Decyl(triphenyl)phosphonium

{{short description|Chemical compound}}

{{Chembox

| ImageFile = Dodecyltriphenylphosphonium.svg

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| PIN = Dodecyltri(phenyl)phosphanium

| OtherNames = Dodecyltriphenylphosphonium, C12TPP(+), DTPP

| Section1 = {{Chembox Identifiers

| index_label = ion

| index1_label = bromide

| CASNo = 17895-72-6

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo1 = 15510-55-1

| CASNo1_Ref = {{cascite|correct|CAS}}

| UNII1 = 2OQV5UAF87

| UNII1_Ref = {{fdacite|correct|FDA}}

| PubChem = 84956

| ChEBI = 82636

| ChEMBL = 3306671

| ChEMBL1 = 3229257

| ChemSpiderID = 76637

| StdInChI=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

| StdInChIKey = VZXRCMCRCZBKEZ-UHFFFAOYSA-N

| SMILES = CCCCCCCCCCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3

}}

| Section2 = {{Chembox Properties

|C=30|H=40|P=1|Formula_Charge=+

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| Section3 = {{Chembox Hazards

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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.{{cite journal |last1=Murphy |first1=MP |title=Targeting lipophilic cations to mitochondria. |journal=Biochimica et Biophysica Acta (BBA) - Bioenergetics |date=2008 |volume=1777 |issue=7–8 |pages=1028–31 |doi=10.1016/j.bbabio.2008.03.029 |pmid=18439417|doi-access=free }}{{cite journal |last1=Leo |first1=S |last2=Szabadkai |first2=G |last3=Rizzuto |first3=R |title=The mitochondrial antioxidants MitoE(2) and MitoQ(10) increase mitochondrial Ca(2+) load upon cell stimulation by inhibiting Ca(2+) efflux from the organelle. |journal=Annals of the New York Academy of Sciences |date=December 2008 |volume=1147 |issue=1 |pages=264–74 |doi=10.1196/annals.1427.019 |pmid=19076448|pmc=2676430 |bibcode=2008NYASA1147..264L }}

DTPP itself can cause mitochondrial swelling in kidney tissue, an action possibly related to increased membrane permeability.{{cite journal |last1=Gottwald |first1=EM |last2=Duss |first2=M |last3=Bugarski |first3=M |last4=Haenni |first4=D |last5=Schuh |first5=CD |last6=Landau |first6=EM |last7=Hall |first7=AM |title=The targeted anti-oxidant MitoQ causes mitochondrial swelling in kidney tissue. It and depolarization in kidney tissue. |journal=Physiological Reports |date=April 2018 |volume=6 |issue=7 |pages=e13667 |doi=10.14814/phy2.13667 |pmid=29611340|pmc=5880956 }}