Decyl(triphenyl)phosphonium

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+1 Key: VZXRCMCRCZBKEZ-UHFFFAOYSA-N;
	SMILES ion: CCCCCCCCCCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3;
Properties
Chemical formula	C30H40P+
Molar mass	431.623 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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.^[1]^[2] DTPP itself can cause mitochondrial swelling in kidney tissue, an action possibly related to increased membrane permeability.^[3]

References

↑ 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.
↑ 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: 264–74. doi:10.1196/annals.1427.019. PMC 2676430. PMID 19076448.
↑ 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.

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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[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: 264–74. 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.

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References

Further reading