WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H571206
CAS#: 116364-81-9
Description: A 83586C is a depsipeptide antibiotic from Streptomyces karnatakensis that shows potent Gram-positive activity in vitro. It functions as a highly potent inhibitor 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).
Hodoodo Cat#: H571206
Name: A 83586C
CAS#: 116364-81-9
Chemical Formula: C47H76N8O14
Exact Mass: 976.55
Molecular Weight: 977.170
Elemental Analysis: C, 57.77; H, 7.84; N, 11.47; O, 22.92
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Synonym: A 83586C; A-83586C; A83586C
IUPAC/Chemical Name: (S)-2-((2R,5S,6S)-6-((S,2E,6E)-4,6-dimethyl-5-oxoocta-2,6-dien-2-yl)-2-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)-2-hydroxy-N-((4aR,7S,10R,16aS,19R,22S,23S)-6-hydroxy-19-((S)-1-hydroxyethyl)-22-isopropyl-7,9,10-trimethyl-5,8,11,17,20,24-hexaoxodocosahydro-13H,22H-dipyridazino[6,1-f:6',1'-o][1]oxa[4,7,10,13,16]pentaazacyclononadecin-23-yl)butanamide
InChi Key: BJRNAAQGIMGUML-IYSUCPQHSA-N
InChi Code: 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
SMILES Code: CC[C@@]([C@@]1(O)CC[C@H](C)[C@@H](/C(C)=C/[C@@H](C(/C(C)=C/C)=O)C)O1)(O)C(N[C@H]2[C@H](C(C)C)OC([C@@H]([C@@H](O)C)NC([C@@H]3CCCNN3C([C@@H](C)N(C)C([C@H](C)N(O)C([C@H]4CCCNN4C2=O)=O)=O)=O)=O)=O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 977.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Smitka TA, Deeter JB, Hunt AH, Mertz FP, Ellis RM, Boeck LD, Yao RC. A83586C, a new depsipeptide antibiotic. J Antibiot (Tokyo). 1988 Jun;41(6):726-33. PubMed PMID: 3403366.
2: Assem ES, Peh KH, Wan BY, Manaviazar S, Walters MA, George JH, Hale KJ. Pharmacological actions of a new synthetic cyclodepsipeptide, the A83586C-citropeptin hybrid, on complement C5a and G-Proteins. Inflamm Res. 2008;57 Suppl 1:S21-2. doi: 10.1007/s00011-007-0610-6. PubMed PMID: 18345507.
3: Hale KJ, Manaviazar S, George JH, Walters MA, Dalby SM. Total synthesis of (+)-azinothricin and (+)-kettapeptin. Org Lett. 2009 Feb 5;11(3):733-6. doi: 10.1021/ol802817t. PubMed PMID: 19175351.
4: Hale KJ, Manaviazar S, George J. Total synthesis of (+)-A83586C, (+)-kettapeptin and (+)-azinothricin: powerful new inhibitors of beta-catenin/TCF4- and E2F-mediated gene transcription. Chem Commun (Camb). 2010 Jun 21;46(23):4021-42. doi: 10.1039/c000603c. Epub 2010 Apr 19. PubMed PMID: 20405066.
5: Hale KJ, Lazarides L. Synthesis of an L-proline modified mimetic of the A83586C antitumour cyclodepsipeptide. Chem Commun (Camb). 2002 Sep 7;(17):1832-3. PubMed PMID: 12271631.
6: Hale KJ, Lazarides L. Synthetic route to the GE3 cyclodepsipeptide. Org Lett. 2002 May 30;4(11):1903-6. PubMed PMID: 12027643.
7: Hale KJ, Manaviazar S, Lazarides L, George J, Walters MA, Cai J, Delisser VM, Bhatia GS, Peak SA, Dalby SM, Lefranc A, Chen YN, Wood AW, Crowe P, Erwin P, El-Tanani M. Synthesis of A83586C analogs with potent anticancer and beta-catenin/ TCF4/osteopontin inhibitory effects and insights into how A83586C modulates E2Fs and pRb. Org Lett. 2009 Feb 5;11(3):737-40. doi: 10.1021/ol802818f. PubMed PMID: 19175352.
