Prostratin
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 523118

CAS#: 60857-08-1

Description: Prostratin is a protein kinase C activator found in the bark of the mamala tree of Samoa, Homalanthus nutans (Euphorbiaceae). While prostratin was originally isolated and identified as a new phorbol from species of the genus Pimelea (Thymelaceae) in Australia, the antiviral activity of prostratin was discovered during research on the traditional knowledge of Samoan healers in Falealupo village by ethnobotanist Paul Alan Cox and a team at the U.S. National Cancer Institute. Samoan healers use the mamala tree to treat hepatitis. Research indicated that prostratin has potential to be useful in the treatment of HIV as it could flush viral reservoirs in latently infected CD4+ T-cells. As a modulator of Protein Kinase C, it has been shown to exhibit promising therapeutic potential against other diseases such as cancer and Alzheimer's disease. In 2015, study showed that orally administrated prostratin repressed human pancreatic tumor. (Source: https://en.wikipedia.org/wiki/Prostratin). (Last update: 4/1/2016).

Chemical Structure

img
Prostratin
CAS# 60857-08-1
Instruction

Theoretical Analysis

MedKoo Cat#: 523118
Name: Prostratin
CAS#: 60857-08-1
Chemical Formula: C22H30O6
Exact Mass: 390.20
Molecular Weight: 390.480
Elemental Analysis: C, 67.67; H, 7.74; O, 24.58

Price and Availability

Size Price Availability Quantity
1mg USD 350 2 Weeks
Bulk inquiry

Synonym: 12-Deoxyphorbol-13-acetate; Prostratin; [dPAc;

IUPAC/Chemical Name: (1aR,1bS,4aR,7aS,7bR,8R,9aS)-9a-(Acetyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one

InChi Key: BOJKFRKNLSCGHY-HXGSDTCMSA-N

InChi Code: 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

SMILES Code: O=C1C(C)=C[C@@]2([H])[C@]3(O)[C@@]([C@@](C4(C)C)([H])[C@@]4(OC(C)=O)C[C@H]3C)([H])C=C(CO)C[C@]12O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 390.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Miana GA, Riaz M, Shahzad-ul-Hussan S, Paracha RZ, Paracha UZ. Prostratin: An Overview. Mini Rev Med Chem. 2015;15(13):1122-30. PubMed PMID: 25963564.

2: Shen X, Xiong GL, Jing Y, Xiao H, Cui Y, Zhang YF, Shan YJ, Xing S, Yang M, Liu XL, Dong B, Wang LS, Luo QL, Yu ZY, Cong YW. 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. doi: 10.1016/j.canlet.2014.10.018. Epub 2014 Oct 22. PubMed PMID: 25449427.

3: Wang H, Zhu X, Zhu Y, Liu J, Hu X, Wang Y, Peng S, Chen Y, Chen R, Ding F, Liu R. 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. doi: 10.1155/2014/968027. Epub 2014 Jul 21. PubMed PMID: 25136641; PubMed Central PMCID: PMC4127265.

4: Chan JK, Bhattacharyya D, Lassen KG, Ruelas D, Greene WC. Calcium/calcineurin synergizes with prostratin to promote NF-κB dependent activation of latent HIV. PLoS One. 2013 Oct 30;8(10):e77749. doi: 10.1371/journal.pone.0077749. eCollection 2013. PubMed PMID: 24204950; PubMed Central PMCID: PMC3813743.

5: Beans EJ, Fournogerakis D, Gauntlett C, Heumann LV, Kramer R, Marsden MD, Murray D, Chun TW, Zack JA, Wender PA. Highly potent, synthetically accessible prostratin analogs induce latent HIV expression in vitro and ex vivo. Proc Natl Acad Sci U S A. 2013 Jul 16;110(29):11698-703. doi: 10.1073/pnas.1302634110. Epub 2013 Jun 28. PubMed PMID: 23812750; PubMed Central PMCID: PMC3718093.

6: Bourjot M, Delang L, Nguyen VH, Neyts J, Guéritte F, Leyssen P, Litaudon M. Prostratin and 12-O-tetradecanoylphorbol 13-acetate are potent and selective inhibitors of Chikungunya virus replication. J Nat Prod. 2012 Dec 28;75(12):2183-7. doi: 10.1021/np300637t. Epub 2012 Dec 7. PubMed PMID: 23215460.

7: Chan CN, McMonagle EL, Hosie MJ, Willett BJ. Prostratin exhibits both replication enhancing and inhibiting effects on FIV infection of feline CD4+ T-cells. Virus Res. 2013 Jan;171(1):121-8. doi: 10.1016/j.virusres.2012.11.004. Epub 2012 Nov 28. PubMed PMID: 23201205; PubMed Central PMCID: PMC3566544.

8: Barrero RA, Chapman B, Yang Y, Moolhuijzen P, Keeble-Gagnère G, Zhang N, Tang Q, Bellgard MI, Qiu D. De novo assembly of Euphorbia fischeriana root transcriptome identifies prostratin pathway related genes. BMC Genomics. 2011 Dec 13;12:600. doi: 10.1186/1471-2164-12-600. PubMed PMID: 22151917; PubMed Central PMCID: PMC3273484.

9: Reuse S, Calao M, Kabeya K, Guiguen A, Gatot JS, Quivy V, Vanhulle C, Lamine A, Vaira D, Demonte D, Martinelli V, Veithen E, Cherrier T, Avettand V, Poutrel S, Piette J, de Launoit Y, Moutschen M, Burny A, Rouzioux C, De Wit S, Herbein G, Rohr O, Collette Y, Lambotte O, Clumeck N, Van Lint C. Synergistic activation of HIV-1 expression by deacetylase inhibitors and prostratin: implications for treatment of latent infection. PLoS One. 2009 Jun 30;4(6):e6093. doi: 10.1371/journal.pone.0006093. PubMed PMID: 19564922; PubMed Central PMCID: PMC2699633.

10: Johnson HE, Banack SA, Cox PA. Variability in content of the anti-AIDS drug candidate prostratin in Samoan populations of Homalanthus nutans. J Nat Prod. 2008 Dec;71(12):2041-4. doi: 10.1021/np800295m. PubMed PMID: 19007283; PubMed Central PMCID: PMC2663895.