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

SGA360
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 555952

CAS#: 680611-86-3

Description: 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

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 555952
Name: SGA360
CAS#: 680611-86-3
Chemical Formula: C19H17F3N2O2
Exact Mass: 362.12
Molecular Weight: 362.350
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	2 Weeks
100mg	USD 950	2 Weeks
200mg	USD 1650	2 Weeks
500mg	USD 2950	2 Weeks
1g	USD 3950	2 Weeks
2g	USD 5950	2 Weeks
5g	USD 9650	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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/

Solubility Data

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

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, 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.

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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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.

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