron. ,vol. 59, pp. 10203- 10211 ,(2003) , 10.1016/J.TET.2003.10.073
Alberto Fernandez-Tejada, Francisco Corzana, Jesus H Busto, Alberto Avenoza, Jesus M Peregrina, None, Conformational Effects of the Non-natural α-Methylserine on Small Peptides and Glycopeptides Journal of Organic Chemistry. ,vol. 74, pp. 9305- 9313 ,(2009) , 10.1021/JO901988W
Joel D. A. Tyndall, Bernhard Pfeiffer, Giovanni Abbenante, David P. Fairlie, Over one hundred peptide-activated G protein-coupled receptors recognize ligands with turn structure. Chemical Reviews. ,vol. 105, pp. 793- 826 ,(2005) , 10.1021/CR040689G
Keld Fosgerau, Torsten Hoffmann, Peptide therapeutics: current status and future directions. Drug Discovery Today. ,vol. 20, pp. 122- 128 ,(2015) , 10.1016/J.DRUDIS.2014.10.003
Yean Jang Lee, Rong Ling, Patrick S. Mariano, Ung Chan Yoon, Dong Uk Kim, Sun Wha Oh, Exploratory Studies of H-Atom Abstraction and Silyl-Transfer Photoreactions of Silylalkyl Ketones and (Silylalkyl)phthalimides Journal of Organic Chemistry. ,vol. 61, pp. 3304- 3314 ,(1996) , 10.1021/JO9522623
Taha Rezai, Bin Yu, Glenn L. Millhauser, Matthew P. Jacobson, R. Scott Lokey, Testing the conformational hypothesis of passive membrane permeability using synthetic cyclic peptide diastereomers. Journal of the American Chemical Society. ,vol. 128, pp. 2510- 2511 ,(2006) , 10.1021/JA0563455