BADGE

CAS# 1675-54-3

BADGE

Catalog No. BCC7022----Order now to get a substantial discount!

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Chemical structure

BADGE

3D structure

Chemical Properties of BADGE

Cas No. 1675-54-3 SDF Download SDF
PubChem ID 2286 Appearance Powder
Formula C21H24O4 M.Wt 340.42
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Bisphenol A diglycidyl ether
Solubility Soluble to 50 mM in ethanol and to 100 mM in DMSO
Chemical Name 2-[[4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenoxy]methyl]oxirane
SMILES CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4
Standard InChIKey LCFVJGUPQDGYKZ-UHFFFAOYSA-N
Standard InChI InChI=1S/C21H24O4/c1-21(2,15-3-7-17(8-4-15)22-11-19-13-24-19)16-5-9-18(10-6-16)23-12-20-14-25-20/h3-10,19-20H,11-14H2,1-2H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of BADGE

DescriptionPPARγ pure antagonist with micromolar affinity in 3T3-L1 and 3T3-F442A preadipocyte cells; selective over PPARδ and PPARα. Antagonizes the ability of rosiglitazone to stimulate transcriptional activity of PPARγ. Acts as a PPARγ agonist in an ECV304 cell line. Also produces PPARγ-independent apoptosis of tumor cells via several mechanisms. Active in vivo.

BADGE Dilution Calculator

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Preparing Stock Solutions of BADGE

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9375 mL 14.6877 mL 29.3755 mL 58.751 mL 73.4387 mL
5 mM 0.5875 mL 2.9375 mL 5.8751 mL 11.7502 mL 14.6877 mL
10 mM 0.2938 mL 1.4688 mL 2.9375 mL 5.8751 mL 7.3439 mL
50 mM 0.0588 mL 0.2938 mL 0.5875 mL 1.175 mL 1.4688 mL
100 mM 0.0294 mL 0.1469 mL 0.2938 mL 0.5875 mL 0.7344 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on BADGE

BETA DOSE EVALUATION ALGORITHM FOR CaSO4:Dy BYSED TLD BADGE USED IN COUNTRYWIDE PERSONNEL MONITORING PROGRAMME IN INDIA.[Pubmed:27765890]

Radiat Prot Dosimetry. 2017 Jun 1;175(1):96-103.

The prevalent algorithm for the estimation of beta dose, which in turn is used for estimation of skin dose for exposures involving beta radiations was observed to significantly overestimate the dose in individual monitoring based on CaSO4:Dy TLD BADGE in India. A new algorithm has been developed by estimating the correction factor from the response of dosemeter to different beta sources at various angles of incidence. The correction factor was observed to vary linearly with the ratio of the responses of dosemeter element without filter (D3) and dosemeter element under Perspex filter (D2). The correction factor determined using the ratio of D3 and D2 was applied to the response (D3) of dosemeter element without filter for estimation of beta dose. Protocol for identification of beta in the mixed gamma beta fields was defined such that it resulted in nearly same correction factor for given beta source in both gamma beta mixed fields and pure beta fields. The beta dose evaluation algorithm has provided the beta dose estimation within the required accuracy for >90% cases obtained from national quality assurance test data from different laboratories.

Determination of BPA, BPB, BPF, BADGE and BFDGE in canned energy drinks by molecularly imprinted polymer cleaning up and UPLC with fluorescence detection.[Pubmed:27855918]

Food Chem. 2017 Apr 1;220:406-412.

A new method for simultaneous determination of five bisphenols in canned energy drinks by UPLC with fluorescence detection, after clean up on molecularly imprinted polymers, is herein described. The method was validated at two concentration levels, calculating trueness, repeatability and within-laboratory reproducibility, specificity, linearity of detector response, the limits of quantifications and the limits of detection for each bisphenol. The method is specific, reliable and very sensitive, allowing for determination of bisphenol F diglycidyl ether (BFDGE), bisphenol A (BPA), bisphenol B (BPB), bisphenol F (BPF) and bisphenol A diglycidyl ether (BADGE) down to 0.50ng/mL; it was employed to determine contamination levels from these bisphenols in forty energy drinks of different brands, collected from the market in Naples. BPA was detected in 17 out of 40 samples (42.5%); in some energy drinks also BPF, BADGE and BFDGE were determined.

Identification badge lanyards as infection control risk: a cross-sectional observation study with epidemiological analysis.[Pubmed:28215625]

J Hosp Infect. 2017 May;96(1):63-66.

Staphylococcus aureus cultures from name BADGE lanyards were phenotypically and genotypically indistinguishable from the wearer's nasal carrier strains by pulsed-field gel electrophoresis and antibiogram. Lanyards had a mean age of 22 months and hygiene was poor with only 9% ever having been laundered. Molecular analysis showed that 26% of S. aureus nasal carriers shared an indistinguishable strain on their lanyard. Lanyards should not be recommended for staff in frontline clinical care.

Rosiglitazone, a ligand of the peroxisome proliferator-activated receptor-gamma, reduces acute inflammation.[Pubmed:14709329]

Eur J Pharmacol. 2004 Jan 1;483(1):79-93.

Peroxisome proliferator-activated receptors (PPARs) are members of the nuclear hormone receptor superfamily of ligand-activated transcription factors that are related to retinoid, steroid and thyroid hormone receptors. The PPAR-gamma receptor subtype appears to play a pivotal role in the regulation of cellular proliferation and inflammation. The thiazolidinedione rosiglitazone (Avandia) is a peroxisome proliferator-activated receptor-gamma (PPAR-gamma) agonist, that was recently approved by the Food and Drug Administration for treatment of type II diabetes mellitus. In the present study, we have investigated the effects of rosiglitazone in animal models of acute inflammation (carrageenan-induced paw oedema and carrageenan-induced pleurisy). We report here for the first time that rosiglitazone (given at 1, 3 or 10 mg/kg i.p. concomitantly with carrageenan injection in the paw oedema model, or at 3, 10 or 30 mg/kg i.p. 15 min before carrageenan administration in the pleurisy model) exerts potent anti-inflammatory effects (e.g. inhibition of paw oedema, pleural exudate formation, mononuclear cell infiltration and histological injury) in vivo. Furthermore, rosiglitazone reduced: (1) the increase in the staining (immunohistochemistry) for nitrotyrosine and poly (ADP-ribose) polymerase (PARP), (2) the expression of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), intercellular adhesion molecules-1 (ICAM-1) and P-selectin in the lungs of carrageenan-treated rats. In order to elucidate whether the protective effect of rosiglitazone is related to activation of the PPAR-gamma receptor, we also investigated the effect of a PPAR-gamma antagonist, bisphenol A diglycidyl ether (BADGE), on the protective effects of rosiglitazone. BADGE (30 mg/kg i.p.) administered 30 min prior to treatment with rosiglitazone significantly antagonized the effect of the PPAR-gamma agonist and thus abolished the anti-inflammatory effects of rosiglitazone. We propose that rosiglitazone and other potent PPAR-gamma agonists may be useful in the therapy of inflammation.

Bisphenol A diglycidyl ether-induced apoptosis involves Bax/Bid-dependent mitochondrial release of apoptosis-inducing factor (AIF), cytochrome c and Smac/DIABLO.[Pubmed:12788809]

Br J Pharmacol. 2003 Jun;139(3):495-500.

(1) Bisphenol A diglycidyl ether (BADGE) is a peroxisome proliferator-activated receptor-gamma (PPAR-gamma) antagonist, which is able to induce apoptosis in tumor cells independently of PPAR-gamma in caspase-dependent and -independent manners. Additionally, BADGE promotes TRAIL-induced apoptosis. (2) We report that BADGE activates via Bax and caspases-2 and -8 both the intrinsic and extrinsic apoptotic pathways using Bid as a shunt. (3) BADGE stimulates the mitochondrial release of apoptosis-inducing factor (AIF), cytochrome c and second mitochondria-derived activator of caspase/direct IAP-binding protein with low pl (Smac/DIABLO). The release of cytochrome c could not be blocked by inhibitors of caspases-3, -8 and -9 indicating that BADGE acts upstream of caspases-3 and -9 and does not involve caspase-8 to release cytochrome c. (4) While the caspase-independent apoptotic effect might be mediated by AIF, the sensitizing effect of BADGE against other apoptotic substances is most likely mediated by the X-linked inhibitor of apoptosis inhibitor Smac/DIABLO. (5) Our data suggest that BADGE or BADGE derivatives could represent promising substances for the treatment of neoplasms improving the antitumoral activity of TRAIL.

Bisphenol A diglycidyl ether (BADGE) is a PPARgamma agonist in an ECV304 cell line.[Pubmed:11030710]

Br J Pharmacol. 2000 Oct;131(4):651-4.

Peroxisome proliferator activated receptors (PPAR)s are nuclear transcription factors of the steroid receptor super-family. One member, PPARgamma, a critical transcription factor in adipogenesis, is expressed in ECV304 cells, and when activated participates in the induction of cell death by apoptosis. Here we describe a clone of ECV304 cells, ECV-ACO.Luc, which stably expresses a reporter gene for PPAR activation. ECV-ACO.Luc respond to the PPARgamma agonists, 15-deoxy-Delta(12,14) PGJ(2), and ciglitizone, by inducing luciferase expression. Furthermore, using ECV-ACO.Luc, we demonstrate that a newly described PPARgamma antagonist, bisphenol A diglycidyl ether (BADGE) has agonist activities. Similar to 15-deoxy-Delta(12,14) PGJ(2), BADGE induces PPARgamma activation, nuclear localization of the receptor, and induces cell death.

A synthetic antagonist for the peroxisome proliferator-activated receptor gamma inhibits adipocyte differentiation.[Pubmed:10636887]

J Biol Chem. 2000 Jan 21;275(3):1873-7.

While searching for natural ligands for the peroxisome proliferator-activated receptor (PPAR) gamma, we identified a synthetic compound that binds to this receptor. Bisphenol A diglycidyl ether (BADGE) is a ligand for PPARgamma with a K(d(app)) of 100 microM. This compound has no apparent ability to activate the transcriptional activity of PPARgamma; however, BADGE can antagonize the ability of agonist ligands such as rosiglitazone to activate the transcriptional and adipogenic action of this receptor. BADGE also specifically blocks the ability of natural adipogenic cell lines such as 3T3-L1 and 3T3-F442A cells to undergo hormone-mediated cell differentiation. These results provide the first pharmacological evidence that PPARgamma activity is required for the hormonally induced differentiation of adipogenic cells.

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