A83586C
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| Category | Antibiotics |
| Catalog number | BBF-03514 |
| CAS | 116364-81-9 |
| Molecular Weight | 977.15 |
| Molecular Formula | C47H76N8O14 |
| Purity | >98% |
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Description
A83586C is an ester peptide antibiotic produced by Streptomyces karnatakensis. It has strong anti-Gram-positive bacteria activity, and the MIC of Staphylococcus aureus and Streptococcus is 0.008-0.06 μg/mL. The IC50 for human T-cell leukemia CCRF-CEM cells is 0.0135 μg/mL.
Specification
| Synonyms | Antibiotic A 83586C |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2-[(2R,5S,6S)-6-[(2E,4S,6E)-4,6-dimethyl-5-oxoocta-2,6-dien-2-yl]-2-hydroxy-5-methyloxan-2-yl]-2-hydroxy-N-[(3R,6S,9R,16S,17S,20R,23S)-7-hydroxy-20-[(1S)-1-hydroxyethyl]-3,4,6-trimethyl-2,5,8,15,19,22-hexaoxo-17-propan-2-yl-18-oxa-1,4,7,13,14,21,27-heptazatricyclo[21.4.0.09,14]heptacosan-16-yl]butanamide |
| Canonical SMILES | CCC(C(=O)NC1C(OC(=O)C(NC(=O)C2CCCNN2C(=O)C(N(C(=O)C(N(C(=O)C3CCCNN3C1=O)O)C)C)C)C(C)O)C(C)C)(C4(CCC(C(O4)C(=CC(C)C(=O)C(=CC)C)C)C)O)O |
| InChI | InChI=1S/C47H76N8O14/c1-13-25(5)36(57)27(7)23-28(8)38-26(6)19-20-47(66,69-38)46(65,14-2)45(64)51-35-37(24(3)4)68-44(63)34(31(11)56)50-39(58)32-17-15-21-48-53(32)41(60)29(9)52(12)40(59)30(10)55(67)42(61)33-18-16-22-49-54(33)43(35)62/h13,23-24,26-27,29-35,37-38,48-49,56,65-67H,14-22H2,1-12H3,(H,50,58)(H,51,64)/b25-13+,28-23+/t26-,27-,29+,30-,31-,32-,33+,34+,35-,37-,38-,46+,47+/m0/s1 |
| InChI Key | BJRNAAQGIMGUML-IYSUCPQHSA-N |
Properties
| Appearance | Colorless Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 189-191°C |
| Density | 1.32 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Synthesis of A83586C analogs with potent anticancer and beta-catenin/ TCF4/osteopontin inhibitory effects and insights into how A83586C modulates E2Fs and pRb
Karl J Hale, Soraya Manaviazar, Linos Lazarides, Jonathan George, Marcus A Walters, Jiaqiang Cai, Vern M Delisser, Gurpreet S Bhatia, S Andrew Peak, Stephen M Dalby, Amandine Lefranc, Ying-Nan P Chen, Alexander W Wood, Paul Crowe, Pauline Erwin, Mohamed El-Tanani Org Lett. 2009 Feb 5;11(3):737-40. doi: 10.1021/ol802818f.
The synthesis of three potent new antitumor agents is described: the A83586C-citropeptin hybrid (1), the A83586C-GE3 hybrid (2), and l-Pro-A83586C (3). Significantly, compounds 1 and 2 function as highly potent inhibitors of beta-catenin/TCF4 signaling within cancer cells, while simultaneously downregulating osteopontin (Opn) expression. A83586C antitumor cyclodepsipeptides also inhibit E2F-mediated transcription by downregulating E2F1 expression and inducing dephosphorylation of the oncogenic hyperphosphorylated retinoblastoma protein (pRb).
2. Total synthesis of (+)-A83586C, (+)-kettapeptin and (+)-azinothricin: powerful new inhibitors of beta-catenin/TCF4- and E2F-mediated gene transcription
Karl J Hale, Soraya Manaviazar, Jonathan George Chem Commun (Camb). 2010 Jun 21;46(23):4021-42. doi: 10.1039/c000603c. Epub 2010 Apr 19.
Herein we describe our asymmetric total syntheses of (+)-A83586C, (+)-kettapeptin and (+)-azinothricin. We also demonstrate that molecules of this class powerfully inhibit beta-catenin/TCF4- and E2F-mediated gene transcription within malignant human colon cancer cells at low drug concentrations.
3. Total synthesis of (+)-azinothricin and (+)-kettapeptin
Karl J Hale, Soraya Manaviazar, Jonathan H George, Marcus A Walters, Stephen M Dalby Org Lett. 2009 Feb 5;11(3):733-6. doi: 10.1021/ol802817t.
Asymmetric total syntheses of (+)-azinothricin and (+)-kettapeptin have been completed through a common new pathway that exploits a highly chemoselective coupling reaction between the fully elaborated cyclodepsipeptide 5 and the glycal activated esters 3 and 4 at the final stages of both respective syntheses.
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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 ╳
