癸基三苯基鏻

癸基三苯基鏻
	IUPAC名; Dodecyltri(phenyl)phosphanium
别名	Dodecyltriphenylphosphonium, C12TPP(+), DTPP
识别
CAS号	17895-72-6
PubChem	84956
ChemSpider	76637
SMILES	CCCCCCCCCCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3;
ChEBI	82636
性质
化学式	C30H40P+
摩尔质量	431.61 g·mol⁻¹
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

癸基三苯基鏻（DTPP）是一种有机磷阳离子，分子式为C₁₀H₂₁P(C₆H₅)₃⁺。它是亲脂性季鏻阳离子。它是许多线粒体靶向药物的基础，包括MitoQ、MitoE和SkQ。它首先插入内膜，再与线粒体基质结合。^[1]^[2]DTPP本身可以导致肾组织中的线粒体肿胀，可能与膜通透性的增加有关。^[3]

常见盐类

常见的癸基三苯基鏻盐如下：


名称	化学式	CAS号
癸基三苯基溴化鏻	C₁₀H₂₁P(C₆H₅)₃Br	15510-55-1
癸基三苯基氯化鏻	C₁₀H₂₁P(C₆H₅)₃Cl	84902-22-7
癸基三苯基碘化鏻	C₁₀H₂₁P(C₆H₅)₃I	123966-50-7
癸基三苯基鏻对甲苯磺酸盐^[4]	C₁₀H₂₁P(C₆H₅)₃(C₇H₇SO₃)	95736-41-7
四氯合铂(II)酸癸基三苯基鏻^[5]	[C₁₀H₂₁P(C₆H₅)₃]₂[PtCl₄]	77773-17-2

参考文献

^ Murphy, MP. Targeting lipophilic cations to mitochondria.. Biochimica et Biophysica Acta (BBA) - Bioenergetics. 2008, 1777 (7–8): 1028–31. PMID 18439417. doi:10.1016/j.bbabio.2008.03.029 .
^ Leo, S; Szabadkai, G; Rizzuto, R. 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. December 2008, 1147: 264–74. PMC 2676430 . PMID 19076448. doi:10.1196/annals.1427.019.
^ Gottwald, EM; Duss, M; Bugarski, M; Haenni, D; Schuh, CD; Landau, EM; Hall, AM. The targeted anti-oxidant MitoQ causes mitochondrial swelling in kidney tissue. It and depolarization in kidney tissue.. Physiological Reports. April 2018, 6 (7): e13667. PMC 5880956 . PMID 29611340. doi:10.14814/phy2.13667.
^ Anderson, J. H.; Bugner, D. E.; DeMejo, L. P.; Guistina, R. A.; Zumbulyadis, N. Charge agent studies: I. Charge agent surface concentration and charging behavior. Journal of Imaging Science and Technology, 1993. 37 (5): 431-439.
^ Brovko, V. S.; Skvortsov, N. K.; Reikhsfel'd, V. O. Phosphonium salt platinites and platinates as hydrosilylation catalysts. Zhurnal Obshchei Khimii, 1981. 51 (2): 487.

延伸阅读

Zielonka, Jacek; Joseph, Joy; Sikora, Adam; Hardy, Micael; Ouari, Olivier; Vasquez-Vivar, Jeannette; Cheng, Gang; Lopez, Marcos; Kalyanaraman, Balaraman. Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications. Chemical Reviews. 27 June 2017, 117 (15): 10043–10120. PMC 5611849 . PMID 28654243. doi:10.1021/acs.chemrev.7b00042.

[1] Murphy, MP. Targeting lipophilic cations to mitochondria.. Biochimica et Biophysica Acta (BBA) - Bioenergetics. 2008, 1777 (7–8): 1028–31. PMID 18439417. doi:10.1016/j.bbabio.2008.03.029 .

[2] Leo, S; Szabadkai, G; Rizzuto, R. 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. December 2008, 1147: 264–74. PMC 2676430 . PMID 19076448. doi:10.1196/annals.1427.019.

[3] Gottwald, EM; Duss, M; Bugarski, M; Haenni, D; Schuh, CD; Landau, EM; Hall, AM. The targeted anti-oxidant MitoQ causes mitochondrial swelling in kidney tissue. It and depolarization in kidney tissue.. Physiological Reports. April 2018, 6 (7): e13667. PMC 5880956 . PMID 29611340. doi:10.14814/phy2.13667.

[4] Anderson, J. H.; Bugner, D. E.; DeMejo, L. P.; Guistina, R. A.; Zumbulyadis, N. Charge agent studies: I. Charge agent surface concentration and charging behavior. Journal of Imaging Science and Technology, 1993. 37 (5): 431-439.

[5] Brovko, V. S.; Skvortsov, N. K.; Reikhsfel'd, V. O. Phosphonium salt platinites and platinates as hydrosilylation catalysts. Zhurnal Obshchei Khimii, 1981. 51 (2): 487.

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