Dp44mT | CAS#152095-12-0 | iron chelator

MedKoo Cat#: 527651 | Name: Dp44mT

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dp44mT is an iron chelator, possessing DNA-damaging activity mediated by top2a inhibition.

Chemical Structure

Dp44mT

CAS#152095-12-0

Theoretical Analysis

MedKoo Cat#: 527651

Name: Dp44mT

CAS#: 152095-12-0

Chemical Formula: C14H15N5S

Exact Mass: 285.1048

Molecular Weight: 285.37

Elemental Analysis: C, 58.93; H, 5.30; N, 24.54; S, 11.23

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,450.00	2 Weeks

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Related CAS #

152095-12-0

Synonym

Dp44mT; NSC744381; NSC 744381; NSC-744381;

IUPAC/Chemical Name

3-(Dipyridin-2-ylmethylideneamino)-1,1-dimethylthiourea

InChi Key

XOBIGRNRXCAMJQ-UHFFFAOYSA-N

InChi Code

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 Code

S=C(N/N=C(C1=NC=CC=C1)/C2=NC=CC=C2)N(C)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Dp44mT is an iron chelator with selective anticancer activity.

In vitro activity:

Dp44mT increased levels of tumour-suppressive PTEN, and decreased phosphorylation of ERK1/2 and SMAD2L, which are regulated by oncogenic Ras/MAPK signalling. Importantly, the effects of Dp44mT on NDRG1 and p-SMAD2L expression were more marked in prostate cancer cells than normal prostate epithelial cells. Reference: Br J Cancer. 2013 Feb 5;108(2):409-19. https://pubmed.ncbi.nlm.nih.gov/23287991/

In vivo activity:

After 17 days of treatment, the tumors derived from Dp44mT-treated mice present reductions of 63.81% in tumor size (120.61 ± 24.08 mm3 vs. 333.31 ± 71.11 mm3, Figure 5B) and 37.32% in tumor weight (683.80 ± 109.06 mg vs. 1090.98 ± 155.04 mg, Figure 5C), as compared with tumors from vehicle-treated animals. Furthermore, results of RT-qPCR assays (Figure 5D) show that mRNA of NDRG1, NDRG3, and Maspin was increased in the xenografted tumors from Dp44mT-treated mice. Reference: Int J Mol Sci. 2016 Aug 31;17(9):1435. https://pubmed.ncbi.nlm.nih.gov/27589737/

	Solvent	mg/mL	mM
Solubility
	DMF	33.0	115.64
	DMSO	66.5	233.03
	Ethanol	33.0	115.64
	Ethanol:PBS (pH 7.2) (1:7)	0.1	0.42

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 285.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Dixon KM, Lui GY, Kovacevic Z, Zhang D, Yao M, Chen Z, Dong Q, Assinder SJ, Richardson DR. Dp44mT targets the AKT, TGF-β and ERK pathways via the metastasis suppressor NDRG1 in normal prostate epithelial cells and prostate cancer cells. Br J Cancer. 2013 Feb 5;108(2):409-19. doi: 10.1038/bjc.2012.582. Epub 2013 Jan 3. PMID: 23287991; PMCID: PMC3566801. 2. Lovejoy DB, Jansson PJ, Brunk UT, Wong J, Ponka P, Richardson DR. 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. doi: 10.1158/0008-5472.CAN-11-1218. Epub 2011 Jul 12. PMID: 21750178. 3. Lee JC, Chiang KC, Feng TH, Chen YJ, Chuang ST, Tsui KH, Chung LC, Juang HH. The Iron Chelator, Dp44mT, Effectively Inhibits Human Oral Squamous Cell Carcinoma Cell Growth in Vitro and in Vivo. Int J Mol Sci. 2016 Aug 31;17(9):1435. doi: 10.3390/ijms17091435. PMID: 27589737; PMCID: PMC5037714. 4. Jansson PJ, Yamagishi T, Arvind A, Seebacher N, Gutierrez E, Stacy A, Maleki S, Sharp D, Sahni S, Richardson DR. Di-2-pyridylketone 4,4-dimethyl-3-thiosemicarbazone (Dp44mT) overcomes multidrug resistance by a novel mechanism involving the hijacking of lysosomal P-glycoprotein (Pgp). J Biol Chem. 2015 Apr 10;290(15):9588-603. doi: 10.1074/jbc.M114.631283. Epub 2015 Feb 26. PMID: 25720491; PMCID: PMC4392262.

In vitro protocol:

In vivo protocol:

1. Lee JC, Chiang KC, Feng TH, Chen YJ, Chuang ST, Tsui KH, Chung LC, Juang HH. The Iron Chelator, Dp44mT, Effectively Inhibits Human Oral Squamous Cell Carcinoma Cell Growth in Vitro and in Vivo. Int J Mol Sci. 2016 Aug 31;17(9):1435. doi: 10.3390/ijms17091435. PMID: 27589737; PMCID: PMC5037714. 2. Jansson PJ, Yamagishi T, Arvind A, Seebacher N, Gutierrez E, Stacy A, Maleki S, Sharp D, Sahni S, Richardson DR. Di-2-pyridylketone 4,4-dimethyl-3-thiosemicarbazone (Dp44mT) overcomes multidrug resistance by a novel mechanism involving the hijacking of lysosomal P-glycoprotein (Pgp). J Biol Chem. 2015 Apr 10;290(15):9588-603. doi: 10.1074/jbc.M114.631283. Epub 2015 Feb 26. PMID: 25720491; PMCID: PMC4392262.

1: Al-Akra L, Bae DH, Sahni S, Huang MLH, Park KC, Lane DJR, Jansson PJ, Richardson DR. Tumor stressors induce two mechanisms of intracellular p-glycoprotein-mediated resistance that are overcome by lysosomal-targeted thiosemicarbazones. J Biol Chem. 2018 Jan 5. pii: jbc.M116.772699. doi: 10.1074/jbc.M116.772699. [Epub ahead of print] PubMed PMID: 29305422. 2: Kang YJ, Kuo CF, Majd S. Nanoparticle-based delivery of an anti-proliferative metal chelator to tumor cells. Conf Proc IEEE Eng Med Biol Soc. 2017 Jul;2017:309-312. doi: 10.1109/EMBC.2017.8036824. PubMed PMID: 29059872. 3: Moussa RS, Kovacevic Z, Bae DH, Lane DJR, Richardson DR. Transcriptional regulation of the cyclin-dependent kinase inhibitor, p21(CIP1/WAF1), by the chelator, Dp44mT. Biochim Biophys Acta. 2017 Oct 13. pii: S0304-4165(17)30330-6. doi: 10.1016/j.bbagen.2017.10.009. [Epub ahead of print] PubMed PMID: 29032246. 4: Abayaweera GS, Wang H, Shrestha TB, Yu J, Angle K, Thapa P, Malalasekera AP, Maurmann L, Troyer DL, Bossmann SH. Synergy of Iron Chelators and Therapeutic Peptide Sequences Delivered via a Magnetic Nanocarrier. J Funct Biomater. 2017 Jun 26;8(3). pii: E23. doi: 10.3390/jfb8030023. PubMed PMID: 28672849; PubMed Central PMCID: PMC5618274. 5: Nam SY, Han NR, Yoon KW, Kim HM, Jeong HJ. Di-2-pyridylketone 4,4-dimethyl-3-thiosemicarbazone (Dp44mT), an anticancer agent, exerts an anti-inflammatory effect in activated human mast cells. Inflamm Res. 2017 Oct;66(10):871-879. doi: 10.1007/s00011-017-1067-x. Epub 2017 Jun 14. PubMed PMID: 28616734. 6: Li P, Zheng X, Shou K, Niu Y, Jian C, Zhao Y, Yi W, Hu X, Yu A. The iron chelator Dp44mT suppresses osteosarcoma's proliferation, invasion and migration: in vitro and in vivo. Am J Transl Res. 2016 Dec 15;8(12):5370-5385. eCollection 2016. PubMed PMID: 28078009; PubMed Central PMCID: PMC5209489. 7: Seebacher NA, Richardson DR, Jansson PJ. A mechanism for overcoming P-glycoprotein-mediated drug resistance: novel combination therapy that releases stored doxorubicin from lysosomes via lysosomal permeabilization using Dp44mT or DpC. Cell Death Dis. 2016 Dec 1;7(12):e2510. doi: 10.1038/cddis.2016.381. PubMed PMID: 27906178; PubMed Central PMCID: PMC5261000. 8: Xu Z, Liu Y, Zhou S, Fu Y, Li C. Response to the Letter to the Editor by D. Richardson: Analysis of the Interaction of Dp44mT with Human Serum Albumin and Calf Thymus DNA Using Molecular Docking and Spectroscopic Techniques. Int J Mol Sci. 2016 Nov 16;17(11). pii: E1917. PubMed PMID: 27854349; PubMed Central PMCID: PMC5133914. 9: Merlot AM, Sahni S, Lane DJ, Richardson V, Huang ML, Kalinowski DS, Richardson DR. Letter to the Editor: "Analysis of the Interaction of Dp44mT with Human Serum Albumin and Calf Thymus DNA Using Molecular Docking and Spectroscopic Techniques". Int J Mol Sci. 2016 Nov 16;17(11). pii: E1916. PubMed PMID: 27854347; PubMed Central PMCID: PMC5133913. 10: Xu Z, Liu Y, Zhou S, Fu Y, Li C. Correction: Zhongjie Xu, et al. Analysis of the Interaction of Dp44mT with Human Serum Albumin and Calf Thymus DNA using Molecular Docking and Spectroscopic Techniques. Int. J. Mol. Sci. 2016, 17, 1042. Int J Mol Sci. 2016 Nov 16;17(11). pii: E1915. PubMed PMID: 27854346; PubMed Central PMCID: PMC5133912. 11: Drummen GP, Christov CZ. Editorial: Analysis of the Interaction of Dp44mT with Human Serum Albumin and Calf Thymus DNA Using Molecular Docking and Spectroscopic Techniques. Int J Mol Sci. 2016 Nov 16;17(11). pii: E1914. PubMed PMID: 27854345; PubMed Central PMCID: PMC5133911. 12: Krishan S, Richardson DR, Sahni S. The Anticancer Agent, Di-2-Pyridylketone 4,4-Dimethyl-3-Thiosemicarbazone (Dp44mT), Up-Regulates the AMPK-Dependent Energy Homeostasis Pathway in Cancer Cells. Biochim Biophys Acta. 2016 Dec;1863(12):2916-2933. doi: 10.1016/j.bbamcr.2016.09.011. Epub 2016 Sep 15. PubMed PMID: 27639899. 13: Guo ZL, Richardson DR, Kalinowski DS, Kovacevic Z, Tan-Un KC, Chan GC. The novel thiosemicarbazone, di-2-pyridylketone 4-cyclohexyl-4-methyl-3-thiosemicarbazone (DpC), inhibits neuroblastoma growth in vitro and in vivo via multiple mechanisms. J Hematol Oncol. 2016 Sep 27;9(1):98. PubMed PMID: 27678372; PubMed Central PMCID: PMC5039880. 14: Akladios FN, Andrew SD, Parkinson CJ. Cytotoxic activity of expanded coordination bis-thiosemicarbazones and copper complexes thereof. J Biol Inorg Chem. 2016 Dec;21(8):931-944. Epub 2016 Sep 19. PubMed PMID: 27645502. 15: Lee JC, Chiang KC, Feng TH, Chen YJ, Chuang ST, Tsui KH, Chung LC, Juang HH. The Iron Chelator, Dp44mT, Effectively Inhibits Human Oral Squamous Cell Carcinoma Cell Growth in Vitro and in Vivo. Int J Mol Sci. 2016 Aug 31;17(9). pii: E1435. doi: 10.3390/ijms17091435. PubMed PMID: 27589737; PubMed Central PMCID: PMC5037714. 16: Stacy AE, Palanimuthu D, Bernhardt PV, Kalinowski DS, Jansson PJ, Richardson DR. Structure-Activity Relationships of Di-2-pyridylketone, 2-Benzoylpyridine, and 2-Acetylpyridine Thiosemicarbazones for Overcoming Pgp-Mediated Drug Resistance. J Med Chem. 2016 Sep 22;59(18):8601-20. doi: 10.1021/acs.jmedchem.6b01050. Epub 2016 Aug 30. PubMed PMID: 27524608. 17: Xu Z, Liu Y, Zhou S, Fu Y, Li C. Analysis of the Interaction of Dp44mT with Human Serum Albumin and Calf Thymus DNA Using Molecular Docking and Spectroscopic Techniques. Int J Mol Sci. 2016 Jun 30;17(7). pii: E1042. doi: 10.3390/ijms17071042. Erratum in: Int J Mol Sci. 2016 Nov 16;17 (11):. PubMed PMID: 27376275; PubMed Central PMCID: PMC4964418. 18: Gutierrez EM, Seebacher NA, Arzuman L, Kovacevic Z, Lane DJ, Richardson V, Merlot AM, Lok H, Kalinowski DS, Sahni S, Jansson PJ, Richardson DR. Lysosomal membrane stability plays a major role in the cytotoxic activity of the anti-proliferative agent, di-2-pyridylketone 4,4-dimethyl-3-thiosemicarbazone (Dp44mT). Biochim Biophys Acta. 2016 Jul;1863(7 Pt A):1665-81. doi: 10.1016/j.bbamcr.2016.04.017. Epub 2016 Apr 19. PubMed PMID: 27102538. 19: Merlot AM, Shafie NH, Yu Y, Richardson V, Jansson PJ, Sahni S, Lane DJ, Kovacevic Z, Kalinowski DS, Richardson DR. Mechanism of the induction of endoplasmic reticulum stress by the anti-cancer agent, di-2-pyridylketone 4,4-dimethyl-3-thiosemicarbazone (Dp44mT): Activation of PERK/eIF2α, IRE1α, ATF6 and calmodulin kinase. Biochem Pharmacol. 2016 Jun 1;109:27-47. doi: 10.1016/j.bcp.2016.04.001. Epub 2016 Apr 6. PubMed PMID: 27059255. 20: Kovacevic Z, Sahni S, Richardson DR. Copper that cancer with lysosomal love! Aging (Albany NY). 2016 Feb;8(2):210-1. PubMed PMID: 26928386; PubMed Central PMCID: PMC4789575.