4-o-methyl-phorbol-12,13-didecanoate profile

4-O-methyl-phorbol-12,13-didecanoate (PMA) is a potent tumor promoter, a member of the phorbol ester family. It is commonly used in research to activate protein kinase C (PKC), a key signaling enzyme involved in cell growth and differentiation. PMA's effects are attributed to its ability to bind to and activate PKC, leading to a cascade of downstream events, including the activation of transcription factors and the production of inflammatory mediators. PMA is synthesized from phorbol, a diterpene compound extracted from the plant Croton tiglium. Its synthesis involves multiple steps, including esterification and methylation reactions. The potent biological activity of PMA, its ability to activate PKC, and its role in tumor promotion make it a valuable tool for studying signal transduction pathways and the development of cancer. PMA is also used as a research tool to study the role of PKC in various cellular processes, including inflammation, immune responses, and apoptosis. Due to its potent activity and its ability to mimic the effects of tumor promoters, PMA is widely used in research to study the molecular mechanisms of cancer development.'

ID Source	ID
PubMed CID	119493
MeSH ID	M0071960

Synonym
54870-24-5
4-o-mepdd
4-o-methyl-phorbol-12,13-didecanoate
5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a-alpha,1b-beta,4,4a,7a-alpha,7b,8,9,9a-decahydro-7b-alpha,9-beta,9a-alpha-trihydroxy-3-hydroxymethyl-1,1,6,8-alpha-tetramethyl-4a-methoxy-, 9,9a-didecanoate
decanoic acid, 1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-7b-hydroxy-3-(hydroxymethyl)-4a-methoxy-1,1,6,8-tetramethyl-5-oxo-9ah-cyclopropa(3,4)benz(1,2-e)azulene-9,9a-diyl ester, (1ar-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
7b-hydroxy-3-(hydroxymethyl)-4a-methoxy-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9ah-cyclopropa[3,4]benzo[1,2-e]azulene-9,9a-diyl didecanoate
DTXSID60970210
[(1s,2s,6r,10s,11r,13s,14r,15r)-13-decanoyloxy-1-hydroxy-8-(hydroxymethyl)-6-methoxy-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] decanoate

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (20.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	2 (40.00)	29.6817
2010's	2 (40.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	5 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
pyridoxal phosphate Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.	2.17	1	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
npc 15437 NPC 15437: interacts with th C1 doamin of protein kinase C	2.02	1
pyridoxal phosphate-6-azophenyl-2',4'-disulfonic acid pyridoxal phosphate-6-azophenyl-2',4'-disulfonic acid: a novel antagonist that selectively blocks P2 purinoceptor receptors; a useful tool to study co-transmission in tissues when ATP and coexisting neurotransmitters act in concert. 5'-phosphopyridoxal-6-azobenzene-2,4-disulfonic acid : An arenesulfonic acid that is pyridoxal 5'-phosphate carrying an additional 2,4-disulfophenylazo substituent at position 6.	2.17	1	arenesulfonic acid; azobenzenes; methylpyridines; monohydroxypyridine; organic phosphate; pyridinecarbaldehyde	purinergic receptor P2X antagonist
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	2.02	1	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal metabolite
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.38	2	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
phorbols Phorbols: The parent alcohol of the tumor promoting compounds from CROTON OIL (Croton tiglium).	1.95	1	diterpene; terpenoid fundamental parent
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	2.02	1	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
arginine vasopressin Arginine Vasopressin: The predominant form of mammalian antidiuretic hormone. It is a nonapeptide containing an ARGININE at residue 8 and two disulfide-linked cysteines at residues of 1 and 6. Arg-vasopressin is used to treat DIABETES INSIPIDUS or to improve vasomotor tone and BLOOD PRESSURE.. argipressin : The predominant form of mammalian vasopressin (antidiuretic hormone). It is a nonapeptide containing an arginine at residue 8 and two disulfide-linked cysteines at residues of 1 and 6.	2.02	1	vasopressin	cardiovascular drug; hematologic agent; mitogen
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	2.02	1	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
piperidines Piperidines: A family of hexahydropyridines.	2.02	1

Condition	Relationship Strength	Studies
Hepatoblastoma A malignant neoplasm occurring in young children, primarily in the liver, composed of tissue resembling embryonal or fetal hepatic epithelium, or mixed epithelial and mesenchymal tissues. (Stedman, 25th ed)	2.02	1
Experimental Leukemia [description not available]	1.95	1
Leukemia, Lymphocytic [description not available]	1.95	1
Leukemia, Lymphoid Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.	1.95	1

4-o-methyl-phorbol-12,13-didecanoate

Cross-References

Synonyms (8)

Research

Studies (5)

Market Indicators

Research Demand Index: 12.53

Study Types