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P0077

Prostratin

Name: Prostratin
Brand: SIGMA

≥98% (HPLC), PKC activator, powder

Synonym(s):

12-Deoxyphorbol-13-acetate, CCRIS 6292, NSC 623310

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₃₀O₆

CAS Number:

60857-08-1

Molecular Weight:

390.47

UNSPSC Code:

12352200

PubChem Substance ID:

329820006

NACRES:

NA.77

MDL number:

MFCD00674138

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Product Name

Prostratin, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

C[C@@H]1C[C@]2(OC(C)=O)[C@H]([C@@H]3C=C(CO)C[C@@]4(O)[C@@H](C=C(C)C4=O)[C@@]13O)C2(C)C

InChI

1S/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17-,20-,21+,22-/m1/s1

InChI key

BOJKFRKNLSCGHY-HXGSDTCMSA-N

Related Categories

Bioactive Small Molecules

Application

Prostratin has been used to reverse the latency of human immunodeficiency virus-1 (HIV-1) and to quantify the transcriptional activation of the long terminal repeat (LTR) in latently HIV-1-infected Jurkat (J-Lat) cell lines.

Biochem/physiol Actions

Prostratin, an unusual non-tumorigenic phorbol ester, is an activator of protein kinase C (PKC) and also an activator of nuclear factor KB (NF-KB) mediated through activation of the IKKs (IKB kinases). Prostratin exhibits potent in vitro activity by inducing HIV expression in latently infected cell lines and primary cells, thus antagonizing HIV latency. Activation of PKC and NF-kB has been proposed as the mechanism of action. Prostratin also inhibits HIV entry into target cells by down-regulating CD4 and CXCR4 receptors.

Features and Benefits

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Variability in content of the anti-AIDS drug candidate prostratin in Samoan populations of Homalanthus nutans.

Holly E Johnson et al.

Journal of natural products, 71(12), 2041-2044 (2008-11-15)

Homalanthus nutans, used by Samoan healers to treat hepatitis, produces the antiviral compound 12-deoxyphorbol 13-acetate, prostratin (1). Prostratin is being developed as an adjuvant therapy to clear latent viral reservoirs, the major obstacle to eradication of HIV-AIDS within the human

Prostratin as a new therapeutic agent targeting HIV viral reservoirs.

Marjan Hezareh

Drug news & perspectives, 18(8), 496-500 (2006-01-05)

The persistence of latent reservoirs of human immunodeficiency virus type 1 (HIV-1) represents a major barrier to virus eradication in patients on combination antiretroviral therapy. It has been suggested that treating infected individuals simultaneously with highly active antiretroviral therapy (HAART)

De novo assembly of Euphorbia fischeriana root transcriptome identifies prostratin pathway related genes.

Roberto A Barrero et al.

BMC genomics, 12, 600-600 (2011-12-14)

Euphorbia fischeriana is an important medicinal plant found in Northeast China. The plant roots contain many medicinal compounds including 12-deoxyphorbol-13-acetate, commonly known as prostratin that is a phorbol ester from the tigliane diterpene series. Prostratin is a protein kinase C

Designed, synthetically accessible bryostatin analogues potently induce activation of latent HIV reservoirs in vitro.

Brian A DeChristopher et al.

Nature chemistry, 4(9), 705-710 (2012-08-24)

Bryostatin is a unique lead in the development of potentially transformative therapies for cancer, Alzheimer's disease and the eradication of HIV/AIDS. However, the clinical use of bryostatin has been hampered by its limited supply, difficulties in accessing clinically relevant derivatives

Bioactive components in the fruits of Ziziphus jujuba Mill. against the inflammatory irritant action of Euphorbia plants.

L Yu et al.

Phytomedicine : international journal of phytotherapy and phytopharmacology, 19(3-4), 239-244 (2011-10-11)

Chinese jujube (also known as Chinese date) is the fruit of Ziziphus jujuba Mill. (Rhamnaceae). As a famous folk medicine, it is used as antidote in traditional Chinese formula, Shi Zao Decoction, to relieve the drastic inflammatory irritant nature of

View All Related Papers

Articles

Protein Kinase C (PKC)

Protein kinase C (PKC) is an AGC kinase that phosphorylates serine and threonine residues in many target proteins.

Global Trade Item Number

SKU	GTIN
P0077-1MG	04061826703557
P0077-5MG	04061833220085

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