Decyl(triphenyl)phosphonium

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Decyl(triphenyl)phosphonium
Dodecyltriphenylphosphonium.svg
Names
Preferred IUPAC name
Dodecyltri(phenyl)phosphanium
Other names
Dodecyltriphenylphosphonium, C12TPP(+), DTPP
Identifiers
3D model (JSmol)
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
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).

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[edit]

  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.

Further reading[edit]