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Merck

SML0186

Dp44mT

≥98% (HPLC)

Synonym(s):

2-(Di-2-pyridinylmethylene)-N,N-dimethyl-hydrazinecarbothioamide, Di-2-pyridylketone-4,4,-dimethyl-3-thiosemicarbazone

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About This Item

Empirical Formula (Hill Notation):
C14H15N5S
CAS Number:
152095-12-0
Molecular Weight:
285.37
NACRES:
NA.77
PubChem Substance ID:
329825215
UNSPSC Code:
12352200
MDL number:
MFCD20527329

Key Documents

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Product Name

Dp44mT, ≥98% (HPLC)

InChI

1S/C14H15N5S/c1-19(2)14(20)18-17-13(11-7-3-5-9-15-11)12-8-4-6-10-16-12/h3-10H,1-2H3,(H,18,20)

SMILES string

CN(C)C(=S)N\N=C(\c1ccccn1)c2ccccn2

InChI key

XOBIGRNRXCAMJQ-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

yellow to orange

solubility

DMSO: ≥5 mg/mL

originator

Bayer

storage temp.

2-8°C

Quality Level

100

Related Categories

Features and Benefits

This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Application

Dp44mT may be used in cell signaling studies.

Biochem/physiol Actions

Cell-permeable iron chelator and top2a activity inhibitor
Dp44mT (di-2-pyridylketone-4,4,-dimethyl-3-thiosemicarbazone) influences lysosome integrity through copper binding. It induces reactive oxygen species (ROS) generation by redox cycling of iron complex. Dp44mT exhibits anti cancer action by attenuating Ndrg-1 (N-myc downstream regulated 1), a metastasis suppressor protein. It also alters the cyclin family of proteins (A, B, D1, D2,D3 and cyclin-dependent kinase 2) known for cell-cycle regulation. Dp44mT is known to promote apoptosis in neuroepithelioma, melanoma and breast cancer.
Dp44mT is an iron chelator that works as a selective anticancer agent. As other iron chelators it can serve as a therapeutic adjunct to doxorubicin treatment. Additionally Dm44mT possess DNA-damaging activity. It appears that that activity is mediated by top2a inhibition.

Disclaimer

Material appears to be unstable in solution; make solutions immediately before use.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000123071
0000123072
0000087753
0000081911
0000082263

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Chaowei Shang et al.
Oncogene, 39(29), 5201-5213 (2020-06-17)
The mammalian target of rapamycin (mTOR) functions as two complexes (mTORC1 and mTORC2), regulating cell growth and metabolism. Aberrant mTOR signaling occurs frequently in cancers, so mTOR has become an attractive target for cancer therapy. Iron chelators have emerged as
Antitumor activity of metal-chelating compound Dp44mT is mediated by formation of a redox-active copper complex that accumulates in lysosomes
Lovejoy DB
Cancer Research, 71(17), 5871-5880 (2011)
Fereshtehsadat Mirab et al.
PloS one, 14(1), e0211078-e0211078 (2019-01-25)
Treatment of glioblastoma, the most common and aggressive type of primary brain tumors, is a major medical challenge and the development of new alternatives requires simple yet realistic models for these tumors. In vitro spheroid models offer attractive platforms to
The iron chelator Dp44mT causes DNA damage and selective inhibition of topoisomerase IIalpha in breast cancer cells
Rao VA, et al.
Cancer Research, 69(3), 948-957 (2009)
Sumit Sahni et al.
Biochimica et biophysica acta. General subjects, 1864(8), 129625-129625 (2020-04-27)
N-myc downstream regulated gene 1 (NDRG1) is an established stress-response protein. This study investigated the effects of NDRG1 on autophagic degradation and how this can be therapeutically exploited. Cell culture, western analysis, confocal microscopy, acridine orange staining, cholesterol determination, cellular
View All Related Papers

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