N,N'-Dihydroxyoctanediamide

Modify Date: 2024-01-02 18:22:06

N,N'-Dihydroxyoctanediamide Structure
N,N'-Dihydroxyoctanediamide structure
 Common Name N,N'-Dihydroxyoctanediamide
CAS Number 38937-66-5 Molecular Weight 204.224
Density 1.2±0.1 g/cm3 Boiling Point N/A
Molecular Formula C8H16N2O4 Melting Point 153-155ºC(lit.)
MSDS USA Flash Point N/A

 Use of N,N'-Dihydroxyoctanediamide


Suberoyl bis-hydroxamic acid (Suberohydroxamic acid; SBHA) is a competitive and cell-permeable HDAC1 and HDAC3 inhibitor with ID50 values of 0.25 μM and 0.30 μM, respectively[1].Suberoyl bis-hydroxamic acid renders MM cells susceptible to apoptosis and facilitates the mitochondrial apoptotic pathways[2].Suberoyl bis-hydroxamic acid can be used for the study of medullary thyroid carcinoma (MTC)[3].

 Names

Name Suberoyl Bis-hydroxamic Acid
Synonym More Synonyms

 N,N'-Dihydroxyoctanediamide Biological Activity

Description Suberoyl bis-hydroxamic acid (Suberohydroxamic acid; SBHA) is a competitive and cell-permeable HDAC1 and HDAC3 inhibitor with ID50 values of 0.25 μM and 0.30 μM, respectively[1].Suberoyl bis-hydroxamic acid renders MM cells susceptible to apoptosis and facilitates the mitochondrial apoptotic pathways[2].Suberoyl bis-hydroxamic acid can be used for the study of medullary thyroid carcinoma (MTC)[3].
Related Catalog
Target

HDAC1:0.25 μM (IC50)

HDAC3:0.30 μM (IC50)
In Vitro Suberoyl bis-hydroxamic acid (10, 20 or 50 μM; 24 hours) combination with TRAIL improves apoptosis extent, and when TRAIL is combined with 20 μM SBHA (itself causing only 10–15% apoptosis), resulting in 45–50% cell death[1]. Suberoyl bis-hydroxamic acid (20-50 μM; 10-20 hours) alone has little effect on the expression of the proteins Bcl-xL, Mcl-1, and has albeit mildeffect on Bax. When it combines with TRAIL,which increases the ratio of relative protein expression of Bcl-xL and Bax in early periods, while the change in the ratio of Mcl-1 and Bax increases later in MM-BI and Ist-Mes2 cells[1]. Suberoyl bis-hydroxamic acid (30 μM; 6 hours) causes accumulation of acetylated histone H4 in MEL cells[2]. Apoptosis Analysis[1] Cell Line: MM-BI and Ist-Mes2 cells Concentration: 10 μM, 20 μM or 50 μM Incubation Time: 24 hours Result: Showed a cooperative effect in cell apoptosis.
In Vivo Suberoyl bis-hydroxamic acid (intraperitoneal injection; 200 mg/kg; every 2 days; 12 days) reveals a marked increase in the active form of Notch1 (NICD) with a concomitant decrease in ASCL1. It reduces the MTC tumor growth[3]. Animal Model: Nude mice injected with human MTC cells[3] Dosage: 200 mg/kg Administration: Intraperitoneal injection; every 2 days; 12 days Result: Resulted in an average 55% inhibition of tumor growth in SBHA treatment group.
References

[1]. Jiri Neuzil, et al. Sensitization of Mesothelioma to TRAIL Apoptosis by Inhibition of Histone Deacetylase: Role of Bcl-xL Down-Regulation. Biochem Biophys Res Commun. 2004 Jan 30;314(1):186-91.

[2]. V M Richon, et al. A Class of Hybrid Polar Inducers of Transformed Cell Differentiation Inhibits Histone Deacetylases.Proc Natl Acad Sci U S A

[3]. Li Ning, et al. Suberoyl Bishydroxamic Acid Activates notch1 Signaling and Suppresses Tumor Progression in an Animal Model of Medullary Thyroid Carcinoma. Ann Surg Oncol. 2008 Sep;15(9):2600-5.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Melting Point 153-155ºC(lit.)
Molecular Formula C8H16N2O4
Molecular Weight 204.224
Exact Mass 204.111008
PSA 98.66000
LogP -1.81
Appearance of Characters lyophilized powder
Index of Refraction 1.502
Storage condition −20°C
Water Solubility H2O: soluble

 Safety Information

Safety Phrases 22-24/25
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2924199090

 Synthetic Route

Dimethyl octanedioate structure

Dimethyl octane...

CAS#:1732-09-8

~92%

N,N'-Dihydroxyoctanediamide Structure

N,N'-Dihydroxyo...

CAS#:38937-66-5
Literature: Bioorganic and Medicinal Chemistry, , vol. 21, # 13 p. 3866 - 3872
Ethyl suberate structure

Ethyl suberate

CAS#:2050-23-9

~%

N,N'-Dihydroxyoctanediamide Structure

N,N'-Dihydroxyo...

CAS#:38937-66-5
Literature: Journal of Chemical & Engineering Data, , vol. 29, # 3 p. 345 - 348
methyl 8-(hydroxyamino)-8-oxooctanoate structure

methyl 8-(hydro...

CAS#:149647-87-0

~%

N,N'-Dihydroxyoctanediamide Structure

N,N'-Dihydroxyo...

CAS#:38937-66-5
Literature: Journal of Medicinal Chemistry, , vol. 53, # 8 p. 3038 - 3047
1,8-di(1H-imidazol-1-yl)octane-1,8-dione structure

1,8-di(1H-imida...

CAS#:122236-58-2

~%

N,N'-Dihydroxyoctanediamide Structure

N,N'-Dihydroxyo...

CAS#:38937-66-5
Literature: Synthetic Communications, , vol. 15, # 13 p. 1159 - 1164
Octanedioic acid structure

Octanedioic acid

CAS#:505-48-6

~%

N,N'-Dihydroxyoctanediamide Structure

N,N'-Dihydroxyo...

CAS#:38937-66-5
Literature: Journal of the Chemical Society. Perkin Transactions 2, , vol. 1996, # 12 p. 2673 - 2679

 Customs

HS Code 2924199090
Summary 2924199090. other acyclic amides (including acyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

 Articles10

More Articles
A regimen combining the Wee1 inhibitor AZD1775 with HDAC inhibitors targets human acute myeloid leukemia cells harboring various genetic mutations.

Leukemia 29(4) , 807-18, (2015)

AZD1775 targets the cell cycle checkpoint kinase Wee1 and potentiates genotoxic agent cytotoxicity through p53-dependent or -independent mechanisms. Here, we report that AZD1775 interacted synergistic...
Reactive oxygen species, glutathione, and thioredoxin influence suberoyl bishydroxamic acid-induced apoptosis in A549 lung cancer cells.

Tumour Biol. 36 , 3429-39, (2015)

Suberoyl bishydroxamic acid (SBHA) as a histone deacetylase (HDAC) inhibitor can induce apoptosis through the formation of reactive oxygen species (ROS). However, there is no report about the regulati...
Down-Regulation of Thioredoxin1 Is Involved in Death of Calu-6 Lung Cancer Cells Treated With Suberoyl Bishydroxamic Acid.

J. Cell. Biochem. 117 , 1250-61, (2016)

Suberoyl bishydroxamic acid (SBHA), a histone deacetylase (HDAC) inhibitor, can show an anticancer effect. In this study, we investigated the effects of SBHA on the growth inhibition and death of Calu...

 Synonyms

Octanediamide, N,N-dihydroxy-
octane-1,8-dihydroxamic acid
N,N'-Dihydroxyoctanediamide
MFCD00192455
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