Home Deuterated Building Blocks 152095-12-0
152095-12-0,MFCD20527329
Catalog No.:AA007JPD

152095-12-0 | Dp44mt

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1mg
97%
in stock  
$8.00   $6.00
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10mg
97%
in stock  
$25.00   $18.00
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25mg
97%
in stock  
$42.00   $29.00
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50mg
97%
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$71.00   $50.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA007JPD
Chemical Name:
Dp44mt
CAS Number:
152095-12-0
Molecular Formula:
C14H15N5S
Molecular Weight:
285.3674
MDL Number:
MFCD20527329
SMILES:
S=C(N(C)C)NN=C(c1ccccn1)c1ccccn1
NSC Number:
744381
Properties
Computed Properties
 
Complexity:
336  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
3  
XLogP3:
2.2  

Downstream Synthesis Route
19437-26-4    6926-58-5   
di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone 

[1]JournalofMedicinalChemistry,2006,vol.49,p.6510-6521

[2]Patent:CN104177288,2020,B.Locationinpatent:Paragraph0169-0171

[3]BioMetals,2016,vol.29,p.157-170

[4]InternationalJournalofMolecularSciences,2016,vol.17

[5]Patent:CN104844632,2017,B.Locationinpatent:Paragraph0033;0034;0035;0036;0037;0051-0052;0054-0055

[6]EuropeanJournalofMedicinalChemistry,2019,vol.171,p.180-194

152095-12-0   
CASUnavailable 
 
CASUnavailable 

[1]Akladios,FadyN.;Andrew,ScottD.;Parkinson,ChristopherJ.[BioMetals,2016,vol.29,#1,p.157-170]

152095-12-0   
CASUnavailable 
 
CASUnavailable 

[1]Akladios,FadyN.;Andrew,ScottD.;Parkinson,ChristopherJ.[BioMetals,2016,vol.29,#1,p.157-170]

152095-12-0   
CASUnavailable 
 
CASUnavailable 
 
CASUnavailable 

[1]Stacy,AlexandraE.;Palanimuthu,Duraippandi;Bernhardt,PaulV.;Kalinowski,DanutaS.;Jansson,PatricJ.;Richardson,DesR.[JournalofMedicinalChemistry,2016,vol.59,#10,p.4965-4984]

Literature

Title: The anticancer agent di-2-pyridylketone 4,4-dimethyl-3-thiosemicarbazone (Dp44mT) overcomes prosurvival autophagy by two mechanisms: persistent induction of autophagosome synthesis and impairment of lysosomal integrity.

Journal: The Journal of biological chemistry 20141128

Title: Distinct mechanisms of cell-kill by triapine and its terminally dimethylated derivative Dp44mT due to a loss or gain of activity of their copper(II) complexes.

Journal: Biochemical pharmacology 20141001

Title: The metastasis suppressor, N-myc downstream-regulated gene 1 (NDRG1), inhibits stress-induced autophagy in cancer cells.

Journal: The Journal of biological chemistry 20140404

Title: The anticancer drug Dp44mT inhibits T-cell activation and CD25 through a copper-dependent mechanism.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20130201

Title: Synthesis and characterization of quinoline-based thiosemicarbazones and correlation of cellular iron-binding efficacy to anti-tumor efficacy.

Journal: Bioorganic & medicinal chemistry letters 20120901

Title: Novel second-generation di-2-pyridylketone thiosemicarbazones show synergism with standard chemotherapeutics and demonstrate potent activity against lung cancer xenografts after oral and intravenous administration in vivo.

Journal: Journal of medicinal chemistry 20120823

Title: The anticancer thiosemicarbazones Dp44mT and triapine lack inhibitory effects as catalytic inhibitors or poisons of DNA topoisomerase IIα.

Journal: Biochemical pharmacology 20120701

Title: Methemoglobin formation by triapine, di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone (Dp44mT), and other anticancer thiosemicarbazones: identification of novel thiosemicarbazones and therapeutics that prevent this effect.

Journal: Molecular pharmacology 20120701

Title: The iron chelators Dp44mT and DFO inhibit TGF-β-induced epithelial-mesenchymal transition via up-regulation of N-Myc downstream-regulated gene 1 (NDRG1).

Journal: The Journal of biological chemistry 20120518

Title: Bp44mT: an orally active iron chelator of the thiosemicarbazone class with potent anti-tumour efficacy.

Journal: British journal of pharmacology 20120101

Title: Investigation of substituted 6-aminohexanoates as skin penetration enhancers.

Journal: Bioorganic & medicinal chemistry 20120101

Title: The iron chelator Dp44mT inhibits the proliferation of cancer cells but fails to protect from doxorubicin-induced cardiotoxicity in spontaneously hypertensive rats.

Journal: Cancer chemotherapy and pharmacology 20111101

Title: Halogenated 2'-benzoylpyridine thiosemicarbazone (XBpT) chelators with potent and selective anti-neoplastic activity: relationship to intracellular redox activity.

Journal: Journal of medicinal chemistry 20111013

Title: Antitumor activity of metal-chelating compound Dp44mT is mediated by formation of a redox-active copper complex that accumulates in lysosomes.

Journal: Cancer research 20110901

Title: The potent and novel thiosemicarbazone chelators di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone and 2-benzoylpyridine-4,4-dimethyl-3-thiosemicarbazone affect crucial thiol systems required for ribonucleotide reductase activity.

Journal: Molecular pharmacology 20110601

Title: Cellular iron depletion stimulates the JNK and p38 MAPK signaling transduction pathways, dissociation of ASK1-thioredoxin, and activation of ASK1.

Journal: The Journal of biological chemistry 20110429

Title: Iron chelators of the di-2-pyridylketone thiosemicarbazone and 2-benzoylpyridine thiosemicarbazone series inhibit HIV-1 transcription: identification of novel cellular targets--iron, cyclin-dependent kinase (CDK) 2, and CDK9.

Journal: Molecular pharmacology 20110101

Title: Investigating the activity of 2-substituted alkyl-6-(2,5-dioxopyrrolidin-1-yl)hexanoates as skin penetration enhancers.

Journal: Bioorganic & medicinal chemistry 20101215

Title: Anti-tumor and radiosensitization activities of the iron chelator HDp44mT are mediated by effects on intracellular redox status.

Journal: Cancer letters 20101208

Title: The iron complex of Dp44mT is redox-active and induces hydroxyl radical formation: an EPR study.

Journal: Journal of inorganic biochemistry 20101101

Title: Novel thiosemicarbazones of the ApT and DpT series and their copper complexes: identification of pronounced redox activity and characterization of their antitumor activity.

Journal: Journal of medicinal chemistry 20100812

Title: Conjugates of desferrioxamine B (DFOB) with derivatives of adamantane or with orally available chelators as potential agents for treating iron overload.

Journal: Journal of medicinal chemistry 20100211

Title: 2-Acetylpyridine thiosemicarbazones are potent iron chelators and antiproliferative agents: redox activity, iron complexation and characterization of their antitumor activity.

Journal: Journal of medicinal chemistry 20090312

Title: Antitumor activity and mechanism of action of the iron chelator, Dp44mT, against leukemic cells.

Journal: American journal of hematology 20090301

Title: The iron chelator Dp44mT causes DNA damage and selective inhibition of topoisomerase IIalpha in breast cancer cells.

Journal: Cancer research 20090201

Title: Iron chelators of the dipyridylketone thiosemicarbazone class: precomplexation and transmetalation effects on anticancer activity.

Journal: Journal of medicinal chemistry 20090122

Title: HPLC methods for determination of two novel thiosemicarbazone anti-cancer drugs (N4mT and Dp44mT) in plasma and their application to in vitro plasma stability of these agents.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090115

Title: Iron behaving badly: inappropriate iron chelation as a major contributor to the aetiology of vascular and other progressive inflammatory and degenerative diseases.

Journal: BMC medical genomics 20090101

Title: Structure-activity relationships of novel iron chelators for the treatment of iron overload disease: the methyl pyrazinylketone isonicotinoyl hydrazone series.

Journal: Journal of medicinal chemistry 20080124

Title: Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: structure-activity relationships of novel thiohydrazone analogues.

Journal: Journal of medicinal chemistry 20071129

Title: Design, synthesis, and characterization of novel iron chelators: structure-activity relationships of the 2-benzoylpyridine thiosemicarbazone series and their 3-nitrobenzoyl analogues as potent antitumor agents.

Journal: Journal of medicinal chemistry 20070726

Title: Development and validation of HPLC-DAD methods for the analysis of two novel iron chelators with potent anti-cancer activity.

Journal: Journal of pharmaceutical and biomedical analysis 20070312

Title: Dipyridyl thiosemicarbazone chelators with potent and selective antitumor activity form iron complexes with redox activity.

Journal: Journal of medicinal chemistry 20061102

Title: Rao VA, et al. The iron chelator Dp44mT causes DNA damage and selective inhibition of topoisomerase IIalpha in breast cancer cells. Cancer Res. 2009 Feb 1;69(3):948-57.

Title: Lovejoy DB, et al. Antitumor activity of metal-chelating compound Dp44mT is mediated by formation of a redox-active copper complex that accumulates in lysosomes. Cancer Res. 2011 Sep 1;71(17):5871-80.

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