Ingenol 3-Hexanoate | CAS#83036-61-7 | reactivator of latent HIV-1

MedKoo Cat#: 561544 | Name: Ingenol 3-Hexanoate

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

Ingenol 3-Hexanoate novel potent reactivator of latent HIV-1.

Chemical Structure

Ingenol 3-Hexanoate

CAS#83036-61-7

Theoretical Analysis

MedKoo Cat#: 561544

Name: Ingenol 3-Hexanoate

CAS#: 83036-61-7

Chemical Formula: C26H38O6

Exact Mass: 446.2668

Molecular Weight: 446.58

Elemental Analysis: C, 69.93; H, 8.58; O, 21.50

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks

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Synonym

Ingenol 3-Hexanoate; Ingenol B

IUPAC/Chemical Name

(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-Dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclpropa[e][10]annulen-6-yl hexanoate

InChi Key

LYWIFBNBLVOVKN-FOJFYXSBSA-N

InChi Code

InChI=1S/C26H38O6/c1-6-7-8-9-19(28)32-23-14(2)12-25-15(3)10-18-20(24(18,4)5)17(22(25)30)11-16(13-27)21(29)26(23,25)31/h11-12,15,17-18,20-21,23,27,29,31H,6-10,13H2,1-5H3/t15-,17+,18-,20+,21-,23+,25+,26+/m1/s1

SMILES Code

CCCCCC(O[C@H]1C(C)=C[C@]23[C@]1(O)[C@H](O)C(CO)=C[C@@](C3=O)([H])[C@@]4([H])[C@@](C4(C)C)([H])C[C@H]2C)=O

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

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ingenol 3-Hexanoate, or Ingenol B, is a novel potent reactivator of latent HIV-1.

In vitro activity:

One of the sgRNAs (LTR5), which binds specifically in the HIV-1 LTR NFκB binding site, was able to promote robust repression of HIV-1 reactivation in latently infected T cells stimulated with Phorbol 12-Myristate 13-Acetate (PMA) and Ingenol B (IngB), both potent protein kinase C (PKC) stimulators. Reference: Retrovirology. 2022 Jun 22;19(1):12. https://pubmed.ncbi.nlm.nih.gov/35733180/

In vivo activity:

However, significant toxicity risks and the lack of evidence supporting their activity in vivo have limited further evaluation of PKC agonists as HIV latency-reversing agents (LRA) in cure strategies. Here this study evaluated whether GSK445A, a stabilized ingenol-B derivative, can induce HIV/simian immunodeficiency virus (SIV) transcription and virus production in vitro and demonstrate pharmacological activity in nonhuman primates (NHP). In vivo, GSK445A tolerability was established in SIV-naïve RM at 15 μg/kg although tolerability was reduced in SIV-infected RM on ART. Increases in plasma viremia following GSK445A administration were suggestive of increased SIV transcription in vivo. Collectively, these results indicate that GSK445A is a potent HIV/SIV LRA in vitro and has a tolerable safety profile amenable for further evaluation in vivo in NHP models of HIV cure/remission. Reference: PLoS Pathog. 2022 Jan 18;18(1):e1010245. https://pubmed.ncbi.nlm.nih.gov/35041707/

Preparing Stock Solutions

The following data is based on the product molecular weight 446.58 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.

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:

1. da Costa LC, Bomfim LM, Dittz UVT, Velozo CA, da Cunha RD, Tanuri A. Repression of HIV-1 reactivation mediated by CRISPR/dCas9-KRAB in lymphoid and myeloid cell models. Retrovirology. 2022 Jun 22;19(1):12. doi: 10.1186/s12977-022-00600-9. PMID: 35733180; PMCID: PMC9215058. 2. Okoye AA, Fromentin R, Takata H, Brehm JH, Fukazawa Y, Randall B, Pardons M, Tai V, Tang J, Smedley J, Axthelm M, Lifson JD, Picker LJ, Favre D, Trautmann L, Chomont N. The ingenol-based protein kinase C agonist GSK445A is a potent inducer of HIV and SIV RNA transcription. PLoS Pathog. 2022 Jan 18;18(1):e1010245. doi: 10.1371/journal.ppat.1010245. PMID: 35041707; PMCID: PMC8797195.

In vitro protocol:

In vivo protocol:

1. Okoye AA, Fromentin R, Takata H, Brehm JH, Fukazawa Y, Randall B, Pardons M, Tai V, Tang J, Smedley J, Axthelm M, Lifson JD, Picker LJ, Favre D, Trautmann L, Chomont N. The ingenol-based protein kinase C agonist GSK445A is a potent inducer of HIV and SIV RNA transcription. PLoS Pathog. 2022 Jan 18;18(1):e1010245. doi: 10.1371/journal.ppat.1010245. PMID: 35041707; PMCID: PMC8797195.

1: Sorg B, Schmidt R, Hecker E. Structure/activity relationships of polyfunctional diterpenes of the ingenane type. I. Tumor-promoting activity of homologous, aliphatic 3-esters of ingenol and of delta 7,8-isoingenol-3-tetradecanoate. Carcinogenesis. 1987 Jan;8(1):1-4. PubMed PMID: 3100081.