Chemistry:Decyl(triphenyl)phosphonium
From HandWiki
Short description: Chemical compound
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| Preferred IUPAC name
Dodecyltri(phenyl)phosphanium | |
| Other names
Dodecyltriphenylphosphonium, C12TPP(+), DTPP
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3D model (JSmol)
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| Properties | |
| 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. 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. PMID 29611340.
Further reading
- Zielonka, Jacek; Joseph, Joy; Sikora, Adam; Hardy, Micael; Ouari, Olivier; Vasquez-Vivar, Jeannette; Cheng, Gang; Lopez, Marcos et al. (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. PMID 28654243.
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