Cat. No.: HY-145748

SYUIQ-5

Name: SYUIQ-5
Brand: MedChemExpress
SKU: HY-145748
Price: 270.00 USD
Availability: InStock
Rating: 5 (1 reviews)

Customer Review

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.

For research use only. We do not sell to patients.

Purity : 99.03%
CAS No.: 188630-47-9
Formula: C₂₀H₂₂N₄
Molecular Weight:318.42

Storage:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

SYUIQ-5 Chemical Structure

CAS No.: 188630-47-9

Size

Price

Stock

Quantity

Amount: USD 0.00

* Please select Quantity before adding items.

Top Publications Citing

Use of MCE Products

Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
Chemical Information
Solvent & Solubility
- In Vitro
Purity & Documentation
References
Help & FAQs
Classifications
Bioz

Biological Activity

Description

IC₅₀ & Target

^[1]^[2]^[3]^[4]^[5]^[6]^[7]

G-quadruplex

c-Myc

VEGF

hTERT

Telomerase

p16

p21

P27

TRF2

All VEGFR Isoforms :

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.

RT-PCR^[1]

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.

Western Blot Analysis^[1]

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.

Western Blot Analysis^[1]

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.

Apoptosis Analysis^[1]

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.

ELISA Assay^[2]

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.

Western Blot Analysis^[2]

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.

Western Blot Analysis^[2]

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.

Immunofluorescence^[3]

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.

Real Time qPCR^[6]

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.

Western Blot Analysis^[6]

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 Cytotoxicity Assay^[7]

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 Proliferation Assay^[7]

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.

Related Protocols :

Chemical Information

CAS No. 188630-47-9
Appearance Solid
Molecular Weight 318.42
Formula C₂₀H₂₂N₄
Color White to yellow
SMILES

CN(C)CCCNC(C1=C(C=CC=C1)N=C23)=C3NC4=C2C=CC=C4
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

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)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.1405 mL

15.7025 mL

31.4051 mL

5 mM

0.6281 mL

3.1405 mL

6.2810 mL

10 mM

0.3141 mL

1.5703 mL

3.1405 mL

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.

Molarity Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Dilution Calculator

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

Concentration _(start) Concentration _(start)

Volume _(start) Volume _(start)

Concentration _(final) Concentration _(final)

Volume _(final) Volume _(final)

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (307 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)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Liu JN, et al. Inhibition of myc promoter and telomerase activity and induction of delayed apoptosis by SYUIQ-5, a novel G-quadruplex interactive agent in leukemia cells. Leukemia. 2007 Jun;21(6):1300-2.

[2]. Zhou JM, et al. Senescence and telomere shortening induced by novel potent G-quadruplex interactive agents, quindoline derivatives, in human cancer cell lines. Oncogene. 2006 Jan 26;25(4):503-11.

[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]

[4]. Wu Y, et al. Stabilization of VEGF G-quadruplex and inhibition of angiogenesis by quindoline derivatives. Biochimica et biophysica acta. 2014 Sep;1840(9):2970-7.

[5]. Liu HY, et al. New Disubstituted Quindoline Derivatives Inhibiting Burkitt's Lymphoma Cell Proliferation by Impeding c-MYC Transcription. Journal of medicinal chemistry. 2017 Jul 13;60(13):5438-5454.

[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]

[7]. Gerosa L, et al. Murine Myoblasts Exposed to SYUIQ-5 Acquire Senescence Phenotype and Differentiate into Sarcopenic-Like Myotubes, an In Vitro Study. The journals of gerontology. Series A, Biological sciences and medical sciences. 2024 Apr 01;79(4):glae022.

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

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

Product Name:
Cat. No.:
Quantity:
MCE Japan Authorized Agent:

Product Name:
CAS No.:
Species:
Purity:
Quantity:

SYUIQ-5

All VEGFR Isoforms