103489-33-4

Usage

Uses

Used in Bioconjugation and Labeling Experiments:
4-(4-Azidophenyl)butyric acid is used as a linking agent for the attachment of proteins, peptides, and other biomolecules to various biological entities. It is chosen for this application due to its ability to selectively modify aliphatic or aromatic groups, thereby facilitating the precise conjugation of target molecules.
Used in Bioorthogonal Chemistry:
In the field of bioorthogonal chemistry, 4-(4-Azidophenyl)butyric acid is utilized as a key component in chemical reactions that occur within living systems without interfering with native biochemical processes. Its unique reactivity allows for the selective modification of biomolecules, which is crucial for the development of innovative diagnostic and therapeutic strategies.
Used in Click Chemistry Applications:
4-(4-Azidophenyl)butyric acid is employed as a reactant in click chemistry, a set of modular and highly efficient reactions that are ideal for the rapid assembly of complex molecules. Its use in this context is driven by the need for biocompatible and highly reactive compounds that can be easily integrated into biological systems for applications such as drug development and molecular imaging.
Used in Biological Imaging:
4-(4-Azidophenyl)butyric acid is used as a contrast agent in biological imaging to enhance the visualization of specific biomolecules or cellular structures. Its incorporation into imaging probes allows for the precise tracking and analysis of biological processes in real-time, providing valuable insights into disease mechanisms and therapeutic responses.
Used in Drug Delivery Systems:
In drug delivery, 4-(4-Azidophenyl)butyric acid is used as a component of targeted drug delivery systems. Its ability to bind selectively to specific biomolecules enables the development of therapies that can be directed to particular cells or tissues, thereby increasing the efficacy and reducing the side effects of treatments.
Used in Diagnostics:
4-(4-Azidophenyl)butyric acid is utilized in the development of diagnostic tools, where its unique chemical properties allow for the sensitive and specific detection of biological markers. This is particularly important in the early identification of diseases and the monitoring of treatment responses.

InChI:InChI=1/C10H11N3O2/c11-13-12-9-6-4-8(5-7-9)2-1-3-10(14)15/h4-7H,1-3H2,(H,14,15)

Upstream product

• 5600-62-4 4-(4-nitrophenyl)butanoic acid 
• 15118-60-2 4-(4-aminophenyl)butyric Acid 

Downstream Products

• 1262304-44-8 4-(4-(4-(4-(3-(4-(1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-indol-1-yl)-butyl)-(1,2,3)triazol-1-yl)-phenyl)-butyric acid 
• 1262304-38-0 4-(4-(4-(3-(3-(4-(1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-indol-1-yl)-propyl)-(1,2,3)triazol-1-yl)-phenyl)-butyric acid 
• 1262304-32-4 4-(4-(4-(4-(3-(4-(1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-indol-1-yl)-butyl)-(1,2,3)triazol-1-yl)-phenyl)-butyric acid 
• 1262304-23-3 4-(4-(4-(3-(3-(4-(1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-indol-1-yl)-propyl)-(1,2,3)triazol-1-yl)-phenyl)-butyric acid 
• 253325-35-8 4-azidophenyl butyric acid 4-nitrophenyl ester 

Relevant academic research and scientific papers

A practical molecular clip for immobilization of receptors and biomolecules on devices' surface: Synthesis, grafting protocol and analytical assay

Deposition of O-succinimidyl 4-(p-azido-phenyl)butanoate (4) onto inorganic device (FTIR-ATR crystal) or polymer material (filtration membrane) followed by irradiation at 254 nm led to surface functionalisation with NHS esters. Further reaction with biomolecules allowed their covalent grafting. The reactivity of the photoactivated surfaces was assayed by two methods: (i) the coupling with 3,5-bis(trifluoromethyl)benzylamine (7) and subsequent XPS analysis; (ii) the coupling with 4,5-bis-tritiated lysine (10) and subsequent LSC measurement of the radioactivity.

Targeting glycolysis: A fragment based approach towards bifunctional inhibitors of hLDH-5

hLDH-5 has emerged as a promising target for anti-glycolytic cancer chemotherapy. Here we report a first generation of bifunctional inhibitors, which show promising activity against hLDH-5.

Synthesis and biological characterization of SQBAzide, a novel biotinylated photoaffinity probe for the study of the human platelet thromboxane A2 receptor

SQBAzide, a biotinylated, azido derivative of the TXA2 receptor antagonist, SQ31,491, was synthesized and characterized. The compound specifically inhibited human platelet aggregation mediated by TXA2 receptor activation and irreversibly labeled platelet TXA2 receptors upon exposure to ultraviolet light. This probe should prove to be of significant value for the study of the receptor-ligand binding domain.

A new series of photoactivatable and iodinatable linear vasopressin antagonists

A series of new linear photoactivatable and iodinatable antagonists of the neuropeptidic hormone vasopressin was designed and synthesized by a combination of PyBOP-mediated Boc/solid-phase peptide synthesis and solution synthesis approaches. These were based on modifications of a previously reported potent and selective antagonist of the vasopressor response (V(1a) receptor) to [arginine]vasopressin, phenylacetyl-D-Tyr(Me)-Phe-Gln-Asn-Arg- Pro-Arg-Tyr-NH2. (Azidophenyl)alkyl substitutions, of the general structure N3-C6H4(CH2)(n)CO (n = 0, 1, 2, or 3), were employed in position 1. The seven new analogues are 4-N3-C6H4CO-D-Tyr(Me)-Phe-Gln-Asn-Arg-Pro-Arg- Tyr-NH2 (3), 3-N3-C6H4CO-D-Tyr(Me)-Phe-Gln-Asn-Arg-Pro-Arg-Tyr-NH2 (12), 4-N3-C6H4CH2CO-D-Tyr(Me)-Phe-Gln-Asn-Arg-Pro-Arg-Tyr-NH2 (13), 3-N3- C6H4CH2CO-D-Tyr(Me)-Phe-Gln-Asn-Arg-Pro-Arg-Tyr-NH2 (14), 4-N3- C6H4(CH2)2CO-D-Tyr(Me)-Phe-Gln-Asn-Arg-Pro-Arg-Tyr-NH2 (15) 3-N3- C6H4(CH2)2CO-D-Tyr(Me)-Phe-Gln-Asn-Arg-Pro-Arg-Tyr-NH2 (16), 4-N3- C6H4(CH2)3CO-D-Tyr(Me)-Phe-Gln-Asn-Arg-Pro-Arg-Tyr-NH2 (17). All analogues were tested for their affinity of the rat hepatic V(1a) receptor. Analogues 3 and 12 have a low affinity (K(i) ? 20 nM) and analogues 13-17 show a high affinity (K(i) between 0.04 and 0.3 nM). The affinity values appear to be mainly a function of the alkyl chain length and to a lesser extent of the meta or para position of the azido group on the aromatic ring. Analogues 13-17 were iodinated on the Tyr-9 residue, giving compounds 18-22. All these five iodinated derivatives exhibited K(i) values of 0.2-1 nM for rat liver membranes. Their affinities for oxytocin and renal V2 vasopressin receptors were much lower. Moreover, all analogues completely antagonized the vasopressin-stimulated inositol phosphates production in WRK1 cells and were devoided of any agonistic potency. Preliminary covalent binding studies showed improved covalent yields as compared to any previously reported results. They are very promising candidates as potential high-affinity, highly selective, photosensitive ligands for the V(1a) receptor. They could serve as useful pharmacological tools for studies on the vasopressin binding site.