Prostratin

Modify Date: 2024-01-02 16:13:50

Prostratin Structure
Prostratin structure
Common Name Prostratin
CAS Number 60857-08-1 Molecular Weight 390.470
Density 1.3±0.1 g/cm3 Boiling Point 550.5±50.0 °C at 760 mmHg
Molecular Formula C22H30O6 Melting Point 216-219℃
MSDS Chinese USA Flash Point 188.7±23.6 °C

 Use of Prostratin


Prostratin, a natural terpenoid compound, is a PKC activator, with a Ki of 12.5 nM and shows inhibitory effect on HIV-1.

 Names

Name 12-deoxyphorbol 13-acetate
Synonym More Synonyms

 Prostratin Biological Activity

Description Prostratin, a natural terpenoid compound, is a PKC activator, with a Ki of 12.5 nM and shows inhibitory effect on HIV-1.
Related Catalog
Target

PKC:12.5 nM (Ki)

HIV-1

In Vitro Prostratin 抑制 [3H]PDBu 与 CEM 细胞的结合,Ki 为 210 nM[1]。 Prostratin (125-1000 nM) 剂量依赖性地抑制急性髓性白血病 (AML) 细胞系 (HL-60、NB4 和 U937 细胞) 的生长。Prostratin (125-100 nM) 诱导 AML 细胞的 G1 期阻滞并影响 HL-60 细胞中的细胞周期相关分子 (pRb 磷酸化、CDK 和 p21)。Prostratin 还通过激活 PKC 导致 AML 细胞系分化。此外,MEK/ERK/MAP 信号通路的 PKC 依赖性激活需要 Prostratin 诱导的分化[2]。 Prostratin 诱导需要 PKD3 活性形式的 HIV-1 转录激活。Prostratin 还通过新型 PKC 亚家族的 PKCε 激活 PKD3[3]。 Cell Viability Assay[2] Cell Line: HL-60, NB4 and U937 cells Concentration: 125 nM, 250 nM, 500 nM, 1000 nM Incubation Time: 24 hours, 48 hours, 72 hours Result: Dose-dependently inhibited the growth of acute myeloid leukemia (AML) cell lines. Cell Cycle Analysis[2] Cell Line: HL-60, NB4 and U937 cells Concentration: 125 nM, 250 nM, 500 nM, 1000 nM Incubation Time: 24 hours Result: Induced a G0/G1 phase accumulation in a concentration-dependent manner. Western Blot Analysis[2] Cell Line: HL-60 cells Concentration: 125 nM, 250 nM, 500 nM, 1000 nM Incubation Time: 24 hours Result: Affected the cell-cycle-related molecules (pRb phosphorylation, CDKs, and p21) in HL-60 cells.
References

[1]. Gustafson KR, et al. A nonpromoting phorbol from the samoan medicinal plant Homalanthus nutans inhibits cell killing by HIV-1. J Med Chem. 1992 May 29;35(11):1978-86.  

[2]. Shen X, et al. The protein kinase C agonist prostratin induces differentiation of human myeloid leukemia cells and enhances cellular differentiation by chemotherapeutic agents. Cancer Lett. 2015 Jan 28;356(2 Pt B):686-96.  

[3]. Wang H, et al. Protein kinase D3 is essential for prostratin-activated transcription of integrated HIV-1 provirus promoter via NF-κB signaling pathway. Biomed Res Int. 2014;2014:968027.  

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 550.5±50.0 °C at 760 mmHg
Melting Point 216-219℃
Molecular Formula C22H30O6
Molecular Weight 390.470
Flash Point 188.7±23.6 °C
Exact Mass 390.204254
PSA 104.06000
LogP 1.84
Vapour Pressure 0.0±3.4 mmHg at 25°C
Index of Refraction 1.600
Storage condition ?20°C
Water Solubility Soluble in DMSO at 30mg/ml

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR NONH for all modes of transport

 Synthetic Route

~90%

Prostratin Structure

Prostratin

CAS#:60857-08-1

Literature: The Board of Trustees of the Leland Stanford Junior University Patent: US2009/187046 A1, 2009 ; Location in patent: Page/Page column 11 ;

~35%

Prostratin Structure

Prostratin

CAS#:60857-08-1

Literature: The Board of Trustees of the Leland Stanford Junior University Patent: US2009/187046 A1, 2009 ; Location in patent: Page/Page column 12-13 ;

~%

Prostratin Structure

Prostratin

CAS#:60857-08-1

Literature: Natural Product Research, , vol. 27, # 16 p. 1459 - 1462

 Precursor & DownStream

Precursor  2

DownStream  0

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 Synonyms

(1aR,1bS,4aR,7aS,7bR,8R,9aS)-4a,7b-Dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl acetate
13-O-Acetyl-12-deoxyphorbol
12-Deoxyphorbol-13-acetate
Stillingia Facto
5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one, 9a-(acetyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1aR,1bS,4aR,7aS,7bR,8R,9aS)-
12-Deoxyphorbol 13-Acetate,dPAc
13-O-Acetylphorbol
Stillingia factor S7
SA 101A
prostratin
12-deoxyphorbal-13-acetate