Dithizone | CAS#60-10-6 | Sulfur-containing ligand

MedKoo Cat#: 463956 | Name: Dithizone

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Description:

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

Dithizone is a sulfur-containing organic compound. It is a good ligand, and forms complexes with many metals such as lead and mercury. Dithizone may be prepared by reacting phenylhydrazine with carbon disulfide, followed by reaction with potassium hydroxide. Dithizone is used to assess the purity of human pancreatic islet preparations used for transplantation into patients with type 1 diabetes. Dithizone binds zinc ions present in the islet's beta cells, and therefore stains the islets red. Exocrine tissue also present in the preparations does not bind dithizone, and is therefore not stained.

Chemical Structure

Dithizone

CAS#60-10-6

Theoretical Analysis

MedKoo Cat#: 463956

Name: Dithizone

CAS#: 60-10-6

Chemical Formula: C13H12N4S

Exact Mass: 256.0783

Molecular Weight: 256.33

Elemental Analysis: C, 60.92; H, 4.72; N, 21.86; S, 12.51

Price and Availability

Size	Price	Availability	Quantity
25g	USD 450.00	2 Weeks

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Synonym

Dithizone; Diphenylthiocarbazone; Dithizon; Ditizon; NSC 215189; NSC-215189; NSC215189;

IUPAC/Chemical Name

1-anilino-3-phenyliminothiourea

InChi Key

UOFGSWVZMUXXIY-BMRADRMJSA-N

InChi Code

InChI=1S/C13H12N4S/c18-13(16-14-11-7-3-1-4-8-11)17-15-12-9-5-2-6-10-12/h1-10,14H,(H,16,18)/b17-15+

SMILES Code

S=C(/N=N/C1=CC=CC=C1)NNC2=CC=CC=C2

Appearance

Solid powder

Purity

>85% (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:

Dithizone is a sulfur-containing organic compound.

In vitro activity:

Application of the newly formulated iDTZ (i stands for islet) over a range of temperatures, time intervals and cell and tissue types found it to be robust for identifying these cells. Through high transition zinc binding, the iDTZ (dithizone) compound concentrated in insulin-producing cells and proved effective at delineating zinc levels in vitro. Reference: Sci Rep. 2019 Jun 26;9(1):9295. https://pubmed.ncbi.nlm.nih.gov/31243300/

In vivo activity:

Collectively, dithizone treatment was associated with alleviation in the severity of liver steatosis in HFD mice, possibly through gut microbiome modulation involving the increase in Bacteroides, suggesting microbiome-targeted therapies may have a role in the treatment of NAFLD. Reference: Front Microbiol. 2022 Feb 25;13:813783. https://pubmed.ncbi.nlm.nih.gov/35283810/

Preparing Stock Solutions

The following data is based on the product molecular weight 256.33 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. Khiatah B, Qi M, Wu Y, Chen KT, Perez R, Valiente L, Omori K, Isenberg JS, Kandeel F, Yee JK, Al-Abdullah IH. Pancreatic human islets and insulin-producing cells derived from embryonic stem cells are rapidly identified by a newly developed Dithizone. Sci Rep. 2019 Jun 26;9(1):9295. doi: 10.1038/s41598-019-45678-y. PMID: 31243300; PMCID: PMC6594947. 2. Tavallali H, Deilamy-Rad G, Parhami A, Kiyani S. Dithizone as novel and efficient chromogenic probe for cyanide detection in aqueous media through nucleophilic addition into diazenylthione moiety. Spectrochim Acta A Mol Biomol Spectrosc. 2014;121:139-46. doi: 10.1016/j.saa.2013.10.083. Epub 2013 Oct 28. PMID: 24231750. 3. Zhang S, Tun HM, Zhang D, Chau HT, Huang FY, Kwok H, Wong DK, Mak LY, Yuen MF, Seto WK. Alleviation of Hepatic Steatosis: Dithizone-Related Gut Microbiome Restoration During Paneth Cell Dysfunction. Front Microbiol. 2022 Feb 25;13:813783. doi: 10.3389/fmicb.2022.813783. PMID: 35283810; PMCID: PMC8914291. 4. Berger JN, Gong H, Good M, McElroy SJ. Dithizone-induced Paneth cell disruption significantly decreases intestinal perfusion in the murine small intestine. J Pediatr Surg. 2019 Nov;54(11):2402-2407. doi: 10.1016/j.jpedsurg.2019.02.021. Epub 2019 Feb 23. PMID: 30857731; PMCID: PMC6707906.

In vitro protocol:

In vivo protocol:

1. Zhang S, Tun HM, Zhang D, Chau HT, Huang FY, Kwok H, Wong DK, Mak LY, Yuen MF, Seto WK. Alleviation of Hepatic Steatosis: Dithizone-Related Gut Microbiome Restoration During Paneth Cell Dysfunction. Front Microbiol. 2022 Feb 25;13:813783. doi: 10.3389/fmicb.2022.813783. PMID: 35283810; PMCID: PMC8914291. 2. Berger JN, Gong H, Good M, McElroy SJ. Dithizone-induced Paneth cell disruption significantly decreases intestinal perfusion in the murine small intestine. J Pediatr Surg. 2019 Nov;54(11):2402-2407. doi: 10.1016/j.jpedsurg.2019.02.021. Epub 2019 Feb 23. PMID: 30857731; PMCID: PMC6707906.

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Generation of Insulin-Producing Cells from Canine Adipose Tissue-Derived Mesenchymal Stem Cells. Stem Cells Int. 2020 Oct 18;2020:8841865. doi: 10.1155/2020/8841865. PMID: 33133196; PMCID: PMC7591982. 5: Camara BOS, Ocarino NM, Bertassoli BM, Malm C, Araújo FR, Reis AMS, Jorge EC, Alves EGL, Serakides R. Differentiation of canine adipose mesenchymal stem cells into insulin-producing cells: comparison of different culture medium compositions. Domest Anim Endocrinol. 2021 Jan;74:106572. doi: 10.1016/j.domaniend.2020.106572. Epub 2020 Sep 17. PMID: 33039930. 6: Ghani MW, Bin L, Jie Y, Yi Z, Jiang W, Ye L, Cun LG, Birmani MW, Zhuangzhi Z, Lilong A, Mei X. Differentiation of rat pancreatic duct stem cells into insulin- secreting islet-like cell clusters through BMP7 inducement. Tissue Cell. 2020 Dec;67:101439. doi: 10.1016/j.tice.2020.101439. Epub 2020 Sep 3. PMID: 32979709. 7: Cun LG, Ghani MW, Yi Z, Jiang W, Ye L, Bin L, Birmani MW, Lilong A, Mei X. 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Deciphering lead tolerance mechanisms in a population of the plant species Biscutella auriculata L. from a mining area: Accumulation strategies and antioxidant defenses. Chemosphere. 2020 Dec;261:127721. doi: 10.1016/j.chemosphere.2020.127721. Epub 2020 Jul 20. PMID: 32745740. 11: Deng G, Deng X, Deng J, Lu X, Kang X, Song Y. Performance Evaluation of an Electrospun Nanofiber Mat as Samplers for the Trap of Trace Heavy Metals in Atmospheric Particles and Its Application. Anal Sci. 2020 Dec 10;36(12):1453-1459. doi: 10.2116/analsci.20P199. Epub 2020 Jul 31. PMID: 32741954. 12: Zhang S, Yin J, Ji H, Wang Q, Yang Q, Lai J, Sun Y, Guan W, Chen P. Functional β-Cell Differentiation of Small-Tail Han Sheep Pancreatic Mesenchymal Stem Cells and the Therapeutic Potential in Type 1 Diabetic Mice. Pancreas. 2020 Aug;49(7):947-954. doi: 10.1097/MPA.0000000000001604. PMID: 32658079. 13: Aali E, Madjd Z, Tekiyehmaroof N, Sharifi AM. 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