Vinylamycin
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| Category | Antibiotics |
| Catalog number | BBF-02962 |
| CAS | 224427-91-2 |
| Molecular Weight | 493.64 |
| Molecular Formula | C26H43N3O6 |
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Description
It is a depsipeptide antibiotic produced by the strain of Streptomyces sp. M1982-63F1. It has activity against gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA) with MIC of 1.56-3.13 μg/mL.
Specification
| Synonyms | (8E,12S,15R)-3-(1-Methylheptyl)-4-(2-hydroxyethyl)-7-methylene-12-methyl-15-isopropyl-2-oxa-6,11,14-triazacyclopentadecane-8-ene-1,5,10,13-tetraone; 1-Oxa-4,7,12-triazacyclotetradec-9-ene-2,5,8,13-tetrone, 14-[1-(2-hydroxyethyl)-2-methyloctyl]-6-methyl-11-methylene-3-(1-methylethyl)-, (3R,6S,9E)- |
| IUPAC Name | (3R,6S,9E)-14-(2-hydroxyethyl)-6-methyl-11-methylidene-15-octan-2-yl-3-propan-2-yl-1-oxa-4,7,12-triazacyclopentadec-9-ene-2,5,8,13-tetrone |
| Canonical SMILES | CCCCCCC(C)C1C(C(=O)NC(=C)C=CC(=O)NC(C(=O)NC(C(=O)O1)C(C)C)C)CCO |
| InChI | InChI=1S/C26H43N3O6/c1-7-8-9-10-11-17(4)23-20(14-15-30)25(33)27-18(5)12-13-21(31)28-19(6)24(32)29-22(16(2)3)26(34)35-23/h12-13,16-17,19-20,22-23,30H,5,7-11,14-15H2,1-4,6H3,(H,27,33)(H,28,31)(H,29,32)/b13-12+/t17?,19-,20?,22+,23?/m0/s1 |
| InChI Key | ONGSLGFACDWAIV-OIXFFAKGSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 784.2±60.0°C at 760 mmHg |
| Melting Point | 182-184°C |
| Density | 1.1±0.1 g/cm3 |
| Solubility | Soluble in Methanol, DMSO |
Reference Reading
1. Total Syntheses and Biological Activities of Vinylamycin Analogues
Jinghan Wang, Beijia Kuang, Xiaoqian Guo, Jianwei Liu, Yahui Ding, Jiangnan Li, Shende Jiang, Ying Liu, Fang Bai, Luyuan Li, Quan Zhang, Xiao-Yu Zhu, Bo Xia, Chun-Qi Li, Liang Wang, Guang Yang, Yue Chen J Med Chem. 2017 Feb 9;60(3):1189-1209. doi: 10.1021/acs.jmedchem.6b01745. Epub 2017 Jan 20.
Natural depsipeptide vinylamycin was reported to be an antibiotic previously. Herein we report vinylamycin to be active against K562 leukemia cells (IC50 = 4.86 μM) and be unstable in plasma (t1/2 = 0.54 h). A total of 24 vinylamycin analogues with modification of the OH group and chiral centers were generated via a combinatorial approach. The lead compound 1a was subsequently characterized as having the following: no antimicrobial activity, significantly higher plasma stability (t1/2 = 14.3 h), improved activity against K562 leukemia cells (IC50 = 0.64 μM), and up to 75% cell inhibition without significant toxicities in K562 cells xenograft zebrafish model. Furthermore, compound 1a maintained its activity against the breast cancer cell line MCF-7 under hypoxic conditions. In comparison, the activity of gemcitabine in the same hypoxic in vitro model of MCF-7 cells was 15-fold lower. Therefore, the present results demonstrate that 1a has great potential as an anticancer agent.
2. Draft genome sequence of Micromonospora sp. DSW705 and distribution of biosynthetic gene clusters for depsipeptides bearing 4-amino-2,4-pentadienoate in actinomycetes
Hisayuki Komaki, Natsuko Ichikawa, Akira Hosoyama, Moriyuki Hamada, Enjuro Harunari, Arisa Ishikawa, Yasuhiro Igarashi Stand Genomic Sci. 2016 Oct 22;11:84. doi: 10.1186/s40793-016-0206-2. eCollection 2016.
Here, we report the draft genome sequence of Micromonospora sp. DSW705 (=NBRC 110037), a producer of antitumor cyclic depsipeptides rakicidins A and B, together with the features of this strain and generation, annotation, and analysis of the genome sequence. The 6.8 Mb genome of Micromonospora sp. DSW705 encodes 6,219 putative ORFs, of which 4,846 are assigned with COG categories. The genome harbors at least three type I polyketide synthase (PKS) gene clusters, one nonribosomal peptide synthetase (NRPS) gene clusters, and three hybrid PKS/NRPS gene clusters. A hybrid PKS/NRPS gene cluster encoded in scaffold 2 is responsible for rakicidin synthesis. DNA database search indicated that the biosynthetic gene clusters for depsipeptides bearing 4-amino-2,4-pentadienoate are widely present in taxonomically diverse actinomycetes.
3. Determination of the Absolute Configurations of Microtermolides A and B
Zhantao Yang, Meiyan Ma, Chun-Hua Yang, Yuan Gao, Quan Zhang, Yue Chen J Nat Prod. 2016 Sep 23;79(9):2408-12. doi: 10.1021/acs.jnatprod.5b01143. Epub 2016 Aug 31.
Absolute configurations of the three consecutive chiral centers in the cyclic depsipeptide microtermolide A have been tentatively assigned as 2‴R, 3‴R, and 4‴R. However, on the basis of a structural comparison with vinylamycin, another depsipeptide with a unique 4-amino-2,4-pentadienolate structure, the chiral centers could also be assigned as 2‴R, 3‴R, and 4‴S. Here, the first total synthesis of microtermolide A is reported and the configurations of the three consecutive chiral centers were confirmed to be 2‴R, 3‴R, and 4‴S. A similar approach was used to determine the analogous centers in microtermolide B as 2‴R, 3‴R, and 4‴S.
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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 ╳
