Synonym
NCH-51; NCH 51; NCH51. PTACH
IUPAC/Chemical Name
S-(7-oxo-7-((4-phenylthiazol-2-yl)amino)heptyl) 2-methylpropanethioate
InChi Key
MDYDGUOQFUQOGE-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H26N2O2S2/c1-15(2)19(24)25-13-9-4-3-8-12-18(23)22-20-21-17(14-26-20)16-10-6-5-7-11-16/h5-7,10-11,14-15H,3-4,8-9,12-13H2,1-2H3,(H,21,22,23)
SMILES Code
CC(C)C(SCCCCCCC(NC1=NC(C2=CC=CC=C2)=CS1)=O)=O
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
Biological target:
PTACH (NCH-51) is a potent HDAC inhibitor with IC50s of 48 nM, 32 nM, and 41 nM for HDAC1, HDAC4, and HDAC6.
In vitro activity:
The novel histone deacetylase inhibitor NCH-51 induced expression of latent HIV-1 with minimal cytotoxicity. Using chromatin immunoprecipitation assays, this study observed a reduction of HDAC1 occupancy, histone hyperacetylation and the recruitment of positive transcription factors at the HIV-1 promoter in latently infected-cells under the treatment with NCH-51. Mutation studies of the long terminal repeat (LTR) revealed NCH-51 mediated gene expression through the Sp1 sites. When Sp1 expression was knocked-down by small interfering RNA, the NCH-51-mediated activation of a stably integrated HIV-1 LTR was attenuated.
Reference: FEBS Lett. 2011 Apr 6;585(7):1103-11. https://pubmed.ncbi.nlm.nih.gov/21402072/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
76.81 |
| DMSO |
40.0 |
102.42 |
| DMSO:PBS (pH 7.2) (1:1) |
0.5 |
1.28 |
| Ethanol |
10.0 |
25.60 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
390.56
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. Victoriano AF, Imai K, Togami H, Ueno T, Asamitsu K, Suzuki T, Miyata N, Ochiai K, Okamoto T. Novel histone deacetylase inhibitor NCH-51 activates latent HIV-1 gene expression. FEBS Lett. 2011 Apr 6;585(7):1103-11. doi: 10.1016/j.febslet.2011.03.017. Epub 2011 Mar 12. PMID: 21402072.
2. Sanda T, Okamoto T, Uchida Y, Nakagawa H, Iida S, Kayukawa S, Suzuki T, Oshizawa T, Suzuki T, Miyata N, Ueda R. Proteome analyses of the growth inhibitory effects of NCH-51, a novel histone deacetylase inhibitor, on lymphoid malignant cells. Leukemia. 2007 Nov;21(11):2344-53. doi: 10.1038/sj.leu.2404902. Epub 2007 Aug 9. PMID: 17690692.
In vitro protocol:
1. Victoriano AF, Imai K, Togami H, Ueno T, Asamitsu K, Suzuki T, Miyata N, Ochiai K, Okamoto T. Novel histone deacetylase inhibitor NCH-51 activates latent HIV-1 gene expression. FEBS Lett. 2011 Apr 6;585(7):1103-11. doi: 10.1016/j.febslet.2011.03.017. Epub 2011 Mar 12. PMID: 21402072.
2. Sanda T, Okamoto T, Uchida Y, Nakagawa H, Iida S, Kayukawa S, Suzuki T, Oshizawa T, Suzuki T, Miyata N, Ueda R. Proteome analyses of the growth inhibitory effects of NCH-51, a novel histone deacetylase inhibitor, on lymphoid malignant cells. Leukemia. 2007 Nov;21(11):2344-53. doi: 10.1038/sj.leu.2404902. Epub 2007 Aug 9. PMID: 17690692.
1: Nageshappa S, Carromeu C, Trujillo CA, Mesci P, Espuny-Camacho I, Pasciuto E,
Vanderhaeghen P, Verfaillie CM, Raitano S, Kumar A, Carvalho CM, Bagni C, Ramocki
MB, Araujo BH, Torres LB, Lupski JR, Van Esch H, Muotri AR. Altered neuronal
network and rescue in a human MECP2 duplication model. Mol Psychiatry. 2016
Feb;21(2):178-88. doi: 10.1038/mp.2015.128. Epub 2015 Sep 8. PubMed PMID:
26347316; PubMed Central PMCID: PMC4720528.
2: Victoriano AF, Imai K, Togami H, Ueno T, Asamitsu K, Suzuki T, Miyata N,
Ochiai K, Okamoto T. Novel histone deacetylase inhibitor NCH-51 activates latent
HIV-1 gene expression. FEBS Lett. 2011 Apr 6;585(7):1103-11. doi:
10.1016/j.febslet.2011.03.017. Epub 2011 Mar 12. PubMed PMID: 21402072.
3: Sanda T, Okamoto T, Uchida Y, Nakagawa H, Iida S, Kayukawa S, Suzuki T,
Oshizawa T, Suzuki T, Miyata N, Ueda R. Proteome analyses of the growth
inhibitory effects of NCH-51, a novel histone deacetylase inhibitor, on lymphoid
malignant cells. Leukemia. 2007 Nov;21(11):2344-53. Epub 2007 Aug 9. PubMed PMID:
17690692.
4: Suzuki T, Hisakawa S, Itoh Y, Maruyama S, Kurotaki M, Nakagawa H, Miyata N.
Identification of a potent and stable antiproliferative agent by the prodrug
formation of a thiolate histone deacetylase inhibitor. Bioorg Med Chem Lett. 2007
Mar 15;17(6):1558-61. Epub 2007 Jan 13. PubMed PMID: 17257837.
