ChemicalBook CAS DataBase List 68003-38-3

68003-38-3

Name	2-[(4-chloro-3-nitrophenyl)sulphonyl]anthranilic acid
CAS	68003-38-3
EINECS(EC#)	268-121-3
Molecular Formula	C13H9ClN2O6S
MDL Number	MFCD00129907
Molecular Weight	356.74
MOL File	68003-38-3.mol

Chemical Properties

Boiling point	564.8±60.0 °C(Predicted)
density	1.660±0.06 g/cm3(Predicted)
storage temp.	Store at -20°C
solubility	DMSO:125 mg/mL(350.40 mM)
form	A solid
pka	3.19±0.36(Predicted)
color	Off-white to light yellow
InChI	1S/C13H9ClN2O6S/c14-10-6-5-8(7-12(10)16(19)20)23(21,22)15-11-4-2-1-3-9(11)13(17)18/h1-7,15H,(H,17,18)
InChIKey	NJTHPOSQGFJTDP-UHFFFAOYSA-N
SMILES	[S](=O)(=O)(Nc2c(cccc2)C(=O)O)c1cc(c(cc1)Cl)[N+](=O)[O-]
EPA Substance Registry System	Benzoic acid, 2-[[(4-chloro-3-nitrophenyl)sulfonyl]amino]- (68003-38-3)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H312-H315-H319-H332-H335
Precautionary statements	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501
WGK Germany	WGK 3
TSCA	TSCA listed
Storage Class	11 - Combustible Solids

Hazard Information

Uses

CTPI-2 is a third-generation mitochondrial citrate carrier SLC25A1 inhibitor with a KD of 3.5 μM. CTPI-2 inhibits glycolysis, PPARγ, and its downstream target the glucose transporter GLUT4. CTPI-2 halts salient alterations of NASH reverting steatosis, preventing the evolution to steatohepatitis, reducing inflammatory macrophage infiltration in the liver and adipose tissue, and starkly mitigating obesity induced by a high-fat diet. Antitumor activity[1][2].

Biological Activity

CTPI-2 is a selective mitochondrial citrate transporter (SLC25A1) inhibitor th at displays H1299 anti-proliferation activity in a SLC25A1-dependent manner (IC50 <10 μM). When compared with CTPI-1CTPI-2 exhibits 20-fold higher target affinity (hSLC25A1 KD = 3.5 μM vs. 63.6 μMrespectively) and is ~1000-fold more potent against H1299 sphere-forming capacity. CTPI-2 inhibits mitochondrial respiration and formation of patient NSCLC tumors-derived CSCs spheres in cultures (10-50 μM)as well as suppresses the growth of patent-derived NSCLC exnografts in mice in vivo (28 mg/kg q.o.d. i.p.).

in vivo

CTPI-2 is a unique regulator of glycolysis that limits the metabolic plasticity of cancer stem cells (CSCs). CTPI-2 (26 mg/kg; i.p.) inhibits tumor growth in in vivo models of non-small cell lung cancer (NSCLC)^[1].
CTPI-2 (50 mg/kg; i.p.; alternate days for 12 weeks) completely averts weight gain in the prevention study and leads to significant weight loss in the reversion study^[2].
CTPI-2 prevents steatohepatitis and normalizes glucose tolerance. CTPI-2 lowers the levels of circulating IL-6 while increasing anti-inflammatory IL-4 and IL-10 and also reduced the monocyte chemoattractant protein-1 and monokine-induced by interferon-γ that attract neutrophils and monocytes. CTPI-2 regulates the citrate pool, the lipogenic and the gluconeogenic pathways^[2].

Animal Model:	C57BL/6J mice (HFD-fed mice)^[2]
Dosage:	50 mg/kg
Administration:	Alternate days via the intraperitoneal route for 12 weeks
Result:	Completely averted weight gain in the prevention study and led to significant weight loss in the reversion study.

References

[1] Tan M, et al. Inhibition of the mitochondrial citrate carrier, Slc25a1, reverts steatosis, glucose intolerance, and inflammation in preclinical models of NAFLD/NASH. Cell Death Differ. 2020;27(7):2143-2157. DOI:10.1038/s41418-020-0491-6
[2] Fernandez HR, et al. The mitochondrial citrate carrier, SLC25A1, drives stemness and therapy resistance in non-small cell lung cancer. Cell Death Differ. 2018;25(7):1239-1258. DOI:10.1038/s41418-018-0101-z

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