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P1269

Sigma-Aldrich

Phorbol 12,13-dibutyrate

≥98% (TLC), powder

Synonym(s):

PDBu

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About This Item

Empirical Formula (Hill Notation):
C28H40O8
CAS Number:
37558-16-0
Molecular Weight:
504.61
Beilstein:
6551234
MDL number:
MFCD00036783
UNSPSC Code:
12352211
PubChem Substance ID:
24898178
NACRES:
NA.77

Quality Level

100

Assay

≥98% (TLC)

form

powder

color

clear light yellow, film

solubility

H2O: 30 μM
DMSO: soluble
acetone: soluble
ethanol: soluble

storage temp.

−20°C

SMILES string

CCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@@H](C=C(CO)C[C@@]3(O)[C@H]2C=C(C)C3=O)[C@@H]4C(C)(C)[C@]14OC(=O)CCC

InChI

1S/C28H40O8/c1-7-9-20(30)35-24-16(4)27(34)18(22-25(5,6)28(22,24)36-21(31)10-8-2)12-17(14-29)13-26(33)19(27)11-15(3)23(26)32/h11-12,16,18-19,22,24,29,33-34H,7-10,13-14H2,1-6H3/t16-,18+,19-,22-,24-,26-,27-,28-/m1/s1

InChI key

BQJRUJTZSGYBEZ-YVQNUNKESA-N

Gene Information

mouse ... Prkcd(18753)

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Application

Phorbol 12,13-dibutyrate has been used as a protein kinase C (PKC) activator to study its effects on human organic anion transporter 4 (hOAT4) activity. It has also been used as a PKC activator to analyze its effects on galectin-3 expression and matrix production in HL-1 cells.

Biochem/physiol Actions

Phorbol 12,13-dibutyrate (PDBu) is a potent activator of protein kinase C (PKC). It is more hydrophilic than phorbol 12-myristate 13-acetate (PMA), which facilitates washing PDBu out of cells in tissue culture. PDBu activates endothelial nitric oxide synthase expression in primary human umbilical vein endothelial cells, which in turn correlates with PKC α and ε expression.

Features and Benefits

Less hydrophobic then PMA, making it easier to wash out of cells in tissue culture.

Caution

Photosensitive

Reconstitution

Stock solution cannot be made in aqueous media; dissolve in a water-miscible organic solvent before dilution to working concentrations in aqueous media.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Carc. 2 - Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mayumi Shindo et al.
The Journal of biological chemistry, 278(20), 18448-18454 (2003-03-07)
Diacylglycerol kinase (DGK) and protein kinase C (PKC) are two distinct enzyme families associated with diacylglycerol. Both enzymes have cysteine-rich C1 domains (C1A, C1B, and C1C) in the regulatory region. Although most PKC C1 domains strongly bind phorbol esters, there
Kazuhiro Irie et al.
Pharmacology & therapeutics, 93(2-3), 271-281 (2002-08-23)
Conventional and novel protein kinase C (PKC) isozymes contain two cysteine-rich C1 domains (C1A and C1B), both of which are candidate phorbol-12, 13-dibutyrate (PDBu)-binding sites. We synthesized C1 peptides of 50-70 residues corresponding to all PKC isozyme C1 domains using
Quynh Nhu Dinh et al.
Aging, 9(6), 1595-1606 (2017-07-01)
Aging is commonly associated with chronic low-grade inflammation and hypertension but it is unknown whether a cause-effect relationship exists between them. We compared the sensitivity of young adult (8-12 w) and aged (23-31 mo) male C57Bl6J mice to develop hypertension
T Hori et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 19(17), 7262-7267 (1999-08-25)
Phorbol ester facilitates transmitter release at a variety of synapses, and the phorbol ester-induced synaptic potentiation (PESP) is a model for presynaptic facilitation. To address the mechanism underlying PESP, we have made paired whole-cell recordings from the giant presynaptic terminal
Vesna Lazarevic et al.
International journal of molecular sciences, 20(17) (2019-09-05)
Major depressive disorder is one of the most common neuropsychiatric disorders worldwide. The treatment of choice that shows good efficacy in mood stabilization is based on selective serotonin reuptake inhibitors (SSRIs). Their primary mechanism of action is considered to be
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