37558-16-0

Usage

Uses

Used in Pharmaceutical Research:
PHORBOL 12,13-DIBUTYRATE is used as a PKC activator for studying its effects on human organic anion transporter 4 (hOAT4) activity. This application is crucial in understanding the role of PKC in the regulation of transporter proteins, which can have implications for drug development and treatment of various diseases.
Used in Cellular and Molecular Biology:
PHORBOL 12,13-DIBUTYRATE is used as a PKC activator to analyze its effects on galectin-3 expression and matrix production in HL-1 cells. This application aids in investigating the intricate relationships between PKC activation and cellular processes, such as cell adhesion, migration, and proliferation, which are essential for understanding various biological phenomena and potential therapeutic targets.

Reactivity Profile

PHORBOL 12,13-DIBUTYRATE may be sensitive to prolonged exposure to air, light and ambient temperatures. PHORBOL 12,13-DIBUTYRATE may also be subject to autooxidation.

Fire Hazard

The flash point of PHORBOL 12,13-DIBUTYRATE has not been determined, but PHORBOL 12,13-DIBUTYRATE is probably combustible.

Biological Activity

phorbol 12,13-dibutyrate, a phorbol ester, is an activator of pkc, including the conventional calcium-dependent subtypes (α and γ), the nonconventional calcium-independent isoforms (δ, ε, η), as well as the atypical calcium-independent and dag or phorbol ester-unresponsive subtype (ζ). pkc plays an important role in the regulation of a variety of cellular processes such as exocytosis, gene expression, cell proliferation and differentiation, as well as tumor promotion, thereby representing the major target for tumor-promoting phorbol esters and chemically unrelated tumor promoters. phorbol esters are able to replace the endogenous activator dag in the stimulation of pkc, and participate in the multistage process of tumor formation and progression.1. geiges d, meyer t, marte b, et al. activation of protein kinase c subtypes alpha, gamma, delta, epsilon, zeta, and eta by tumor-promoting and nontumor-promoting agents. biochemical pharmacology, 1997, 53(6): 865-875.2. middleton jp, khan wa, collinsworth g, et al. heterogeneity of protein kinase c-mediated rapid regulation of na/k-atpase in kidney epithelial cells. journal of biological chemistry, 1993, 268(21): 15958-15964.3. scribner jd, boutwell rk. inflammation and tumor promotion: selective protein induction in mouse skin by tumor promoters. european journal of cancer, 1972, 8(6): 617-621.

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.

InChI:InChI=1/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

Upstream product

• 325781-13-3 Butyric acid (1aR,1bS,4aR,5S,7aS,7bS,8R,9S,9aS)-9-butyryloxy-4a,5,7b-trihydroxy-1,1,6,8-tetramethyl-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 325781-12-2 Butyric acid (1aR,1bS,4aR,5S,7aS,7bS,8R,9S,9aS)-4a,5,7b,9-tetrahydroxy-1,1,6,8-tetramethyl-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 325781-10-0 Butyric acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5,9-dioxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 325781-09-7 Butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9-trihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 325781-11-1 Butyric acid (1aR,1bS,4aR,5S,7aS,7bR,8S,9aS)-4a,5,7b-trihydroxy-1,1,6,8-tetramethyl-9-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 82400-03-1 phorbol-20-trityl ether 
• 17673-25-5 phorbol 
• 325781-14-4 Butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9S,9aS)-9-butyryloxy-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 17673-25-5 phorbol 

Relevant academic research and scientific papers

A new class of simplified phorbol ester analogues: Synthesis and binding to PKC and ηPKC-C1B (ηPKC-CRD2)

(matrix presented) A unique class of simplified phorbol ester analogues is described for the first time. A highly efficient retro-annelation sequence was developed in order to remove the five-membered ring from the phorbol diterpene core, allowing access

Studies on the regio- and diastereo-selective epoxidation of daphnanes and tiglianes

Daphnanes and tiglianes are diterpenes with a shared tricyclic 5-7-6 ring system. Many members exhibit significant biological activities often associated with protein kinase C signaling. Many of these natural products (～100) have a C6-C7 α-epoxide whose i

Modulation of the transient receptor potential vanilloid channel TRPV4 by 4α-phorbol esters: A structure-activity study

The mechanism of activation of the transient receptor potential vanilloid 4 (TRPV4) channel by 4α-phorbol esters was investigated by combining information from chemical modification of 4α-phorbol-didecanoate (4α-PDD, 2a), site-directed mutagenesis, Casup

Synthesis and tumor-promoting activities of 12-Epi-phorbol-12,13-dibutyrate.

12-Epi-phorbol-12,13-dibutyrate (1), the C12-epimer of the most frequently used phorbol ester probe, phorbol-12,13-dibutyrate (PDBu), has been synthesized from phorbol in 9 steps in order to investigate the structural requirements for tumor-promoting acti