A new boronic acid-based fluorescent sensor for L-dihydroxy-phenylalanine
Catecholamines, such as dopamine and L-dihydroxyphenylalanine (L-DOPA), are associated with different physiological functions and diseases. In our recent studies, a novel water-soluble boronic acid compound 3c was identified as a selective fluorescent sensor for L-DOPA. This compound not only has th...
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| Published in | Drug Discoveries & Therapeutics Vol. 6; no. 5; pp. 238 - 241 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
International Research and Cooperation Association for Bio & Socio-Sciences Advancement
01.01.2012
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| Subjects | |
| Online Access | Get full text |
| ISSN | 1881-7831 1881-784X |
| DOI | 10.5582/ddt.2012.v6.5.238 |
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| Abstract | Catecholamines, such as dopamine and L-dihydroxyphenylalanine (L-DOPA), are associated with different physiological functions and diseases. In our recent studies, a novel water-soluble boronic acid compound 3c was identified as a selective fluorescent sensor for L-DOPA. This compound not only has the ability to interact with dopamine and catechol, but also has no fluorescence intensity change for L-DOPA precursors in vivo, such as L-tyrosine. |
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| AbstractList | Catecholamines, such as dopamine and L-dihydroxyphenylalanine (L-DOPA), are associated with different physiological functions and diseases. In our recent studies, a novel water-soluble boronic acid compound 3c was identified as a selective fluorescent sensor for L-DOPA. This compound not only has the ability to interact with dopamine and catechol, but also has no fluorescence intensity change for L-DOPA precursors in vivo, such as L-tyrosine. |
| Author | Wang, Binghe Fang, Hao Wu, Zhongyu Yang, Xinying Xu, Wenfang |
| Author_xml | – sequence: 1 fullname: Wu, Zhongyu organization: Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmacy, Shandong University – sequence: 1 fullname: Wang, Binghe organization: Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University – sequence: 1 fullname: Xu, Wenfang organization: Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmacy, Shandong University – sequence: 1 fullname: Yang, Xinying organization: Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmacy, Shandong University – sequence: 1 fullname: Fang, Hao organization: Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmacy, Shandong University |
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| DOI | 10.5582/ddt.2012.v6.5.238 |
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| References | 18. Wu Z, Li M, Fang H, Wang B. A new boronic acid based fluorescent reporter for catechol. Bioorg Med Chem Lett. 2012; 23:7179-7182. 17. Coskun A, Akkaya EU. Three-point recognition and selective fluorescence sensing of L-DOPA. Org Lett. 2004; 6:3107-3109. 13. Karimi M, Carl JL, Loftin S, Perlmutter JS. Modified high-performance liquid chromatography with electrochemical detection method for plasma measurement of levodopa, 3-O-methyldopa, dopamine, carbidopa and 3,4-dihydroxyphenyl acetic acid. J Chromatogr B Analyt Technol Biomed Life Sci. 2006; 836:120-123. 14. Talebpour Z, Haghgoo S, Shamsipur M. 1H nuclear magnetic resonance spectroscopy analysis for simultaneous determination of levodopa, carbidopa and methyldopa in human serum and pharmaceutical formulations. Anal Chim Acta. 2004; 506:97-104. 19. Jin S, Li M, Zhu C, Tran V, Wang B. Computer-based de novo design, synthesis, and evaluation of boronic acid-based artificial receptors for selective recognition of dopamine. Chembiochem. 2008; 9:1431-1438. 10. Paisán-Ruiz C, Guevara R, Federoff M, Hanagasi H, Sina F, Elahi E, Schneider SA, Schwingenschuh P, Bajaj N, Emre M. Early-onset L-dopa-responsive parkinsonism with pyramidal signs due to ATP13A2, PLA2G6, FBXO7 and spatacsin mutations. Mov Disord. 2010; 25:1791-1800. 9. Cotzias GC, Papavasiliou PS, Gellene R. Modification of Parkinsonism-chronic treatment with L-dopa. N Engl J Med.1969; 280:337-345. 2. Hamdy NM, El-Wakeel L, Suwailem SM. Involvement of depressive catecholamines as thrombosis risk/inflammatory markers in non-smoker, non-obese congestive heart failure, linked to increased epidermal growth factor-receptor (EGF-R) production. Indian J Clin Biochem. 2011; 26:140-145. 1. Gorina AS, Kolesnichenko LS, Mikhnovich VI. Catecholamines and their metabolites in children with Asperger and Kanner syndromes. Biomed Khim. 2011; 57:562-570. 4. Vuda M, Brander L, Schroder R, Jakob SM, Takala J, Djafarzadeh S. Effects of catecholamines on hepatic and skeletal muscle mitochondrial respiration after prolonged exposure to faecal peritonitis in pigs. Innate Immun. 2012; 18:217-230. 3. Riva R, Mork PJ, Westgaard RH, Johansen TO, Lundberg U. Catecholamines and heart rate in female fibromyalgia patients. J Psychosom Res. 2012; 72:51-57. 16. Seto D, Maki T, Soh N, Nakano K, Ishimatsu R, Imato T. A simple and selective fluorometric assay for dopamine using a calcein blue-Fe2+ complex fluorophore. Talanta. 2012; 94:36-43. 6. Kotecha R, Toledo-Pereyra LH. The effect of catecholamines on hepatic artery vasospasm in small-for-size syndrome liver grafts. J Surg Res. 2012; 172:77-79. 12. Sagar KA, Smyth MR. Simultaneous determination of levodopa, carbidopa and their metabolites in human plasma and urine samples using LC-EC. J Pharm Biomed Anal. 2000; 22:613-624. 8. Lv H, Li A, Liu F, Ma H, Yao B. Effects of gastrodin on the dopamine system of Tourette's syndrome rat models. Biosci Trends. 2009; 3:58-62. 11. Pistonesi M, Centurion ME, Fernandez Band BS, Damiani PC, Olivieri AC. Simultaneous determination of levodopa and benserazide by stopped-flow injection analysis and three-way multivariate calibration of kinetic-spectrophotometric data. J Pharm Biomed Anal. 2004; 36:541-547. 7. Holloway EL, Polumbo RA, Harrison DC. Acute circulatory effects of dopamine in patients with pulmonary hypertension. Br Heart J. 1975; 37:482-485. 20. Huang S, Jia M, Xie Y, Wang J, Xu W, Fang H. The progress of selective fluorescent chemosensors by boronic acid. Curr Med Chem. 2012; 19:2621-2637. 5. Peterson G, Kumar A, Gart E, Narayanan S. Catecholamines increase conjugative gene transfer between enteric bacteria. Microb Pathog. 2011; 51:1-8. 15. Ha PT, Van Schepdael A, Hauta-Aho T, Roets E, Hoogmartens J. Simultaneous determination of dopa and carbidopa enantiomers by capillary zone electrophoresis. Electrophoresis. 2002; 23:3404-3409. |
| References_xml | – reference: 3. Riva R, Mork PJ, Westgaard RH, Johansen TO, Lundberg U. Catecholamines and heart rate in female fibromyalgia patients. J Psychosom Res. 2012; 72:51-57. – reference: 13. Karimi M, Carl JL, Loftin S, Perlmutter JS. Modified high-performance liquid chromatography with electrochemical detection method for plasma measurement of levodopa, 3-O-methyldopa, dopamine, carbidopa and 3,4-dihydroxyphenyl acetic acid. J Chromatogr B Analyt Technol Biomed Life Sci. 2006; 836:120-123. – reference: 15. Ha PT, Van Schepdael A, Hauta-Aho T, Roets E, Hoogmartens J. Simultaneous determination of dopa and carbidopa enantiomers by capillary zone electrophoresis. Electrophoresis. 2002; 23:3404-3409. – reference: 2. Hamdy NM, El-Wakeel L, Suwailem SM. Involvement of depressive catecholamines as thrombosis risk/inflammatory markers in non-smoker, non-obese congestive heart failure, linked to increased epidermal growth factor-receptor (EGF-R) production. Indian J Clin Biochem. 2011; 26:140-145. – reference: 11. Pistonesi M, Centurion ME, Fernandez Band BS, Damiani PC, Olivieri AC. Simultaneous determination of levodopa and benserazide by stopped-flow injection analysis and three-way multivariate calibration of kinetic-spectrophotometric data. J Pharm Biomed Anal. 2004; 36:541-547. – reference: 20. Huang S, Jia M, Xie Y, Wang J, Xu W, Fang H. The progress of selective fluorescent chemosensors by boronic acid. Curr Med Chem. 2012; 19:2621-2637. – reference: 19. Jin S, Li M, Zhu C, Tran V, Wang B. Computer-based de novo design, synthesis, and evaluation of boronic acid-based artificial receptors for selective recognition of dopamine. Chembiochem. 2008; 9:1431-1438. – reference: 8. Lv H, Li A, Liu F, Ma H, Yao B. Effects of gastrodin on the dopamine system of Tourette's syndrome rat models. Biosci Trends. 2009; 3:58-62. – reference: 16. Seto D, Maki T, Soh N, Nakano K, Ishimatsu R, Imato T. A simple and selective fluorometric assay for dopamine using a calcein blue-Fe2+ complex fluorophore. Talanta. 2012; 94:36-43. – reference: 6. Kotecha R, Toledo-Pereyra LH. The effect of catecholamines on hepatic artery vasospasm in small-for-size syndrome liver grafts. J Surg Res. 2012; 172:77-79. – reference: 10. Paisán-Ruiz C, Guevara R, Federoff M, Hanagasi H, Sina F, Elahi E, Schneider SA, Schwingenschuh P, Bajaj N, Emre M. Early-onset L-dopa-responsive parkinsonism with pyramidal signs due to ATP13A2, PLA2G6, FBXO7 and spatacsin mutations. Mov Disord. 2010; 25:1791-1800. – reference: 17. Coskun A, Akkaya EU. Three-point recognition and selective fluorescence sensing of L-DOPA. Org Lett. 2004; 6:3107-3109. – reference: 12. Sagar KA, Smyth MR. Simultaneous determination of levodopa, carbidopa and their metabolites in human plasma and urine samples using LC-EC. J Pharm Biomed Anal. 2000; 22:613-624. – reference: 5. Peterson G, Kumar A, Gart E, Narayanan S. Catecholamines increase conjugative gene transfer between enteric bacteria. Microb Pathog. 2011; 51:1-8. – reference: 7. Holloway EL, Polumbo RA, Harrison DC. Acute circulatory effects of dopamine in patients with pulmonary hypertension. Br Heart J. 1975; 37:482-485. – reference: 4. Vuda M, Brander L, Schroder R, Jakob SM, Takala J, Djafarzadeh S. Effects of catecholamines on hepatic and skeletal muscle mitochondrial respiration after prolonged exposure to faecal peritonitis in pigs. Innate Immun. 2012; 18:217-230. – reference: 14. Talebpour Z, Haghgoo S, Shamsipur M. 1H nuclear magnetic resonance spectroscopy analysis for simultaneous determination of levodopa, carbidopa and methyldopa in human serum and pharmaceutical formulations. Anal Chim Acta. 2004; 506:97-104. – reference: 9. Cotzias GC, Papavasiliou PS, Gellene R. Modification of Parkinsonism-chronic treatment with L-dopa. N Engl J Med.1969; 280:337-345. – reference: 1. Gorina AS, Kolesnichenko LS, Mikhnovich VI. Catecholamines and their metabolites in children with Asperger and Kanner syndromes. Biomed Khim. 2011; 57:562-570. – reference: 18. Wu Z, Li M, Fang H, Wang B. A new boronic acid based fluorescent reporter for catechol. Bioorg Med Chem Lett. 2012; 23:7179-7182. |
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| Title | A new boronic acid-based fluorescent sensor for L-dihydroxy-phenylalanine |
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