From Wikipedia, the free encyclopedia
Chemical compound
Decyl(triphenyl)phosphonium
Names
Preferred IUPAC name
Dodecyltri(phenyl)phosphanium
Other names
Dodecyltriphenylphosphonium, C12TPP(+), DTPP
Identifiers
ChEBI
ChEMBL
ChemSpider
UNII
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
ion: CCCCCCCCCCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
Properties
C 30 H 40 P +
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).
Chemical compound
Decyl(triphenyl)phosphonium (DTPP) is the
organophosphorus cation with the formula C10 H21 P(C6 H5 )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]
^ 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 .