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Decyl(triphenyl)phosphonium

Names
Preferred IUPAC name Dodecyltri(phenyl)phosphanium
Other names Dodecyltriphenylphosphonium, C12TPP(+), DTPP
Identifiers
CAS Number	ion: 17895-72-6 bromide: 15510-55-1
3D model (JSmol)	ion: Interactive image
ChEBI	ion: CHEBI:82636
ChEMBL	ion: ChEMBL3306671 bromide: ChEMBL3229257
ChemSpider	ion: 76637
PubChem CID	ion: 84956
UNII	bromide: 2OQV5UAF87
CompTox Dashboard (EPA)	ion: DTXSID70904622
InChI InChI=1S/C30H40P/c1-2-3-4-5-6-7-8-9-10-20-27-31(28-21-14-11-15-22-28,29-23-16-12-17-24-29)30-25-18-13-19-26-30/h11-19,21-26H,2-10,20,27H2,1H3/q+1Key: VZXRCMCRCZBKEZ-UHFFFAOYSA-N
SMILES ion: CCCCCCCCCCCC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
Properties
Chemical formula	C30H40P
Molar mass	431.623 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Decyl(triphenyl)phosphonium (DTPP) is the organophosphorus cation with the formula C₁₀H₂₁P(C₆H₅)₃. It is a lipophilic quaternary phosphonium cation. It forms the basis for many mitochondrial-targeted drugs, including MitoQ, MitoE, and SkQ. It binds to the mitochondrial matrix by insertion into the inner membrane. DTPP itself can cause mitochondrial swelling in kidney tissue, an action possibly related to increased membrane permeability.

References

1. Murphy, MP (2008). "Targeting lipophilic cations to mitochondria". Biochimica et Biophysica Acta (BBA) - Bioenergetics. 1777 (7–8): 1028–31. doi:10.1016/j.bbabio.2008.03.029. PMID 18439417.
2. Leo, S; Szabadkai, G; Rizzuto, R (December 2008). "The mitochondrial antioxidants MitoE(2) and MitoQ(10) increase mitochondrial Ca(2+) load upon cell stimulation by inhibiting Ca(2+) efflux from the organelle". Annals of the New York Academy of Sciences. 1147 (1): 264–74. Bibcode:2008NYASA1147..264L. doi:10.1196/annals.1427.019. PMC 2676430. PMID 19076448.
3. Gottwald, EM; Duss, M; Bugarski, M; Haenni, D; Schuh, CD; Landau, EM; Hall, AM (April 2018). "The targeted anti-oxidant MitoQ causes mitochondrial swelling in kidney tissue. It and depolarization in kidney tissue". Physiological Reports. 6 (7): e13667. doi:10.14814/phy2.13667. PMC 5880956. PMID 29611340.

Further reading

• Zielonka, Jacek; Joseph, Joy; Sikora, Adam; Hardy, Micael; Ouari, Olivier; Vasquez-Vivar, Jeannette; Cheng, Gang; Lopez, Marcos; Kalyanaraman, Balaraman (27 June 2017). "Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications". Chemical Reviews. 117 (15): 10043–10120. doi:10.1021/acs.chemrev.7b00042. PMC 5611849. PMID 28654243.

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