38937-66-5

38937-66-5 structure

Name: N,N'-Dihydroxyoctanediamide
Chemical Name: Suberoyl Bis-hydroxamic Acid
CAS Number: 38937-66-5
Molecular Formula: C₈H₁₆N₂O₄
Molecular Weight: 204.224
Catalog: Chemical reagent Organic reagent Hydroxylamine
Create Date: 2018-06-12 11:45:17
Modify Date: 2024-01-02 18:22:06
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].

Name	Suberoyl Bis-hydroxamic Acid
Synonyms	Octanediamide, N,N-dihydroxy- octane-1,8-dihydroxamic acid N,N'-Dihydroxyoctanediamide MFCD00192455

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	Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> HDAC Signaling Pathways >> Epigenetics >> HDAC
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.

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	lyophilized powder
Index of Refraction	1.502
Storage condition	−20°C
Water Solubility	H2O: soluble

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

1732-09-8

~92%

38937-66-5

Literature: Bioorganic and Medicinal Chemistry, , vol. 21, # 13 p. 3866 - 3872

2050-23-9

38937-66-5

Literature: Journal of Chemical & Engineering Data, , vol. 29, # 3 p. 345 - 348

149647-87-0

38937-66-5

Literature: Journal of Medicinal Chemistry, , vol. 53, # 8 p. 3038 - 3047

122236-58-2

38937-66-5

Literature: Synthetic Communications, , vol. 15, # 13 p. 1159 - 1164

505-48-6

38937-66-5

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

Precursor 4
1732-09-8 2050-23-9 122236-58-2 505-48-6
DownStream 0

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%

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