Vicenistatin
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| Category | Antibiotics |
| Catalog number | BBF-02959 |
| CAS | 150999-05-6 |
| Molecular Weight | 500.71 |
| Molecular Formula | C30H48N2O4 |
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Description
It is a macrocyclic lipid antibiotic produced by the strain of Str. sp. HC34. In vitro it is cytotoxic to human leukemia HL-60 cells and human colon cancer Co-LO205 cells with IC50 (μg/mL) of 0.12 and 0.19, respectively.
Specification
| Synonyms | Azacycloeicosa-3,5,10,13,15-pentaen-2-one, 7,11,13,19-tetramethyl-8-[[2,4,6-trideoxy-4-(methylamino)-β-D-ribo-hexopyranosyl]oxy]-, (3E,5E,7S,8S,10E,13E,15E,19S)-; Antibiotic HC34; NSC 641691; Vicenistatine |
| IUPAC Name | (3E,5E,7S,8S,10E,13E,15E,19S)-8-[(2R,4S,5S,6R)-4-hydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy-7,11,13,19-tetramethyl-1-azacycloicosa-3,5,10,13,15-pentaen-2-one |
| Canonical SMILES | CC1CCC=CC=C(CC(=CCC(C(C=CC=CC(=O)NC1)C)OC2CC(C(C(O2)C)NC)O)C)C |
| InChI | InChI=1S/C30H48N2O4/c1-21-12-8-7-9-13-23(3)20-32-28(34)15-11-10-14-24(4)27(17-16-22(2)18-21)36-29-19-26(33)30(31-6)25(5)35-29/h7-8,10-12,14-16,23-27,29-31,33H,9,13,17-20H2,1-6H3,(H,32,34)/b8-7+,14-10+,15-11+,21-12+,22-16+/t23-,24-,25+,26-,27-,29-,30+/m0/s1 |
| InChI Key | FINGADBUNZWVLV-KVAOKYIVSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 678.3°C at 760 mmHg |
| Melting Point | 151-153°C (dec.) |
| Density | 1.05 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Characterization of the Aminosugar Biosynthetic and Regulatory Genes of Vicenistatin in Monodonata labio-Associated Streptomyces parvus SCSIO Mla-L010
Zhicheng Liang, Jun Li, Chunyao Ling, Run Xu, Xiangxi Yi, Jianhua Ju, Qinglian Li J Nat Prod. 2022 Jan 28;85(1):256-263. doi: 10.1021/acs.jnatprod.1c01044. Epub 2022 Jan 18.
Vicenistatin (1) is a potent polyketide antitumor antibiotic composed of a 20-membered macrolactam core appended to a unique aminosugar, vicenisamine. In this study, vicenistatin was isolated and its biosynthetic gene cluster identified from Monodonata labio-associated Streptomyces parvus SCSIO Mla-L010. A set of five genes, vicC, vicD, vicE, vicF, and vicG, was confirmed to be involved in the biosynthesis of the aminosugar by gene inactivations. VicG was characterized as an N-methyltransferase that catalyzes the methylation of the 4'-amino group in the last step of the aminosugar biosynthetic pathway; the N-demethyl intermediate 4'-N-demethylvicenistatin (2) was isolated from the ΔvicG mutant strain. In addition, vicR1 was characterized as a positive pathway-specific regulatory gene. Notably, N-demethyl compound 2 was found to exert impressive antibacterial activities, with MIC values spanning 0.06-4 μg/mL, against a panel of Gram-positive bacteria including methicillin-resistant Staphylococcus aureus, Gram-negative Helicobacter pylori, and mycobacterium Mycobacterium smegmatis and the fungal pathogen Candida albicans. Compound 2 was also found to display reduced cytotoxicities relative to vicenistatin, especially against noncancerous human cell lines.
2. Vicenistatin induces early endosome-derived vacuole formation in mammalian cells
Yuko Nishiyama, Tomohiro Ohmichi, Sayaka Kazami, Hiroki Iwasaki, Kousuke Mano, Yoko Nagumo, Fumitaka Kudo, Sosaku Ichikawa, Yoshiharu Iwabuchi, Naoki Kanoh, Tadashi Eguchi, Hiroyuki Osada, Takeo Usui Biosci Biotechnol Biochem. 2016 May;80(5):902-10. doi: 10.1080/09168451.2015.1132152. Epub 2016 Feb 1.
Homotypic fusion of early endosomes is important for efficient protein trafficking and sorting. The key controller of this process is Rab5 which regulates several effectors and PtdInsPs levels, but whose mechanisms are largely unknown. Here, we report that vicenistatin, a natural product, enhanced homotypic fusion of early endosomes and induced the formation of large vacuole-like structures in mammalian cells. Unlike YM201636, another early endosome vacuolating compound, vicenistatin did not inhibit PIKfyve activity in vitro but activated Rab5-PAS pathway in cells. Furthermore, vicenistatin increased the membrane surface fluidity of cholesterol-containing liposomes in vitro, and cholesterol deprivation from the plasma membrane stimulated vicenistatin-induced vacuolation in cells. These results suggest that vicenistatin is a novel compound that induces the formation of vacuole-like structures by activating Rab5-PAS pathway and increasing membrane fluidity.
3. Protein-Protein Recognition Involved in the Intermodular Transacylation Reaction in Modular Polyketide Synthase in the Biosynthesis of Vicenistatin
Taichi Chisuga, Akimasa Miyanaga, Tadashi Eguchi Chembiochem. 2022 Jul 19;23(14):e202200200. doi: 10.1002/cbic.202200200. Epub 2022 May 16.
The ketosynthase (KS) domain is a core domain found in modular polyketide synthases (PKSs). To maintain the polyketide biosynthetic fidelity, the KS domain must only accept an acyl group from the acyl carrier protein (ACP) domain of the immediate upstream module even when they are separated into different polypeptides. Although it was reported that both the docking domain-based interactions and KS-ACP compatibility are important for the interpolypeptide transacylation reaction in 6-deoxyerythronolide B synthase, it is not clear whether these findings are broadly applied to other modular PKSs. Herein, we describe the importance of protein-protein recognition in the intermodular transacylation between VinP1 module 3 and VinP2 module 4 in vicenistatin biosynthesis. We compared the transacylation activity and crosslinking efficiency of VinP2 KS4 against the cognate VinP1 ACP3 with the noncognate one. As a result, it appeared that VinP2 KS4 distinguishes the cognate ACP3 from other ACPs.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
