SGA360 | CAS#680611-86-3 | AHR modulator

MedKoo Cat#: 555952 | Name: SGA360

Description:

WARNING: This product is for research use only, not for human or veterinary use.

SGA360 is a selective AHR modulator, which is a ligand-dependent transcription factor that mediates the toxicity of certain xenobiotics and polyaromatic hydrocarbons.

Chemical Structure

SGA360

CAS#680611-86-3

Theoretical Analysis

MedKoo Cat#: 555952

Name: SGA360

CAS#: 680611-86-3

Chemical Formula: C19H17F3N2O2

Exact Mass: 362.1242

Molecular Weight: 362.35

Elemental Analysis: C, 62.98; H, 4.73; F, 15.73; N, 7.73; O, 8.83

Price and Availability

Size	Price	Availability
50mg	USD 550.00	2 Weeks
100mg	USD 950.00	2 Weeks
200mg	USD 1,650.00	2 Weeks
500mg	USD 2,950.00	2 Weeks
1g	USD 3,950.00	2 Weeks
2g	USD 5,950.00	2 Weeks
5g	USD 9,650.00	2 Weeks

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Related CAS #

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Synonym

SGA360; SGA-360; SGA 360;

IUPAC/Chemical Name

3-(2,4-dimethoxyphenyl)-1-(2-propen-1-yl)-7-(trifluoromethyl)-1H-indazole

InChi Key

BMIOASGFHBRKJL-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H17F3N2O2/c1-4-10-24-18-14(6-5-7-15(18)19(20,21)22)17(23-24)13-9-8-12(25-2)11-16(13)26-3/h4-9,11H,1,10H2,2-3H3

SMILES Code

FC(C1=CC=CC2=C1N(CC=C)N=C2C3=CC=C(OC)C=C3OC)(F)F

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SGA360 competitively binds to AhR (IC50 = 3 µM) and represses serum amyloid A 1 (SAA1) gene expression induced by IL-1β in Huh7 cells.

In vitro activity:

To be determined

In vivo activity:

SGA360 is a selective Ah receptor modulator (SAhRM) that exhibits anti-inflammatory properties in vivo. SGA360 significantly inhibited 2-O-tetradecanoylphorbol-13-acetate (TPA)-mediated ear swelling and induction of a number of inflammatory genes in C57BL6/J mice. SGA360 had no effect on TPA-mediated ear swelling or inflammatory gene expression in Ahr(-/-) mice. Reference: Chem Res Toxicol. 2010 May 17;23(5):955-66. https://pubmed.ncbi.nlm.nih.gov/20423157/

	Solvent	mg/mL	mM
Solubility
	DMSO	10.0	27.60
	DMF	20.0	55.20
	Ethanol	2.5	6.90

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 362.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Muku GE, Lahoti TS, Murray IA, Podolsky MA, Smith KJ, Hubbard TD, Kuzu G, Gowda K, Amin SG, Perdew GH. Ligand-mediated cytoplasmic retention of the Ah receptor inhibits macrophage-mediated acute inflammatory responses. Lab Invest. 2017 Dec;97(12):1471-1487. doi: 10.1038/labinvest.2017.92. Epub 2017 Sep 11. PMID: 28892097; PMCID: PMC5711556. 2. Murray IA, Krishnegowda G, DiNatale BC, Flaveny C, Chiaro C, Lin JM, Sharma AK, Amin S, Perdew GH. Development of a selective modulator of aryl hydrocarbon (Ah) receptor activity that exhibits anti-inflammatory properties. Chem Res Toxicol. 2010 May 17;23(5):955-66. doi: 10.1021/tx100045h. PMID: 20423157; PMCID: PMC2871980.

In vitro protocol:

To be determined

In vivo protocol:

1: Muku GE, Blazanin N, Dong F, Smith PB, Thiboutot D, Gowda K, Amin S, Murray IA, Perdew GH. Selective Ah receptor ligands mediate enhanced SREBP1 proteolysis to restrict lipogenesis in sebocytes. Toxicol Sci. 2019 Jun 21;171(1):146–58. doi: 10.1093/toxsci/kfz140. Epub ahead of print. PMID: 31225620; PMCID: PMC6736396. 2: Muku GE, Lahoti TS, Murray IA, Podolsky MA, Smith KJ, Hubbard TD, Kuzu G, Gowda K, Amin SG, Perdew GH. Ligand-mediated cytoplasmic retention of the Ah receptor inhibits macrophage-mediated acute inflammatory responses. Lab Invest. 2017 Dec;97(12):1471-1487. doi: 10.1038/labinvest.2017.92. Epub 2017 Sep 11. PMID: 28892097; PMCID: PMC5711556. 3: van den Bogaard EH, Podolsky MA, Smits JP, Cui X, John C, Gowda K, Desai D, Amin SG, Schalkwijk J, Perdew GH, Glick AB. Genetic and pharmacological analysis identifies a physiological role for the AHR in epidermal differentiation. J Invest Dermatol. 2015 May;135(5):1320-1328. doi: 10.1038/jid.2015.6. Epub 2015 Jan 20. PMID: 25602157; PMCID: PMC4402116. 4: Smith KJ, Murray IA, Tanos R, Tellew J, Boitano AE, Bisson WH, Kolluri SK, Cooke MP, Perdew GH. Identification of a high-affinity ligand that exhibits complete aryl hydrocarbon receptor antagonism. J Pharmacol Exp Ther. 2011 Jul;338(1):318-27. doi: 10.1124/jpet.110.178392. Epub 2011 Apr 14. PMID: 21493753; PMCID: PMC3126639. 5: Murray IA, Krishnegowda G, DiNatale BC, Flaveny C, Chiaro C, Lin JM, Sharma AK, Amin S, Perdew GH. Development of a selective modulator of aryl hydrocarbon (Ah) receptor activity that exhibits anti-inflammatory properties. Chem Res Toxicol. 2010 May 17;23(5):955-66. doi: 10.1021/tx100045h. PMID: 20423157; PMCID: PMC2871980.