Azumamide E | CAS#585535-37-1 | HDAC inhibitor

MedKoo Cat#: 561261 | Name: Azumamide E

Description:

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

Azumamide E is a carboxylic acid containing natural histone deacetylase (HDAC) inhibitor. It is a cyclotetrapeptide isolated from the sponge Mycale izuensis.

Chemical Structure

Azumamide E

CAS#585535-37-1

Theoretical Analysis

MedKoo Cat#: 561261

Name: Azumamide E

CAS#: 585535-37-1

Chemical Formula: C27H38N4O6

Exact Mass: 514.2791

Molecular Weight: 514.62

Elemental Analysis: C, 63.02; H, 7.44; N, 10.89; O, 18.65

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

Azumamide E

IUPAC/Chemical Name

(Z)-6-[(2R,5R,8R,11R,12S)-8-Benzyl-5,12-dimethyl-3,6,9,13-tetraoxo-2-propan-2-yl-1,4,7,10-tetrazacyclotridec-11-yl]hex-4-enoic acid

InChi Key

DMXROUYLQHFRCS-GIORXHJXSA-N

InChi Code

InChI=1S/C27H38N4O6/c1-16(2)23-27(37)28-18(4)25(35)30-21(15-19-11-7-5-8-12-19)26(36)29-20(17(3)24(34)31-23)13-9-6-10-14-22(32)33/h5-9,11-12,16-18,20-21,23H,10,13-15H2,1-4H3,(H,28,37)(H,29,36)(H,30,35)(H,31,34)(H,32,33)/b9-6-/t17-,18+,20+,21+,23+/m0/s1

SMILES Code

O=C(O)CC/C=C\C[C@H]([C@@H]1C)NC([C@@H](CC2=CC=CC=C2)NC([C@@H](C)NC([C@@H](C(C)C)NC1=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 514.62 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: Chandrasekhar S, Rao CL, Seenaiah M, Naresh P, Jagadeesh B, Manjeera D, Sarkar A, Bhadra MP. Total synthesis of azumamide E and sugar amino acid-containing analogue. J Org Chem. 2009 Jan 2;74(1):401-4. doi: 10.1021/jo8020264. PubMed PMID: 19053574. 2: Wen S, Carey KL, Nakao Y, Fusetani N, Packham G, Ganesan A. Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue. Org Lett. 2007 Mar 15;9(6):1105-8. Epub 2007 Feb 21. PubMed PMID: 17311393. 3: Maulucci N, Chini MG, Micco SD, Izzo I, Cafaro E, Russo A, Gallinari P, Paolini C, Nardi MC, Casapullo A, Riccio R, Bifulco G, Riccardis FD. Molecular insights into azumamide e histone deacetylases inhibitory activity. J Am Chem Soc. 2007 Mar 14;129(10):3007-12. Epub 2007 Feb 21. PubMed PMID: 17311384. 4: Terracciano S, Di Micco S, Bifulco G, Gallinari P, Riccio R, Bruno I. Synthesis and biological activity of cyclotetrapeptide analogues of the natural HDAC inhibitor FR235222. Bioorg Med Chem. 2010 May 1;18(9):3252-60. doi: 10.1016/j.bmc.2010.03.022. Epub 2010 Mar 15. PubMed PMID: 20381359. 5: Maolanon AR, Villadsen JS, Christensen NJ, Hoeck C, Friis T, Harris P, Gotfredsen CH, Fristrup P, Olsen CA. Methyl effect in azumamides provides insight into histone deacetylase inhibition by macrocycles. J Med Chem. 2014 Nov 26;57(22):9644-57. doi: 10.1021/jm501399d. Epub 2014 Nov 7. PubMed PMID: 25380299. 6: Villadsen JS, Stephansen HM, Maolanon AR, Harris P, Olsen CA. Total synthesis and full histone deacetylase inhibitory profiling of Azumamides A-E as well as β²- epi-Azumamide E and β³-epi-Azumamide E. J Med Chem. 2013 Aug 22;56(16):6512-20. doi: 10.1021/jm4008449. Epub 2013 Aug 5. Erratum in: J Med Chem. 2013 Sep 12;56(17):7135. PubMed PMID: 23865683. 7: Nakao Y, Narazaki G, Hoshino T, Maeda S, Yoshida M, Maejima H, Yamashita JK. Evaluation of antiangiogenic activity of azumamides by the in vitro vascular organization model using mouse induced pluripotent stem (iPS) cells. Bioorg Med Chem Lett. 2008 May 1;18(9):2982-4. doi: 10.1016/j.bmcl.2008.03.053. Epub 2008 Mar 21. PubMed PMID: 18397826.