178181-33-4

Basic information

• Product Name: 4-nitrophenyl 2-fluoropropionate
• Synonyms: 4-nitrophenyl 2-fluoropropionate
• CAS NO: 178181-33-4
• Molecular Formula: C₉H₈FNO₄
• Molecular Weight: 213.16
• Mol File: 178181-33-4.mol

Chemical Properties

• Boiling Point: 309.3°Cat760mmHg
• Flash Point: 140.9°C
• Appearance: /
• Density: 1.322g/cm³
• Vapor Pressure: 0.000644mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: 4-nitrophenyl 2-fluoropropionate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitrophenyl 2-fluoropropionate(178181-33-4)
• EPA Substance Registry System: 4-nitrophenyl 2-fluoropropionate(178181-33-4)

Safety Data

• Hazardous Substances Data: 178181-33-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H8FNO4/c1-6(10)9(12)15-8-4-2-7(3-5-8)11(13)14/h2-6H,1H3

Upstream product

• 100-02-7 4-nitro-phenol 
• 57965-29-4 2-fluoropropanoic acid 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 

Relevant articles and documents

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Synthesis and evaluation of [18F]FP-Lys-GE11 as a new radiolabeled peptide probe for epidermal growth factor receptor (EGFR) imaging

Introduction: The epidermal growth factor receptor (EGFR) has emerged as an attractive target in the treatment of various cancers. Radiolabeled small molecules, antibodies, and peptides that specifically target EGFR are promising probes for tumor imaging to guide personalized treatment with EGFR-targeted drugs. This study aimed to radiolabel GE11 (an EGFR-specific targeting peptide) with 18-fluorine to develop a new EGFR-targeting positron emission tomography (PET) probe, [18F]FP-Lys-GE11, for imaging tumors overexpressing EGFR. Methods: [18F]FP-Lys-GE11 was produced by radiolabeling a GE11 peptide with the prosthetic group 4-nitrophenyl-2-[18F]fluoropropionate ([18F]NFP). Stability in PBS and mice serum, affinity for A431 cell line, U87 and PC-3 cells uptake and blocking studies, and biodistribution of [18F]FP-Lys-GE11 were determined. 2 h dynamic and static PET scans of probe for tumor-bearing mice normal and inhibition uptake were performed. Results: [18F]FP-Lys-GE11 was stable in PBS and mice serum. The Kd and Bmax values of probe for A431 were 42.43 ± 3.75 nM and 3383 ± 81.73 CPM, respectively. In cell uptake and blocking experiments, a significant reduction in radioactivity accumulation (over 4-fold) was observed by blocking U87 and PC-3 cells with unlabeled peptide. PET imaging of U87 and PC-3 tumor-bearing mice revealed clear tumor imaging (tumor radioactivity accumulation was 3.48 ± 0.44 and 3.68 ± 0.76%ID/g respectively, tumor-to-muscle ratio was 3.45 ± 0.43 and 3.64 ± 0.76 respectively). Blocking imaging revealed that the U87 tumor uptake was significantly inhibited (2.21 ± 0.41%ID/g). The biodistribution and dynamic PET imaging showed that [18F]FP-Lys-GE11 was mainly excreted by the kidneys and the rest was excreted through the bile and intestines. Conclusion: The current results showed that [18F]FP-Lys-GE11was a good radiolabeled peptide probe for EGFR overexpression tumor's imaging.

A novel aliphatic 18F-labeled probe for PET imaging of melanoma

Radiofluorinated benzamide and nicotinamide analogues are promising molecular probes for the positron emission tomography (PET) imaging of melanoma. Compounds containing aromatic (benzene or pyridine) and N,N- diethylethylenediamine groups have been successfully used for development of melanin targeted PET and single-photon emission computed tomography (SPECT) imaging agents for melanoma. The objective of this study was to determine the feasibility of using aliphatic compounds as a molecular platform for the development of a new generation of PET probes for melanoma detection. An aliphatic N,N-diethylethylenediamine precursor was directly coupled to a radiofluorination synthon, p-nitrophenyl 2-18F-fluoropropionate (18F-NFP), to produce the probe N-(2-(diethylamino)ethyl)-2- 18F-fluoropropanamide (18F-FPDA). The melanoma-targeting ability of 18F-FPDA was further evaluated both in vitro and in vivo through cell uptake assays, biodistribution studies, and small animal PET imaging in C57BL/6 mice bearing B16F10 murine melanoma tumors. Beginning with the precursor 18F-NFP, the total preparation time for 18F-FPDA, including the final high-performance liquid chromatography purification step, was approximately 30 min, with a decay-corrected radiochemical yield of 79.8%. The melanin-targeting specificity of 18F-FPDA was demonstrated by significantly different uptake rates in tyrosine-treated and untreated B16F10 cells in vitro. The tumor uptake of 18F-FPDA in vivo reached 2.65 ± 0.48 %ID/g at 2 h postinjection (p.i.) in pigment-enriched B16F10 xenografts, whereas the tumor uptake of 18F-FPDA was close to the background levels, with rates of only 0.37 ± 0.07 %ID/g at 2 h p.i. in the nonpigmented U87MG tumor mouse model. Furthermore, small animal PET imaging studies revealed that 18F-FPDA specifically targeted the melanotic B16F10 tumor, yielding a tumor-to-muscle ratio of approximately 4:1 at 1 h p.i. and 7:1 at 2 h p.i. In summary, we report the development of a novel 18F-labeled aliphatic compound for melanoma imaging that can be easily synthesized in high yields using the radiosynthon 18F-NFP. The PET probe 18F-FPDA exhibits high B16F10 tumor-targeting efficacy and favorable in vivo pharmacokinetics. Our study demonstrates that aliphatic compounds can be used as a new generation molecular platform for the development of novel melanoma targeting agents. Further evaluation and optimization of 18F-FPDA for melanin targeted molecular imaging are therefore warranted.

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