A 83586C | CAS# 116364-81-9 | Antibiotic antitumor agent

MedKoo Cat#: 571206 | Name: A 83586C

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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).

Chemical Structure

A 83586C

CAS#116364-81-9

Theoretical Analysis

MedKoo Cat#: 571206

Name: A 83586C

CAS#: 116364-81-9

Chemical Formula: C47H76N8O14

Exact Mass: 976.5481

Molecular Weight: 977.17

Elemental Analysis: C, 57.77; H, 7.84; N, 11.47; O, 22.92

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

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

Instruction

View handling instruction

Preparing Stock Solutions

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

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.