1206711-16-1

1206711-16-1 structure

Name: DMH-1
Chemical Name: 4-[6-(4-propan-2-yloxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline
CAS Number: 1206711-16-1
Molecular Formula: C₂₄H₂₀N₄O
Molecular Weight: 380.442
Catalog: Biochemical Inhibitor TGF-beta/Smad signaling pathway inhibitor (TGF-beta/Smad) TGF-beta/Smad inhibitor
Create Date: 2016-08-19 22:27:47
Modify Date: 2025-08-24 12:02:51
DMH-1 is a potent and selective BMP inhibitor with IC50s of 27/107.9/<5/47.6 nM for ALK1/ALK2/ALK3/ALK6, respectively.

Name	4-[6-(4-propan-2-yloxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline
Synonyms	4-[6-(4-Isopropoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline DMH1 Quinoline, 4-[6-[4-(1-methylethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]- DMH-1

Description	DMH-1 is a potent and selective BMP inhibitor with IC50s of 27/107.9/<5/47.6 nM for ALK1/ALK2/ALK3/ALK6, respectively.
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> TGF-beta/Smad >> TGF-β Receptor Research Areas >> Cancer
Target	IC50: 27 nM (ALK1), 107.9 nM (ALK2), <5 nM (ALK3), 47.6 nM (ALK6)[1]
In Vitro	DMH-1 (0.5 μM) induces regulation of OCT4, Nanog, and PAX6 protein expression. DMH-1 significantly reduces the percentage of cells expressing the pluripotency marker proteins OCT4 and Nanog in both SM3 and CA6 cells. PAX6 expression is significantly up-regulated by day 5 and day 7 in CA6 and SM3 cells, respectively. DMH-1 induces regulation of pluripotency and neural precursor marker mRNAs. PAX6 can regulate the expression of SOX1 independently by manipulating the DMH-1 concentration during the neural induction of hiPSCs[2]. DMH-1 (5 μM and 10 μM) inhibits CDDP-induced autophagy in HeLa cells and enhances the ability of CDDP to reduce HeLa cell viability, inhibits tamoxifen-induced autophagy in MCF-7 cells and enhances the ability of tamoxifen to reduce MCF-7 cell viability, inhibits 5-FU-induced autophagy in both MCF-7 and HeLa cells but does not affect the inhibitory effects of 5-FU on MCF-7 and HeLa cell viability. DMH-1 enhances the apoptotic induction effects of CDDP on HeLa cells after 24 h treatment. DMH-1 inhibits HeLa and MCF-7 cell proliferation[3]. DMH-1 (20 μM) reduces the canonical phosphorylation of Smads 1,5 and 9. DMH-1 in combination with Cisplatin significantly decreases Ki-67 positive staining in the OVCAR8 cells. DMH-1 (20 µM) upregulates JAG1, reduces CYP1B1 and increases HAPLN1 expression in both OVCAR8 and NCI-RES cells[4].
In Vivo	DMH1 (5 mg/kg, i.p.) treatment significantly reduces the tumor growth in human lung cancer xenograft model[5].
Cell Assay	Cells are seeded in 96-well plates and treated with different drugs for appropriate time. Then 5 mg/mL MTT is added and incubated for 4 h at 37°C. Medium is then removed and 200 μL of DMSO is added to dissolve the crystal. Absorbance is measured at a wavelength of 490 nm with a plate reader.
Animal Admin	Sub-confluent A549 cells are trypsinized and then suspended in serum free RPMI 1640 medium. The cell suspension (1×106 cells in 100 µL medium for each injection) is injected subcutaneously into both the right and left flanks of eight-week old NOD SCID mice (n=5 for each group). Mice are given Intraperitoneal (i.p.) injection of the vehicle (12.5% 2-hydroxypropyl-β-cyclodextrin) or 5 mg/kg DMH1 every other day. The tumor sizes are measured with a vernier caliper from the sixth day to the fourth week after tumor implantation. The tumor volume (V) is calculated according to the formulation: Volume=(width)2×length/2. The tumor tissues are dissected at the end of study, and are sectioned and stained with H & E, and for immunohistochemical analysis.
References	[1]. Engers DW, et al. Synthesis and structure-activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of dorsomorphin: the discovery of mL347 as an ALK2 versus ALK3 selective mLPCN probe. Bioorg Med Chem Lett. 2013 Jun 1;23(11):3248-52. [2]. Neely MD, et al. DMH1, a highly selective small molecule BMP inhibitor promotes neurogenesis of hiPSCs: comparison of PAX6 and SOX1 expression during neural induction. ACS Chem Neurosci. 2012 Jun 20;3(6):482-91. [3]. Sheng Y, et al. DMH1 (4-[6-(4-isopropoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline) inhibits chemotherapeutic drug-induced autophagy. Acta Pharm Sin B. 2015 Jul;5(4):330-6. [4]. Hover LD, et al. Small molecule inhibitor of the bone morphogenetic protein pathway DMH1 reduces ovarian cancer cell growth. Cancer Lett. 2015 Nov 1;368(1):79-87. [5]. Hao J, et al. DMH1, a small molecule inhibitor of BMP type i receptors, suppresses growth and invasion of lung cancer. PLoS One. 2014 Mar 6;9(6):e90748.

Density	1.2±0.1 g/cm3
Molecular Formula	C₂₄H₂₀N₄O
Molecular Weight	380.442
Exact Mass	380.163696
PSA	52.31000
LogP	3.62
Appearance	light yellow to orange
Index of Refraction	1.672
Storage condition	Store at +4°C
Water Solubility	DMSO: soluble5mg/mL, clear (warmed)

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301
Precautionary Statements	P301 + P310
Hazard Codes	T
Risk Phrases	25
Safety Phrases	45
RIDADR	UN 2811 6.1 / PGIII

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