NSC139021

Names

[ Name ]:
NSC139021

[Synonym ]:
TAN
1,2-thiazoylazo-2-naphthol
MFCD00021611
1-(2-Thiazolylazo)-2-naphthol
1-thiazol-2-ylazo-naphthalen-2-ol
EINECS 214-555-3
NSC139021

Biological Activity

[Description]:

NSC139021 (ERGi-USU) is a highly selective inhibitor for the growth of ERG-positive cancer cells with IC50s ranging from 30 to 400 nM.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

[Target]

IC50: 30 to 400 nM (ERG-positive cancer cells)[1]

[In Vitro]

NSC139021 selectively inhibits growth of ERGpositive cancer cell lines with minimal effect on normal prostate or endothelial cells or ERG-negative tumor cell lines. The IC50 of NSC139021 for cell growth inhibition of responsive cell lines range between 30 nM to 400 nM. Combination of NSC139021 with enzalutamide shows additive effects in inhibiting growth of VCaP cells. A screen of kinases reveal that NSC139021 directly bound the ribosomal biogenesis regulator atypical kinase RIOK2 and induces ribosomal stress signature[1].

[In Vivo]

NSC139021 treatment inhibits growth of ERG-positive VCaP tumor xenografts with no apparent toxicity. Significant (P<0.05, P<0.005) inhibition of tumor growth is noted at day 26 in treatment groups indicating 44% (100 mg/kg) and 65% (150 mg/kg) reduction of tumor burden. At 100 mg/kg and 150 mg/kg, no apparent toxicity including weight loss, lethargy, diarrhea, loss of appetite, respiratory distress, or overall drug related toxicity is observed. [1].

[Cell Assay]

To assess cell growth, To evaluate the ERG selectivity of the NSC139021, a panel of the following cell lines are assessed: ERG positive tumor cell lines (prostate cancer: VCaP; colon cancer: COLO320; leukemia: KG-1, MOLT-4; ERG negative prostate cancer cell lines (LNCaP, LAPC4, MDA PCa2b); normal prostate epithelium derived cell lines (BPH-1, RWPE-1); and primary endothelium derived cells (HUVEC). Monolayer of adherent cells are grown in their respective medium for 48 h followed by treatment with indicated dosage and time for the small molecule inhibitor NSC139021. Medium is replaced every 24 h containing the same concentration of the small molecule compound. Cells are counted by using trypan blue exclusion method. Cell morphology is documented by photography in all indicated time points. IC50 is calculated using GraphPad Prism 6 software[1].

[Animal admin]

Mice[1] The VCaP prostate cancer cells are injected into lower right dorsal flank of the male athymic nude mice (6-8 weeks old and weighing 27 to 30g). when tumors are palpable, mice are randomly separated into 2 experimental groups and into one control group of 6 mice in each group. In the treatment groups mice are injected intraperitoneally (I.P) with 100 mg/kg of NSC139021 or 150 mg/kg of NSC139021 while the control group are injected with vehicle (1:1[v/v], DMSO/PEG300) only. Growth in tumor volume is recorded weekly by using digital calipers and tumor volumes are calculated[1].

[References]

[1]. Mohamed AA, et al. Identification of a small molecule that selectively inhibits ERG-positive cancer cell growth. Cancer Res. 2018 Apr 30. pii: canres.2949.2017.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4g/cm3

[ Boiling Point ]:
523.251ºC at 760 mmHg

[ Melting Point ]:
138-139 °C

[ Molecular Formula ]:
C₁₃H₉N₃OS

[ Molecular Weight ]:
255.29500

[ Flash Point ]:
270.253ºC

[ Exact Mass ]:
255.04700

[ PSA ]:
86.08000

[ LogP ]:
4.41730

[ Vapour Pressure ]:
0mmHg at 25°C

[ Index of Refraction ]:
1.728

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
methanol: 10 mg/mL, clear

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2934100090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934100090

[ Summary ]:
2934100090 other compounds containing an unfused thiazole ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

Articles

Planar triazinium cations from vanadyl-mediated ring cyclizations: the thiazole species for efficient nuclear staining and photocytotoxicity.

Dalton Trans. 42(13) , 4436-49, (2013)

Planar triazinium cationic species from vanadyl-assisted cyclization of 1-(2-thiazolylazo)-2-naphthol (H-TAN, 1), 1-(2-pyridylazo)-2-naphthol (H-PAN, 2), 2-(2'-thiazolylazo)-p-cresol (H-TAC, 3) and 6-...

Study on the determination of heavy metals in water samples with ultrasound-assisted dispersive liquid-liquid microextraction prior to FAAS.

Water Sci. Technol. 67(2) , 247-53, (2013)

A new, simple and rapid method based on dispersive liquid-liquid microextraction (DLLME) was developed for extracting and preconcentrating copper (Cu), nickel (Ni), lead (Pb) and cadmium (Cd) in water...

Determination of manganese in water samples by flame atomic absorption spectrometry after cloud point extraction.

Analyst 126(4) , 534-7, (2001)

Cloud point extraction has been used for the preconcentration of manganese, after the formation of a complex with 1-(2-thiazolylazo)-2-naphthol (TAN), and later analysis by flame atomic absorption spe...