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157945

Sigma-Aldrich

(4-Carboxybutyl)triphenylphosphonium bromide

98%

Sinonimo/i:

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

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About This Item

Formula condensata:
(C6H5)3P(Br)(CH2)4COOH
Numero CAS:
17814-85-6
Peso molecolare:
443.31
Beilstein:
3586477
Numero CE:
241-782-5
Numero MDL:
MFCD00011906
Codice UNSPSC:
12352107
ID PubChem:
24849711
NACRES:
NA.22

Livello qualitativo

200

Saggio

98%

Stato

powder

Impiego in reazioni chimiche

reaction type: C-C Bond Formation

Punto di fusione

204-207 °C (lit.)

Gruppo funzionale

carboxylic acid
phosphine

Stringa SMILE

[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
MLOSJPZSZWUDSK-UHFFFAOYSA-N

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Applicazioni

  • 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

Pittogrammi

Skull and crossbonesCorrosion
GHS06,GHS05

Avvertenze

Danger

Indicazioni di pericolo

H301,H318

Classi di pericolo

Acute Tox. 3 Oral - Eye Dam. 1

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
STBH0658
0000217293
STBH0658
0000184026
0000118461

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Sigma-Aldrich

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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
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
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)
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
Victoria López et al.
ACS applied materials & interfaces, 9(32), 26697-26706 (2017-08-02)
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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