Total synthesis and cyclization strategy of samoamide A, a cytotoxic cyclic octapeptide rich in proline and phenlalanine isolated from marine cyanobacterium

2018 ◽  
Vol 21 (2) ◽  
pp. 171-177 ◽  
Author(s):  
Qi Chang ◽  
Yu-Lei Li ◽  
Xia Zhao
Keyword(s):  
Total Synthesis ◽  
Marine Cyanobacterium ◽  
Cyclic Octapeptide

Isolation and Total Synthesis of Bromoiesol sulfates, Antitrypanosomal arylethers from a Salileptolyngbya sp. Marine Cyanobacterium

2021 ◽  
Author(s):  
Akira Ebihara ◽  
Arihiro Iwasaki ◽  
Youhei Miura ◽  
Ghulam Jeelani ◽  
Tomoyoshi Nozaki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Marine Cyanobacterium

scholarly journals Gatorbulin-1, a distinct cyclodepsipeptide chemotype, targets a seventh tubulin pharmacological site

2021 ◽  
Vol 118 (9) ◽  
pp. e2021847118
Author(s):  
Susan Matthew ◽  
Qi-Yin Chen ◽  
Ranjala Ratnayake ◽  
Charles S. Fermaintt ◽  
Daniel Lucena-Agell ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Wide Spectrum ◽  
Targeted Chemotherapy ◽  
Structural Determination ◽  
Marine Cyanobacterium ◽  
Microtubule Stabilization ◽  
Biochemical Studies ◽  
Β Tubulin

Tubulin-targeted chemotherapy has proven to be a successful and wide spectrum strategy against solid and liquid malignancies. Therefore, new ways to modulate this essential protein could lead to new antitumoral pharmacological approaches. Currently known tubulin agents bind to six distinct sites at α/β-tubulin either promoting microtubule stabilization or depolymerization. We have discovered a seventh binding site at the tubulin intradimer interface where a novel microtubule-destabilizing cyclodepsipeptide, termed gatorbulin-1 (GB1), binds. GB1 has a unique chemotype produced by a marine cyanobacterium. We have elucidated this dual, chemical and mechanistic, novelty through multidimensional characterization, starting with bioactivity-guided natural product isolation and multinuclei NMR-based structure determination, revealing the modified pentapeptide with a functionally critical hydroxamate group; and validation by total synthesis. We have investigated the pharmacology using isogenic cancer cell screening, cellular profiling, and complementary phenotypic assays, and unveiled the underlying molecular mechanism by in vitro biochemical studies and high-resolution structural determination of the α/β-tubulin−GB1 complex.

Total Synthesis of Proline-Rich Cyclic Octapeptide Stylissamide X

2015 ◽  
Vol 51 (3) ◽  
pp. 523-526 ◽  
Author(s):  
Ting Huang ◽  
Yan Zou ◽  
Mao-cheng Wu ◽  
Qing-jie Zhao ◽  
Hong-gang Hu
Keyword(s):  
Total Synthesis ◽  
Cyclic Octapeptide

Total synthesis of lyngbyabellin A, a potent cytotoxic metabolite from the marine cyanobacterium Lyngbya majuscula

2001 ◽  
Vol 42 (25) ◽  
pp. 4171-4174 ◽  
Author(s):  
Fumiaki Yokokawa ◽  
Hirofumi Sameshima ◽  
Takayuki Shioiri
Keyword(s):  
Total Synthesis ◽  
Marine Cyanobacterium ◽  
Lyngbya Majuscula

scholarly journals Towards the First Total Synthesis and Anticancer Screening of Polycarponin C: A Cyclic Octapeptide

2016 ◽  
Vol 32 (1) ◽  
pp. 515-521 ◽  
Author(s):  
Nirmala Shinde ◽  
Avinash Dhake ◽  
Kishan Haval
Keyword(s):  
Total Synthesis ◽  
Cyclic Octapeptide

scholarly journals Discovery and Total Synthesis of Doscadenamide A: A Quorum Sensing Signaling Molecule from a Marine Cyanobacterium

2019 ◽  
Vol 21 (18) ◽  
pp. 7274-7278 ◽  
Author(s):  
Xiao Liang ◽  
Susan Matthew ◽  
Qi-Yin Chen ◽  
Jason C. Kwan ◽  
Valerie J. Paul ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Total Synthesis ◽  
Marine Cyanobacterium ◽  
Signaling Molecule
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