Synthesis, binding ability, and cell cytotoxicity of fluorescent probes for l‐arginine detection based on naphthalene derivatives: Experiment and theory

• Published in: Journal of molecular recognition 2018-01, Vol.31 (1), p.n/a
• Main Authors: Li, Jie, Zhang, Yang, Chen, Yanmei, Shang, Xuefang, Ti, Tongyu, Chen, Hongli, Wang, Tianyun, Zhang, Jinlian, Xu, Xiufang
• Format: Article
• Language: English
• Subjects: Alanine; Amino acids; Arginine; Arginine - analysis; Arginine - chemistry; Asparagine; Aspartic acid; Binding; Biocompatibility; cell cytotoxicity; Cell Survival - drug effects; Chemical modification; Combining ability; Cytotoxicity; Derivatives; Fluorescence; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - toxicity; Fluorescent indicators; fluorescent probe; Functional groups; Glutamic acid; Glutamine; Glycine; Histidine; Humans; Imines; Isoleucine; Leucine; Lysine; MCF-7 Cells; Methionine; Naphthalene; naphthalene derivatives; Naphthalenes - chemical synthesis; Naphthalenes - toxicity; Nitrogen dioxide; Phenylalanine; Proline; Selectivity; Serine; Toxicity; Tryptophan; Valine
• ISSN: 0952-3499; 1099-1352
• DOI: 10.1002/jmr.2657

Inspired by biological related parts, Schiff base derivatives and functional groups of chemical modification can provide efficient detection method of amino acids. Therefore, we have designed and prepared 4 compounds based on Schiff base derivatives involving ─NO2, ─OH, and naphthyl group. Results indicated that compound 4 containing 2 nitro groups showed strong sensitivity and high selectivity for arginine (Arg) among normal 18 kinds of standard amino acids (alanine, valine, leucine, isoleucine, methionine, aspartic acid, glutamic acid, arginine, glycine, serine, asparagine, phenylalanine, histidine, tryptophan, proline, lysine, glutamine, and cysteine). Theoretical investigation also approved the strong binding ability of compound 4 for Arg. In addition, compound 4 displayed high combining ability of Arg and low cytotoxicity of MCF‐7 cell in the 0 to 150 μg mL−1 of concentration range; it can be used for Arg in vivo detection of fluorescent probe. Four compounds involving naphthyl, nitro and hydroxyl groups have been synthesized and optimized. The compound containing two nitro and hydroxyl showed high binding ability for l‐arginine and low cytotoxicity for MCF‐7 cells.