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MedKoo Cat#: 461783 | Name: Sapintoxin A

Description:

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

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

Sapintoxin A
Sapintoxin A
CAS#79083-69-5

Theoretical Analysis

MedKoo Cat#: 461783

Name: Sapintoxin A

CAS#: 79083-69-5

Chemical Formula: C30H37NO7

Exact Mass: 523.2570

Molecular Weight: 23.62

Elemental Analysis: C, 68.81; H, 7.12; N, 2.68; O, 21.39

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 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
More Info

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
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.