MedKoo Cat#: 461784 | Name: Sapintoxin D

Description:

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

Sapintoxin D is a fluorescent phorbol ester and selective activator of protein kinase C.

Chemical Structure

Sapintoxin D
Sapintoxin D
CAS#80998-07-8

Theoretical Analysis

MedKoo Cat#: 461784

Name: Sapintoxin D

CAS#: 80998-07-8

Chemical Formula: C30H37NO8

Exact Mass: 539.2519

Molecular Weight: 539.62

Elemental Analysis: C, 66.77; H, 6.91; N, 2.60; O, 23.72

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
Sapintoxin D;
IUPAC/Chemical Name
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl 2-(methylamino)benzoate
InChi Key
UPAIGGMQTARRMN-CSSCWBSHSA-N
InChi Code
InChI=1S/C30H37NO8/c1-15-11-22-28(36,24(15)34)13-18(14-32)12-20-23-27(4,5)30(23,39-17(3)33)25(16(2)29(20,22)37)38-26(35)19-9-7-8-10-21(19)31-6/h7-12,16,20,22-23,25,31-32,36-37H,13-14H2,1-6H3/t16-,20+,22-,23-,25-,28-,29-,30-/m1/s1
SMILES Code
O=C(O[C@H]([C@H]1C)[C@]2(OC(C)=O)[C@@]([C@@](C=C(CO)C[C@]34O)([H])[C@@]1(O)[C@]4([H])C=C(C)C3=O)([H])C2(C)C)C5=CC=CC=C5NC
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 539.62 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.

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: McLean JR, Plant M, Lecuyer DW, Davidson C, Truong J. Sapintoxin D is a weak tumour promoter in Sencar mouse skin. J Pharm Pharmacol. 1995 Mar;47(3):263. PubMed PMID: 7602494. 2: Wickley PJ, Yuge R, Martin BA, Meyer JS, Damron DS. Propofol activates and allosterically modulates recombinant protein kinase C epsilon. Anesthesiology. 2009 Jul;111(1):36-43. doi: 10.1097/ALN.0b013e3181a3274b. PubMed PMID: 19512879; PubMed Central PMCID: PMC2747769. 3: Glover KP, Chen Z, Markell LK, Han X. Synergistic Gene Expression Signature Observed in TK6 Cells upon Co-Exposure to UVC-Irradiation and Protein Kinase C-Activating Tumor Promoters. PLoS One. 2015 Oct 2;10(10):e0139850. doi: 10.1371/journal.pone.0139850. eCollection 2015. PubMed PMID: 26431317; PubMed Central PMCID: PMC4592187. 4: Brooks G, Birch M, Hart IR. Effects of biologically active tumour-promoting and non-promoting phorbol esters on in vitro growth of melanocytic cells. Pigment Cell Res. 1990 Mar-Apr;3(2):98-100. PubMed PMID: 2385570. 5: Slater SJ, Taddeo FJ, Mazurek A, Stagliano BA, Milano SK, Kelly MB, Ho C, Stubbs CD. Inhibition of membrane lipid-independent protein kinase Calpha activity by phorbol esters, diacylglycerols, and bryostatin-1. J Biol Chem. 1998 Sep 4;273(36):23160-8. PubMed PMID: 9722545. 6: Brooks G, Evans AT, Aitken A, Evans FJ. Tumour-promoting and hyperplastic effects of phorbol and daphnane esters in CD-1 mouse skin and a synergistic effect of calcium ionophore with the non-promoting activator of protein kinase C, sapintoxin A. Carcinogenesis. 1989 Feb;10(2):283-8. PubMed PMID: 2912580. 7: Kedei N, Lubart E, Lewin NE, Telek A, Lim L, Mannan P, Garfield SH, Kraft MB, Keck GE, Kolusheva S, Jelinek R, Blumberg PM. Some phorbol esters might partially resemble bryostatin 1 in their actions on LNCaP prostate cancer cells and U937 leukemia cells. Chembiochem. 2011 May 16;12(8):1242-51. doi: 10.1002/cbic.201100064. Epub 2011 May 3. PubMed PMID: 21542090; PubMed Central PMCID: PMC3313843. 8: Pedron T, Girard R, Chaby R. Down-modulation through protein kinase C-alpha of lipopolysaccharide-induced expression of membrane CD14 in mouse bone marrow granulocytes. Biochem Pharmacol. 2000 Dec 15;60(12):1837-43. PubMed PMID: 11108799. 9: Slater SJ, Ho C, Kelly MB, Larkin JD, Taddeo FJ, Yeager MD, Stubbs CD. Protein kinase Calpha contains two activator binding sites that bind phorbol esters and diacylglycerols with opposite affinities. J Biol Chem. 1996 Mar 1;271(9):4627-31. PubMed PMID: 8617724. 10: Das J, Addona GH, Sandberg WS, Husain SS, Stehle T, Miller KW. Identification of a general anesthetic binding site in the diacylglycerol-binding domain of protein kinase Cdelta. J Biol Chem. 2004 Sep 3;279(36):37964-72. Epub 2004 Jul 2. PubMed PMID: 15234976. 11: Husøy T, Mikalsen SO, Sanner T. Effects of five phorbol esters on gap junctional intercellular communication, morphological transformation and epidermal growth factor binding in Syrian hamster embryo cells. Carcinogenesis. 1993 Jan;14(1):73-7. PubMed PMID: 8425273. 12: Brooks G, Brooks SF. Both tumour-promoting and non-promoting phorbol esters inhibit [125I]EGF binding and stimulate the phosphorylation of an 80 kd protein kinase C substrate protein in intact quiescent swiss 3T3 cells. Carcinogenesis. 1990 Apr;11(4):667-72. PubMed PMID: 2323005. 13: Evans AT, Gordge PC, Sahni V, Evans FJ. The potent irritancy of the daphnane orthoester, resiniferatoxin, exhibits features of a mixed aetiology. J Pharm Pharmacol. 1992 Apr;44(4):361-3. PubMed PMID: 1355552. 14: Das J, Pany S, Rahman GM, Slater SJ. PKC epsilon has an alcohol-binding site in its second cysteine-rich regulatory domain. Biochem J. 2009 Jul 15;421(3):405-13. doi: 10.1042/BJ20082271. Erratum in: Biochem J. 2009 Nov 1;423(3):442. PubMed PMID: 19432558. 15: Ho C, Slater SJ, Stagliano B, Stubbs CD. The C1 domain of protein kinase C as a lipid bilayer surface sensing module. Biochemistry. 2001 Aug 28;40(34):10334-41. PubMed PMID: 11513612. 16: Ho C, Slater SJ, Stagliano BA, Stubbs CD. Conformation of the C1 phorbol-ester-binding domain participates in the activating conformational change of protein kinase C. Biochem J. 1999 Dec 1;344 Pt 2:451-60. PubMed PMID: 10567228; PubMed Central PMCID: PMC1220663. 17: Majhi A, Rahman GM, Panchal S, Das J. Binding of curcumin and its long chain derivatives to the activator binding domain of novel protein kinase C. Bioorg Med Chem. 2010 Feb 15;18(4):1591-8. doi: 10.1016/j.bmc.2009.12.075. Epub 2010 Jan 6. PubMed PMID: 20100661; PubMed Central PMCID: PMC2843403. 18: Geiges D, Meyer T, Marte B, Vanek M, Weissgerber G, Stabel S, Pfeilschifter J, Fabbro D, Huwiler A. Activation of protein kinase C subtypes alpha, gamma, delta, epsilon, zeta, and eta by tumor-promoting and nontumor-promoting agents. Biochem Pharmacol. 1997 Mar 21;53(6):865-75. PubMed PMID: 9113106. 19: Slater SJ, Seiz JL, Stagliano BA, Cook AC, Milano SK, Ho C, Stubbs CD. Low- and high-affinity phorbol ester and diglyceride interactions with protein kinase C: 1-O-alkyl-2-acyl-sn-glycerol enhances phorbol ester- and diacylglycerol-induced activity but alone does not induce activity. Biochemistry. 2001 May 22;40(20):6085-92. PubMed PMID: 11352745.