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.
Nur für Forschungszwecke. Wir verkaufen nicht an Patienten.
- Reinheit : 99.03%
- CAS. Nr.: 188630-47-9
- Formel: C20H22N4
- Molecular Weight:318.42
-
Speicherung:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
Alle VEGFR Isoform-spezifische Produkte anzeigen
More
Biologische Aktivität
Beschreibung
|
G-quadruplex |
c-Myc |
VEGF |
hTERT |
Telomerase |
p16 |
p21 |
P27 |
TRF2 |
Cellular Effect
|
Cell Line
|
Type | Value | Description | References |
|---|---|---|---|---|
| HL-60 | IC50 |
1.6 mg/mL
|
Cytotoxicity against human HL-60 cells in a 3-day cytotoxic assay.
Cytotoxicity against human HL-60 cells in a 3-day cytotoxic assay.
|
17392822 |
| K562 | IC50 |
2.65 μM
|
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.
|
16170347 |
| SW-620 | IC50 |
1.68 μM
|
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.
|
16170347 |
| CNE-2 | IC50 |
0.9322 μg/mL
|
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.
|
19996277 |
| HeLa | IC50 |
0.5508 μg/mL
|
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.
|
19996277 |
In Vitro
SYUIQ-5 (0.6-10 mg/mL) dose-dependently inhibits cell-free PCR product formation from the c-myc promoter Pu22myc G-quadruplex-forming oligomer, while the mutant Pu22mu control is not inhibited[1].
SYUIQ-5 (0.4-1.0 µM; 72 h) increases SA-β-galactosidase activity in C2C12 myoblasts[7].
SYUIQ-5 (0.4-1.0 μg/mL for HL-60; 0.4-1.2 μg/mL for K562; 72 h) inhibits c-myc mRNA and protein expression in HL-60 and K562 leukemia cells[1].
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 (0.4 mg/mL; 6-12 days) upregulates P16, P21, and P27 in HL-60 cells, associating with growth arrest[1].
SYUIQ-5 (0.05-0.4 μM; 18-35 days) upregulates p16, p21 and p27 in K562 and SW620 cells[2].
SYUIQ-5 (0.4 mg/mL; 9 days) induces delayed apoptosis in HL-60 cells, with caspase-3 and PARP cleavage and sub-G1 accumulation[1].
SYUIQ-5 (0.5-4 μg/mL; 24-48 h) induces autophagy in CNE2 and HeLa cancer cells, increasing LC3-II, MDC-labeled autophagosomes, and YFP-LC3 puncta[3].
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].
SYUIQ-5 (0.5-4 μg/mL; 24-48 h) delocalizes TRF2 from telomeres and promotes its proteasomal degradation in CNE2 and HeLa cells, while TRF1 remains telomere-bound[3].
SYUIQ-5 (0.4-1.0 µM; 72 h) reduces C2C12 myoblast proliferation and increases p21 expression at 1 µM[7].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
-
Cell Line:HL-60 and K562 leukemia cells
-
Concentration:0.4, 0.6, 0.8, 1.0 μg/mL
-
Incubation Time:72 h
-
Result:Inhibited the expression of c-myc mRNA in HL-60 and K562 leukemia cells.
-
Cell Line:HL-60 and K562 leukemia cells
-
Concentration:0.4, 0.6, 0.8, 1.0 μg/mL
-
Incubation Time:72 h
-
Result:Inhibited the expression of c-myc protein in HL-60 and K562 leukemia cells.
-
Cell Line:HL-60 cells
-
Concentration:0.4 μg/mL
-
Incubation Time:6, 9, 12 days
-
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.
-
Cell Line:HL-60 cells
-
Concentration:0.4 μg/mL
-
Incubation Time:6, 9, 12 days (caspase-3/PARP); 3, 6, 9, 12 days (flow cytometry)
-
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.
-
Cell Line:K562 and SW620 cells
-
Concentration:0.15, 0.3, 0.6 μM SYUIQ-5
-
Incubation Time:72 h
-
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.
-
Cell Line:K562 and SW620 cells
-
Concentration:0.4 μM (K562); 0.05, 0.1, 0.2, 0.4 μM (SW620)
-
Incubation Time:35 days (K562); 18 days (SW620)
-
Result:p16, p21 and p27 protein levels were upregulated by SYUIQ-5 in K562 and SW620 cells.
-
Cell Line:K562 and SW620 cells
-
Concentration:0.2, 0.4 μM (K562); 0.1, 0.2 μM (SW620)
-
Incubation Time:3 days
-
Result:hTERT protein expression was decreased after SYUIQ-5 exposure in K562 and SW620 cells.
-
Cell Line:CNE2 and HeLa cells
-
Concentration:2 μg/mL
-
Incubation Time:24 h
-
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.
-
Cell Line:Ramos and CA46 cells
-
Concentration:0.1 μM
-
Incubation Time:1, 2, 3, 4 days
-
Result:Down-regulated c-myc transcription and further down-regulated hTERT in Ramos cells; no inhibitory activity on transcription was found in CA46 cells.
-
Cell Line:Ramos and CA46 cells
-
Concentration:0.05 or 0.1 μM
-
Incubation Time:1, 2, 3, 4 days
-
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.
-
Cell Line:C2C12 mouse myoblasts
-
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)
-
Incubation Time:72 h (LDH and AlamarBlue chronic); 2 h (acute AlamarBlue)
-
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.
-
Cell Line:C2C12 mouse myoblasts
-
Concentration:0.4 and 1.0 µM (SYUIQ-5)
-
Incubation Time:72 h (SYUIQ-5); 6 h (BrdU labeling); 90 min (anti-BrdU-POD); 10 min (substrate)
-
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.
Chemical Information
-
CAS. Nr. 188630-47-9
-
Appearance Solid
-
Molecular Weight 318.42
-
Formel C20H22N4
-
Color White to yellow
-
SMILES
CN(C)CCCNC(C1=C(C=CC=C1)N=C23)=C3NC4=C2C=CC=C4
-
Versand
Room temperature in continental US; may vary elsewhere.
-
Speicherung
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Lösungsmittel & Löslichkeit
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.
Konzentration (Stammlösung) × Volumen (Stammlösung) = Konzentration (Ziellösung) × Volumen (Ziellösung)
Protokoll
-
RNA extraction experimental
By lysing cells, releasing RNA, and removing impurities such as proteins and DNA, high-purity RNA products are finally obtained. The commonly used traditional method is the guanidine isothiocyanate/phenol/chloroform method (Trizol), which is suitable for a variety of animal materials including animal tissues, microorganisms, cultured cells, etc., and most plant materials.
-
Detection of Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
-
TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
-
Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
-
Autophagy
Autophagy is a process in which eukaryotic cells use lysosomes to degrade their own cytoplasmic proteins and damaged organelles under the regulation of autophagy related gene (Atg). Microtubule-associated proteins light chain 3 (LC3) is recognized as autophagy marker, which transfers from cytoplasmic LC3 (LC3-I) to membrane type (LC3-II). LC3-II/I ratio could be detected by Western Blot and fluorescence microscopy.
-
Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
-
Lysosome and acidic-vesicle live-cell staining
Lysosome and acidic-vesicle live-cell staining detects acidic intracellular compartments by using membrane-permeant acidotropic probes that accumulate in low-pH vesicles, including lysosomes, late endosomes, autolysosomes, and acidic phagosomes. LysoTracker staining is commonly used as an intensity-based readout of acidic lysosomal compartment abundance or enlargement, while acridine orange produces green fluorescence in less concentrated compartments and red fluorescence after concentration-dependent accumulation in acidic vesicular organelles. Loss or reduction of acridine-orange red signal can be used as a readout of lysosomal membrane permeabilization or reduced acidic-vesicle integrity. This protocol is designed for live cultured cells and can be adapted for fluorescence microscopy, high-content imaging, plate-reader readout, or flow cytometry when the selected literature supports the readout. Because these dyes report acidotropic accumulation rather than lysosome identity alone,
-
Macroautophagy Solutions
Macroautophagy is a conserved lysosome-dependent degradation pathway in which cytoplasmic material is sequestered into double-membrane autophagosomes and delivered to lysosomes for degradation and recycling. The pathway supports cellular homeostasis during nutrient limitation, organelle stress, protein-aggregate accumulation, infection, differentiation, and tissue remodeling by coupling cargo sequestration, autophagosome maturation, lysosomal fusion, and degradation of cargo-derived macromolecules. The core molecular sequence includes initiation by nutrient- and stress-regulated autophagy machinery, autophagosome nucleation, LC3/ATG8-family conjugation to autophagosomal membranes, cargo selection through receptors such as SQSTM1/p62, autophagosome-lysosome fusion, and lysosomal degradation. LC3 was identified as a mammalian homolog of yeast Atg8 that localizes to autophagosomal membranes after processing, and p62/SQSTM1 was shown to connect ubiquitinated cargo with autophagic degradati
-
Senescence-associated β-galactosidase staining
Senescence-associated β-galactosidase staining detects β-galactosidase activity that is histochemically visible at pH 6. 0 in senescent cells, where X-gal cleavage produces an insoluble blue precipitate observable by bright-field microscopy. This activity reflects increased lysosomal β-galactosidase/lysosomal mass rather than a senescence-essential enzyme, because GLB1 depletion or genetic lysosomal β-galactosidase deficiency can abolish SA-β-gal staining while cells still undergo senescence. SA-β-gal was originally reported in senescent but not presenescent fibroblasts and keratinocytes, absent from quiescent fibroblasts and terminally differentiated keratinocytes, and increased with donor age in human skin samples. Because SA-β-gal can also appear in some non-senescent or tissue-specific contexts, interpretation should be paired with experimental controls and, when possible, independent senescence markers.
-
Genotoxicity/Mutagenicity Study
The bacterial reverse mutation assay detects point mutations that restore amino-acid prototrophy in auxotrophic Salmonella typhimurium or Escherichia coli tester strains; after exposure to a test article, mutagenic activity is read out as an increased number of revertant colonies on minimal agar compared with the vehicle control. The assay uses tester strains with different mutation targets so that base-substitution and frameshift mutagens can be detected, and testing is performed with and without exogenous mammalian metabolic activation because some chemicals require biotransformation to become mutagenic.
Reinheit & Dokumentation
-
Data Sheet (295 KB)
-
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)
-
Handling Instructions (2659 KB)
Verweise
[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 |