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157945

Sigma-Aldrich

(4-Carboxybutyl)triphenylphosphonium bromide

98%

Synonym(s):

5-(Triphenylphosphonio)pentanoic acid bromide, Carboxybutyltriphenylphosphonium bromide, NSC 147756

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About This Item

Linear Formula:
(C6H5)3P(Br)(CH2)4COOH
CAS Number:
17814-85-6
Molecular Weight:
443.31
Beilstein:
3586477
EC Number:
241-782-5
MDL number:
MFCD00011906
UNSPSC Code:
12352107
PubChem Substance ID:
24849711
NACRES:
NA.22

Quality Level

200

Assay

98%

form

powder

reaction suitability

reaction type: C-C Bond Formation

mp

204-207 °C (lit.)

SMILES string

[Br-].OC(=O)CCCC[P+](c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C23H23O2P.BrH/c24-23(25)18-10-11-19-26(20-12-4-1-5-13-20,21-14-6-2-7-15-21)22-16-8-3-9-17-22;/h1-9,12-17H,10-11,18-19H2;1H

InChI key

MLOSJPZSZWUDSK-UHFFFAOYSA-N

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Application

  • Used as a platform for delivery of pro-apoptotic peptides into the mitochondria of tumor cells

Reactant for preparation of:
  • Ring skeletons via ring closing metathesis and double bond migration ring closing metathesis reactions
  • Methyl alkenyl quinolones as antimycobacterial agents
  • Prostaglandins and their drug analogs via Gold-catalyzed Meyer-Schuster rearrangement
  • Diphenylmethylpiperazines as N-type calcium channel blockers as potential therapeutic agents
  • Folate receptor-specific glycinamide ribonucleotide formyltransferase (GARFTase) inhibitors with antitumor activity
  • Cycloalkylidene alkanols with antileishmanial activity, via Wittig reaction

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H318

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000356493
0000356494
0000356495
0000356495
SDBB0275

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Raquel Palao-Suay et al.
Journal of materials science. Materials in medicine, 28(10), 152-152 (2017-09-02)
Active targeting not only of a specific cell but also a specific organelle maximizes the therapeutic activity minimizing adverse side effects in healthy tissues. The present work describes the synthesis, characterization, and in vitro biological activity of active targeting nanoparticles (NP)
Gantumur Battogtokh et al.
Nanomedicine : nanotechnology, biology, and medicine, 13(2), 733-743 (2016-11-07)
The objective of this study was to develop a mitochondria-targeted photosensitizer (PS) for photodynamic therapy (PDT). Herein, a porphyrin-derivative photosensitizer, pheophorbide-a (PheoA), was conjugated to carboxybutyltriphenylphosphonium (TPP) via a carbodiimide linkage to enhance mitochondrial targeting and TPP-PheoA conjugate was further
Sabah Haq et al.
OncoTargets and therapy, 10, 2427-2447 (2017-05-13)
Prostaspheres-based three dimensional (3D) culture models have provided insight into prostate cancer (PCa) biology, highlighting the importance of cell-cell interactions and the extracellular matrix (EMC) in the tumor microenvironment. Although these 3D classical spheroid platforms provide a significant advance over
O O Koloskova et al.
Colloids and surfaces. B, Biointerfaces, 167, 328-336 (2018-04-24)
Development of efficient biodegradable, environmentally responsive, biocompatible and non-toxic delivery system is needed for efficient gene delivery. As well known, properties of the vehicle are determined by the structure of carrier components. The aim of the current study was to
Ningqiang Gong et al.
Nature nanotechnology, 14(4), 379-387 (2019-02-20)
Mitochondrial redox homeostasis, the balance between reactive oxygen species and antioxidants such as glutathione, plays critical roles in many biological processes, including biosynthesis and apoptosis, and thus is a potential target for cancer treatment. Here, we report a mitochondrial oxidative
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