Prostratin

Names

[ Name ]:
Prostratin

[Synonym ]:
(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

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]:

Signaling Pathways >> Epigenetics >> PKC

Research Areas >> Cancer

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

Signaling Pathways >> TGF-beta/Smad >> PKC

[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

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

IFI44 suppresses HIV-1 LTR promoter activity and facilitates its latency.

Virology 481 , 142-50, (2015)

IFI44 is an interferon-alfa inducible protein, and is associated with infection of several viruses. However, IFI44 elicits minimal antiviral effects on these viruses, and its exact role is still unkno...

Sulfonation pathway inhibitors block reactivation of latent HIV-1.

Virology 471-473 , 1-12, (2014)

Long-lived pools of latently infected cells are a significant barrier to the development of a cure for HIV-1 infection. A better understanding of the mechanisms of reactivation from latency is needed ...

Synergistic activation of HIV-1 expression by deacetylase inhibitors and prostratin: implications for treatment of latent infection.

PLoS ONE 4(6) , e6093, (2009)

The persistence of transcriptionally silent but replication-competent HIV-1 reservoirs in Highly Active Anti-Retroviral Therapy (HAART)-treated infected individuals, represents a major hurdle to virus...