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905186

Sigma-Aldrich

(9-Bromononyl)triphenylphosphonium bromide

Synonym(s):

Bromononane TPP mitochondrial tag, Mitochondria-targeting probe building block, Phosphonium lipocation tag

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About This Item

Empirical Formula (Hill Notation):
C27H33Br2P
CAS Number:
90052-38-3
Molecular Weight:
548.33
UNSPSC Code:
12352200

form

liquid

storage temp.

2-8°C

InChI

1S/C27H33BrP.BrH/c28-23-15-4-2-1-3-5-16-24-29(25-17-9-6-10-18-25,26-19-11-7-12-20-26)27-21-13-8-14-22-27;/h6-14,17-22H,1-5,15-16,23-24H2;1H/q+1;/p-1

InChI key

ACKJFSDDEOFXHT-UHFFFAOYSA-M

Application

Mitochondria perform several functions in the cell, and dysfunction has been implicated in various organ systems and disease states, including neurodegenerative disorders and cancers. The targeting of small molecules to the mitochondria can help to probe and better understand this relationship. This bromononane triphenylphosphine (TPP) tag is conjugated to small molecules to localize them to the mitochondria in cells where the TPP cations facilitate both cellular uptake and accumulation in the mitochondria.

Other Notes

Conjugates of 2,4-Dihydroxybenzoate and Salicylhydroxamate and Lipocations Display Potent Antiparasite Effects by Efficiently Targeting the Trypanosoma brucei and Trypanosoma congolense Mitochondrion

Targeting lipophilic cations to mitochondria

Photoswitchable polyfluorophores based on perylenemonoimide-dithienylethene conjugates as super-resolution MitoTrackers

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Francisco José Fueyo González et al.
Journal of medicinal chemistry, 60(4), 1509-1522 (2017-01-24)
We investigated a chemical strategy to boost the trypanocidal activity of 2,4-dihydroxybenzoic acid (2,4-DHBA)- and salicylhydroxamic acid (SHAM)-based trypanocides with triphenylphosphonium and quinolinium lipophilic cations (LC). Three series of LC conjugates were synthesized that were active in the submicromolar (5a-d
Michael P Murphy
Biochimica et biophysica acta, 1777(7-8), 1028-1031 (2008-04-29)
Mitochondrial function and dysfunction contributes to a range of important aspects of biomedical research. Consequently there is considerable interest in developing approaches to modify and report on mitochondria in cells and in vivo. One approach has been to target bioactive

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