Darinaparsin
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MedKoo CAT#: 200850

CAS#: 69819-86-9

Description: Darinaparsin, also know as ZIO-101 and SP-02, is a small-molecule organic arsenical with potential antineoplastic activity. Although the exact mechanism of action is unclear, darinaparsin, a highly toxic metabolic intermediate of inorganic arsenicals (iAs) that occurs in vivo, appears to generate volatile cytotoxic arsenic compounds when glutathione (GSH) concentrations are low. The arsenic compounds generated from darinaparsin disrupt mitochondrial bioenergetics, producing reactive oxygen species (ROS) and inducing ROS-mediated tumor cell apoptosis; in addition, this agent or its byproducts may initiate cell death by interrupting the G2/M phase of the cell cycle and may exhibit antiangiogenic effects.


Chemical Structure

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Darinaparsin
CAS# 69819-86-9

Theoretical Analysis

MedKoo Cat#: 200850
Name: Darinaparsin
CAS#: 69819-86-9
Chemical Formula: C12H22AsN3O6S
Exact Mass: 411.04453
Molecular Weight: 411.31
Elemental Analysis: C, 35.04; H, 5.39; As, 18.22; N, 10.22; O, 23.34; S, 7.80

Price and Availability

Size Price Availability Quantity
5.0mg USD 90.0 Same day
10.0mg USD 150.0 Same day
25.0mg USD 250.0 Same day
50.0mg USD 450.0 Same day
100.0mg USD 750.0 Same day
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500.0mg USD 2450.0 Same day
1.0g USD 3850.0 Same day
2.0g USD 7450.0 Same day
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Synonym: ZIO 101; ZIO101; ZIO-101; SP-02; SP 02; SP02; Darinaparsin; Zinapar.

IUPAC/Chemical Name: (S)-2-amino-5-(((R)-1-((carboxymethyl)amino)-3-((dimethylarsino)thio)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid

InChi Key: JGDXFQORBMPJGR-YUMQZZPRSA-N

InChi Code: InChI=1S/C12H22AsN3O6S/c1-13(2)23-6-8(11(20)15-5-10(18)19)16-9(17)4-3-7(14)12(21)22/h7-8H,3-6,14H2,1-2H3,(H,15,20)(H,16,17)(H,18,19)(H,21,22)/t7-,8-/m0/s1

SMILES Code: O=C(O)[C@@H](N)CCC(N[C@@H](CS[As](C)C)C(NCC(O)=O)=O)=O

Appearance: White to off-white 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 water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in water

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

Preparing Stock Solutions

The following data is based on the product molecular weight 411.31 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.

Recalculate based on batch purity %
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

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1: Bansal N, Farley NJ, Wu L, Lewis J, Youssoufian H, Bertino JR. Darinaparsin inhibits prostate tumor-initiating cells and du145 xenografts and is an inhibitor of hedgehog signaling. Mol Cancer Ther. 2015 Jan;14(1):23-30. doi: 10.1158/1535-7163.MCT-13-1040. Epub 2014 Nov 7. PubMed PMID: 25381261.

2: Ravi D, Bhalla S, Gartenhaus RB, Crombie J, Kandela I, Sharma J, Mazar A, Evens AM. The novel organic arsenical darinaparsin induces MAPK-mediated and SHP1-dependent cell death in T-cell lymphoma and Hodgkin lymphoma cells and human xenograft models. Clin Cancer Res. 2014 Dec 1;20(23):6023-33. doi: 10.1158/1078-0432.CCR-14-1532. Epub 2014 Oct 14. PubMed PMID: 25316819; PubMed Central PMCID: PMC4281835.

3: Yehiayan L, Stice S, Liu G, Matulis S, Boise LH, Cai Y. Dimethylarsinothioyl glutathione as a metabolite in human multiple myeloma cell lines upon exposure to Darinaparsin. Chem Res Toxicol. 2014 May 19;27(5):754-64. doi: 10.1021/tx400386c. Epub 2014 Mar 26. PubMed PMID: 24624948; PubMed Central PMCID: PMC4027956.

4: Garnier N, Redstone GG, Dahabieh MS, Nichol JN, del Rincon SV, Gu Y, Bohle DS, Sun Y, Conklin DS, Mann KK, Miller WH Jr. The novel arsenical darinaparsin is transported by cystine importing systems. Mol Pharmacol. 2014 Apr;85(4):576-85. doi: 10.1124/mol.113.089433. Epub 2014 Jan 15. PubMed PMID: 24431147.

5: Tian J, Doi H, Saar M, Santos J, Li X, Peehl DM, Knox SJ. Radioprotection and cell cycle arrest of intestinal epithelial cells by darinaparsin, a tumor radiosensitizer. Int J Radiat Oncol Biol Phys. 2013 Dec 1;87(5):1179-85. doi: 10.1016/j.ijrobp.2013.08.051. Epub 2013 Oct 24. PubMed PMID: 24210080.

6: Garnier N, Petruccelli LA, Molina MF, Kourelis M, Kwan S, Diaz Z, Schipper HM, Gupta A, del Rincon SV, Mann KK, Miller WH Jr. The novel arsenical Darinaparsin circumvents BRG1-dependent, HO-1-mediated cytoprotection in leukemic cells. Leukemia. 2013 Nov;27(11):2220-8. doi: 10.1038/leu.2013.54. Epub 2013 Feb 21. PubMed PMID: 23426167.

7: Nielsen TH, Johnson N, Garnier N, Kwan S, Yao L, Cocolakis E, Hébert J, Morgan RA, Paquet E, Callahan KP, Jordan CT, Assouline S, Miller WH Jr, Mann KK. Monitoring Response and Resistance to the Novel Arsenical Darinaparsin in an AML Patient. Front Pharmacol. 2013 Feb 12;4:9. doi: 10.3389/fphar.2013.00009. eCollection 2013. PubMed PMID: 23408639; PubMed Central PMCID: PMC3570070.

8: Tian J, Zhao H, Nolley R, Reese SW, Young SR, Li X, Peehl DM, Knox SJ. Darinaparsin: solid tumor hypoxic cytotoxin and radiosensitizer. Clin Cancer Res. 2012 Jun 15;18(12):3366-76. doi: 10.1158/1078-0432.CCR-11-3179. Epub 2012 Apr 25. PubMed PMID: 22535156.

9: Mason TA, Kolobova E, Liu J, Roland JT, Chiang C, Goldenring JR. Darinaparsin is a multivalent chemotherapeutic which induces incomplete stress response with disruption of microtubules and Shh signaling. PLoS One. 2011;6(11):e27699. doi: 10.1371/journal.pone.0027699. Epub 2011 Nov 15. PubMed PMID: 22110729; PubMed Central PMCID: PMC3216988.

10: Hosein PJ, Craig MD, Tallman MS, Boccia RV, Hamilton BL, Lewis JJ, Lossos IS. A multicenter phase II study of darinaparsin in relapsed or refractory Hodgkin's and non-Hodgkin's lymphoma. Am J Hematol. 2012 Jan;87(1):111-4. doi: 10.1002/ajh.22232. Epub 2011 Nov 12. PubMed PMID: 22081459.



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