Phorbol 12,13-dibutyrate
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.
References:
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.
| Physical Appearance | White lyophilised solid |
| Storage | Store at -20°C |
| M.Wt | 504.61 |
| Cas No. | 37558-16-0 |
| Formula | C28H40O8 |
| Solubility | <25.23mg/ml in DMSO |
| Chemical Name | (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulene-9,9a-diyl dibutyrate |
| SDF | Download SDF |
| Canonical SMILES | O[C@@]1([C@H](C=C(C)C2=O)[C@]32O)[C@@H](C=C(CO)C3)[C@H](C4(C)C)[C@]4([C@@H]([C@H]1C)OC(CCC)=O)OC(CCC)=O |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment:[2] | |
|
Cell lines |
OK and LLC-PK1 cells expressing detectable levels of PKCα and PKCζ |
|
Reaction Conditions |
1 mM phorbol 12,13-dibutyrate for 10 min incubation |
|
Applications |
Phorbol 12,13-dibutyrate activated PKC, and inhibited Na/K-ATPase transport activity in OK cells, but not in LLC-PK1 cells. |
| Animal experiment:[3] | |
|
Animal models |
Female CD-1 mice, 8 weeks of age |
|
Dosage form |
9.7 µmol; 0.067 µmol/ear Topical administration |
|
Applications |
Phorbol 12,13-dibutyrate induced papilloma formation in mice with a total dose of 9.7 µmol required to produce papillomas in 50% of survivors after eight weeks. Phorbol 12,13-dibutyrate also induced inflammation in 50% of mice when administered topically to the ear at a dose of 0.067 µmol/ear. |
|
Note |
The technical data provided above is for reference only. |
|
References: 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. |
|
Quality Control & MSDS
- View current batch:
-
Purity = 98.00%
- COA (Certificate Of Analysis)
- MSDS (Material Safety Data Sheet)
Chemical structure
