![2-[(1,2-Dihydro-2-oxo-3H-indol-3-ylidene)methyl]-4-methyl-1H-pyrrole-3-propanoic acid structure, CAS 215543-92-3](/structures/60000/55619_1_215543_92_3.png)
CAS Number215543-92-3
SynonymsS1479_Selleck; 3-{4-Methyl-2-[(Z)-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl}propanoic acid; SU-5402; SU 5402
Molecular FormulaC17H16N2O3
Molecular Weight296.32
Purity≥98 (HPLC)%
Density1.4±0.1 g/cm3
Boiling Point592.6±50.0 °C at 760 mmHg
Melting Point>222ºC (dec.)
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 215543-92-3 |
| Catalog No. | 2A-9055619 |
| Chinese Name | 3-四聚丙烯基二氢-2,5-呋喃二酮 |
| Synonyms | S1479_Selleck; 3-{4-Methyl-2-[(Z)-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl}propanoic acid; SU-5402; SU 5402 |
| Molecular Formula | C17H16N2O3 |
| Molecular Weight | 296.32 |
| Purity | ≥98 (HPLC) |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 592.6±50.0 °C at 760 mmHg |
| Melting Point | >222ºC (dec.) |
| Appearance | powder |
| Storage Condition | -20℃ |
| Application | SU 5402 is a potent multi-target receptor tyrosine kinase inhibitor targeting VEGFR2, FGFR1 and PDGFRβ with IC50 of 20 nM, 30 nM and 510 nM respectively. |
| PubChem ID | 329824725 |
| MDL Number | MFCD08235144 |
| SMILES | Cc1c[nH]c(\C=C2/C(=O)Nc3ccccc23)c1CCC(O)=O |
| InChI | 1S/C17H16N2O3/c1-10-9-18-15(11(10)6-7-16(20)21)8-13-12-4-2-3-5-14(12)19-17(13)22/h2-5,8-9,18H,6-7H2,1H3,(H,19,22)(H,20,21)/b13-8- |
| InChI Key | JNDVEAXZWJIOKB-JYRVWZFOSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 51111800 |
| Hazard Symbols | transportation |
| MSDS | msds/55619_1_215543_92_3.pdf |
| Bioactivity | SU 5402 is a potent multi-targeted receptor tyrosine kinase inhibitor with IC50 of 20 nM, 30 nM, and 510 nM for VEGFR2, FGFR1, and PDGFRβ, respectively. Related Catalog Signaling Pathways >> Protein Tyrosine Kinase/RTK >> FGFR Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PDGFR Research Areas >> Cancer Target VEGFR2:20 nM (IC50) FGFR1:30 nM (IC50) PDGFRβ:510 nM (IC50) In Vitro SU 5402 is cocrystallized with the catalytic domain of FGF-R1 (flg-1) and is found to inhibit tyrosine phosphorylation of VEGF-R2 (Flk-1/KDR) and PDGF-R in NIH 3T3 cells with IC50 values of 0.4 and 60.9 μM, respectively[1]. In order to investigate whether phosphorylation of PKM2 and LDHA is mediated in FGFR1-specific manner, FTC-133 are treated with receptor tyrosine kinase inhibitors Dovitinib and SU 5402 (SU-5402). Dovitinib treatment results in significant decrease of phosphorylation status at a concentration of 100 nM after four hours of incubation for both PKM2 and LDHA. No significant changes are seen when administered at concentrations of 1 nM and 10 nM. SU 5402 administration leads to a sigificant decrease of PKM2 and LDHA phosphorylation at a concentration of 20 μM[2]. In Vivo Inhibition of FGFR1 with SU 5402 (SU5402) administered to ΔF508-CFTR homozygous mice results in partial ΔF508-CFTR rescue, as shown by an increase in saliva secretion, a surrogate "sweat test" assay in mice. As salivary secretion is often sex dependent, only male mice are chosen for these experiments. Our results indicate that treatment of the ΔF508-CFTR mice with SU 5402 restores the saliva secretion level to ~10% of that observed for the wild-type CFTR mice, which suggests that SU 5402 can have therapeutic benefits to Cystic Fibrosis (CF)[3]. The selective FGFR1 inhibitor SU 5402 (SU5402) prevents and/or reverses PH induced by MCT (monocrotaline) in rats. In rats treated with SU 5402 on days 21 to 42 after the MCT injection, evaluations on day 42 show marked decreases in pulmonary artery pressure (PAP), RV/(LV+S), and distal artery muscularization compare with rats treated with the vehicle (saline)[4]. Cell Assay 8505C and FTC133 cells are grown in DMEM/F12 suppplemented with 10% FCS and 1% PenStrep and incubated at 37°C, 5% CO2. For B-CPAP RPMI 1640 medium is used. FGFR1 inhibition experiments are performed on FTC133 cells by employment of Receptor Tyrosine Kinase Inhibitors TKI-258 (Dovitinib) and SU 5402 (20μM). Inhibition is conducted over 4 h with the indicated inhibitor concentrations. Control cells receive corresponding concentrations of DMSO[2]. Animal Admin Mice[3] Male ΔF508 mice (CFTRtm1Eur on a 129/FVB background) and their wild-type littermates of 9-12 weeks are intraperitoneally injected with DMSO or SU 5402 (dissolved in DMSO at the concentration of 6 mg/mL) at 25 mg/kg body weight, every day for 1 week. The mice are weighed daily and the dosages adjusted accordingly. The mice are then anesthetized by inhaling isoflurane until the end of the procedure. Cholinergic antagonist, Atropine (1 mM, 50 μL) is subcutaneously injected into the right cheek to block potential cholinergic stimulation of the salivary gland. A small strip of filter paper is placed against the injected cheek, for 4 min. Isoprenaline (10 mM, 37.5 μL) is subsequently injected in the same spot to stimulate an adrenergic secretion of saliva (time 0). Filter strips (pre-weighed in an Eppendorf tube) are replaced every 5 min, over a period of 30 min. All six filter strips are weighed at the end of the collection and the results are normalized relative to mg/g body weight. Rats[4] To assess the potential effects of the FGFR1 inhibitor SU 5402 on established PH, adult male Wistar rats (200-250 g) are given MCT (60 mg/kg s.c.), left untreated for 21 days, then randomly divided into 2 groups (10 animals in each group), of which one is treated with SU 5402 (25 mg/kg/day) and the other given the vehicle, from day 21 to day 42. All treatments are given once a day by s.c. injection. References [1]. Sun L, et al. Design, synthesis, and evaluations of substituted 3-[(3- or 4-carboxyethylpyrrol-2-yl)methylidenyl]indolin-2-ones as inhibitors of VEGF, FGF, and PDGF receptor tyrosine kinases. J Med Chem. 1999 Dec 16;42(25):5120-30. [2]. Kachel P, et al. Phosphorylation of pyruvate kinase M2 and lactate dehydrogenase A by fibroblast growth factor receptor 1 in benign and malignant thyroid tissue. BMC Cancer. 2015 Mar 18;15:140. [3]. Trzcińska-Daneluti AM, et al. RNA Interference Screen to Identify Kinases That Suppress Rescue of ΔF508-CFTR. Mol Cell Proteomics. 2015 Jun;14(6):1569-83. [4]. Izikki M, et al. Endothelial-derived FGF2 contributes to the progression of pulmonary hypertension in humans and rodents. J Clin Invest. 2009 Mar;119(3):512-23. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Boiling Point 592.6±50.0 °C at 760 mmHg Melting Point >222ºC (dec.) Molecular Formula C17H16N2O3 Molecular Weight 296.320 Flash Point 312.2±30.1 °C Exact Mass 296.116089 PSA 82.19000 LogP 2.03 Vapour Pressure 0.0±1.8 mmHg at 25°C Index of Refraction 1.688 InChIKey JNDVEAXZWJIOKB-JYRVWZFOSA-N SMILES Cc1c[nH]c(C=C2C(=O)Nc3ccccc32)c1CCC(=O)O Storage condition -20℃ |
| Use of | SU 5402 is a potent multi-targeted receptor tyrosine kinase inhibitor with IC50 of 20 nM, 30 nM, and 510 nM for VEGFR2, FGFR1, and PDGFRβ, respectively. Properties Name 3-[4-methyl-2-[(Z)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl]propanoic acid Synonym More Synonyms SU 5402 Biological Activity Description SU 5402 is a potent multi-targeted receptor tyrosine kinase inhibitor with IC50 of 20 nM, 30 nM, and 510 nM for VEGFR2, FGFR1, and PDGFRβ, respectively. Related Catalog Signaling Pathways >> Protein Tyrosine Kinase/RTK >> FGFR Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PDGFR Research Areas >> Cancer VEGFR2:20 nM (IC50) FGFR1:30 nM (IC50) PDGFRβ:510 nM (IC50) References [1]. Sun L, et al. Design, synthesis, and evaluations of substituted 3-[(3- or 4-carboxyethylpyrrol-2-yl)methylidenyl]indolin-2-ones as inhibitors of VEGF, FGF, and PDGF receptor tyrosine kinases. J Med Chem. 1999 Dec 16;42(25):5120-30. [2]. Kachel P, et al. Phosphorylation of pyruvate kinase M2 and lactate dehydrogenase A by fibroblast growth factor receptor 1 in benign and malignant thyroid tissue. BMC Cancer. 2015 Mar 18;15:140. [3]. Trzcińska-Daneluti AM, et al. RNA Interference Screen to Identify Kinases That Suppress Rescue of ΔF508-CFTR. Mol Cell Proteomics. 2015 Jun;14(6):1569-83. Chemical & Physical Properties Molecular Formula C17H16N2O3 Exact Mass 296.116089 PSA 82.19000 Index of Refraction 1.688 InChIKey JNDVEAXZWJIOKB-JYRVWZFOSA-N Storage condition -20℃ |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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