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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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Colloids and surfaces. B, Biointerfaces, 167, 328-336 (2018-04-24)
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The development of targeted nanocarriers able to be selectively internalized within tumor cells, and therefore to deliver anti-tumor drugs specifically to diseased cells, constitutes one of the most important goals in nano-oncology. Herein, the development of Janus mesoporous silica particles
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