50889-29-7

Usage

Uses

Used in Pharmaceutical Industry:
(5-Carboxypentyl)(triphenyl)phosphonium bromide is used as a pharmaceutical intermediate for the synthesis of various drugs and compounds with therapeutic potential.
Used in Catalyst Applications:
(5-Carboxypentyl)(triphenyl)phosphonium bromide is employed as a catalyst in various chemical reactions, facilitating the conversion of reactants to products and improving the efficiency of the process.
Used in Medicine for Diabetes and Obesity Treatment:
(5-Carboxypentyl)(triphenyl)phosphonium bromide is used as a reactant in the preparation of inhibitors of protein tyrosine phosphatase 1B, which have potential therapeutic applications in the treatment of diabetes and obesity.
Used in Anticancer Applications:
(5-Carboxypentyl)(triphenyl)phosphonium bromide is used in the synthesis of folate receptor-specific glycinamide ribonucleotide formyltransferase inhibitors, which possess antitumor activity and can be employed in cancer treatment.
Used in Nucleic Acid Synthesis:
(5-Carboxypentyl)(triphenyl)phosphonium bromide is utilized in the preparation of peptide nucleic acids (PNAs) with high specific activity, which have potential applications in molecular biology and medicine.
Used in Organic Synthesis:
(5-Carboxypentyl)(triphenyl)phosphonium bromide is employed in the synthesis of roseophilin, an antibiotic with potential antimicrobial properties, through Wittig/aldol methodology, a widely used organic reaction for the synthesis of complex molecules.

InChI:InChI=1/C24H25O2P.BrH/c25-24(26)19-11-4-12-20-27(21-13-5-1-6-14-21,22-15-7-2-8-16-22)23-17-9-3-10-18-23;/h1-3,5-10,13-18H,4,11-12,19-20H2;1H

Upstream product

• 4224-70-8 6-bromohexanoic acid 
• 603-35-0 triphenylphosphine 
• 502-44-3 hexahydro-2H-oxepin-2-one 
• 6399-81-1 triphenylphosphine hydrobromide 
• 4286-55-9 1-bromo-6-hexanol 
• 108-94-1 cyclohexanone 
• 105-60-2 caprolactam 
• 60-32-2 6-aminohexanoic acid 
• 60633-18-3 (3-carboxy-propyl)triphenylphosphonium chloride 
• 1191-25-9 6-Hydroxyhexanoic acid 
• 629-11-8 1,6-hexanediol 

Downstream Products

• 1027086-34-5 cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid 
• 73367-77-8 (5-carboxypentyl)diphenylphosphine oxide 
• 75040-58-3 butyl (Z)-4⁽⁵⁾-(6-carboxyhex-1-enyl)imidazole-5⁽⁴⁾-carboxylate 
• 75040-57-2 butyl (E)-4⁽⁵⁾-(6-carboxyhex-1-enyl)imidazole-5⁽⁴⁾-carboxylate 
• 82302-57-6 11α-hydroxy-13-oxaprostanoic acid 
• 153732-05-9 (E)-7-[4-(2-{[(4-chlorophenyl)sulfonyl]amino}ethyl)phenyl]-7-(3-pyridyl)hept-6-enoic acid 
• 157020-35-4 cis-4(R)-(6-Carboxyhex-1-enyl)-2(R)-phenylthiazolidine-3-carboxylic acid tert-butyl ester 
• 72009-36-0 Sodium; 6-(triphenyl-λ⁵-phosphanylidene)-hexanoate 
• 93943-87-4 7-phenyl-7-(3-pyridyl)-6-heptenic acid 
• 93943-82-9 (E)-7-(3-Bromo-phenyl)-7-pyridin-3-yl-hept-6-enoic acid 
• 93943-86-3 (E)-7-(3-Nitro-phenyl)-7-pyridin-3-yl-hept-6-enoic acid 
• 1026858-27-4 (E)-7-(3-Methoxy-phenyl)-7-pyridin-3-yl-hept-6-enoic acid 
• 163163-85-7 (E)-7-(3-pyridyl)-7-(4-formylphenyl)hept-6-enoic acid 
• 5771-68-6 7-phenyl-6-heptenoic acid 

Relevant academic research and scientific papers

Synergistic antitumor efficacy of hybrid micelles with mitochondrial targeting and stimuli-responsive drug release behavior

The term synergism means that the overall therapeutic benefits should be greater than the sum of the effects of individual agents and that the optimal therapeutic efficacy can be achieved at reduced doses. Micellar systems usually fail to deliver multiple drugs to target sites at synergistic doses and thus are not able to maximize the antitumor efficacy. In the current study, we demonstrate a strategy to coordinate the release of camptothecin (CPT) and α-tocopheryl succinate (TOS) from hybrid micelles for nucleus and mitochondrion interferences. TOS is decorated with cationic triphenylphosphonium (TPP) to promote the targeting capability of TOS-TPP to mitochondria. The combination of CPT and TOS-TPP shows strong synergistism with a combination index of 0.186. Hyaluronic acid (HA) is conjugated with CPT or TOS-TPP via disulfide linkages for tumor cell targeting and intracellular reduction-triggered release. Both conjugates either separately self-assemble into MC and MT micelles, or are blended at different ratios to form MC-T hybrid micelles. In response to elevated intracellular glutathione levels, the coordinated release of CPT and TOS-TPP from MC-T results in a combination index of 0.26 and the dose-reduction indexes of CPT and TOS are 7.7 and 3.4, respectively. Compared with MC and MT, MC-T micelles with 5 fold lower doses exhibit higher intracellular reactive oxygen species (ROS) levels, comparable tumor growth inhibition and animal survival, indicating no hematologic and intestinal toxicities. Moreover, the HA conjugates of MC-T are linked to polylactide via acid-labile linkages and electrospun into short fibers (MC-T@SF) as an injectable depot to release MC-T in response to the acidic tumor microenvironment. At a predetermined synergistic ratio, MC-T@SF with 5 fold lower doses achieves antitumor profiles comparable to those of individual micelle-loaded short fibers. Therefore, the hybrid micelles and micelle-releasing short fibers represent a feasible strategy to synergistically enhance the therapeutic efficacy and enable significant reduction in effective doses of chemotherapeutic agents.

Tuning the Hydrophobicity of a Mitochondria-Targeted NO Photodonor

A few compounds in which the nitric oxide (NO) photodonor N-[4-nitro-3-(trifluoromethyl)phenyl]propane-1,3-diamine is joined to the mitochondria-targeting alkyltriphenylphosphonium moiety via flexible spacers of variable length were synthesized. The lipop

Radiation protection compound as well as synthesis method and application thereof

The invention discloses a radiation protection compound with a structural general formula (I) or (II). The synthesis method comprises the steps: enabling triphenylphosphine to react with 6-bromohexanoic acid or 1,6-dibromohexane to obtain a triphenylphosp

A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA1), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration

Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA1) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA1 agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA1 receptor agonist described so far (Emax = 118%, EC50 = 0.24 μM, KD = 19.6 nM; inactive at autotaxin and LPA2-6 receptors). This compound induces characteristic LPA1-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.

Synthesis and chemiluminescent properties of amino-acylated luminol derivatives bearing phosphonium cations

The monitoring of reactive oxygen species in living cells provides valuable information on cell function and performance. Lately, the development of chemiluminescence-based reactive oxygen species monitoring has gained increased attention due to the advantages posed by chemiluminescence, including its rapid measurement and high sensitivity. In this respect, specific organelle-targeting trackers with strong chemiluminescence performance are of high importance. We herein report the synthesis and chemiluminescence properties of eight novel phosphonium-functionalized amino-acylated luminol and isoluminol derivatives, designed as mitochondriotropic chemiluminescence reactive oxygen species trackers. Three different phosphonium cationic moieties were employed (phenyl, p-tolyl, and cyclohexyl), as well as two alkanoyl chains (hexanoyl and undecanoyl) as bridges/linkers. Synthesis is accomplished via the acylation of the corresponding phthalimides, as phthalhydrazide precursors, followed by hydrazinolysis. This method was chosen because the direct acylation of (iso)luminol was discouraging. The new derivatives’ chemiluminescence was evaluated and compared with that of the parent molecules. A relatively poor chemiluminescence performance was observed for all derivatives, with the isoluminol-based ones being the poorest. This result is mainly attributed to the low yield of the fluorescence species formation during the chemiluminescence oxidation reaction.

Precise delivery of therapeutic agents to cell mitochondria for anti-cancer therapy

Described is a targeted molecular scaffold for construction of a metabolic inhibitor loaded with cancer-cell specific activity and anti-tumor immunity. Incorporation of a mitochondria targeting moiety such as triphenylphosphonium cation through a biodegra

Rational design of mitochondria-targeted pyruvate dehydrogenase kinase 1 inhibitors with improved selectivity and antiproliferative activity

Herein, triphenylphosphonium cation moieties were incorporated into a dichloroacetophenone derivative, leading to the discovery of novel mitochondria-targeted and tumor-specific pyruvate dehydrogenase kinase 1 (PDK1) inhibitors. Biological studies suggest

Preparation of mitochondrion-targeting radioprotectant and application of mitochondrion-targeted radioprotectant in radiation damage protection

The invention relates to preparation of a mitochondrion-targeting radioprotectant and an application of the mitochondrion-targeting radioprotectant in radiation damage protection and belongs to the technical field of medicine. The medicine combines free r

Aliphatic hydroxylation and epoxidation of capsaicin by cytochrome P450 CYP505X

Microbial cytochrome P450 enzymes (CYPs) are able to mimic the metabolism of human CYPs. One challenge is to identify the respective drug metabolites and to compare substrate specificities to those of the human enzymes. In this study, a class VIII self-sufficient CYP from Aspergillus fumigatus (CYP505X) and variants of this enzyme were heterologously expressed in E. coli. The substrate scope of the variants was determined using active pharmaceutical ingredients (APIs) and (hetero)cyclic compounds. Capsaicin – the active compound in chili peppers – was oxidized most efficiently (4.36 μM/min) in a whole cell mediated biotransformation. The products were isolated, purified and their structures elucidated by 1D and 2D NMR. The two major metabolites showed modifications on the lipophilic side chain. Specifically, capsaicin was hydroxylated at position 8 to give (E)-8-hydroxy-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide and epoxidized at the double bond to give N-(4-hydroxy-3-methoxybenzyl)-5-(3-isopropyloxiran-2-yl)-pentanamide.

BACKGROUND-FREE FLUORESCENT PROBES FOR LIVE CELL IMAGING

BODIPY (boron-dipyrromethene) containing fluorescent compounds for use in live cell intracellular imaging are described. Methods of producing the compounds, methods of labeling tagged organelles, and methods of live cell intracellular imaging using the compounds/probes are described herein.