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Merck

P1269

Sigma-Aldrich

Phorbol 12,13-dibutyrate

≥98% (TLC), powder, PKC activator

Sinónimos:

PDBu

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About This Item

Fórmula empírica (notación de Hill):
C28H40O8
Número de CAS:
Peso molecular:
504.61
Beilstein/REAXYS Number:
6551234
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77

product name

Phorbol 12,13-dibutyrate, ≥98% (TLC), powder

Quality Level

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.

signalword

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

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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
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
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
Chengyin Li et al.
Journal of ethnopharmacology, 242, 112035-112035 (2019-06-22)
Dangguibuxue decoction (DGBX), is a well-known traditional Chinese medicine that contains two types of materials used to treat anemia. In this study, we aimed to explore the effect and mechanism of DGBX on abolishing erythroid progenitor cell (Ter119+CD71+) accumulation induced

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