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P0077

Prostratin

≥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

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, 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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Certificates of Analysis (COA)

Lot/Batch Number
0000546277
0000534009
0000546277
0000534009
0000519391

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Articles

Protein Kinase C (PKC)

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

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)
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
Zichong Li et al.
Nucleic acids research, 41(1), 277-287 (2012-10-23)
Latent HIV reservoirs are the primary hurdle to eradication of infection. Identification of agents, pathways and molecular mechanisms that activate latent provirus may, in the presence of highly active antiretroviral therapy, permit clearance of infected cells by the immune system.
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