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MedKoo Cat#: 597903 | Name: Calyculin A

Description:

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

Calyculin A is a natural, cell-permeable inhibitor of the serine-threonine protein phosphatases (PP) PP1 and PP2A (IC50s = 0.3-0.7 and 0.5-1 nM, respectively). It is without significant effect against PP2B, PP2C, and PP4.2 Through its effects on PP1 and PP2A, calyculin A has been shown to either promote or inhibit cancer cell growth in tumor cell lines and animal models.

Chemical Structure

Calyculin A
Calyculin A
CAS#101932-71-2

Theoretical Analysis

MedKoo Cat#: 597903

Name: Calyculin A

CAS#: 101932-71-2

Chemical Formula: C50H81N4O15P

Exact Mass: 1008.5436

Molecular Weight: 1009.18

Elemental Analysis: C, 59.51; H, 8.09; N, 5.55; O, 23.78; P, 3.07

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
Calyculin A; Hemicalyculin A;
IUPAC/Chemical Name
(2R,3R,5R,7S,8S,9R)-2-((1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraen-1-yl)-7-((E)-3-(2-((S)-4-((2S,3S,4S)-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanamido)butan-2-yl)oxazol-4-yl)allyl)-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-3-yl dihydrogen phosphate
InChi Key
FKAWLXNLHHIHLA-YCBIHMBMSA-N
InChi Code
InChI=1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m0/s1
SMILES Code
O[C@@H]([C@H]([C@@H](N(C)C)COC)O)C(NCC[C@@H](C1=NC(/C=C/C[C@@H]([C@@H](C)[C@H](O)C2)O[C@@]32C(C)(C)[C@@H](OP(O)(O)=O)[C@@H]([C@@H](OC)C[C@H](O)[C@H](C)[C@H](O)[C@H](C)/C=C(C)/C(C)=C/C=C/C(C)=C\C#N)O3)=CO1)C)=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
>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 1,009.18 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: Wakimoto T, Egami Y, Nakashima Y, Wakimoto Y, Mori T, Awakawa T, Ito T, Kenmoku H, Asakawa Y, Piel J, Abe I. Calyculin biogenesis from a pyrophosphate protoxin produced by a sponge symbiont. Nat Chem Biol. 2014 Aug;10(8):648-55. doi: 10.1038/nchembio.1573. Epub 2014 Jun 29. PubMed PMID: 24974231. 2: Almasry M, Jemaà M, Mischitelli M, Faggio C, Lang F. Stimulation of Suicidal Erythrocyte Death by Phosphatase Inhibitor Calyculin A. Cell Physiol Biochem. 2016;40(1-2):163-171. Epub 2016 Nov 18. PubMed PMID: 27855413. 3: Chartier L, Rankin LL, Allen RE, Kato Y, Fusetani N, Karaki H, Watabe S, Hartshorne DJ. Calyculin-A increases the level of protein phosphorylation and changes the shape of 3T3 fibroblasts. Cell Motil Cytoskeleton. 1991;18(1):26-40. PubMed PMID: 1848484. 4: Edelson JR, Brautigan DL. The Discodermia calyx toxin calyculin a enhances cyclin D1 phosphorylation and degradation, and arrests cell cycle progression in human breast cancer cells. Toxins (Basel). 2011 Jan;3(1):105-19. doi: 10.3390/toxins3010105. Epub 2011 Jan 24. PubMed PMID: 22069692; PubMed Central PMCID: PMC3210456. 5: Gutierrez LM, Quintanar JL, Rueda J, Viniegra S, Reig JA. The protein phosphatase inhibitor calyculin-A affects catecholamine secretion and granular distribution in cultured adrenomedullary chromaffin cells. Eur J Cell Biol. 1995 Sep;68(1):88-95. PubMed PMID: 8549595. 6: Holy M, Brautigan DL. Calyculin A from Discodermia calyx is a dual action toxin that blocks calcium influx and inhibits protein Ser/Thr phosphatases. Toxins (Basel). 2012 Oct;4(10):940-54. doi: 10.3390/toxins4100940. Epub 2012 Oct 22. PubMed PMID: 23162706; PubMed Central PMCID: PMC3496997. 7: Leopoldt D, Yee HF Jr, Rozengurt E. Calyculin-A induces focal adhesion assembly and tyrosine phosphorylation of p125(Fak), p130(Cas), and paxillin in Swiss 3T3 cells. J Cell Physiol. 2001 Jul;188(1):106-19. PubMed PMID: 11382927. 8: Pozuelo-Rubio M, Leslie NR, Murphy J, Mackintosh C. Mechanism of activation of PKB/Akt by the protein phosphatase inhibitor Calyculin A. Cell Biochem Biophys. 2010 Dec;58(3):147-56. doi: 10.1007/s12013-010-9101-4. PubMed PMID: 20717744; PubMed Central PMCID: PMC3627045. 9: Yu G, Li Y, Tian Q, Liu R, Wang Q, Wang JZ, Wang X. Berberine attenuates calyculin A-induced cytotoxicity and Tau hyperphosphorylation in HEK293 cells. J Alzheimers Dis. 2011;24(3):525-35. doi: 10.3233/JAD-2011-101779. PubMed PMID: 21297267. 10: Kramer JM, Evans A, Drury K, Moore K. Calyculin-A improves chromosome condensation for cytogenetic analysis of blastomeres from bovine and murine eight-cell stage embryos. Theriogenology. 2008 Sep 1;70(4):692-703. doi: 10.1016/j.theriogenology.2008.04.048. Epub 2008 Jun 16. PubMed PMID: 18556054. 11: Kita A, Matsunaga S, Takai A, Kataiwa H, Wakimoto T, Fusetani N, Isobe M, Miki K. Crystal structure of the complex between calyculin A and the catalytic subunit of protein phosphatase 1. Structure. 2002 May;10(5):715-24. Erratum in: Structure (Camb). 2002 Aug;10(8):1149.. PubMed PMID: 12015153. 12: Wakimoto T, Egami Y, Abe I. Calyculin: Nature's way of making the sponge-derived cytotoxin. Nat Prod Rep. 2016 Jun 2;33(6):751-60. doi: 10.1039/c5np00123d. Review. PubMed PMID: 26923942. 13: Okamura H, Yoshida K, Morimoto H, Haneji T. PTEN expression elicited by EGR-1 transcription factor in calyculin A-induced apoptotic cells. J Cell Biochem. 2005 Jan 1;94(1):117-25. PubMed PMID: 15517593. 14: Lindvall MK, Pihko PM, Koskinen AM. The binding mode of calyculin A to protein phosphatase-1. A novel spiroketal vector model. J Biol Chem. 1997 Sep 12;272(37):23312-6. PubMed PMID: 9287341. 15: Kowalska A, Srebniak M, Wawrzkiewicz A, Kamiński K. The influence of calyculin A on lymphocytes in vitro. J Appl Genet. 2003;44(3):413-8. PubMed PMID: 12923316. 16: Tosuji H, Fusetani N, Seki Y. Calyculin A causes the activation of histone H1 kinase and condensation of chromosomes in unfertilized sea urchin eggs independently of the maturation-promoting factor. Comp Biochem Physiol C Toxicol Pharmacol. 2003 Aug;135(4):415-24. PubMed PMID: 12965186. 17: Qiu L, Yoshida K, Amorim BR, Okamura H, Haneji T. Calyculin A stimulates the expression of TNF-alpha mRNA via phosphorylation of Akt in mouse osteoblastic MC3T3-E1 cells. Mol Cell Endocrinol. 2007 Jun 15;271(1-2):38-44. Epub 2007 Apr 4. PubMed PMID: 17482757. 18: Yang IC, Cheng TH, Wang F, Price EM, Hwang TC. Modulation of CFTR chloride channels by calyculin A and genistein. Am J Physiol. 1997 Jan;272(1 Pt 1):C142-55. PubMed PMID: 9038820. 19: Volter KE, Pierens GK, Quinn RJ, Wakimoto T, Matsunaga S, Fusetani N. The solution structures of calyculin A and dephosphonocalyculin A by NMR. Bioorg Med Chem Lett. 1999 Mar 8;9(5):717-22. PubMed PMID: 10201835. 20: Ishihara H, Martin BL, Brautigan DL, Karaki H, Ozaki H, Kato Y, Fusetani N, Watabe S, Hashimoto K, Uemura D, et al. Calyculin A and okadaic acid: inhibitors of protein phosphatase activity. Biochem Biophys Res Commun. 1989 Mar 31;159(3):871-7. PubMed PMID: 2539153.