Skip to Content
Merck
CN

Key Documents

View All Documentation

P0077

Prostratin

≥98% (HPLC), PKC activator, powder

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

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
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
116M4758V
056M4707V
085M4704V
054M4727V
044M4707V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Articles

Protein Kinase C (PKC)

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

Sheena M Saayman et al.
Molecular therapy : the journal of the American Society of Gene Therapy, 24(3), 488-498 (2015-11-20)
HIV-1 provirus integration results in a persistent latently infected reservoir that is recalcitrant to combined antiretroviral therapy (cART) with lifelong treatment being the only option. The "shock and kill" strategy aims to eradicate latent HIV by reactivating proviral gene expression
Joaquín Rullas et al.
Antiviral therapy, 9(4), 545-554 (2004-10-01)
Induction of HIV expression through lymphocyte activation has been proposed as a strategy to purge latent reservoirs. Prostratin is a non-tumourogenic phorbol ester that delays HIV replication in vitro, but paradoxically activates HIV expression in latently infected cells. To get
Samuel A Williams et al.
The Journal of biological chemistry, 279(40), 42008-42017 (2004-07-31)
A subset of quiescent memory CD4 T cells harboring integrated but transcriptionally silent proviruses poses a currently insurmountable barrier to the eradication of the human immunodeficiency virus (HIV) in infected patients. Induction of HIV gene expression in these latently infected
View All Related Papers

Global Trade Item Number

SKUGTIN
P0077-1MG04061826703557
P0077-5MG04061833220085