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P1269

Sigma-Aldrich

Phorbol 12,13-dibutyrate

≥98% (TLC), powder, PKC activator

Synonyme(s) :

PDBu

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About This Item

Formule empirique (notation de Hill):
C28H40O8
Numéro CAS:
37558-16-0
Poids moléculaire :
504.61
Numéro Beilstein :
6551234
Numéro MDL:
MFCD00036783
Code UNSPSC :
12352211
ID de substance PubChem :
24898178
Nomenclature NACRES :
NA.77

product name

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

Niveau de qualité

100

Pureté

≥98% (TLC)

Forme

powder

Couleur

clear light yellow, film

Solubilité

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

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

BQJRUJTZSGYBEZ-YVQNUNKESA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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

Attention

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.

Pictogrammes

Skull and crossbonesHealth hazardCorrosion
GHS06,GHS08,GHS05

Mention d'avertissement

Danger

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "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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