Phorbol-12-myristate-13-acetate

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Structural formula
Structural formula of phorbol-12-myristate-13-acetate
General
Surname Phorbol-12-myristate-13-acetate
other names
  • 12- O -Tetradecanoylphorbol-13-acetate
  • 4 β , 9 α , 12 β , 13 α , 20-pentahydroxytiglia-1,6-diene-3-one-12-tetradecanoate-13-acetate
  • PMA
  • TPA
Molecular formula C 36 H 56 O 8
Brief description

colorless powder

External identifiers / databases
CAS number 16561-29-8
EC number 605-413-5
ECHA InfoCard 100.109.485
PubChem 27924
Wikidata Q416716
properties
Molar mass 616.83 g mol −1
Physical state

firmly

Melting point

50-60 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315
P: no P-phrases
Toxicological data

0.309 mg kg −1 ( LD 50 ,  mouse ,  iv )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phorbol-12-myristate-13-acetate (PMA), alternatively also 12- O -tetradecanoylphorbol-13-acetate or tetradecanoylphorbol-acetate (TPA), belongs to the group of phorbol esters. The molecule is used in biochemical research to activate protein kinase C (PKC) as a structural analog of diacylglycerol. The effect of PMA results from its structural similarity to one of the natural activators of the PKC isoforms, diacylglycerol .

PMA is a subject of study in the treatment of leukemia . It is particularly useful in cancer diagnostics because it can serve as a B-cell -specific mitogen in a cytogenetic test. In ELISPOT , phorbol esters such as PMA are used as positive controls to demonstrate cell viability and the secretion of cytokines in the cells used.

PMA was first found in a Southeast Asian plant belonging to the Croton genus , which, when touched, causes a rash similar to poison sumac . Plants with higher contents of phorbol esters are problematic feedstuffs in the animal fattening of herbivores.

Individual evidence

  1. ↑ a b c d e f data sheet Phorbol 12-myristate 13-acetate, ≥99% (TLC), film or powder from Sigma-Aldrich , accessed on October 18, 2012 ( PDF ).
  2. ↑ M. Castagna, Y. Takai, K. Kaibuchi, K. Sano, U. Kikkawa, Y. Nishizuka: Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters . In: Journal of Biological Chemistry . tape 257 , no. 13 , October 7, 1982, pp. 7847-7851 .
  3. ↑ Peter M. Blumberg: Protein Kinase C as the Receptor for the Phorbol Ester Tumor Promoters: Sixth Rhoads Memorial Award Lecture . In: Cancer Research . tape 48 , no. 1 , 1988, p. 1-8 .
  4. ↑ JE Niedel, LJ Kuhn, GR Vandenbark: phorbol diesters receptor copurifies with protein kinase C . In: Proceedings of the National Academy of Sciences . tape 80 , no. 1 , 1983, p. 36-40 , doi : 10.1073 / pnas.80.1.36 .
  5. ↑ Margaret J. Barch, T. Knutsen, Jack L. Spurbeck et al. (Ed.): The AGT cytogenetics laboratory manual . 3. Edition. tape 666 . Lippincott-Raven Publishers, Philadelphia 1997.
  6. ^ S. Palzer, T. Bailey, C. Hartnett, A. Grant, M. Tsang, AE Kalyuzhny: Simultaneous detection of multiple cytokines in ELISPOT assays. In: Methods in Molecular Biology (2005), Vol. 302, pp. 273-288. PMID 15937361 .
  7. ↑ XL Zhang, L. Wang, F. Li, K. Yu, MK Wang: Cytotoxic Phorbol Esters of Croton tiglium. In: J Nat Prod . (2013), Volume 76, Issue 5, pp. 858-864. doi: 10.1021 / np300832n . PMID 23701597 .
  8. ↑ G. Goel, HP Makkar, G. Francis, K. Becker: Phorbol esters: structure, biological activity, and toxicity in animals. In: Int J Toxicol . (2007), Volume 26, Issue 4, pp. 279-288. PMID 17661218 .