SYUIQ-5
Based on 1 Customer Validation
SYUIQ-5 is a G-quadruplex stabilizer. SYUIQ-5 stabilizes the c-myc promoter G-quadruplex, the VEGF promoter G-quadruplex, and the telomeric G-quadruplex. SYUIQ-5 selectively inhibits telomerase but not Taq polymerase, while decreasing c-myc/hTERT expression and dissociating NM23-H2. SYUIQ-5 induces growth arrest, senescence, autophagy, DNA damage response, telomere shortening, and apoptosis, accompanied by upregulation of p16/p21/p27, decreased TRF2, and pro-catabolic myotube changes. SYUIQ-5 can be used for research on leukemia, colon cancer, cervical cancer, nasopharyngeal carcinoma, Burkitt lymphoma, and sarcopenia.
Nos produits utilisent uniquement pour la recherche. Nous ne vendons pas aux patients.
- Pureté : 99.03%
- CAS No.: 188630-47-9
- Formule: C20H22N4
- Masse moléculaire:318.42
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Stockage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Activité biologique
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Chemical Information
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Solvant et solubilité
- Protocole
- Pureté et documentation
- Références
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Help & FAQs
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Activité biologique
Description
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G-quadruplex |
c-Myc |
VEGF |
hTERT |
Telomerase |
p16 |
p21 |
P27 |
TRF2 |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HL-60 | IC50 |
1.6 mg/mL
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Cytotoxicity against human HL-60 cells in a 3-day cytotoxic assay.
Cytotoxicity against human HL-60 cells in a 3-day cytotoxic assay.
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17392822 |
| K562 | IC50 |
2.65 μM
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Cytotoxicity against human K562 cells assessed as viability reduction after 68 hrs exposure followed by 4 hrs MTT incubation.
Cytotoxicity against human K562 cells assessed as viability reduction after 68 hrs exposure followed by 4 hrs MTT incubation.
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16170347 |
| SW-620 | IC50 |
1.68 μM
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Cytotoxicity against human SW620 cells assessed as viability reduction after 68 hrs exposure followed by 4 hrs MTT incubation.
Cytotoxicity against human SW620 cells assessed as viability reduction after 68 hrs exposure followed by 4 hrs MTT incubation.
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16170347 |
| CNE-2 | IC50 |
0.9322 μg/mL
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Cytotoxicity against human nasopharyngeal carcinoma CNE2 cells assessed as viability reduction after 72 hrs incubation with SYUIQ-5 by MTT assay.
Cytotoxicity against human nasopharyngeal carcinoma CNE2 cells assessed as viability reduction after 72 hrs incubation with SYUIQ-5 by MTT assay.
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19996277 |
| HeLa | IC50 |
0.5508 μg/mL
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Cytotoxicity against human cervix cancer HeLa cells assessed as viability reduction after 72 hrs incubation with SYUIQ-5 by MTT assay.
Cytotoxicity against human cervix cancer HeLa cells assessed as viability reduction after 72 hrs incubation with SYUIQ-5 by MTT assay.
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19996277 |
In Vitro
SYUIQ-5 (0.4-1.0 μg/mL; 72 h) dose-dependently inhibits E2F1 and hTERT and decreases TRF2, with only a slight decrease in TRF1 in HL-60 cells[1].
SYUIQ-5 (3 days) inhibits telomerase activity in HL-60 cells, with reported inhibition of 22.6-64.2%[1].
SYUIQ-5 (3 days) has an IC50 of 1.6 mg/mL in a cytotoxic assay against HL-60 cells[1].
SYUIQ-5 (0.05-0.8 μM; 30 min) is a potent cell-free telomerase inhibitor in K562 extract, with an IC50 of 0.44 μM[2].
SYUIQ-5 (0.15-0.6 μM; 72 h) inhibits telomerase activity in K562 and SW620 cells, with 0.6 μM producing 84.1% and 79.5% inhibition, respectively[2].
SYUIQ-5 (3 days) has MTT IC50 values of 2.65 μM in K562 cells and 1.68 μM in SW620 cells[2].
SYUIQ-5 (0.1-0.4 μM; 16-35 days) induces growth arrest and senescence-associated β-galactosidase in K562 and SW620 cells under continuous nonacute exposure[2].
SYUIQ-5 (0.2-0.4 μM; long-term exposure) shortens telomeres by about 6.1 kbp in K562 cells and about 2.5 kbp in SW620 cells[2].
SYUIQ-5 (0.1-0.4 μM; 3 days) decreases hTERT protein expression in K562 and SW620 cells[2].
SYUIQ-5 (0.5508-0.9322 μg/mL; 72 h) inhibits proliferation of CNE2 and HeLa cancer cells with IC50 values of 0.9322 and 0.5508 μg/mL, respectively[3].
SYUIQ-5 (0.5-4 μg/mL; 24-48 h) induces telomere DNA damage with γ-H2AX foci that colocalize with TRF1 in CNE2 and HeLa cells[3].
SYUIQ-5 (0.1 μM; 4 days) down-regulates c-myc and hTERT transcription in Ramos lymphoma cells but not in CA46 cells[6].
SYUIQ-5 (0.05-0.1 μM; 4 days) inhibits c-Myc and hTERT protein expression in Ramos cells and c-Myc expression in CA46 cells[6].
SYUIQ-5 (0.1 μM; 4 days) interferes with NM23-H2 binding to the c-myc promoter but not with POT-1 binding to telomeric ssDNA in HeLa S3 cells[6].
SYUIQ-5 (0.1 μM; 24 h) dissociates NM23-H2 from the wild-type c-myc promoter but not from a mutant promoter in HeLa cells[6].
SYUIQ-5 (0.05-0.1 μM; 16 days) shortens telomeres more strongly in Ramos cells (~1.6 kb) than in CA46 cells (0.8 kb)[6].
SYUIQ-5 (0.05-0.1 μM; 16 days) induces senescence in Ramos cells but has no obvious effect in CA46 cells[6].
SYUIQ-5 inhibits proliferation of diverse tumor cell lines with IC50 values of 0.24-4.8 μM[6].
SYUIQ-5 (0.4-2.0 µM; 72 h) did not exert toxic effects on C2C12 myoblasts below 2 µM, whereas 2 µM was toxic after 72 h[7].
SYUIQ-5 (0.4-1.0 µM; 72 h) activates DNA damage response in C2C12 myoblasts, increasing γ-H2AX and phosphorylated p53[7].
SYUIQ-5 (4 μg/mL for 24 h; 0.5-4 μg/mL for 48 h)-mediated telomere DNA damage, autophagy, and cell death in CNE2 and HeLa cells is antagonized by overexpression of wild-type TRF2[3].
SYUIQ-5 (4 μg/mL) induces telomere DNA damage and autophagy in an ATM-dependent manner in CNE2 and HeLa cells[3].
SYUIQ-5 (2 μg/mL for 24 h; various concentrations for 72 h) induces autophagy and cytotoxicity in CNE2 and HeLa cells that is attenuated by ATG5 knockdown, indicating autophagic cell death[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:HL-60 and K562 leukemia cells
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Concentration:0.4, 0.6, 0.8, 1.0 μg/mL
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Incubation Time:72 h
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Result:Inhibited the expression of c-myc mRNA in HL-60 and K562 leukemia cells.
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Cell Line:HL-60 and K562 leukemia cells
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Concentration:0.4, 0.6, 0.8, 1.0 μg/mL
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Incubation Time:72 h
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Result:Inhibited the expression of c-myc protein in HL-60 and K562 leukemia cells.
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Cell Line:HL-60 cells
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Concentration:0.4 μg/mL
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Incubation Time:6, 9, 12 days
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Result:P16, P21, and P27 were upregulated by SYUIQ-5 in HL-60 cells, suggesting growth arrest could be due to upregulation of these proteins.
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Cell Line:HL-60 cells
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Concentration:0.4 μg/mL
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Incubation Time:6, 9, 12 days (caspase-3/PARP); 3, 6, 9, 12 days (flow cytometry)
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Result:Caspase-3 and PARP were cleaved.
Pro-caspase-3 was cleaved to yield a 17 kDa fragment and PARP was cleaved to an 89 kDa fragment after incubation for 9 days.
A sub-G1 peak obviously appeared after HL-60 cells were exposed to 0.4 μg/mL SYUIQ-5 for 9 days.
Delayed apoptosis was not detected in the first 6 days.
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Cell Line:K562 and SW620 cells
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Concentration:0.15, 0.3, 0.6 μM SYUIQ-5
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Incubation Time:72 h
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Result:In K562 cells, SYUIQ-5 inhibited telomerase activity by 43.7%, 65.4% and 84.1% at 0.15, 0.3 and 0.6 μM, respectively.
In SW620 cells, SYUIQ-5 inhibited telomerase activity by 38.7%, 62.3% and 79.5%, respectively.
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Cell Line:K562 and SW620 cells
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Concentration:0.4 μM (K562); 0.05, 0.1, 0.2, 0.4 μM (SW620)
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Incubation Time:35 days (K562); 18 days (SW620)
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Result:p16, p21 and p27 protein levels were upregulated by SYUIQ-5 in K562 and SW620 cells.
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Cell Line:K562 and SW620 cells
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Concentration:0.2, 0.4 μM (K562); 0.1, 0.2 μM (SW620)
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Incubation Time:3 days
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Result:hTERT protein expression was decreased after SYUIQ-5 exposure in K562 and SW620 cells.
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Cell Line:CNE2 and HeLa cells
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Concentration:2 μg/mL
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Incubation Time:24 h
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Result:After SYUIQ-5 at 2 μg/mL for 24 h, 71.7% of CNE2 cells and 67.2% of HeLa cells showed YFP-LC3 dots, compared with 21.1% of DMSO-exposed CNE2 cells and 15.9% of DMSO-exposed HeLa cells.
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Cell Line:Ramos and CA46 cells
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Concentration:0.1 μM
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Incubation Time:1, 2, 3, 4 days
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Result:Down-regulated c-myc transcription and further down-regulated hTERT in Ramos cells; no inhibitory activity on transcription was found in CA46 cells.
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Cell Line:Ramos and CA46 cells
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Concentration:0.05 or 0.1 μM
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Incubation Time:1, 2, 3, 4 days
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Result:Inhibited c-Myc and hTERT expression in Ramos cells.
In CA46 cells, inhibited c-Myc expression, while hTERT expression was too low to detect.
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Cell Line:C2C12 mouse myoblasts
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Concentration:0.4, 0.7, 1.0, 2.0 µM (LDH and AlamarBlue chronic); 0.4, 0.7, 1.0, 2.0 µM (acute AlamarBlue)
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Incubation Time:72 h (LDH and AlamarBlue chronic); 2 h (acute AlamarBlue)
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Result:At 2 µM, SYUIQ-5 was toxic; intracellular LDH decreased to 0.2078 compared with untreated mean = 1, and supernatant/cellular LDH ratio increased to 9.032 compared with untreated mean = 1.
Concentrations 0.4, 0.7, and 1.0 µM had no toxic effects.
No differences among SYUIQ-5 0.4, 0.7, 1.0, and 2.0 µM were observed at 2 h or 72 h in AlamarBlue.
Protein content decreased after chronic exposure with increasing SYUIQ-5 concentration, but AlamarBlue normalized to protein content showed no differences.
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Cell Line:C2C12 mouse myoblasts
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Concentration:0.4 and 1.0 µM (SYUIQ-5)
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Incubation Time:72 h (SYUIQ-5); 6 h (BrdU labeling); 90 min (anti-BrdU-POD); 10 min (substrate)
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Result:BrdU ELISA showed dose-dependent reduction in C2C12 proliferation: −22% with 0.4 µM SYUIQ-5 and −56% with 1 µM SYUIQ-5 compared with untreated cells.
p21 transcript and p21 protein levels were higher after 1 µM SYUIQ-5 exposure.
- RNA extraction experimental
- Detection of Apoptosis
- TUNEL staining for apoptotic DNA fragmentation
- Annexin V plus membrane-impermeant dye apoptosis staining
- Autophagy
- Apoptosis Solutions
- Lysosome and acidic-vesicle live-cell staining
- Macroautophagy Solutions
- Senescence-associated β-galactosidase staining
- Genotoxicity/Mutagenicity Study
Chemical Information
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CAS No. 188630-47-9
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Appearance Solid
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Masse moléculaire 318.42
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Formule C20H22N4
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Color White to yellow
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SMILES
CN(C)CCCNC(C1=C(C=CC=C1)N=C23)=C3NC4=C2C=CC=C4
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Solvant et solubilité
In Vitro:
DMSO : 100 mg/mL (314.05 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, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
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, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Pureté et documentation
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Fiche technique (307 KB)
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SDS (398 KB)
- English - EN (398 KB)
- Français - FR (398 KB)
- Deutsch - DE (398 KB)
- Norwegian - NO (398 KB)
- Español - ES (398 KB)
- Swedish - SV (398 KB)
- Italian - IT (398 KB)
- Korean - KR (398 KB)
- Portuguese - PT (398 KB)
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Instruction de manipulation (2659 KB)
Références
[3]. Zhou WJ, et al. G-quadruplex ligand SYUIQ-5 induces autophagy by telomere damage and TRF2 delocalization in cancer cells. Molecular cancer therapeutics. 2009 Dec;8(12):3203-13. [Content Brief]
[6]. Ou TM, et al. Inhibition of cell proliferation by quindoline derivative (SYUIQ-05) through its preferential interaction with c-myc promoter G-quadruplex. Journal of medicinal chemistry. 2011 Aug 25;54(16):5671-9. [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, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 3.1405 mL | 15.7025 mL | 31.4051 mL | 78.5127 mL |
| 5 mM | 0.6281 mL | 3.1405 mL | 6.2810 mL | 15.7025 mL | |
| 10 mM | 0.3141 mL | 1.5703 mL | 3.1405 mL | 7.8513 mL | |
| 15 mM | 0.2094 mL | 1.0468 mL | 2.0937 mL | 5.2342 mL | |
| 20 mM | 0.1570 mL | 0.7851 mL | 1.5703 mL | 3.9256 mL | |
| 25 mM | 0.1256 mL | 0.6281 mL | 1.2562 mL | 3.1405 mL | |
| 30 mM | 0.1047 mL | 0.5234 mL | 1.0468 mL | 2.6171 mL | |
| 40 mM | 0.0785 mL | 0.3926 mL | 0.7851 mL | 1.9628 mL | |
| 50 mM | 0.0628 mL | 0.3141 mL | 0.6281 mL | 1.5703 mL | |
| 60 mM | 0.0523 mL | 0.2617 mL | 0.5234 mL | 1.3085 mL | |
| 80 mM | 0.0393 mL | 0.1963 mL | 0.3926 mL | 0.9814 mL | |
| 100 mM | 0.0314 mL | 0.1570 mL | 0.3141 mL | 0.7851 mL |
SYUIQ-5 Related Classifications
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