Synonym
Mifobate; SR 202; SR-202
IUPAC/Chemical Name
Phosphoric acid, (4-chlorophenyl)(dimethoxyphosphinyl)methyl dimethyl ester
InChi Key
VQHUQHAPWMNBLP-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H17ClO7P2/c1-15-20(13,16-2)11(19-21(14,17-3)18-4)9-5-7-10(12)8-6-9/h5-8,11H,1-4H3
SMILES Code
O=P(OC)(OC)OC(C1=CC=C(Cl)C=C1)P(OC)(OC)=O
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
2934.99.9001
Biological target:
Mifobate (SR-202) is a potent and specific PPARγ antagonist.
In vitro activity:
Inhibition of p38 signalling pathway by chemical inhibitor SB202190 and small interfering RNA (siRNA) ameliorated LPS-induced iNOS generation, while suppression of PPARγ pathway by SR-202 boosted LPS-elicited iNOS expression.
Reference: PLoS One. 2013 Dec 2;8(12):e80997. https://pubmed.ncbi.nlm.nih.gov/24312512/
In vivo activity:
In vivo, decreasing PPARgamma activity, either by treatment with SR-202 or by invalidation of one allele of the PPARgamma gene, leads to a reduction of both high fat diet-induced adipocyte hypertrophy and insulin resistance. These effects are accompanied by a smaller size of the adipocytes and a reduction of TNFalpha and leptin secretion. Treatment with SR-202 also dramatically improves insulin sensitivity in the diabetic ob/ob mice.
Reference: Mol Endocrinol. 2002 Nov;16(11):2628-44. https://pubmed.ncbi.nlm.nih.gov/12403851/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
86.0 |
239.79 |
|
| Ethanol |
72.0 |
200.75 |
|
| Water |
47.9 |
133.59 |
|
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
358.65
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. Feng A, Zhou G, Yuan X, Huang X, Zhang Z, Zhang T. Inhibitory effect of baicalin on iNOS and NO expression in intestinal mucosa of rats with acute endotoxemia. PLoS One. 2013 Dec 2;8(12):e80997. doi: 10.1371/journal.pone.0080997. PMID: 24312512; PMCID: PMC3846647.
2. Wu HS, Yu JH, Li YY, Yang YS, He QJ, Lou YJ, Ji RY. Insulin-sensitizing effects of a novel alpha-methyl- alpha -phenoxylpropionate derivative in vitro. Acta Pharmacol Sin. 2007 Mar;28(3):417-22. doi: 10.1111/j.1745-7254.2007.00506.x. PMID: 17303006.
3. Rieusset J, Touri F, Michalik L, Escher P, Desvergne B, Niesor E, Wahli W. A new selective peroxisome proliferator-activated receptor gamma antagonist with antiobesity and antidiabetic activity. Mol Endocrinol. 2002 Nov;16(11):2628-44. doi: 10.1210/me.2002-0036. Erratum in: Mol Endocrinol 2002 Dec;16(12):2745. PMID: 12403851.
In vitro protocol:
1. Feng A, Zhou G, Yuan X, Huang X, Zhang Z, Zhang T. Inhibitory effect of baicalin on iNOS and NO expression in intestinal mucosa of rats with acute endotoxemia. PLoS One. 2013 Dec 2;8(12):e80997. doi: 10.1371/journal.pone.0080997. PMID: 24312512; PMCID: PMC3846647.
2. Wu HS, Yu JH, Li YY, Yang YS, He QJ, Lou YJ, Ji RY. Insulin-sensitizing effects of a novel alpha-methyl- alpha -phenoxylpropionate derivative in vitro. Acta Pharmacol Sin. 2007 Mar;28(3):417-22. doi: 10.1111/j.1745-7254.2007.00506.x. PMID: 17303006.
In vivo protocol:
1. Rieusset J, Touri F, Michalik L, Escher P, Desvergne B, Niesor E, Wahli W. A new selective peroxisome proliferator-activated receptor gamma antagonist with antiobesity and antidiabetic activity. Mol Endocrinol. 2002 Nov;16(11):2628-44. doi: 10.1210/me.2002-0036. Erratum in: Mol Endocrinol 2002 Dec;16(12):2745. PMID: 12403851.
1: Doggrell S. Do peroxisome proliferation receptor-gamma antagonists have clinical potential as combined antiobesity and antidiabetic drugs? Expert Opin Investig Drugs. 2003 Apr;12(4):713-6. Review. PubMed PMID: 12665425.
2: Nguyen LM, Niesor E, Bentzen CL. gem-Diphosphonate and gem-phosphonate-phosphate compounds with specific high density lipoprotein inducing activity. J Med Chem. 1987 Aug;30(8):1426-33. PubMed PMID: 3612689.
3: Liniger C, Pometta D, Burger AG. Interference of dimethyl alpha-(dimethoxyphosphinyl) p-chlorobenzyl phosphate (SR-202) in thyroid hormone metabolism: evidence of inhibition of monodeiodination. J Endocrinol. 1987 Jan;112(1):171-5. PubMed PMID: 3102663.
4: Rieusset J, Touri F, Michalik L, Escher P, Desvergne B, Niesor E, Wahli W. A new selective peroxisome proliferator-activated receptor gamma antagonist with antiobesity and antidiabetic activity. Mol Endocrinol. 2002 Nov;16(11):2628-44. Erratum in: Mol Endocrinol 2002 Dec;16(12):2745. PubMed PMID: 12403851.
5: Hodis J, Vaclavíková R, Farghali H. Beta-3 agonist-induced lipolysis and nitric oxide production: relationship to PPARgamma agonist/antagonist and AMP kinase modulation. Gen Physiol Biophys. 2011 Mar;30(1):90-9. doi: 10.4149/gpb_2011_01_90. PubMed PMID: 21460417.
6: Winn RA, Van Scoyk M, Hammond M, Rodriguez K, Crossno JT Jr, Heasley LE, Nemenoff RA. Antitumorigenic effect of Wnt 7a and Fzd 9 in non-small cell lung cancer cells is mediated through ERK-5-dependent activation of peroxisome proliferator-activated receptor gamma. J Biol Chem. 2006 Sep 15;281(37):26943-50. Epub 2006 Jul 11. PubMed PMID: 16835228.
7: Soller M, Tautenhahn A, Brüne B, Zacharowski K, John S, Link H, von Knethen A. Peroxisome proliferator-activated receptor gamma contributes to T lymphocyte apoptosis during sepsis. J Leukoc Biol. 2006 Jan;79(1):235-43. PubMed PMID: 16380602.
8: Matsuwaki Y, Ueki S, Adachi T, Oyamada H, Kamada Y, Yamaguchi K, Kanda A, Hamada K, Kayaba H, Chihara J. The synthetic PPARgamma agonist troglitazone inhibits IL-5-induced CD69 upregulation and eosinophil-derived neurotoxin release from eosinophils. Pharmacology. 2005 Jul;74(4):169-73. Epub 2005 Apr 7. PubMed PMID: 15818060.
