Phorbol 12,13-dibutyrate | CAS#37558-16-0 | protein kinase C activator

MedKoo Cat#: 561541 | Name: Phorbol 12,13-dibutyrate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phorbol 12,13-dibutyrate, also known as PDBu, is a phorbol ester which is one of the constituents of croton oil. As an activator of protein kinase C, it is a weak tumor promoter compared to 12-O-tetradecanoylphorbol-13-acetate.

Chemical Structure

Phorbol 12,13-dibutyrate

CAS#37558-16-0

Theoretical Analysis

MedKoo Cat#: 561541

Name: Phorbol 12,13-dibutyrate

CAS#: 37558-16-0

Chemical Formula: C28H40O8

Exact Mass: 504.2723

Molecular Weight: 504.62

Elemental Analysis: C, 66.65; H, 7.99; O, 25.36

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 600.00
10mg	USD 975.00

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Synonym

PDBu; Phorbol 12,13-dibutyrate; Phorbol dibutyrate;

IUPAC/Chemical Name

Phorbol 12,13-dibutanoate

InChi Key

BQJRUJTZSGYBEZ-YVQNUNKESA-N

InChi Code

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

SMILES Code

OCC1=C[C@@]2([H])[C@H](C3(C)C)[C@@]3(OC(CCC)=O)[C@H](OC(CCC)=O)[C@@H](C)[C@@]2([C@@]([H])([C@@]4(C1)O)C=C(C4=O)C)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Phorbol 12,13-dibutyrate (Phorbol dibutyrate) is a PKC activator and a potent skin tumor promoter.

In vitro activity:

This study determined the effects of PDBu (10(-7) M), the PKC activator, on PKCα and RhoA and ROCK II translocation in the human IAS SMCs. PDBu caused significant translocation of PKCα, RhoA, and ROCK II. PDBu-induced translocation of PKCα was attenuated by calphostin C and not by C3 exoenzyme and Y 27632. However, PDBu-induced translocation of RhoA was blocked by C3 exoenzyme, and that of ROCK II was attenuated by both C3 exoenzyme and Y 27632. Reference: Am J Physiol Gastrointest Liver Physiol. 2011 Aug;301(2):G317-25. https://pubmed.ncbi.nlm.nih.gov/21566015/

In vivo activity:

To explore the role of protein kinase C (PKC) in the augmented bronchial smooth muscle (BSM) contraction observed in the antigen-induced airway hyperresponsive (AHR) mice, the effects of a PKC activator, phorbol 12,13-dibutylate (PDBu), on BSM contraction were compared between the AHR and control mice. Actively sensitized mice were repeatedly challenged by antigen inhalation. In BSMs of control mice, PDBu caused a significant increase in tension when the tissues were precontracted with high K(+), although PDBu itself had no effect on basal tone. The PDBu-mediated contraction was markedly augmented in BSMs of the AHR mice. Reference: J Smooth Muscle Res. 2010;46(5):259-66. https://pubmed.ncbi.nlm.nih.gov/21187674/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	75.1	148.85

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 504.62 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Singh J, Maxwell PJ 4th, Rattan S. Immunocytochemical evidence for PDBu-induced activation of RhoA/ROCK in human internal anal sphincter smooth muscle cells. Am J Physiol Gastrointest Liver Physiol. 2011 Aug;301(2):G317-25. doi: 10.1152/ajpgi.00084.2011. Epub 2011 May 12. PMID: 21566015; PMCID: PMC3154599. 2. Middleton JP, Khan WA, Collinsworth G, Hannun YA, Medford RM. Heterogeneity of protein kinase C-mediated rapid regulation of Na/K-ATPase in kidney epithelial cells. J Biol Chem. 1993 Jul 25;268(21):15958-64. PMID: 8393456. 3. Xiao D, Huang X, Zhang L. Chronic hypoxia differentially up-regulates protein kinase C-mediated ovine uterine arterial contraction via actin polymerization signaling in pregnancy. Biol Reprod. 2012 Dec 21;87(6):142. doi: 10.1095/biolreprod.112.104448. PMID: 23136295; PMCID: PMC4435429. 4. Sakai H, Kurihara Y, Hashimoto Y, Chiba Y, Misawa M. Augmented PDBu-mediated contraction of bronchial smooth muscle of mice with antigen-induced airway hyperresponsiveness. J Smooth Muscle Res. 2010;46(5):259-66. doi: 10.1540/jsmr.46.259. PMID: 21187674.

In vitro protocol:

In vivo protocol:

1. Xiao D, Huang X, Zhang L. Chronic hypoxia differentially up-regulates protein kinase C-mediated ovine uterine arterial contraction via actin polymerization signaling in pregnancy. Biol Reprod. 2012 Dec 21;87(6):142. doi: 10.1095/biolreprod.112.104448. PMID: 23136295; PMCID: PMC4435429. 2. Sakai H, Kurihara Y, Hashimoto Y, Chiba Y, Misawa M. Augmented PDBu-mediated contraction of bronchial smooth muscle of mice with antigen-induced airway hyperresponsiveness. J Smooth Muscle Res. 2010;46(5):259-66. doi: 10.1540/jsmr.46.259. PMID: 21187674.

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