4,4'-Sulfonyldiphenol
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4,4'-Sulfonyldiphenol (Bisphenol S; Bis(4-hydroxyphenyl) sulfone), a substitute for Bisphenol A (HY-18260), is widely used in industrial and consumer products. 4,4'-Sulfonyldiphenol is an oally ative estrogen receptor (ER) agonist and can competitively bind to thyroid hormone receptors (TR) with IC50 values for TRα and TRβ are 2650 μM and 2294 μM respectively, thereby affecting breast development and reducing the expression of androgen receptor (AR) in fetal testes. 4,4'-Sulfonyldiphenol promotes the progression of glioblastoma by upregulating the EZH2 mediated PI3K/AKT/mTOR pathway. Under chronic exposure, 4,4'-Sulfonyldiphenol can cause significant lipid deposition and dyslipidemia in the mouse liver by upregulating JunB and Atf3, and has a role in causing obesity at low doses. 4,4'-Sulfonyldiphenol induces intestinal inflammation by altering the intestinal microbiome. 4,4'-Sulfonyldiphenol accelerates the progression of atherosclerosis in zebrafish embryo larvae.
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- Pureté: 99.44%
- CAS No.: 80-09-1
- Formule: C12H10O4S
- Masse moléculaire:250.28
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Stockage:
Store at room temperature 3 years.
In solvent -80°C, 2 years , -20°C, 1 year
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Activité biologique
4,4'-Sulfonyldiphenol (0-50 μM) induces thyroid hormone (TH)-dependent GH3 cell proliferation, and inhibits T3 (HY-A0070A) induction in the presence of T3[3].
4,4'-Sulfonyldiphenol (100 μM, 24 h) Significantly increases lipid deposition in AML12 and primary hepatocytes via the JunB/ATF3 axis[4].
4,4'-Sulfonyldiphenol (0.001-100 μM, 4-24 h) promotes the proliferation and migration of U-87 MG cells at a concentration of 0.1 µM and appears to be linked to the activation of the EZH2-mediated PI3K/ AKT/mTOR pathway[6].
4,4'-Sulfonyldiphenol (0.01-1 μM, 0-24 h) exhibits enhanced formation of foam cells with oxidized lowdensity lipoprotein (oxLDL) in macrophages[7].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:U-87 MG cells
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Concentration:0, 0.001, 0.01, 0.1, 1, 10 and 100 μM
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Incubation Time:4 and 8 h
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Result:Significantly increased the proliferation rate at 0.1 μM, and the effect was more significant after 8 hours of treatment than after 4 hours.
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Cell Line:U-87 MG cells
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Concentration:0.1 μM
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Incubation Time:0, 2, 4, 6, 8, 10 and 12 h
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Result:Significantly increased the mobility within 12 hours.
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Cell Line:U-87 MG cells
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Concentration:0.1, 1 and 10 μM
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Incubation Time:24 h
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Result:Induced glioblastoma invasion in U-87 MG cells.
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Cell Line:U-87 MG cells
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Concentration:0.1 μM
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Incubation Time:4 and 8 h
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Result:Increased the mRNA level of EZH2.
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Cell Line:U-87 MG cells
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Concentration:0.1 μM
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Incubation Time:4 and 8 h
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Result:Increased the expression of EZH2, p-PI3K, p-AKT, p-mTOR and p-4E-BP1.
Decreased the expression of PIK3IP1.
4,4'-Sulfonyldiphenol (0.2-50 μg/kg, p.o., once daily beginning at gestational day 0 and continuing in offspring up to 23-weeks old) can be an obesogen at low doses and after perinatal and chronic exposure for the male mice[2].
4,4'-Sulfonyldiphenol (0-10 μM, single dose) induces TH-response gene transcription in Pelophylax nigromaculatus tadpoles, but in the presence of T3 altered T3-induced gene transcription in a biphasic concentration-response manner[3].
4,4'-Sulfonyldiphenol (0.1-1 mg/kg, i.g., once daily for 3 months) induces mice to show significant lipid deposition in the liver and dyslipidemia and were predisposed to metabolic dysfunction-associated steatotic liver disease (MASLD)[4].
4,4'-Sulfonyldiphenol (0.1-1 mg/kg, i.g., once daily for 3 months) induces intestinal inflammation via altering gut microbiome in mice[5].
4,4'-Sulfonyldiphenol (0-100 μg/L, for 15-45 days) accelerates the progression of atherosclerotic cardiovascular disease (ASCVD) using zebrafish embryo-larvae as a model[7].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Long-term and short-term exposure effect assessment established in female CD-1 mice[1]
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Dosage:2 and 200 μg/kg (long-term); 2, 200, and 2000 μg/kg (short-term)
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Administration:Oral administration (p.o.), once daily starting on pregnancy day 9 through lactation day 20 (long-term) and starting on pregnancy day 9 through lactation day 2 (short-term)
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Result:Showed signs of ductal formation in the mammary gland and significantly enlarged the intercellular spaces between the tissues.
Increased ERα expression in epithelial cells and dose-dependently decreased AR expression in the stroma.
Increased the right duct area in all groups, and the left duct area also increased significantly in the high-dose group.
Altered the response of male mice to a pre-pubertal estrogen challenge.
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Animal Model:High fat diet model established in pregnant C57Bl/6J mice[2]
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Dosage:0.2, 1.5, 50 µg/kg
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Administration:Oral administration (p.o.) with water, once daily beginning at gestational day 0 and continuing in offspring up to 23-weeks old
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Result:Significantly increased in body weight and fat mass on a high-fat diet.
Had no effect on the food intake and energy expenditure.
Exhibited a weak but significant hypercholesterolemia with a fold increase of 1.21 and 1.29 at 1.5 and 50 µg/kg, respectively.
Showed a significant decrease of the AUC (increase of blood TG clearance).
Significantly increased the calculated HOMA-IR index in mice exposed to 1.5 and 50 µg/kg.
Induced a significant overexpression of SOCS3 mRNA and a significant mRNA down-regulation of INSR and adiponectin.
Induced a weak but significant decrease in mRNA expression of HSL and PPARγ genes in adipose tissue of male mice fed with a HFD.
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Animal Model:MASLD model established in 7-week-old C57BL/6 male mice[4]
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Dosage:0.1 and 1 mg/kg
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Administration:Oral gavage (i.g.), once daily for 3 months
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Result:Induced MASLD phenotype: elevated LDL, increased NEFA, and elevated ALT.
Showed obvious lipid droplet accumulation.
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Animal Model:Intestinal inflammation model established in 6-7 week old male C57BL/6 mice[5]
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Dosage:0.1 and 1 mg/kg alone and 1 mg/kg with antibiotic cocktail (ABX)
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Administration:Oral gavage (i.g.), once daily for 3 months alone and also for 3 months, during the exposure process, every two-week ABX treatment was followed by a two-week recovery in cycles
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Result:Led to typical features of intestinal inflammation: significant shortening of colon length, tissue pathological damage, increased immune cell infiltration and apoptosis.
Induced bacterial imbalance, increasing pro-inflammatory bacteria and decreasing anti-inflammatory bacteria.
Caused an increase in arachidonic acid (pro-inflammatory) and a decrease in madecainic acid (anti-inflammatory).
Normalized intestinal inflammation, improved metabolism after antibiotic intervention.
Chemical Information
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CAS No. 80-09-1
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Appearance Solid
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Masse moléculaire 250.28
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Formule C12H10O4S
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Color White to yellow
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SMILES
O=S(C1=CC=C(O)C=C1)(C2=CC=C(O)C=C2)=O
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Synonyms
Bisphenol S; Bis(4-hydroxyphenyl) sulfone
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
Store at room temperature 3 years
In solvent -80°C 2 years -20°C 1 year
Solvant et solubilité
DMSO : 100 mg/mL (399.55 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (9.99 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (9.99 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Pureté et documentation
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Fiche technique (286 KB)
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SDS (419 KB)
- English - EN (419 KB)
- Français - FR (419 KB)
- Deutsch - DE (419 KB)
- Norwegian - NO (419 KB)
- Español - ES (419 KB)
- Swedish - SV (419 KB)
- Italian - IT (419 KB)
- Korean - KR (419 KB)
- Portuguese - PT (419 KB)
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Instruction de manipulation (2659 KB)
Références
[1]. Kolla S, et al. Bisphenol S alters development of the male mouse mammary gland and sensitizes it to a peripubertal estrogen challenge. Toxicology. 2019 Aug 1;424:152234. [Content Brief]
[2]. Ivry Del Moral L, et al. Obesogen effects after perinatal exposure of 4,4'-sulfonyldiphenol (Bisphenol S) in C57BL/6 mice. Toxicology. 2016 May 16;357-358:11-20. [Content Brief]
[3]. Zhang YF, et al. Bisphenol A alternatives bisphenol S and bisphenol F interfere with thyroid hormone signaling pathway in vitro and in vivo. Environ Pollut. 2018 Jun;237:1072-1079. [Content Brief]
[4]. Li S, et al. Bisphenol S Exposure and MASLD: A Mechanistic Study in Mice. Environ Health Perspect. 2025 May;133(5):57009. [Content Brief]
[5]. Ko MY, et al. Bisphenol S (BPS) induces glioblastoma progression via regulation of EZH2-mediated PI3K/AKT/mTOR pathway in U87-MG cells. Toxicology. 2024 Sep;507:153898. [Content Brief]
[6]. Wang W, et al. Bisphenol S exposure accelerates the progression of atherosclerosis in zebrafish embryo-larvae. J Hazard Mater. 2022 Mar 15;426:128042. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 3.9955 mL | 19.9776 mL | 39.9553 mL | 99.8881 mL |
| 5 mM | 0.7991 mL | 3.9955 mL | 7.9911 mL | 19.9776 mL | |
| 10 mM | 0.3996 mL | 1.9978 mL | 3.9955 mL | 9.9888 mL | |
| 15 mM | 0.2664 mL | 1.3318 mL | 2.6637 mL | 6.6592 mL | |
| 20 mM | 0.1998 mL | 0.9989 mL | 1.9978 mL | 4.9944 mL | |
| 25 mM | 0.1598 mL | 0.7991 mL | 1.5982 mL | 3.9955 mL | |
| 30 mM | 0.1332 mL | 0.6659 mL | 1.3318 mL | 3.3296 mL | |
| 40 mM | 0.0999 mL | 0.4994 mL | 0.9989 mL | 2.4972 mL | |
| 50 mM | 0.0799 mL | 0.3996 mL | 0.7991 mL | 1.9978 mL | |
| 60 mM | 0.0666 mL | 0.3330 mL | 0.6659 mL | 1.6648 mL | |
| 80 mM | 0.0499 mL | 0.2497 mL | 0.4994 mL | 1.2486 mL | |
| 100 mM | 0.0400 mL | 0.1998 mL | 0.3996 mL | 0.9989 mL |