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MedKoo Cat#: 563160 | Name: m-3M3FBS
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Description:

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

m-3M3FBS is an activator of phospholipase C (PLC). It acts by stimulating superoxide generation, Ca2+ release and inositol phosphate formation in a variety of cell types.

Chemical Structure

m-3M3FBS
m-3M3FBS
CAS#200933-14-8

Theoretical Analysis

MedKoo Cat#: 563160

Name: m-3M3FBS

CAS#: 200933-14-8

Chemical Formula: C16H16F3NO2S

Exact Mass: 343.0854

Molecular Weight: 343.36

Elemental Analysis: C, 55.97; H, 4.70; F, 16.60; N, 4.08; O, 9.32; S, 9.34

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 weeks
25mg USD 450.00 2 weeks
50mg USD 750.00 2 weeks
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Related CAS #
No Data
Synonym
m-3M3FBS; m 3M3FBS; m3M3FBS;
IUPAC/Chemical Name
2,4,6-Trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide
InChi Key
ZIIUUSVHCHPIQD-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H16F3NO2S/c1-10-7-11(2)15(12(3)8-10)23(21,22)20-14-6-4-5-13(9-14)16(17,18)19/h4-9,20H,1-3H3
SMILES Code
O=S(C1=C(C)C=C(C)C=C1C)(NC2=CC=CC(C(F)(F)F)=C2)=O
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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#A21M12B09
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
m-3M3FBS is a potent phospholipase C (PLC) activator.
In vitro activity:
m-3M3FBS inhibited the growth of the leukemic cell lines U937 and THP-1, but not primary monocytes. m-3M3FBS induced the apoptosis of U937 cells, which was accompanied by chromatin condensation and DNA fragmentation. Moreover, m-3M3FBS-induced apoptosis appeared to involve the down-regulation of anti-apoptotic Bcl-2, the up-regulation of pro-apoptotic Bax, the release of cytochrome c, and caspase activation. m-3M3FBS-induced apoptosis of U937 cells was also partly inhibited by BAPTA-AM and EGTA, indicating the involvement of intracellular calcium signaling on the apoptosis in U937 cells. Reference: Cancer Lett. 2005 May 26;222(2):227-35. https://pubmed.ncbi.nlm.nih.gov/15863272/
In vivo activity:
Application of the PLCβ activator, m-3M3FBS, in rat hippocampal slices reinstated PLCβ1 protein levels to fully restore S-eCB mobilization and NMDAR-mediated tLTP. In addition, direct hippocampal injection of m-3M3FBS in 5XFAD mice reinstated PLCβ1 protein levels to those observed in wild type control mice and fully restored hippocampus-dependent contextual fear memory in vivo in 5XFAD mice. Reference: Alzheimers Res Ther. 2021 Oct 8;13(1):165. https://pubmed.ncbi.nlm.nih.gov/34625112/
Solvent mg/mL mM
Solubility
DMF 30.0 87.37
DMSO 55.8 162.61
Ethanol 44.5 129.44
Ethanol:PBS (pH 7.2) (1:3) 0.3 0.73
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 343.36 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.

Recalculate based on batch purity %
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. Lee YN, Lee HY, Kim JS, Park C, Choi YH, Lee TG, Ryu SH, Kwak JY, Bae YS. The novel phospholipase C activator, m-3M3FBS, induces monocytic leukemia cell apoptosis. Cancer Lett. 2005 May 26;222(2):227-35. doi: 10.1016/j.canlet.2004.09.017. PMID: 15863272. 2. Krjukova J, Holmqvist T, Danis AS, Akerman KE, Kukkonen JP. Phospholipase C activator m-3M3FBS affects Ca2+ homeostasis independently of phospholipase C activation. Br J Pharmacol. 2004 Sep;143(1):3-7. doi: 10.1038/sj.bjp.0705911. Epub 2004 Aug 9. PMID: 15302681; PMCID: PMC1575272. 3. Lee J, Kwag J. Activation of PLCβ1 enhances endocannabinoid mobilization to restore hippocampal spike-timing-dependent potentiation and contextual fear memory impaired by Alzheimer's amyloidosis. Alzheimers Res Ther. 2021 Oct 8;13(1):165. doi: 10.1186/s13195-021-00901-9. PMID: 34625112; PMCID: PMC8501622. 4. Zhong W, Darmani NA. The Contribution of Phospholipase C in Vomiting in the Least Shrew (Cryptotis Parva) Model of Emesis. Front Pharmacol. 2021 Sep 10;12:736842. doi: 10.3389/fphar.2021.736842. PMID: 34566660; PMCID: PMC8461300.
In vitro protocol:
1. Lee YN, Lee HY, Kim JS, Park C, Choi YH, Lee TG, Ryu SH, Kwak JY, Bae YS. The novel phospholipase C activator, m-3M3FBS, induces monocytic leukemia cell apoptosis. Cancer Lett. 2005 May 26;222(2):227-35. doi: 10.1016/j.canlet.2004.09.017. PMID: 15863272. 2. Krjukova J, Holmqvist T, Danis AS, Akerman KE, Kukkonen JP. Phospholipase C activator m-3M3FBS affects Ca2+ homeostasis independently of phospholipase C activation. Br J Pharmacol. 2004 Sep;143(1):3-7. doi: 10.1038/sj.bjp.0705911. Epub 2004 Aug 9. PMID: 15302681; PMCID: PMC1575272.
In vivo protocol:
1. Lee J, Kwag J. Activation of PLCβ1 enhances endocannabinoid mobilization to restore hippocampal spike-timing-dependent potentiation and contextual fear memory impaired by Alzheimer's amyloidosis. Alzheimers Res Ther. 2021 Oct 8;13(1):165. doi: 10.1186/s13195-021-00901-9. PMID: 34625112; PMCID: PMC8501622. 2. Zhong W, Darmani NA. The Contribution of Phospholipase C in Vomiting in the Least Shrew (Cryptotis Parva) Model of Emesis. Front Pharmacol. 2021 Sep 10;12:736842. doi: 10.3389/fphar.2021.736842. PMID: 34566660; PMCID: PMC8461300.
1: Wang Y, Tu L, Li Y, Chen D, Liu Z, Hu X, Wang S. Notoginsenoside R1 Alleviates Oxygen-Glucose Deprivation/Reoxygenation Injury by Suppressing Endoplasmic Reticulum Calcium Release via PLC. Sci Rep. 2017 Nov 24;7(1):16226. doi: 10.1038/s41598-017-16373-7. PubMed PMID: 29176553; PubMed Central PMCID: PMC5701215. 2: Grześk E, Szadujkis-Szadurska K, Bloch-Bogusławska E, Wiciński M, Malinowski B, KołTan S, Tejza B, Pujanek M, GrześK G. 2,4,6-Trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide increases calcium influx in lipopolisaccharide-pre-treated arteries. Exp Ther Med. 2017 Feb;13(2):766-770. doi: 10.3892/etm.2016.3986. Epub 2016 Dec 19. PubMed PMID: 28352364; PubMed Central PMCID: PMC5348699. 3: Fukuda T, Kuroda T, Kono M, Hyoguchi M, Tajiri S, Tanaka M, Mine Y, Matsui T. Adenine attenuates the Ca(2+) contraction-signaling pathway via adenine receptor-mediated signaling in rat vascular smooth muscle cells. Naunyn Schmiedebergs Arch Pharmacol. 2016 Sep;389(9):999-1007. doi: 10.1007/s00210-016-1264-0. Epub 2016 Jun 18. PubMed PMID: 27318925. 4: Sturgeon RM, Magoski NS. Diacylglycerol-mediated regulation of Aplysia bag cell neuron excitability requires protein kinase C. J Physiol. 2016 Oct 1;594(19):5573-92. doi: 10.1113/JP272152. Epub 2016 Jun 30. PubMed PMID: 27198498; PubMed Central PMCID: PMC5043051. 5: Grześk E, Szadujkis-Szadurska K, Wiciński M, Malinowski B, Sinjab TA, Tejza B, Pujanek M, Janiszewska E, Kopczyńska A, Grześk G. Effect of 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzene-sulfonamide on calcium influx in three contraction models. Biomed Rep. 2016 Jan;4(1):117-121. Epub 2015 Nov 10. PubMed PMID: 26870347; PubMed Central PMCID: PMC4726898. 6: Yang H, Xu S, Li J, Wang L, Wang X. Potassium 2-(1-hydroxypentyl)-benzoate inhibits ADP-induced rat platelet aggregation through P2Y1-PLC signaling pathways. Naunyn Schmiedebergs Arch Pharmacol. 2015 Sep;388(9):983-90. doi: 10.1007/s00210-015-1113-6. Epub 2015 Mar 19. PubMed PMID: 25787305. 7: Szebenyi SA, Ogura T, Sathyanesan A, AlMatrouk AK, Chang J, Lin W. Increases in intracellular calcium via activation of potentially multiple phospholipase C isozymes in mouse olfactory neurons. Front Cell Neurosci. 2014 Oct 21;8:336. doi: 10.3389/fncel.2014.00336. eCollection 2014. PubMed PMID: 25374507; PubMed Central PMCID: PMC4204526. 8: Al-Momany A, Li L, Alexander RT, Ballermann BJ. Clustered PI(4,5)P₂ accumulation and ezrin phosphorylation in response to CLIC5A. J Cell Sci. 2014 Dec 15;127(Pt 24):5164-78. doi: 10.1242/jcs.147744. Epub 2014 Oct 24. PubMed PMID: 25344252. 9: Chen WC, Chou CT, Liou WC, Liu SI, Lin KL, Lu T, Lu YC, Hsu SS, Tsai JY, Liao WC, Liang WZ, Jan CR. Rise of [Ca²⁺]i and apoptosis induced by M-3M3FBS in SCM1 human gastric cancer cells. Chin J Physiol. 2014 Feb 28;57(1):31-40. doi: 10.4077/CJP.2014.BAB141. PubMed PMID: 24621336. 10: Semple-Rowland S, Madorsky I, Bolch S, Berry J, Smith WC. Activation of phospholipase C mimics the phase shifting effects of light on melatonin rhythms in retinal photoreceptors. PLoS One. 2013 Dec 26;8(12):e83378. doi: 10.1371/journal.pone.0083378. eCollection 2013. PubMed PMID: 24386190; PubMed Central PMCID: PMC3873303. 11: Albarrán L, Dionisio N, López E, Salido GM, Rosado JA. The membrane potential modulates thrombin-stimulated Ca²⁺ mobilization and platelet aggregation. Arch Biochem Biophys. 2013 Oct 15;538(2):130-7. doi: 10.1016/j.abb.2013.08.007. Epub 2013 Aug 27. PubMed PMID: 23988350. 12: Kusaka E, Sugiyama M, Senoo N, Yamamoto A, Sugimoto Y. Genomic and non-genomic effects of glucocorticoids on allergic rhinitis model in mice. Int Immunopharmacol. 2013 Jun;16(2):279-87. doi: 10.1016/j.intimp.2013.03.030. Epub 2013 Apr 10. PubMed PMID: 23583558. 13: Fujita F, Uchida K, Takaishi M, Sokabe T, Tominaga M. Ambient temperature affects the temperature threshold for TRPM8 activation through interaction of phosphatidylinositol 4,5-bisphosphate. J Neurosci. 2013 Apr 3;33(14):6154-9. doi: 10.1523/JNEUROSCI.5672-12.2013. PubMed PMID: 23554496. 14: Liu SI, Lin KL, Lu T, Lu YC, Hsu SS, Tsai JY, Liao WC, Huang FD, Chi CC, Liang WZ, Tseng LL, Chiang AJ, Jan CR. M-3M3FBS-induced Ca² ⁺ movement and apoptosis in HA59T human hepatoma cells. Chin J Physiol. 2013 Feb 28;56(1):26-35. doi: 10.4077/CJP.2013.BAA091. PubMed PMID: 23347013. 15: Kim SD, Kim HJ, Shim JW, Lee HY, Lee SK, Kwon S, Jung YS, Baek SH, Park JS, Zabel BA, Bae YS. Phospholipase C activator m-3M3FBS protects against morbidity and mortality associated with sepsis. J Immunol. 2012 Aug 15;189(4):2000-5. doi: 10.4049/jimmunol.1200635. Epub 2012 Jul 13. PubMed PMID: 22798676. 16: Chi CC, Chou CT, Kuo CC, Hsieh YD, Liang WZ, Tseng LL, Su HH, Chu ST, Ho CM, Jan CR. Effect of m-3m3FBS on Ca2+ handling and viability in OC2 human oral cancer cells. Acta Physiol Hung. 2012 Mar;99(1):74-86. doi: 10.1556/APhysiol.99.2012.1.8. PubMed PMID: 22425810. 17: Brown RA, Leung E, Kankaanranta H, Moilanen E, Page CP. Effects of heparin and related drugs on neutrophil function. Pulm Pharmacol Ther. 2012 Apr;25(2):185-92. doi: 10.1016/j.pupt.2012.01.006. Epub 2012 Feb 4. PubMed PMID: 22327105. 18: Morita T, Okada M, Hara Y, Yamawaki H. Mechanisms underlying impairment of endothelium-dependent relaxation by fetal bovine serum in organ-cultured rat mesenteric artery. Eur J Pharmacol. 2011 Oct 15;668(3):401-6. doi: 10.1016/j.ejphar.2011.07.040. Epub 2011 Aug 10. PubMed PMID: 21854767. 19: Tsai JY, Shieh P, Kuo DH, Chen FA, Kuo CC, Jan CR. Effect of m-3M3FBS on Ca²⁺ movement in PC3 human prostate cancer cells. Chin J Physiol. 2010 Jun 30;53(3):151-9. PubMed PMID: 21793323. 20: Kang YH, Shin HM. Cinnamomi ramulus Ethanol Extract Exerts Vasorelaxation through Inhibition of Ca Influx and Ca Release in Rat Aorta. Evid Based Complement Alternat Med. 2012;2012:513068. doi: 10.1155/2012/513068. Epub 2011 Jul 13. PubMed PMID: 21785647; PubMed Central PMCID: PMC3137977.

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