Sapintoxin A

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

MedKoo CAT#: 461783

CAS#: 79083-69-5

Description: Sapintoxin A is a naturally occurring, highly fluorescent phorbol ester that potently binds to and activates the phorbol ester receptor, protein kinase C (PKC).


Chemical Structure

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Sapintoxin A
CAS# 79083-69-5

Theoretical Analysis

MedKoo Cat#: 461783
Name: Sapintoxin A
CAS#: 79083-69-5
Chemical Formula: C30H37NO7
Exact Mass: 523.257
Molecular Weight: 23.62
Elemental Analysis: C, 68.81; H, 7.12; N, 2.68; O, 21.39

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Sapintoxin A;

IUPAC/Chemical Name: (1aR,1bS,4aS,7aR,7bR,8R,9R,9aS)-9a-acetoxy-7b-hydroxy-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: KBSBUGUKMIUBEE-WQYXQGCUSA-N

InChi Code: InChI=1S/C30H37NO7/c1-15-11-21-20(24(15)34)12-18(14-32)13-22-25-28(4,5)30(25,38-17(3)33)26(16(2)29(21,22)36)37-27(35)19-9-7-8-10-23(19)31-6/h7-11,13,16,20-22,25-26,31-32,36H,12,14H2,1-6H3/t16-,20+,21-,22+,25-,26-,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@]34[H])([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

Preparing Stock Solutions

The following data is based on the product molecular weight 23.62 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

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1: Brooks G, Evans AT, Aitken A, Evans FJ. Sapintoxin A. A fluorescent phorbol ester that is a potent activator of protein kinase C but is not a tumour promoter. Cancer Lett. 1987 Dec;38(1-2):165-70. PubMed PMID: 3690506.

2: Taylor SE, Gafur MA, Choudhury AK, Evans FJ. Sapintoxin A, a new biologically active nitrogen containing phorbol ester. Experientia. 1981;37(7):681-2. PubMed PMID: 7274376.

3: 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.

4: Dimitrijević SM, Ryves WJ, Parker PJ, Evans FJ. Characterization of phorbol ester binding to protein kinase C isotypes. Mol Pharmacol. 1995 Aug;48(2):259-67. PubMed PMID: 7651359.

5: 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.

6: Duyster J, Schwende H, Fitzke E, Hidaka H, Dieter P. Different roles of protein kinase C-beta and -delta in arachidonic acid cascade, superoxide formation and phosphoinositide hydrolysis. Biochem J. 1993 May 15;292 ( Pt 1):203-7. PubMed PMID: 8389125; PubMed Central PMCID: PMC1134289.

7: Evans AT, Brooks G, Evans FJ. Non-promoting diterpene esters can induce Epstein-Barr virus early antigen expression in the Raji cell line. Cancer Lett. 1990 Jan;49(1):25-9. PubMed PMID: 2302694.

8: 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.

9: 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.

10: Ryves WJ, Evans AT, Olivier AR, Parker PJ, Evans FJ. Activation of the PKC-isotypes alpha, beta 1, gamma, delta and epsilon by phorbol esters of different biological activities. FEBS Lett. 1991 Aug 19;288(1-2):5-9. PubMed PMID: 1879564.

11: Brooks G, Goss MW, Hart IR. Differential induction of 12-O-tetradecanoylphorbol-13-acetate sequence gene expression in murine melanocytes and melanoma cells. Mol Carcinog. 1992;5(4):328-33. PubMed PMID: 1379817.

12: Merritt JE, Moores KE, Evans AT, Sharma P, Evans FJ, MacPhee CH. Involvement of calcium in modulation of neutrophil function by phorbol esters that activate protein kinase C isotypes and related enzymes. Biochem J. 1993 Feb 1;289 ( Pt 3):919-26. PubMed PMID: 8435086; PubMed Central PMCID: PMC1132263.