38937-66-5 Usage
Description
OCTANE-1,8-DIHYDROXAMIC ACID, also known as Suberohydroxamic acid (SBHA), is a histone deacetylase (HDAC) inhibitor derived from natural sources. It possesses the ability to inhibit HDAC1 and HDAC3, leading to cell differentiation, cell cycle arrest, or apoptosis. Its unique properties make it a promising compound for various applications in the pharmaceutical and biotechnology industries.
Uses
Used in Pharmaceutical Industry:
OCTANE-1,8-DIHYDROXAMIC ACID is used as a histone deacetylase inhibitor for its ability to suppress the growth of proliferating keratinocytes and squamous cell carcinoma cells. It modulates cellular processes by inhibiting histone deacetylation, which is crucial for the regulation of gene expression and has implications in cancer therapy.
Used in Cancer Treatment:
OCTANE-1,8-DIHYDROXAMIC ACID is used as an anticancer agent for its synergistic effects when combined with conventional cytostatic drugs. This combination allows for lower doses of both inhibitors and drugs to be used, potentially reducing side effects and improving treatment outcomes.
Used in Drug Delivery Systems:
In the field of drug delivery, OCTANE-1,8-DIHYDROXAMIC ACID is used to enhance the efficacy of cancer treatments. It can be incorporated into various organic and metallic nanoparticles as a carrier, aiming to improve its delivery, bioavailability, and therapeutic outcomes in cancer treatment.
Biological Activity
Suberoyl bis-hydroxamic acid (SBHA) is a Histone deacetylase (HDAC) inhibitor. SBHA inhibits the activity of HDAC1 and HDAC3 with IC50 values of 250 and 300 nM, respectively. SBHA inhibits proliferation, and induces apoptosis in several cancer cell lines. SBHA has been shown to activate Notch signaling in medullary thyroid carcinoma (MTC) cells.
Biochem/physiol Actions
Suberoyl bis-hydroxamic acid (SBHA) is a Histone deacetylase (HDAC) inhibitor. SBHA inhibits the activity of HDAC1 and HDAC3 with IC50 values of 250 and 300 nM, respectively. SBHA inhibits proliferation, and induces apoptosis in several cancer cell lines. SBHA has been shown to activate Notch signaling in medullary thyroid carcinoma (MTC) cells.
references
1. richon vm, 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. zhang xd, gillespie sk, borrow jm, hersey p. the histone deacetylase inhibitor suberic bishydroxamate regulates the expression of multiple apoptotic mediators and induces mitochondria-dependent apoptosis of melanoma cells. mol cancer ther. 2004 apr; 3(4):425-35.
Check Digit Verification of cas no
The CAS Registry Mumber 38937-66-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,8,9,3 and 7 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 38937-66:
(7*3)+(6*8)+(5*9)+(4*3)+(3*7)+(2*6)+(1*6)=165
165 % 10 = 5
So 38937-66-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H20N2O4/c13-9(11-15)7-5-3-1-2-4-6-8-10(14)12-16/h15-16H,1-8H2,(H,11,13)(H,12,14)
38937-66-5Relevant articles and documents
Cross metathesis with hydroxamate and benzamide BOC-protected alkenes to access HDAC inhibitors and their biological evaluation highlighted intrinsic activity of BOC-protected dihydroxamates
Zwick, Vincent,Nurisso, Alessandra,Sim?es-Pires, Claudia,Bouchet, Samuel,Martinet, Nadine,Lehotzky, Attila,Ovadi, Judit,Cuendet, Muriel,Blanquart, Christophe,Bertrand, Philippe
supporting information, p. 154 - 159 (2015/12/18)
Conditions for the metathesis of alkenes in the convergent synthesis of HDAC inhibitors have been improved by continuous catalyst flow injection in the reaction media. Intermediate and target compounds obtained were tested for their ability to induce HDAC
An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives
Mocci, Rita,De Luca, Lidia,Delogu, Francesco,Porcheddu, Andrea
supporting information, p. 3135 - 3144 (2016/10/09)
An operationally simple, and cost efficient conversion of carboxylic acids into hydroxamic acid derivatives via a high-energy mechanochemical activation is presented. This ball milling methodology was applied to a wide variety of carboxylic acids dramatically improving purification issues associated with this class of molecules, which still remain one of the main bottlenecks of classical methodologies. (Figure presented.).
Modified cap group suberoylanilide hydroxamic acid histone deacetylase inhibitor derivatives reveal improved selective antileukemic activity
Salmi-Smail, Chanaz,Fabre, Aurélie,Dequiedt, Franck,Restouin, Audrey,Castellano, Rémy,Garbit, Slaveia,Roche, Philippe,Morelli, Xavier,Brunel, Jean Michel,Collette, Yves
experimental part, p. 3038 - 3047 (2010/09/07)
A series of SAHA cap derivatives was designed and prepared in good-to-excellent yields that varied from 49% to 95%. These derivatives were evaluated for their antiproliferative activity in several human cancer cell lines. Antiproliferative activity was observed for concentrations varying from 0.12 to >100 μM, and a molecular modeling approach of selected SAHA derivatives, based on available structural information of human HDAC8 in complex with SAHA, was performed. Strikingly, two compounds displayed up to 10-fold improved antileukemic activity with respect to SAHA; however, these compounds displayed antiproliferative activity similar to SAHA when assayed against solid tumor-derived cell lines. A 10-fold improvement in the leukemic vs peripheral blood mononuclear cell therapeutic ratio, with no evident in vivo toxicity toward blood cells, was also observed. The herein-described compounds and method of synthesis will provide invaluable tools to investigate the molecular mechanism responsible for the reported selectively improved antileukemic activity.
