Compounds > 12-deoxyphorbol-13-isobutyrate-20-acetate
Page last updated: 2024-12-10

12-deoxyphorbol-13-isobutyrate-20-acetate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## 12-deoxyphorbol-13-isobutyrate-20-acetate (DPBA)

**12-deoxyphorbol-13-isobutyrate-20-acetate (DPBA)** is a potent **tumor promoter** and a **protein kinase C (PKC) activator**. It's a derivative of **phorbol ester**, a class of compounds derived from the plant **Croton tiglium**.

**Here's why DPBA is important for research:**

**1. Studying Tumor Promotion:**

* DPBA is a valuable tool for **investigating the mechanisms of tumor promotion**. It mimics the action of naturally occurring tumor promoters, enabling researchers to study how these compounds contribute to cancer development.
* By understanding the molecular pathways involved in tumor promotion, scientists can develop **strategies for preventing and treating cancer**.

**2. Activating Protein Kinase C (PKC):**

* DPBA acts as a **potent activator of PKC**, a family of enzymes involved in various cellular processes, including cell growth, differentiation, and apoptosis.
* Studying the effects of DPBA on PKC activity helps researchers understand the role of PKC in various physiological and pathological conditions, including cancer.

**3. Understanding Signal Transduction Pathways:**

* DPBA triggers a cascade of events involving various signaling pathways within cells. Researchers use this compound to **study signal transduction pathways** and understand how they are affected by tumor promoters.

**4. Drug Discovery and Development:**

* DPBA serves as a **lead compound for developing new drugs** that target PKC or other pathways involved in cancer development.
* By understanding the mechanism of action of DPBA, scientists can design drugs that **specifically target tumor promoters** or other cancer-related pathways.

**However, it's important to note that:**

* DPBA is **highly toxic** and should be handled with extreme caution in a laboratory setting.
* It's a **powerful tumor promoter** and should not be used in humans or animals without proper scientific oversight.

**Overall, 12-deoxyphorbol-13-isobutyrate-20-acetate (DPBA) is a valuable research tool that has significantly contributed to our understanding of tumor promotion, PKC activation, and signal transduction pathways.** It continues to play a vital role in advancing cancer research and drug development.

12-deoxyphorbol-13-isobutyrate-20-acetate: RN given refers to (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9aalpha))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3035003
CHEMBL ID486418
MeSH IDM0138115

Synonyms (12)

Synonym
12-deoxyphorbol-13-(2-methylpropionate)-20-acetate
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-3-(acetoxymethyl)-1,1,6,8-alpha-tetramethyl-4a-beta,7b-alpha,9a-alpha-trihydroxy-, 9a-isobutyrate
propanoic acid, 2-methyl-, 3-((acetyloxy)methyl)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-9ah-cyclopropa(3,4)benz(1,2-e)azulen-9a-yl ester, (1ar-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9aalpha))-
12-deoxy-phorbol, 20-acetate-13-isobutyrate
12-deoxy-phorbol-13-isobutyrate-20-acetate
12-deoxyphorbol-13-isobutyrate-20-acetate
25090-71-5
CHEMBL486418
propanoic acid,2-methyl-,(1ar,1bs,4ar,7as,7br,8r,9as)-3-[(acetyloxy)methyl]-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-9ah-cyclopropa[3,4]benz[1,2-e]azulen-9a-ylester
[(1r,2s,6r,10s,11r,13s,15r)-8-(acetyloxymethyl)-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] 2-methylpropanoate
DTXSID10947952
3-[(acetyloxy)methyl]-4a,7b-dihydroxy-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]azulen-9a-yl 2-methylpropanoate
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID334633Skin irritant activity in NMRI mouse ear assessed as irritancy 50 after 24 hrs
AID334632Skin irritant activity in NMRI mouse ear assessed as irritant dose 50 per ear after 24 hrs
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (33.33)18.7374
1990's9 (50.00)18.2507
2000's3 (16.67)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.28

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.28 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index4.33 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.28)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
histamine
[no description available]		1.9710aralkylamino compound;
imidazoles		human metabolite;
mouse metabolite;
neurotransmitter
verapamil
Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.		1.9810aromatic ether;
nitrile;
polyether;
tertiary amino compound
halothane
[no description available]		1.9910haloalkane;
organobromine compound;
organochlorine compound;
organofluorine compound		inhalation anaesthetic
isoflurane
Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.		1.9910organofluorine compoundinhalation anaesthetic
nicardipine
Nicardipine: A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents.. nicardipine : A racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension.. 2-[benzyl(methyl)amino]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine substituted by a methyl, {2-[benzyl(methyl)amino]ethoxy}carbonyl, 3-nitrophenyl, methoxycarbonyl and methyl groups at positions 2, 3, 4, 5 and 6, respectively.		1.9810benzenes;
C-nitro compound;
diester;
dihydropyridine;
methyl ester;
tertiary amino compound
potassium chloride
Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.		2.6930inorganic chloride;
inorganic potassium salt;
potassium salt		fertilizer
ro 31-8220
Ro 31-8220: a protein kinase C inhibitor		1.9810imidothiocarbamic ester;
indoles;
maleimides		EC 2.7.11.13 (protein kinase C) inhibitor
thymeleatoxin
thymeleatoxin: causes translocation & down-regulation of multiple protein kinase C isozymes		1.9810
w 7
W 7: RN given refers to parent cpd; structure; calmodulin antagonist		1.9710
carbachol
Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.		210ammonium salt;
carbamate ester		cardiotonic drug;
miotic;
muscarinic agonist;
nicotinic acetylcholine receptor agonist;
non-narcotic analgesic
sucrose
Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.		1.9810glycosyl glycosidealgal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
sweetening agent
phenylephrine
Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.		3.2460phenols;
phenylethanolamines;
secondary amino compound		alpha-adrenergic agonist;
cardiotonic drug;
mydriatic agent;
nasal decongestant;
protective agent;
sympathomimetic agent;
vasoconstrictor agent
egtazic acid
Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.		1.9810diether;
tertiary amino compound;
tetracarboxylic acid		chelator
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.		1.9710acetate 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
colforsin
Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.		1.9710acetate ester;
cyclic ketone;
labdane diterpenoid;
organic heterotricyclic compound;
tertiary alpha-hydroxy ketone;
triol		adenylate cyclase agonist;
anti-HIV agent;
antihypertensive agent;
plant metabolite;
platelet aggregation inhibitor;
protein kinase A agonist
fura-2
Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.		2.3920
leupeptin
[no description available]		1.9710aldehyde;
tripeptide		bacterial metabolite;
calpain inhibitor;
cathepsin B inhibitor;
EC 3.4.21.4 (trypsin) inhibitor;
serine protease inhibitor
12-deoxyphorbolphenylacetate
12-deoxyphorbolphenylacetate: RN given refers to (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9aalpha))-isomer		1.9810
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		1.9710
leupeptins
Leupeptins: A group of acylated oligopeptides produced by Actinomycetes that function as protease inhibitors. They have been known to inhibit to varying degrees trypsin, plasmin, KALLIKREINS, papain and the cathepsins.		1.9710
inositol 1,4,5-trisphosphate
Inositol 1,4,5-Trisphosphate: Intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane. Inositol 1,4,5-trisphosphate is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin.		1.9810myo-inositol trisphosphatemouse metabolite
phalloidine
Phalloidine: Very toxic polypeptide isolated mainly from AMANITA phalloides (Agaricaceae) or death cup; causes fatal liver, kidney and CNS damage in mushroom poisoning; used in the study of liver damage.. phalloidin : A homodetic bicyclic heptapeptide having a sulfide bridge.		2.0410homodetic cyclic peptide
oleic acid
Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.		1.9910octadec-9-enoic acidantioxidant;
Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
Escherichia coli metabolite;
mouse metabolite;
plant metabolite;
solvent
dinoprost
Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.		1.9810monocarboxylic acid;
prostaglandins Falpha		human metabolite;
mouse metabolite
thromboxane a2
Thromboxane A2: An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).. thromboxane A2 : A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.		1.9910epoxy monocarboxylic acid;
thromboxanes A		mouse metabolite
15-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic acid
15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid: A stable prostaglandin endoperoxide analog which serves as a thromboxane mimetic. Its actions include mimicking the hydro-osmotic effect of VASOPRESSIN and activation of TYPE C PHOSPHOLIPASES. (From J Pharmacol Exp Ther 1983;224(1): 108-117; Biochem J 1984;222(1):103-110)		1.9910
1-oleoyl-2-acetylglycerol
[no description available]		1.96101,2-diglyceride
staurosporine
staurosporinium : Conjugate acid of staurosporine.		2.3920ammonium ion derivative
jasplakinolide
jasplakinolide: cyclodepsipeptide isolated from marine sponge Jaspis; active against Candida; RN refers to 2S-(2R*,4E,6S*,8R*)-isomer; structure in first source. jaspamide : A cyclodepsipeptide isolated from Jaspis splendens and has been shown to exhibit antineoplastic activity. It is an actin polymerization and stabilization inducer.		2.0410cyclodepsipeptide;
phenols		actin polymerisation inducer;
animal metabolite;
antifungal agent;
antineoplastic agent;
apoptosis inducer;
marine metabolite;
neuroprotective agent
calcimycin
Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.		1.9810benzoxazole
pituitrin
Pituitrin: A substance or extract from the neurohypophysis (PITUITARY GLAND, POSTERIOR).		1.9710
ConditionIndicatedRelationship StrengthStudiesTrials
Coarctation of Aorta
[description not available]		01.9810
Aortic Coarctation
A birth defect characterized by the narrowing of the AORTA that can be of varying degree and at any point from the transverse arch to the iliac bifurcation. Aortic coarctation causes arterial HYPERTENSION before the point of narrowing and arterial HYPOTENSION beyond the narrowed portion.		01.9810
Hypertrophy
General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).		01.9810
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		03.2360
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		0210
Cardiac Diseases
[description not available]		01.9710
Spasmophilia
[description not available]		01.9710
Heart Diseases
Pathological conditions involving the HEART including its structural and functional abnormalities.		01.9710
Blood Pressure, High
[description not available]		01.9710
Hypertension
Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.		01.9710