Argyrin A

Argyrin A

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Category Enzyme inhibitors
Catalog number BBF-00080
CAS
Molecular Weight 824.90
Molecular Formula C40H44N10O8S

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Description

Argyrin A has weak antibacterial activity, but has obvious effects on Pseudomonas bacteria. It can inhibit the growth of mammalian cell culture.

Specification

IUPAC Name (4S,7S,13R,22R)-4-(1H-indol-3-ylmethyl)-7-[(4-methoxy-1H-indol-3-yl)methyl]-13,18,22-trimethyl-16-methylidene-24-thia-3,6,9,12,15,18,21,26-octazabicyclo[21.2.1]hexacosa-1(25),23(26)-diene-2,5,8,11,14,17,20-heptone
Canonical SMILES CC1C(=O)NC(=C)C(=O)N(CC(=O)NC(C2=NC(=CS2)C(=O)NC(C(=O)NC(C(=O)NCC(=O)N1)CC3=CNC4=C3C(=CC=C4)OC)CC5=CNC6=CC=CC=C65)C)C
InChI InChI=1S/C40H44N10O8S/c1-20-35(53)46-22(3)40(57)50(4)18-33(52)45-21(2)39-49-30(19-59-39)38(56)48-29(13-23-15-41-26-10-7-6-9-25(23)26)37(55)47-28(36(54)43-17-3
InChI Key MXGWDBFUMHUPTG-SKZNYKRCSA-N

Reference Reading

1. Therapeutic effects of Argyrin F in pancreatic adenocarcinoma
Xi Chen, Khac Cuong Bui, Samarpita Barat, Mai Ly Thi Nguyen, Przemyslaw Bozko, Bence Sipos, Markus Kalesse, Nisar P Malek, Ruben R Plentz Cancer Lett. 2017 Jul 28;399:20-28. doi: 10.1016/j.canlet.2017.04.003. Epub 2017 Apr 10.
Pancreatic ductal adenocarcinoma (PDAC) is an aggressive disease with limited treatment options. The proteasome inhibitor Argyrin A, a cyclic peptide derived from the myxobacterium Archangium gephyra, shows antitumoral activities. We hypothesize that his analogue Argyrin F (AF) may also prevent PDAC progression. We have used PDAC cells and engineered mice (Pdx1-Cre; LSL-KrasG12D; p53 lox/+) to assess AF anticancer activity. We analyzed the effect of AF on proliferation and epithelial plasticity using MTT-, wound healing-, invasion-, colony formation-, apoptosis-, cell cycle- and senescence assays. In vivo treatment with AF, Gemcitabine (G) and combinational treatment (AF + G) was performed for survival analysis. AF inhibited cell proliferation, migration, invasion and colony formation in vitro. AF impaired epithelial-mesenchymal transition (EMT), caused considerable apoptosis and senescence in a dose- and time-dependent manner and affected cell cycle G1/S phase transition. G treatment achieved longest mice survival, followed by AF + G and AF compared to vehicle group. However, AF + G treatment induced the largest reduction in tumor spread and ascites. In conclusion, we have demonstrated that AF prevents PDAC progression and that combined therapy was superior to AF monotherapy. Therefore, AF treatment might be useful as an additional therapy for PDAC.
2. Computational inhibition studies of the human proteasome by argyrin-based analogues with subunit specificity
Eriketi Z Loizidou, Constantinos D Zeinalipour-Yazdi Chem Biol Drug Des. 2014 Jul;84(1):99-107. doi: 10.1111/cbdd.12298. Epub 2014 May 12.
A computational procedure was developed to study the subunit-specific interactions of the proteasome inhibitors argyrin A and F, with the aim of indentifying the determinants of subunit selectivity. Three-dimensional models of humanized proteasome active sites β1 , β2 and β5 were developed and subsequently used in molecular docking simulations with the argyrin analogues. The subunit selectivity exhibited by each analogue could be explained based on the site-specific interactions and a probability-based specificity parameter derived in this study. A rational approach that involved maximizing site-specific interactions was followed to guide the design of new argyrin analogues as specific inhibitors of the caspase-like (β1 site) activity.
3. A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues
Chou-Hsiung Chen, Sivaneswary Genapathy, Peter M Fischer, Weng C Chan Org Biomol Chem. 2014 Dec 28;12(48):9764-8. doi: 10.1039/c4ob02107j.
A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated were (S)-methylbenzylamine and related derivatives. To illustrate the robustness of the method, eight optically pure (S)-tryptophan analogues were synthesized, which were subsequently used for the convergent synthesis of a potent antibacterial agent, argyrin A and its analogues.

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