RGFP966
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MedKoo CAT#: 510215

CAS#: 1357389-11-7

Description: RGFP966 is a selective HDAC3 inhibitor . S ystemic treatment with RGFP966 facilitates extinction in mice in a manner resistant to reinstatement. A single treatment of RGFP966 enhances extinction of a previously established cocaine-conditioned place preference, while simultaneously enhancing long-term object-location memory within subjects. During extinction consolidation, HDAC3 inhibition promotes a distinct pattern of histone acetylation linked to gene expression within the infralimbic cortex, hippocampus, and nucleus accumbens. Thus, the facilitated extinction of drug-seeking cannot be explained by adverse effects on performance.

Chemical Structure

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RGFP966
CAS# 1357389-11-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 510215
Name: RGFP966
CAS#: 1357389-11-7
Chemical Formula: C21H19FN4O
Exact Mass: 362.15
Molecular Weight: 362.400
Elemental Analysis: C, 69.60; H, 5.28; F, 5.24; N, 15.46; O, 4.41

Price and Availability

Size Price Availability Quantity
5mg USD 90 Ready to ship
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2850 Ready to ship
1g USD 4250 Ready to ship
2g USD 6550 2 Weeks
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Related CAS #: 1396841-57-8  

Synonym: RGFP966; RGFP 966; RGFP-966

IUPAC/Chemical Name: (E)-N-(2-amino-4-fluorophenyl)-3-(1-cinnamyl-1H-pyrazol-4-yl)acrylamide

InChi Key: BLVQHYHDYFTPDV-VCABWLAWSA-N

InChi Code: InChI=1S/C21H19FN4O/c22-18-9-10-20(19(23)13-18)25-21(27)11-8-17-14-24-26(15-17)12-4-7-16-5-2-1-3-6-16/h1-11,13-15H,12,23H2,(H,25,27)/b7-4+,11-8+

SMILES Code: O=C(NC1=CC=C(F)C=C1N)/C=C/C2=CN(C/C=C/C3=CC=CC=C3)N=C2.

Appearance: White 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: RGFP966 is an HDAC3 inhibitor with IC50 of 0.08 μM in cell-free assay, exhibits > 200-fold selectivity over other HDAC.
In vitro activity: RGFP966 was applied in cell-based model systems for inflammatory lung diseases using mouse RAW 264.7 macrophages, human bronchial epithelial (HBE) cells and human airway smooth muscle (hASM) cells that were subjected to LPS/IFNγ-stimulation. First, cytotoxicity of RGFP966 was investigated in these cell types and there was no significant observed decrease in cell viability at the applied concentrations, as compared to control cells (data not shown). In LPS/IFNγ-stimulated RAW 264.7 macrophages treatment with RGFP966 did not change the expression of the genes TNFα, iNOS, and IL-10 but provided a significant downregulation of the expression of the pro-inflammatory genes IL-1β, IL-6 and IL-12b (Fig. 2C). This effect was specific for macrophages as in HBE cells and hASM cells the expression of the investigated genes was not affected except for pro-inflammatory gene IL-6, which was upregulated in HBE cells. Reference: Biochem Pharmacol. 2016 May 15;108:58-74. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4844503/
In vivo activity: The effects of RGFP966 ((E)-N-(2-amino-4-fluorophenyl)-3-(1-cinnamyl-1H-pyrazol-4-yl)acrylamide), a benzamide-type HDAC inhibitor that selectively targets HDAC3, was tested in the N171-82Q transgenic mouse model of HD. It was found that RGFP966 at doses of 10 and 25 mg/kg improves motor deficits on rotarod and in open field exploration, accompanied by neuroprotective effects on striatal volume. In light of previous studies implicating HDAC3 in immune function, gene expression changes were measured for 84 immune-related genes elicited by RGFP966 using quantitative PCR arrays. RGFP966 treatment did not cause widespread changes in cytokine/chemokine gene expression patterns, but did significantly alter the striatal expression of macrophage migration inhibitory factor (Mif), a hormone immune modulator associated with glial cell activation, in N171-82Q transgenic mice, but not WT mice. Accordingly, RGFP966-treated mice showed decreased glial fibrillary acidic protein (GFAP) immunoreactivity, a marker of astrocyte activation, in the striatum of N171-82Q transgenic mice compared to vehicle-treated mice. Reference: PLoS One. 2016 Mar 31;11(3):e0152498. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/27031333/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 137.97
DMF 50.0 137.97

Preparing Stock Solutions

The following data is based on the product molecular weight 362.40 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: 1. Leus NG, van der Wouden PE, van den Bosch T, Hooghiemstra WTR, Ourailidou ME, Kistemaker LE, Bischoff R, Gosens R, Haisma HJ, Dekker FJ. HDAC 3-selective inhibitor RGFP966 demonstrates anti-inflammatory properties in RAW 264.7 macrophages and mouse precision-cut lung slices by attenuating NF-κB p65 transcriptional activity. Biochem Pharmacol. 2016 May 15;108:58-74. doi: 10.1016/j.bcp.2016.03.010. Epub 2016 Mar 16. PMID: 26993378; PMCID: PMC4844503. 2. Jia H, Wang Y, Morris CD, Jacques V, Gottesfeld JM, Rusche JR, Thomas EA. The Effects of Pharmacological Inhibition of Histone Deacetylase 3 (HDAC3) in Huntington's Disease Mice. PLoS One. 2016 Mar 31;11(3):e0152498. doi: 10.1371/journal.pone.0152498. PMID: 27031333; PMCID: PMC4816519. 3. Bieszczad KM, Bechay K, Rusche JR, Jacques V, Kudugunti S, Miao W, Weinberger NM, McGaugh JL, Wood MA. Histone Deacetylase Inhibition via RGFP966 Releases the Brakes on Sensory Cortical Plasticity and the Specificity of Memory Formation. J Neurosci. 2015 Sep 23;35(38):13124-32. doi: 10.1523/JNEUROSCI.0914-15.2015. PMID: 26400942; PMCID: PMC4579377.
In vitro protocol: 1. Leus NG, van der Wouden PE, van den Bosch T, Hooghiemstra WTR, Ourailidou ME, Kistemaker LE, Bischoff R, Gosens R, Haisma HJ, Dekker FJ. HDAC 3-selective inhibitor RGFP966 demonstrates anti-inflammatory properties in RAW 264.7 macrophages and mouse precision-cut lung slices by attenuating NF-κB p65 transcriptional activity. Biochem Pharmacol. 2016 May 15;108:58-74. doi: 10.1016/j.bcp.2016.03.010. Epub 2016 Mar 16. PMID: 26993378; PMCID: PMC4844503.
In vivo protocol: 1. Jia H, Wang Y, Morris CD, Jacques V, Gottesfeld JM, Rusche JR, Thomas EA. The Effects of Pharmacological Inhibition of Histone Deacetylase 3 (HDAC3) in Huntington's Disease Mice. PLoS One. 2016 Mar 31;11(3):e0152498. doi: 10.1371/journal.pone.0152498. PMID: 27031333; PMCID: PMC4816519. 2. Bieszczad KM, Bechay K, Rusche JR, Jacques V, Kudugunti S, Miao W, Weinberger NM, McGaugh JL, Wood MA. Histone Deacetylase Inhibition via RGFP966 Releases the Brakes on Sensory Cortical Plasticity and the Specificity of Memory Formation. J Neurosci. 2015 Sep 23;35(38):13124-32. doi: 10.1523/JNEUROSCI.0914-15.2015. PMID: 26400942; PMCID: PMC4579377.

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1: Wells CE, Bhaskara S, Stengel KR, Zhao Y, Sirbu B, Chagot B, Cortez D, Khabele D, Chazin WJ, Cooper A, Jacques V, Rusche J, Eischen CM, McGirt LY, Hiebert SW. Inhibition of histone deacetylase 3 causes replication stress in cutaneous T cell lymphoma. PLoS One. 2013 Jul 22;8(7):e68915. doi: 10.1371/journal.pone.0068915. Print 2013. PubMed PMID: 23894374; PubMed Central PMCID: PMC3718806.