SCS

Names

[ Name ]:
SCS

[Synonym ]:
2-hydroxybenzoylhydrazone of 2-hydroxybenzoylhydrazine
SCS
salicylaldehyde o-hydroxybenzoylhydrazone
MFCD00043494
N'-Salicylidenesalicylic hydrazide
SALICYLIDENE SALICYLHYDRAZONE
salicylaldehyde 2-hydroxybenzoylhydrazone
1-Salicylidene-2-salicyloylhydrazine
EINECS 221-773-2
Salicylidene salicylhydrazide
1-Salicyloyl-2-salicylidenehydrazine
SALICYLIC (2-HYDROXYBENZYLIDENE)HYDRAZIDE
2-HYDROXYBENZYLIDENE SALICYLHYDRAZIDE
2-hydroxybenzoylhydrazine 2-hydroxybenzoylhydrazone
2-Hydroxybenzylidene 2-hydroxybenzhydrazide

Biological Activity

[Description]:

SCS (Salicylidene salicylhydrazide) is a potent, allosteric and selective inhibitor of β1-containing GABAA receptors with an IC50 of 32 nM against α2β1γ1θ by VIPR measurement. SCS is also a chelator of metal ions[1].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[Target]

IC50: 32 nM (α2β1γ1θ; by VIPR measurement) IC50: 4.5 nM (α2β1γ1θ), 5.3 nM (α2β1γ1), 7.9 nM (α1β1γ2s) (Measured by using whole-cell patch clamp)[1]

[In Vitro]

SCS (0.1 nM-3 μM) 对表达 α2β1γ1θ、α2β1γ1 和 α1β1γ2s 受体的 Ltk- 细胞的 GABA EC20 电流有浓度依赖性抑制作用，而对 α2β3γ2s 和 α1β2γ2s 受体无影响[1]。 SCS 的抑制不依赖于电压或使用 (not voltage or use dependent)[1]。 SCS 抑制 GABAA 受体所必需的结构决定因素位于 β1 亚基的精氨酸 238 和甘氨酸 335 区域。β1 亚基的 T255 和 I308 对于 SCS 的抑制是必需的[1]。

[In Vivo]

SCS (Salicylidene salicylhydrazide; 500-1000 mg/kg, i.p. or 800-1000 mg/kg, oral) 使小鼠产生腹部收缩[2]。 SCS (10-75 mg/kg; i.p.; once) 在小鼠中显示出抗强直性和阶段性疼痛和辣椒素痛觉的抗痛觉活性[2]。 SCS (10-75 mg/kg; i.p.; once) 显示小鼠抗炎活性[2]。SCS (50 and 75 mg/kg; i.p.; once) 显示对神经性痛觉的抗痛觉活性[2]。 Animal Model: BALB/c mice; tonic, phasic and Capsaicin (HY-10448) nociception model[2] Dosage: 10, 25, 50, and 75 mg/kg Administration: IP, single dose Result: Produced a significant protection on tonic, phasic and capsaicin nociception in a dose-dependent manner. Animal Model: BALB/c mice, Oxaliplatin (HY-17371)-induced neuropathic nociception model[2] Dosage: 50 and 75 mg/kg Administration: IP, single dose Result: Significantly attenuated the paw withdrawal threshold changes associated with Oxaliplatin. Significantly increased the percent antinociception during 30-120 min.

[References]

[1]. Thompson SA, et al. Salicylidene salicylhydrazide, a selective inhibitor of beta 1-containing GABAA receptors. Br J Pharmacol. 2004 May;142(1):97-106.

[2]. Rukh L, et al. Efficacy assessment of salicylidene salicylhydrazide in chemotherapy associated peripheral neuropathy. Eur J Pharmacol. 2020 Dec 5;888:173481.

Chemical & Physical Properties

[ Density]:
1.406g/cm3

[ Boiling Point ]:
427.3ºC at 760mmHg

[ Melting Point ]:
280-284°C

[ Molecular Formula ]:
C₁₄H₁₂N₂O₃

[ Molecular Weight ]:
256.25700

[ Flash Point ]:
212.2ºC

[ Exact Mass ]:
256.08500

[ PSA ]:
81.92000

[ LogP ]:
2.25260

[ Appearance of Characters ]:
solid | off-white

[ Index of Refraction ]:
1.615

[ Storage condition ]:
Store at RT

[ Water Solubility ]:
DMSO: ~20 mg/mL

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2928000090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2928000090

[ Summary ]:
2928000090 other organic derivatives of hydrazine or of hydroxylamine VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

Articles

Cytotoxicity of salicylaldehyde benzoylhydrazone analogs and their transition metal complexes: quantitative structure-activity relationships.

J. Inorg. Biochem. 77 , 125-133 , (1999)

A series of salicylaldehyde benzoylhydrazone derivatives, their copper(II) complexes and a range of transition metal complexes of the unsubstituted ligand has been synthesized and evaluated for cytoto...

Salicylidene salicylhydrazide, a selective inhibitor of beta 1-containing GABAA receptors.

Br. J. Pharmacol. 142 , 97-106 , (2004)

1. A high-throughput assay utilizing the voltage/ion probe reader (VIPR) technology identified salicylidene salicylhydrazide (SCS) as being a potent selective inhibitor of alpha2beta1gamma1 GABA(A) re...

GABAA receptor subunit beta1 is involved in the formation of protease-resistant prion protein in prion-infected neuroblastoma cells.

FEBS Lett. 584(6) , 1193-8, (2010)

Gamma-aminobutyric acid type A (GABAA) receptor beta1 (gabrb1), a subunit of GABAA receptors involved in inhibitory effects on neurotransmission, was found to associate with the formation of protease-...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.