174664-65-4 Usage
Description
Benzamide, N-hydroxy-3-[3-(hydroxyamino)-3-oxo-1-propen-1-yl]is a second-generation hybrid polar agent with cell permeability. It functions as a histone deacetylase (HDAC) inhibitor, which is believed to inhibit HDAC activity through the binding of its hydroxamic moiety to the active site zinc. Benzamide, N-hydroxy-3-[3-(hydroxyamino)-3-oxo-1-propen-1-yl]has the potential to induce apoptosis and Fas/Fas ligand expression in human neuroblastoma cells.
Uses
Used in Pharmaceutical Industry:
Benzamide, N-hydroxy-3-[3-(hydroxyamino)-3-oxo-1-propen-1-yl]is used as a histone deacetylase inhibitor for its ability to inhibit HDAC activity, which is crucial in the regulation of gene expression. The compound's interaction with the active site zinc leads to the modulation of cellular processes, making it a valuable tool in the development of therapeutic strategies for various diseases, particularly those involving altered gene expression patterns.
Used in Cancer Research and Treatment:
Benzamide, N-hydroxy-3-[3-(hydroxyamino)-3-oxo-1-propen-1-yl]is used as an apoptosis inducer and Fas/Fas ligand expression stimulator in human neuroblastoma. Its ability to induce apoptosis and modulate the Fas/Fas ligand system makes it a promising candidate for the development of targeted cancer therapies, particularly for neuroblastoma and potentially other cancer types with similar molecular mechanisms.
Biological Activity
cbha is a potent and selective inhibitor with id50 values of 0.01 and 0.07 μm for hdac1 and hdac3, respectively [1].histone deacetylases (hdacs) are a class of enzymes that remove acetyl groups from lysine amino acid on histone, allowing the histones to wrap the dna more tightly. hdac inhibitors hyperacetylate histones and increase transcriptional activity in target genes. hdac inhibitors have both apoptotic and differentiating effects on various tumor cells [2].m-carboxycinnamic acid bishydroxamide (cbha) is a potent and selective hdac inhibitor. cbha is a hybrid polar compound that is synthesized to induce terminal differentiation and/or apoptosis in various transformed cells. in mel cells, cbha caused accumulation of acetylated histone h4 [1]. in neuroblastoma cell lines, cbha induced acetylated histone h3 and h4 accumulation. cbha also led to extensive cell death with ld50 ranged between 1 μm and 4 μm, and induced apoptosis [2].in human neuroblastoma xenograft scid mice, cbha (100 mg/kg and 200 mg/kg) resulted in reductions of average final tumor volume of ~50% and 75%, respectively [3].
references
[1]. richon vm1, emiliani s, verdin e, et al. a class of hybrid polar inducers of transformed cell differentiation inhibits histone deacetylases. proc natl acad sci u s a. 1998 mar 17;95(6):3003-7.[2]. glick rd1, swendeman sl, coffey dc, et al. hybrid polar histone deacetylase inhibitor induces apoptosis and cd95/cd95 ligand expression in human neuroblastoma. cancer res. 1999 sep 1;59(17):4392-9.[3]. coffey dc, kutko mc, glick rd, et al. the histone deacetylase inhibitor, cbha, inhibits growth of human neuroblastoma xenografts in vivo, alone and synergistically with all-trans retinoic acid. cancer res. 2001 may 1;61(9):3591-4.
Check Digit Verification of cas no
The CAS Registry Mumber 174664-65-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,4,6,6 and 4 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 174664-65:
(8*1)+(7*7)+(6*4)+(5*6)+(4*6)+(3*4)+(2*6)+(1*5)=164
164 % 10 = 4
So 174664-65-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H10N2O4/c13-9(11-15)5-4-7-2-1-3-8(6-7)10(14)12-16/h1-6,15-16H,(H,11,13)(H,12,14)/b5-4+
