Synonym
Diphenyleneiodonium Chloride; Dibenziodolium chloride; DPI;
IUPAC/Chemical Name
8-iodoniatricyclo[7.4.0.02,7]trideca-1(13),2,4,6,9,11-hexaene;chloride
InChi Key
FCFZKAVCDNTYID-UHFFFAOYSA-M
InChi Code
InChI=1S/C12H8I.ClH/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11;/h1-8H;1H/q+1;/p-1
SMILES Code
C12=CC=CC=C1C3=CC=CC=C3[I+]2.[Cl-]
Purity
>95% (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
Biological target:
Diphenyleneiodonium chloride is a NADPH oxidase (NOX) inhibitor and also functions as a TRPA1 activator with an EC50 of 1 to 3 μM.
In vitro activity:
Together, these data suggest that DPI (diphenyleneiodonium) reduces cell growth by inhibiting cell division in an apoptosis-dependent manner, and that cells with high OxPhos metabolism are more sensitive to DPI-induced apoptosis.
Reference: Cancers (Basel). 2022 May 18;14(10):2485. https://pubmed.ncbi.nlm.nih.gov/35626090/
In vivo activity:
Next, this study used diphenyleneiodonium (DPI), a flavoenzyme inhibitor, to pharmacologically manipulate the ROS levels in HSV-1-infected mice. Surprisingly, the neutrophils from peripheral blood and corneas of the DPI-treated group exhibited an increased level of ROS than the vehicle-treated group of infected B6 mice. Excessive ROS is known to cause cell death. Accordingly, DPI treatment resulted in a significant decrease in neutrophil frequency in peripheral blood and corneas of infected mice and was associated with reduced corneal pathology. Together, these results suggest that regulating ROS levels in neutrophils can ameliorate HSK severity.
Reference: J Virol. 2022 Sep 14;96(17):e0101422. https://pubmed.ncbi.nlm.nih.gov/35946937/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
7.4 |
23.46 |
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
314.55
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. Dakik H, El Dor M, Bourgeais J, Kouzi F, Herault O, Gouilleux F, Zibara K, Mazurier F. Diphenyleneiodonium Triggers Cell Death of Acute Myeloid Leukemia Cells by Blocking the Mitochondrial Respiratory Chain, and Synergizes with Cytarabine. Cancers (Basel). 2022 May 18;14(10):2485. doi: 10.3390/cancers14102485. PMID: 35626090; PMCID: PMC9140039.
2. Monzur S, Hassan G, Afify SM, Kumon K, Mansour H, Nawara HM, Sheta M, Abu Quora HA, Zahra MH, Xu Y, Fu X, Seno A, Wikström P, Szekeres FLM, Seno M. Diphenyleneiodonium efficiently inhibits the characteristics of a cancer stem cell model derived from induced pluripotent stem cells. Cell Biochem Funct. 2022 Apr;40(3):310-320. doi: 10.1002/cbf.3696. Epub 2022 Mar 14. PMID: 35285948.
3. Rana M, Setia M, Suvas PK, Chakraborty A, Suvas S. Diphenyleneiodonium Treatment Inhibits the Development of Severe Herpes Stromal Keratitis Lesions. J Virol. 2022 Sep 14;96(17):e0101422. doi: 10.1128/jvi.01014-22. Epub 2022 Aug 10. PMID: 35946937; PMCID: PMC9472634.
4. Liu Y, Qin X, Lei Z, Chai H, Wu Z. Diphenyleneiodonium ameliorates acute liver rejection during transplantation by inhibiting neutrophil extracellular traps formation in vivo. Transpl Immunol. 2021 Oct;68:101434. doi: 10.1016/j.trim.2021.101434. Epub 2021 Jun 30. PMID: 34216758.
In vitro protocol:
1. Dakik H, El Dor M, Bourgeais J, Kouzi F, Herault O, Gouilleux F, Zibara K, Mazurier F. Diphenyleneiodonium Triggers Cell Death of Acute Myeloid Leukemia Cells by Blocking the Mitochondrial Respiratory Chain, and Synergizes with Cytarabine. Cancers (Basel). 2022 May 18;14(10):2485. doi: 10.3390/cancers14102485. PMID: 35626090; PMCID: PMC9140039.
2. Monzur S, Hassan G, Afify SM, Kumon K, Mansour H, Nawara HM, Sheta M, Abu Quora HA, Zahra MH, Xu Y, Fu X, Seno A, Wikström P, Szekeres FLM, Seno M. Diphenyleneiodonium efficiently inhibits the characteristics of a cancer stem cell model derived from induced pluripotent stem cells. Cell Biochem Funct. 2022 Apr;40(3):310-320. doi: 10.1002/cbf.3696. Epub 2022 Mar 14. PMID: 35285948.
In vivo protocol:
1. Rana M, Setia M, Suvas PK, Chakraborty A, Suvas S. Diphenyleneiodonium Treatment Inhibits the Development of Severe Herpes Stromal Keratitis Lesions. J Virol. 2022 Sep 14;96(17):e0101422. doi: 10.1128/jvi.01014-22. Epub 2022 Aug 10. PMID: 35946937; PMCID: PMC9472634.
2. Liu Y, Qin X, Lei Z, Chai H, Wu Z. Diphenyleneiodonium ameliorates acute liver rejection during transplantation by inhibiting neutrophil extracellular traps formation in vivo. Transpl Immunol. 2021 Oct;68:101434. doi: 10.1016/j.trim.2021.101434. Epub 2021 Jun 30. PMID: 34216758.
1: Peng JJ, Liu B, Xu JY, Peng J, Luo XJ. NADPH oxidase: its potential role in promotion of pulmonary arterial hypertension. Naunyn Schmiedebergs Arch Pharmacol. 2017 Apr;390(4):331-338. doi: 10.1007/s00210-017-1359-2. Epub 2017 Feb 11. Review. PubMed PMID: 28190244.
2: Kraaij T, Tengström FC, Kamerling SW, Pusey CD, Scherer HU, Toes RE, Rabelink TJ, van Kooten C, Teng YK. A novel method for high-throughput detection and quantification of neutrophil extracellular traps reveals ROS-independent NET release with immune complexes. Autoimmun Rev. 2016 Jun;15(6):577-84. doi: 10.1016/j.autrev.2016.02.018. Epub 2016 Feb 27. Review. PubMed PMID: 26925759.
3: Suzuki N, Mittler R. Reactive oxygen species-dependent wound responses in animals and plants. Free Radic Biol Med. 2012 Dec 15;53(12):2269-76. doi: 10.1016/j.freeradbiomed.2012.10.538. Epub 2012 Oct 17. Review. PubMed PMID: 23085520.
4: MacFarlane PM, Satriotomo I, Windelborn JA, Mitchell GS. NADPH oxidase activity is necessary for acute intermittent hypoxia-induced phrenic long-term facilitation. J Physiol. 2009 May 1;587(Pt 9):1931-42. doi: 10.1113/jphysiol.2008.165597. Epub 2009 Feb 23. Review. PubMed PMID: 19237427; PubMed Central PMCID: PMC2689334.
5: Aldieri E, Riganti C, Polimeni M, Gazzano E, Lussiana C, Campia I, Ghigo D. Classical inhibitors of NOX NAD(P)H oxidases are not specific. Curr Drug Metab. 2008 Oct;9(8):686-96. Review. PubMed PMID: 18855607.
6: Ragan CI. The molecular organization of NADH dehydrogenase. Subcell Biochem. 1980;7:267-307. Review. PubMed PMID: 7003824.
