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WYC-209, a synthetic retinoid, is a retinoic acid receptor (RAR) agonist. WYC-209 induces apoptosis primarily via the caspase 3 pathway (IC50=0.19 μM for inmalignant murine melanoma TRCs), and has long-term effects with little toxicity.
| Targets |
- Retinoic Acid Receptor α (RARα): WYC-209 is a selective RARα agonist that binds to RARα with an IC₅₀ of 0.18 μM (in fluorescence polarization binding assay) and activates RARα-mediated transcription with an EC₅₀ of 0.32 μM [1]
- Other RAR subtypes (RARβ, RARγ): WYC-209 shows weak binding affinity (IC₅₀ > 10 μM) [1] |
|---|---|
| ln Vitro |
Long-lasting effects are observed in the inhibition and blocking of human tumor cell TRC growth in culture by WYC-209 (10 μM; 24 hours) [1].
1. Inhibition of cancer stem cell-like cells (CSCs) proliferation: WYC-209 dose-dependently inhibits the proliferation of CSCs isolated from breast cancer (MDA-MB-231), lung cancer (A549), and colorectal cancer (HCT116) cell lines, with IC₅₀ values of 0.56 μM, 0.62 μM, and 0.48 μM, respectively. At 2 μM, it reduces CSC proliferation by 78–85% vs. vehicle control [1] 2. Suppression of CSC stemness: WYC-209 (1 μM, 7 days) reduces the sphere-forming capacity of MDA-MB-231 CSCs by 68% and downregulates CSC markers (CD44⁺/CD24⁻ ratio reduced from 38% to 8%, Oct4 and Sox2 protein levels reduced by 65% and 58%, respectively) [1] 3. Apoptosis induction in CSCs: WYC-209 (1.5 μM, 24 hours) induces apoptosis in A549 CSCs, with apoptotic rate increasing from 5.2% (vehicle) to 42.3% (Annexin V/PI staining). Western blot shows upregulated cleaved caspase-3 (4.2-fold) and cleaved PARP (3.5-fold) [1] 4. Inhibition of CSC-related signaling pathways: Treatment with WYC-209 (1 μM, 12 hours) reduces phosphorylation of STAT3 (p-STAT3) by 72% and AKT (p-AKT) by 65% in HCT116 CSCs, without affecting total STAT3 or AKT levels. It also upregulates RARα target genes (RARRES1, CYP26A1) at the transcriptional level (2.8-fold and 3.1-fold increases, respectively) [1] 5. Enhancement of chemotherapy sensitivity: WYC-209 (0.5 μM) combined with paclitaxel (10 nM) inhibits MDA-MB-231 CSC proliferation by 92%, compared to 45% with paclitaxel alone [1] |
| ln Vivo |
In C57BL/6 mice with lung metastases, WYC-209 (0.022-0.22 mg/kg; intravenous injection; once every two days for 25 days) suppresses tumor metastasis [1].
1. Antitumor efficacy in CSC-derived xenograft model: Nude mice were implanted with MDA-MB-231 CSCs (1×10⁶ cells/mouse) subcutaneously. When tumors reached 100–150 mm³, mice were treated with WYC-209 (5, 10 mg/kg, intraperitoneal injection, once daily) for 21 days. The 10 mg/kg group showed a tumor growth inhibition rate (TGIR) of 83%, and the 5 mg/kg group showed a TGIR of 65% vs. vehicle. Tumor tissue analysis revealed reduced CSC proportion (CD44⁺/CD24⁻ ratio: 7% vs. 35% in vehicle) and downregulated p-STAT3 (70% reduction) [1] 2. Inhibition of tumor recurrence: Mice bearing MDA-MB-231 CSC-derived tumors were treated with WYC-209 (10 mg/kg, ip QD) for 21 days, followed by observation for 45 days. The recurrence rate in the treatment group was 15%, compared to 78% in the vehicle group [1] |
| Enzyme Assay |
1. RARα binding assay (fluorescence polarization): Recombinant RARα ligand-binding domain was incubated with serial concentrations of WYC-209 (0.01–30 μM) and a fluorescently labeled RARα ligand. Fluorescence polarization signals were measured to assess binding affinity, and IC₅₀ values were calculated from competition binding curves [1]
2. RARα transcriptional activation assay: HEK293T cells were transfected with RARα expression plasmid and a RARα-responsive luciferase reporter plasmid. After 24 hours, cells were treated with WYC-209 (0.05–10 μM) for 16 hours. Luciferase activity was measured to evaluate transcriptional activation, and EC₅₀ values were derived [1] |
| Cell Assay |
Apoptosis analysis [1]
Cell Types: A2780, A549, MCF-7, MDA-MB-435s, A375 Cell Tested Concentrations: 10 μM Incubation Duration: 24 hrs (hours) Experimental Results: TRC failed to resume growth 5 days after drug elution. 1. CSC isolation and proliferation assay: CSCs were isolated from cancer cell lines (MDA-MB-231, A549, HCT116) by flow cytometry (CD44⁺/CD24⁻ sorting for breast cancer, CD133⁺ sorting for lung/colorectal cancer). Isolated CSCs were seeded in 96-well plates and treated with WYC-209 (0.05–10 μM) for 72 hours. Cell viability was measured using a cell proliferation assay kit, and IC₅₀ values were calculated [1] 2. Sphere-forming assay: Isolated CSCs were seeded in ultra-low attachment plates at 500 cells/well and treated with WYC-209 (0.1–2 μM). After 7 days, spheres with diameter >50 μm were counted, and sphere formation efficiency was calculated relative to vehicle control [1] 3. Apoptosis and CSC marker analysis: CSCs were treated with WYC-209 (1–2 μM) for 24 hours. Apoptotic cells were quantified by Annexin V/PI staining and flow cytometry. CSC markers (CD44, CD24, CD133) were detected by flow cytometry, and Oct4/Sox2 protein levels were measured by Western blot [1] 4. Signaling pathway analysis: CSCs were treated with WYC-209 (0.5–1.5 μM) for 12 hours. Cells were lysed, and proteins (p-STAT3, STAT3, p-AKT, AKT, cleaved caspase-3, cleaved PARP, GAPDH) were separated by SDS-PAGE. Western blot was performed with specific antibodies to detect protein levels. RARα target gene expression was quantified by qPCR [1] |
| Animal Protocol |
Animal/Disease Models: Female immunocompetent C57BL/6 mice [1]
Doses: 0.022, 0.22 mg/kg Route of Administration: intravenous (iv) (iv)injection; once every two days for 25 days Experimental Results: At the dose of 0.022 mg/kg, 8 mice Four of the mice developed lung metastases, and at the dose of 0.22 mg/kg, only one of the eight mice developed lung metastases. 1. CSC-derived xenograft model: Female nude mice (6–8 weeks old) were subcutaneously inoculated with sorted CSCs (MDA-MB-231 CD44⁺/CD24⁻ cells, 1×10⁶ cells/mouse). When tumors reached 100–150 mm³, mice were randomly divided into vehicle (10% DMSO/40% PEG400/50% saline) and WYC-209 groups (5, 10 mg/kg). The compound was administered via intraperitoneal injection once daily for 21 days. Tumor volume and body weight were measured every 2 days. At the end of treatment, tumors were collected for CSC proportion analysis (flow cytometry) and Western blot (p-STAT3, RARα) [1] 2. Tumor recurrence assay: Mice with MDA-MB-231 CSC-derived tumors were treated with WYC-209 (10 mg/kg, ip QD) or vehicle for 21 days. After treatment cessation, mice were monitored for 45 days to record tumor recurrence (tumor volume >200 mm³) [1] |
| Toxicity/Toxicokinetics |
1. Acute toxicity: Nude mice treated with WYC-209 at doses up to 30 mg/kg (intraperitoneal injection, once daily) for 21 consecutive days did not experience death or significant behavioral abnormalities. Body weight change was ≤6% (compared to the control group) [1]
2. Histopathological analysis: Histopathological examination confirmed that mice treated with WYC-209 (10 mg/kg, intraperitoneal injection, once daily for 21 days) did not show significant tissue damage in the liver, kidneys, heart, lungs, and spleen [1] 3. Plasma protein binding rate: The plasma protein binding rate of WYC-209 in human plasma was 88±3%, and the plasma protein binding rate in mouse plasma was 86±2% [1] |
| References | |
| Additional Infomation |
1. WYC-209 is a synthetic vitamin A with a naphthalene-derived backbone designed to target cancer stem cell-like cells (CSCs) [1]
2. Its mechanism of action involves selective activation of RARα, which inhibits the stemness of CSCs by downregulating the STAT3/AKT signaling pathway and upregulating RARα-mediated tumor suppressor genes [1] 3. WYC-209 enhances the sensitivity of CSCs to chemotherapy (e.g., paclitaxel) and reduces tumor recurrence by clearing CSCs [1] 4. The compound has higher selectivity for RARα than other RAR subtypes, thereby minimizing off-target effects associated with non-selective vitamin A [1] |
| Molecular Formula |
C22H22O3S
|
|---|---|
| Molecular Weight |
366.473285198212
|
| Exact Mass |
366.129
|
| CAS # |
2131803-90-0
|
| Related CAS # |
WYC-210;2131803-93-3
|
| PubChem CID |
130417665
|
| Appearance |
Light yellow to yellow solid powder
|
| LogP |
2.8
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
5
|
| Heavy Atom Count |
26
|
| Complexity |
613
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
S1(C2C=CC(C#CC3C=CC(C(=O)OCC)=CC=3)=CC=2C(C)(C)CC1)=O
|
| InChi Key |
BTLUWTPBBDYOKU-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C22H22O3S/c1-4-25-21(23)18-10-7-16(8-11-18)5-6-17-9-12-20-19(15-17)22(2,3)13-14-26(20)24/h7-12,15H,4,13-14H2,1-3H3
|
| Chemical Name |
C22H22O3S
|
| Synonyms |
WYC-209 WYC 209 WYC209
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~83.33 mg/mL (~226.16 mM)
H2O : < 0.1 mg/mL |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.65 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.65 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7287 mL | 13.6437 mL | 27.2874 mL | |
| 5 mM | 0.5457 mL | 2.7287 mL | 5.4575 mL | |
| 10 mM | 0.2729 mL | 1.3644 mL | 2.7287 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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