SM-7368 | CAS#380623-76-7 | MMP-9 upregulation inhibitor

SM-7368
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561285

CAS#: 380623-76-7

Description: SM-7368 inhibits TNF-alpha-induced MMP-9 upregulation in a concentration-dependent manner. SM-7368 strongly inhibits the TNF-alpha-induced invasion of HT1080 human fibrosarcoma cell line.

Chemical Structure

SM-7368

CAS# 380623-76-7

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 561285
Name: SM-7368
CAS#: 380623-76-7
Chemical Formula: C10H5ClN4O5S
Exact Mass: 327.97
Molecular Weight: 328.680
Elemental Analysis: C, 36.54; H, 1.53; Cl, 10.79; N, 17.05; O, 24.34; S, 9.75

Price and Availability

Size	Price	Availability
1mg	USD 200	2 Weeks
5mg	USD 420	2 weeks
10mg	USD 500	2 weeks
25mg	USD 730	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: SM-7368; SM 7368; SM7368; NF-kappaB Activation Inhibitor III

IUPAC/Chemical Name: 3-Chloro-4-nitro-N-(5-nitro-1,3-thiazol-2-yl)benzamide

InChi Key: XCHLNGBTHLJLFG-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H5ClN4O5S/c11-6-3-5(1-2-7(6)14(17)18)9(16)13-10-12-4-8(21-10)15(19)20/h1-4H,(H,12,13,16)

SMILES Code: O=C(NC1=NC=C([N+]([O-])=O)S1)C2=CC=C([N+]([O-])=O)C(Cl)=C2

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: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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:

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Biological target:	SM-7368 targets downstream of MAPK p38 activation and inhibits TNF-α-induced MMP-9 upregulation.
In vitro activity:	SM-7368 has promise for developing chemotherapies targeting TNF-alpha-mediated tumor invasion and metastasis. In HT1080 human fibrosarcoma cells, SM-7368 concentration-dependently inhibited TNF-alpha-induced MMP-9 upregulation by suppressing mRNA transcript accumulation and protein expression. Additionally, SM-7368 strongly hindered TNF-alpha-induced NF-kappaB activity without affecting AP-1 activity, leading to a significant inhibition of cell invasion. Reference: Biochem Biophys Res Commun. 2005 Oct 21;336(2):716-22. https://pubmed.ncbi.nlm.nih.gov/16140265/
In vivo activity:	To be determined

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	83.3	253.52

Preparing Stock Solutions

The following data is based on the product molecular weight 328.68 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. Morizane Y, Thanos A, Takeuchi K, Murakami Y, Kayama M, Trichonas G, Miller J, Foretz M, Viollet B, Vavvas DG. AMP-activated protein kinase suppresses matrix metalloproteinase-9 expression in mouse embryonic fibroblasts. J Biol Chem. 2011 May 6;286(18):16030-8. doi: 10.1074/jbc.M110.199398. Epub 2011 Mar 14. PMID: 21402702; PMCID: PMC3091212. 2. Lee HY, Park KS, Kim MK, Lee T, Ryu SH, Woo KJ, Kwon TK, Bae YS. A small compound that inhibits tumor necrosis factor-alpha-induced matrix metalloproteinase-9 upregulation. Biochem Biophys Res Commun. 2005 Oct 21;336(2):716-22. doi: 10.1016/j.bbrc.2005.08.154. PMID: 16140265.
In vitro protocol:	1. Morizane Y, Thanos A, Takeuchi K, Murakami Y, Kayama M, Trichonas G, Miller J, Foretz M, Viollet B, Vavvas DG. AMP-activated protein kinase suppresses matrix metalloproteinase-9 expression in mouse embryonic fibroblasts. J Biol Chem. 2011 May 6;286(18):16030-8. doi: 10.1074/jbc.M110.199398. Epub 2011 Mar 14. PMID: 21402702; PMCID: PMC3091212. 2. Lee HY, Park KS, Kim MK, Lee T, Ryu SH, Woo KJ, Kwon TK, Bae YS. A small compound that inhibits tumor necrosis factor-alpha-induced matrix metalloproteinase-9 upregulation. Biochem Biophys Res Commun. 2005 Oct 21;336(2):716-22. doi: 10.1016/j.bbrc.2005.08.154. PMID: 16140265.
In vivo protocol:	To be determined

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1: Lee HY, Park KS, Kim MK, Lee T, Ryu SH, Woo KJ, Kwon TK, Bae YS. A small compound that inhibits tumor necrosis factor-alpha-induced matrix metalloproteinase-9 upregulation. Biochem Biophys Res Commun. 2005 Oct 21;336(2):716-22. PubMed PMID: 16140265.

2: Samuel T, Fadlalla K, Gales DN, Putcha BD, Manne U. Variable NF-κB pathway responses in colon cancer cells treated with chemotherapeutic drugs. BMC Cancer. 2014 Aug 18;14:599. doi: 10.1186/1471-2407-14-599. PubMed PMID: 25134433; PubMed Central PMCID: PMC4152571.

3: Wang X, Li C, Liang A, Peng Y, Sun J, Huang D, Xu K, Ye W. Regulation of a disintegrins and metalloproteinase with thrombospondin motifs 7 during inflammation in nucleus pulposus (NP) cells: role of AP-1, Sp1 and NF-κB signaling. Inflamm Res. 2016 Dec;65(12):951-962. Epub 2016 Aug 11. PubMed PMID: 27516213.

4: Kuntz S, Kunz C, Rudloff S. Carbonyl compounds methylglyoxal and glyoxal affect interleukin-8 secretion in intestinal cells by superoxide anion generation and activation of MAPK p38. Mol Nutr Food Res. 2010 Oct;54(10):1458-67. doi: 10.1002/mnfr.200900408. PubMed PMID: 20397192.

5: Strand ME, Herum KM, Rana ZA, Skrbic B, Askevold ET, Dahl CP, Vistnes M, Hasic A, Kvaløy H, Sjaastad I, Carlson CR, Tønnessen T, Gullestad L, Christensen G, Lunde IG. Innate immune signaling induces expression and shedding of the heparan sulfate proteoglycan syndecan-4 in cardiac fibroblasts and myocytes, affecting inflammation in the pressure-overloaded heart. FEBS J. 2013 May;280(10):2228-47. doi: 10.1111/febs.12161. Epub 2013 Feb 24. PubMed PMID: 23374111.

6: Wang J, Markova D, Anderson DG, Zheng Z, Shapiro IM, Risbud MV. TNF-α and IL-1β promote a disintegrin-like and metalloprotease with thrombospondin type I motif-5-mediated aggrecan degradation through syndecan-4 in intervertebral disc. J Biol Chem. 2011 Nov 18;286(46):39738-49. doi: 10.1074/jbc.M111.264549. Epub 2011 Sep 23. PubMed PMID: 21949132; PubMed Central PMCID: PMC3220535.

7: Morizane Y, Thanos A, Takeuchi K, Murakami Y, Kayama M, Trichonas G, Miller J, Foretz M, Viollet B, Vavvas DG. AMP-activated protein kinase suppresses matrix metalloproteinase-9 expression in mouse embryonic fibroblasts. J Biol Chem. 2011 May 6;286(18):16030-8. doi: 10.1074/jbc.M110.199398. Epub 2011 Mar 14. PubMed PMID: 21402702; PubMed Central PMCID: PMC3091212.

8: Mulla MJ, Yu AG, Cardenas I, Guller S, Panda B, Abrahams VM. Regulation of Nod1 and Nod2 in first trimester trophoblast cells. Am J Reprod Immunol. 2009 Apr;61(4):294-302. doi: 10.1111/j.1600-0897.2009.00694.x. PubMed PMID: 19260860.

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