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MedKoo Cat#: 598040 | Name: Didemnin A

Description:

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

Didemnin A is an antiviral & antitumor depsipeptide from Carribean tunicate.

Chemical Structure

Didemnin A
CAS#77327-04-9

Theoretical Analysis

MedKoo Cat#: 598040

Name: Didemnin A

CAS#: 77327-04-9

Chemical Formula: C49H78N6O12

Exact Mass: 942.5678

Molecular Weight: 943.19

Elemental Analysis: C, 62.40; H, 8.34; N, 8.91; O, 20.36

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 #
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Synonym
Didemnin A; Didemnins; NSC 325319; NSC-325319; NSC325319;
IUPAC/Chemical Name
(R)-N-((3S,6R,7S,10R,11S,15S,17S,20S,25aS)-10-((S)-sec-butyl)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-1,4,8,13,16,18,21-heptaoxodocosahydro-15H-pyrrolo[2,1-f][1,15]dioxa[4,7,10,20]tetraazacyclotricosin-7-yl)-4-methyl-2-(methylamino)pentanamide
InChi Key
XQZOGOCTPKFYKC-VSZULPIASA-N
InChi Code
InChI=1S/C49H78N6O12/c1-14-29(8)40-38(56)25-39(57)67-43(28(6)7)42(58)30(9)44(59)51-35(23-27(4)5)47(62)55-21-15-16-36(55)48(63)54(12)37(24-32-17-19-33(65-13)20-18-32)49(64)66-31(10)41(46(61)52-40)53-45(60)34(50-11)22-26(2)3/h17-20,26-31,34-38,40-41,43,50,56H,14-16,21-25H2,1-13H3,(H,51,59)(H,52,61)(H,53,60)/t29-,30-,31+,34+,35-,36-,37-,38-,40+,41-,43-/m0/s1
SMILES Code
COc1ccc(C[C@H](N(C)C([C@H]2N(CCC2)C([C@H](CC(C)C)NC([C@@H](C)C([C@H](C(C)C)OC(C[C@H](O)[C@@H]([C@@H](C)CC)NC([C@@H](NC([C@H](NC)CC(C)C)=O)[C@@H](C)O3)=O)=O)=O)=O)=O)=O)C3=O)cc1
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 943.19 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.

Recalculate based on batch purity %
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: Xu Y, Kersten RD, Nam SJ, Lu L, Al-Suwailem AM, Zheng H, Fenical W, Dorrestein PC, Moore BS, Qian PY. Bacterial biosynthesis and maturation of the didemnin anti-cancer agents. J Am Chem Soc. 2012 May 23;134(20):8625-32. doi: 10.1021/ja301735a. Epub 2012 Apr 6. PubMed PMID: 22458477; PubMed Central PMCID: PMC3401512. 2: Molinski TF, Ko J, Reynolds KA, Lievens SC, Skarda KR. N,N'-methyleno-didemnin A from the ascidian Trididemnum solidum. Complete NMR assignments and confirmation of the imidazolidinone ring by strategic analysis of 1J(CH). J Nat Prod. 2011 Apr 25;74(4):882-7. doi: 10.1021/np100846s. Epub 2011 Feb 22. PubMed PMID: 21341712; PubMed Central PMCID: PMC3694603. 3: Potts MB, McMillan EA, Rosales TI, Kim HS, Ou YH, Toombs JE, Brekken RA, Minden MD, MacMillan JB, White MA. Mode of action and pharmacogenomic biomarkers for exceptional responders to didemnin B. Nat Chem Biol. 2015 Jun;11(6):401-8. doi: 10.1038/nchembio.1797. Epub 2015 Apr 13. PubMed PMID: 25867045; PubMed Central PMCID: PMC4433765. 4: Henne WA, Kularatne SA, Ayala-López W, Doorneweerd DD, Stinnette TW, Lu Y, Low PS. Synthesis and activity of folate conjugated didemnin B for potential treatment of inflammatory diseases. Bioorg Med Chem Lett. 2012 Jan 1;22(1):709-12. doi: 10.1016/j.bmcl.2011.10.042. Epub 2011 Oct 21. PubMed PMID: 22100311. 5: Crampton SL, Adams EG, Kuentzel SL, Li LH, Badiner G, Bhuyan BK. Biochemical and cellular effects of didemnins A and B. Cancer Res. 1984 May;44(5):1796-801. PubMed PMID: 6713383. 6: Tsukimoto M, Nagaoka M, Shishido Y, Fujimoto J, Nishisaka F, Matsumoto S, Harunari E, Imada C, Matsuzaki T. Bacterial production of the tunicate-derived antitumor cyclic depsipeptide didemnin B. J Nat Prod. 2011 Nov 28;74(11):2329-31. doi: 10.1021/np200543z. Epub 2011 Oct 28. PubMed PMID: 22035372. 7: Hossain MB, Van Der Helm D, Antel J, Sheldrick GM, Weinheimer AJ, Sanduja SK. Crystal and molecular structure of didemnin A, an antiviral depsipeptide. Int J Pept Protein Res. 1996 Jan-Feb;47(1-2):20-7. PubMed PMID: 8907495. 8: Hetherington AM, Sawyez CG, Sutherland BG, Robson DL, Arya R, Kelly K, Jacobs RL, Borradaile NM. Treatment with didemnin B, an elongation factor 1A inhibitor, improves hepatic lipotoxicity in obese mice. Physiol Rep. 2016 Sep;4(17). pii: e12963. doi: 10.14814/phy2.12963. PubMed PMID: 27613825; PubMed Central PMCID: PMC5027364. 9: Xiao D, Vera MD, Liang B, Joullié MM. Total synthesis of a conformationally constrained didemnin B analog. J Org Chem. 2001 Apr 20;66(8):2734-42. PubMed PMID: 11304195. 10: Baker MA, Grubb DR, Lawen A. Didemnin B induces apoptosis in proliferating but not resting peripheral blood mononuclear cells. Apoptosis. 2002 Oct;7(5):407-12. PubMed PMID: 12207173. 11: Cain JM, Liu PY, Alberts DE, Gallion HH, Laufman L, O'Sullivan J, Weiss G, Bickers JN. Phase II trial of didemnin-B in advanced epithelial ovarian cancer. A Southwest Oncology Group study. Invest New Drugs. 1992 Apr;10(1):23-4. PubMed PMID: 1607250. 12: SirDeshpande BV, Toogood PL. Mechanism of protein synthesis inhibition by didemnin B in vitro. Biochemistry. 1995 Jul 18;34(28):9177-84. PubMed PMID: 7619818. 13: Stewart JA, Low JB, Roberts JD, Blow A. A phase I clinical trial of didemnin B. Cancer. 1991 Dec 15;68(12):2550-4. PubMed PMID: 1933801. 14: Weiss RB, Peterson BL, Allen SL, Browning SM, Duggan DB, Schiffer CA. A phase II trial of didemnin B in myeloma. A Cancer and Leukemia Group B (CALGB) study. Invest New Drugs. 1994;12(1):41-3. PubMed PMID: 7960604. 15: Williamson SK, Wolf MK, Eisenberger MA, O'Rourke M, Brannon W, Crawford ED. Phase II evaluation of didemnin B in hormonally refractory metastatic prostate cancer. A Southwest Oncology Group study. Invest New Drugs. 1995;13(2):167-70. PubMed PMID: 8617581. 16: Li LH, Timmins LG, Wallace TL, Krueger WC, Prairie MD, Im WB. Mechanism of action of didemnin B, a depsipeptide from the sea. Cancer Lett. 1984 Jul;23(3):279-88. PubMed PMID: 6744252. 17: Crews CM, Collins JL, Lane WS, Snapper ML, Schreiber SL. GTP-dependent binding of the antiproliferative agent didemnin to elongation factor 1 alpha. J Biol Chem. 1994 Jun 3;269(22):15411-4. PubMed PMID: 8195179. 18: Vera MD, Joullié MM. Natural products as probes of cell biology: 20 years of didemnin research. Med Res Rev. 2002 Mar;22(2):102-45. Review. PubMed PMID: 11857636. 19: Meng L, Sin N, Crews CM. The antiproliferative agent didemnin B uncompetitively inhibits palmitoyl protein thioesterase. Biochemistry. 1998 Jul 21;37(29):10488-92. PubMed PMID: 9671519. 20: Dorr FA, Kuhn JG, Phillips J, von Hoff DD. Phase I clinical and pharmacokinetic investigation of didemnin B, a cyclic depsipeptide. Eur J Cancer Clin Oncol. 1988 Nov;24(11):1699-706. PubMed PMID: 3208814.

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