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SML0186

Sigma-Aldrich

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
MDL number:
MFCD20527329
UNSPSC Code:
12352200
PubChem Substance ID:
329825215
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

yellow to orange

solubility

DMSO: ≥5 mg/mL

originator

Bayer

storage temp.

2-8°C

SMILES string

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

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)

InChI key

XOBIGRNRXCAMJQ-UHFFFAOYSA-N

Application

Dp44mT may be used in cell signaling studies.

Biochem/physiol Actions

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.

Features and Benefits

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.
This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Caution

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Pengcheng Li et al.
American journal of translational research, 8(12), 5370-5385 (2017-01-13)
Di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone (Dp44mT), the novel iron chelator, has been reported to inhibit the tumorigenesis and progression of various cancer cells, including neuroblastoma, neuroepithelioma and prostate cancer. However, whether Dp44mT has anticancer effects in osteosarcoma is still unknown. Here, we investigated the
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)
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