Diphenyleneiodonium | CAS# 244-54-2 (cation) | NADPH oxidase inhibitor

MedKoo Cat#: 413674 | Name: Diphenyleneiodonium

Description:

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

Diphenyleneiodonium (free base) is an NADPH oxidase inhibitor.

Chemical Structure

Diphenyleneiodonium

CAS#244-54-2 (cation)

Theoretical Analysis

MedKoo Cat#: 413674

Name: Diphenyleneiodonium

CAS#: 244-54-2 (cation)

Chemical Formula: C12H8I+

Exact Mass: 278.9665

Molecular Weight: 279.09

Elemental Analysis: C, 51.64; H, 2.89; I, 45.47

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

244-54-2 (cation) 4673-26-1 (chloride)

Synonym

Diphenyleneiodonium; Diphenylene iodonium; Dibenziodolium;

IUPAC/Chemical Name

(1,1'-Biphenyl)-2,2'-diyliodonium

InChi Key

QFXKXRXFBRLLPQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H8I/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H/q+1

SMILES Code

C12=CC=CC=C1[I+]C3=CC=CC=C32

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 279.09 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

1: Pandey M, Singh AK, Thakare R, Talwar S, Karaulia P, Dasgupta A, Chopra S, Pandey AK. Diphenyleneiodonium chloride (DPIC) displays broad-spectrum bactericidal activity. Sci Rep. 2017 Sep 14;7(1):11521. doi: 10.1038/s41598-017-11575-5. Erratum in: Sci Rep. 2018 Apr 12;8(1):6126. PMID: 28912539; PMCID: PMC5599662. 2: Fu Q, Gao N, Che F, Xu G, Han H, Su Q, Ma G. Diphenyleneiodonium chloride synergizes with diazoxide to enhance protection against amyloid β induced neurotoxicity. J Integr Neurosci. 2019 Dec 30;18(4):445-449. doi: 10.31083/j.jin.2019.04.1174. PMID: 31912704. 3: Yeware A, Gample S, Agrawal S, Sarkar D. Using diphenyleneiodonium to induce a viable but non-culturable phenotype in Mycobacterium tuberculosis and its metabolomics analysis. PLoS One. 2019 Aug 1;14(8):e0220628. doi: 10.1371/journal.pone.0220628. PMID: 31369628; PMCID: PMC6675104. 4: Fuchs TA, Abed U, Goosmann C, Hurwitz R, Schulze I, Wahn V, Weinrauch Y, Brinkmann V, Zychlinsky A. Novel cell death program leads to neutrophil extracellular traps. J Cell Biol. 2007 Jan 15;176(2):231-41. doi: 10.1083/jcb.200606027. Epub 2007 Jan 8. PMID: 17210947; PMCID: PMC2063942. 5: Sharma M, Sharma KB, Chauhan S, Bhattacharyya S, Vrati S, Kalia M. Diphenyleneiodonium enhances oxidative stress and inhibits Japanese encephalitis virus induced autophagy and ER stress pathways. Biochem Biophys Res Commun. 2018 Jul 12;502(2):232-237. doi: 10.1016/j.bbrc.2018.05.149. Epub 2018 May 24. PMID: 29792860. 6: Kim SK, Rho SJ, Kim SH, Kim SY, Song SH, Yoo JY, Kim CH, Lee SH. Protective effects of diphenyleneiodonium, an NADPH oxidase inhibitor, on lipopolysaccharide-induced acute lung injury. Clin Exp Pharmacol Physiol. 2019 Feb;46(2):153-162. doi: 10.1111/1440-1681.13050. Epub 2018 Nov 22. PMID: 30403294. 7: Chung JW, Kim SY, Park HJ, Chung CS, Lee HW, Lee SM, Kim I, Pak JH, Lee GH, Jeong JY. In Vitro Activity of Diphenyleneiodonium toward Multidrug- Resistant Helicobacter pylori Strains. Gut Liver. 2017 Sep 15;11(5):648-654. doi: 10.5009/gnl16503. PMID: 28750485; PMCID: PMC5593327. 8: Ji ZH, Liu ZJ, Liu ZT, Zhao W, Williams BA, Zhang HF, Li L, Xu SY. Diphenyleneiodonium Mitigates Bupivacaine-Induced Sciatic Nerve Damage in a Diabetic Neuropathy Rat Model by Attenuating Oxidative Stress. Anesth Analg. 2017 Aug;125(2):653-661. doi: 10.1213/ANE.0000000000002186. PMID: 28682956. 9: Nguyen N, Wilson DW, Nagalingam G, Triccas JA, Schneider EK, Li J, Velkov T, Baell J. Broad activity of diphenyleneiodonium analogues against Mycobacterium tuberculosis, malaria parasites and bacterial pathogens. Eur J Med Chem. 2018 Mar 25;148:507-518. doi: 10.1016/j.ejmech.2017.10.010. Epub 2017 Oct 6. PMID: 29269132. 10: Singh AK, Thakare R, Karaulia P, Das S, Soni I, Pandey M, Pandey AK, Chopra S, Dasgupta A. Biological evaluation of diphenyleneiodonium chloride (DPIC) as a potential drug candidate for treatment of non-tuberculous mycobacterial infections. J Antimicrob Chemother. 2017 Nov 1;72(11):3117-3121. doi: 10.1093/jac/dkx277. PMID: 28961864.