硼酸类化学传感器的研究进展
收稿日期: 2017-09-22
修回日期: 2017-12-22
网络出版日期: 2018-01-03
基金资助
山东省自然科学基金(No.ZR2014YL035)资助项目.
Research Progress of Boronic Acid in Chemsensors
Received date: 2017-09-22
Revised date: 2017-12-22
Online published: 2018-01-03
Supported by
Project supported by the Shandong Provincial Natural Science Foundation (No. ZR2014YL035).
王浩 , 王凯 , 孙捷 , 方桂迁 , 姚庆强 , 吴忠玉 . 硼酸类化学传感器的研究进展[J]. 有机化学, 2018 , 38(5) : 1035 -1051 . DOI: 10.6023/cjoc201709037
The detection and fluorescent identification of some substances such as sLea/x in vivo can provide important reference for the diagnosis, treatment and prognosis of disease, molecular tracing and further research on the mechanism of related diseases. Therefore, the development and discovery of high selectivity and high sensitivity chemsensors is of great value. Due to the special structure, phenyl boronic acid compounds could interact and bind with sugar, catecholamine containing catechol structure, fluoride or alkali cyanide. So boronic acids could be develeped as fluorescence sensors selectively for related substances, while have the advantages of high selectivity, high efficiency, rapid analysis and so on. In recent years, boronic acid has been functioned with new materials such as nanoparticles and quantum dots to design novel sensors for better performance. In this paper, the recent progress in the study of boronic acid compounds in sensors is reviewed.
Key words: boronic acid; chemsensor; fluorescence; carbohydrate; electrochemistry
[1] Hu, X.; Wang, Y.; Liu, H.; Wang, J.; Tan, Y., Wang, F.; Tan, W. Chem. Sci. 2017, 8, 466.
[2] Verly, I. R. N.; Kuilenburg, A. B. P. V.; Abeling, N. G. G. M. Eur. J. Cancer 2017, 235.
[3] Bergenstal, R. M.; Bailey, T. S.; Rodbard, D.; Ziemen, M.; Guo, H.; Muehlen-Bartmer, I.; Ahmann, A. J. Diabetes Care 2017, 40, 554.
[4] Rojas, L. J.; Taracila, M. A.; Papp-Wallace, K. M.; Bethel, C. R.; Caselli, E.; Romagnoli, C.; Bonomo, R. A. Antimicrob. Agents Chemother. 2016, 60, 1751.
[5] Whyte, G. F.; Vilar, R.; Woscholski, R. ChemBioChem 2013, 6, 161.
[6] Nishiyabu, R.; Shimizu, A. Chem. Commun. 2016, 52, 9765.
[7] Imperio, D.; Del Grosso, E.; Fallarini, S.; Lombardi, G.; Panza, L. Org. Lett. 2017, 19, 1678.
[8] Guan, Y.; Zhang, Y. Chem. Soc. Rev. 2013, 42, 8106.
[9] Wu, X.; Chen, X. X.; Jiang, Y. B. Analyst 2017, 142, 1403.
[10] Wang, L.; Zhang, J.; Kim, B.; Peng, J.; Berry, S. N.; Ni, Y.; Chang, Y. T. J. Am. Chem. Soc. 2016, 138, 10394.
[11] Wu, S.; Guo, H.; Wang, L.; Xin, Y.; Cheng, Y.; Fan, W. Sens. Actuators, B 2017, 245, 11.
[12] Tanaka-Okamoto, M.; Mukai, M.; Takahashi, H.; Fujiwara, Y.; Ohue, M.; Miyamoto, Y. Glycobiology 2017, 27, 400.
[13] Springsteen, G.; Wang, B. Tetrahedron 2002, 58, 5291.
[14] Springsteen, G.; Wang, B. Chem. Commun. 2001, 17, 1608.
[15] James, T. D.; Shinkai, S. In Host-Guest Chemistry, Vol. 218, Ed.:Penadés, S., Springer-Verlag, Berlin, 2002, p. 159.
[16] Zhai, W.; Male, L.; Fossey, J. S. Chem. Commun. 2017, 53, 2218.
[17] Li, H.; Yang, C.; Zhu, X. Spectrochim. Acta, Part A 2017, 180, 199.
[18] Hosseinzadeh, R.; Mohadjerani, M.; Pooryousef, M. Spectrochim. Acta, Part A 2015, 144, 53.
[19] Teichert, J. F.; Mazunin, D.; Bode, J. W. J. Am. Chem. Soc. 2013, 135, 113.
[20] Basiruddin, S. K.; Swain, S. K. Mater. Sci. Eng., C 2016, 58, 103.
[21] Solís-Delgado, L. E.; Ochoa-Terán, A.; Yatsimirsky, A. K. Anal. Lett. 2016, 49, 2301.
[22] Hansen, J. S.; Hoeg, J. T.; Christensen, J. B. Tetrahedron 2017, 73, 3010.
[23] Karaku?, E.; Üçüncü, M.; Eanes, R. C.; Emrullaho?lu, M. New J. Chem. 2013, 37, 2632.
[24] Wang, X. K.; Peng, Y.; Tao, H. R.; Zhou, F. F.; Zhang, C.; Su, F.; Xie, W. J. Huazhong Univ. Sci.-Med. 2017, 37, 343(in Chinese). (王小康, 彭燕, 陶浩冉, 周芬芳, 张弛, 苏飞, 谢伟, 华中科技大学学报, 2017, 37, 343.)
[25] Trinchera, M.; Aronica, A.; Dall'Olio, F. Biol. 2017, 6, 16.
[26] Chang, M. H.; Chang, C. N. Tetrahedron Lett. 2014, 55, 4437.
[27] Suazette, R. Sci. China:Chem. 2010, 53, 3.
[28] Xu, X. D.; Cheng, H.; Chen, W. H.; Cheng, S. X.; Zhuo, R. X.; Zhang, X. Z. Sci. Rep. 2013, 3, 2679.
[29] Chu, Y.; Wang, D.; Wang, K.; Liu, Z. L.; Weston, B.; Wang, B. Bioorg. Med. Chem. Lett. 2013, 23, 6307.
[30] Varki, A.; Gagneux, P.; Ann, N. Y. Acad. Sci. 2012, 1253, 16.
[31] Dan, W.; Ozhegov, E.; Lin, W.; Zhou, A.; Nie, H.; Yu, L. Glycoconjugate J. 2016, 33, 725.
[32] Zhang, X.; Chen, B.; He, M.; Zhang, Y.; Peng, L.; Hu, B. Analyst 2016, 141, 1286.
[33] Matsumoto, A.; Stephenson-Brown, A. J.; Khan, T. Chem. Sci. 2017, 8, 6165.
[34] Yang, L.; Zhu, S.; Hang, W.; Wu, L.; Yan, X.; Chem, A. Anal. Chem. 2009, 81, 2555.
[35] Miyata, K.; Christie, R. J.; Kataoka, K. React. Funct. Polym. 2011, 71, 227.
[36] Perdicchio, M.; Ilarregui, J. M.; Verstege, M. I.; Cornelissen, L. A.; Schetters, S. T.; Engels, S.; van Berkel, L. A. Proc. Natl. Acad. Sci. U. S. A. 2016, 113, 3329.
[37] Xu, Y.; Sette, A.; Sidney, J.; Gendler, S. J.; Franco, A. Immunol. Cell Biol. 2005, 83, 440.
[38] Matsumoto, A.; Cabral, H.; Sato, N.; Kataoka, K.; Miyahara, Y. Angew. Chem., Int. Ed. 2010, 49, 5494.
[39] Deshayes, S.; Cabral, H.; Ishii, T.; Miura, Y.; Kobayashi, S.; Yamashita, T.; Kataoka, K. J. Am. Chem. Soc. 2013, 135, 15501.
[40] Zhang, L.; Yu, C.; Gao, R.; Niu, Y. Y.; Li, Y. L.; Chen, J.; He, J. L. Biosens. Bioelectron. 2016, 92, 434.
[41] Zhang, L.; Yu, C.; Gao, R. Biosens. Bioelectron. 2017, 92, 434.
[42] Erickson, J. M.; Messer, T. M.; Scand, J. Plast. Reconstr. Surg. 2013, 38, 1638.
[43] Richy, F.; Bruyere, O.; Ethgen, O.; Cucherat, M.; Henrotin, Y.; Reginster, J. Y. Arch. Intern. Med. 2003, 163, 1514.
[44] Wandel, S.; Jüni, P.; Tendal, B.; Nüesch, E.; Villiger, P. M.; Welton, N. J.; Trelle, S. Br. Med. J. 2010, 341, 4675.
[45] Hwang, J. S.; Kwon, M. Y.; Kim, K. H.; Lee, Y.; Lyoo, I. K.; Kim, J. E.; Han, I. O. J. Biol. Chem. 2017, 292, 1724.
[46] Singh, G.; Alekseeva, L.; Alekseev, V.; Goriachev, D.; Barinov, A.; Nasonov, E.; Pyanykh, S. Ann. Rheum. Dis. 2016, 75, 852.
[47] Reginster, J. Y.; Cooper, C.; Bruyère, O. Curr. Med. Res. Opin. 2016, 32, 1771.
[48] Kantor, E. D.; Zhang, X.; Wu, K.; Signorello, L. B.; Chan, A. T.; Fuchs, C. S.; Giovannucci, E. L. Int. J. Cancer. 2016, 139, 1949.
[49] Saegnipanthkul, S.; Waikakul, S.; Rojanasthien, S.; Totemchokyakarn, K.; Srinkapaibulaya, A.; Chin, T. C.; Lwin, M. Int. J. Rheum. Dis. 2017, 1.
[50] Tran, T. M.; Alan, Y.; Glass, T. E. Chem. Commun. 2015, 51, 7915.
[51] Suk, K. T.; Kim, H. S.; Kim, M. Y.; Kim, J. W.; Uh, Y.; Jang, I. H.; Baik, S. K. J. Korean Med. Sci. 2010, 25, 399.
[52] Huey, E. D.; Putnam, K. T.; Grafman, J. Neurology 2006, 66, 17.
[53] Beck, G. C.; Brinkkoetter, P.; Hanusch, C.; Schulte, J.; van Ackern, K.; van der Woude, F. J.; Yard, B. A. Crit. Care 2004, 8, 485.
[54] Rye, D. B. Neurology 2004, 63, S2.
[55] Nagatsu, T. Cell. Mol. Neurobiol. 2017, 1, 535.
[56] Jenkins, P. O.; Mehta, M. A.; Sharp, D. J. Brain 2016, 139, 2345.
[57] Ali, S. R.; Ma, Y.; Parajuli, R. R.; Balogun, Y.; Lai, W. Y. C.; He, H. Anal. Chem. 2007, 79, 2583.
[58] Nikolajsen, R. P. H.; Hansen, Å. M. Anal. Chim. Acta 2001, 449, 1.
[59] Seto, D.; Maki, T.; Soh, N.; Nakano, K.; Ishimatsu, R.; Imato, T. Talanta 2012, 94, 36.
[60] Wu, Z.; Li, M.; Fang, H.; Wang, B. Bioorg. Med. Chem. Lett. 2012, 22, 7179.
[61] Wu, Z.; Yang, X.; Xu, W.; Wang, B.; Fang, H. Drug Discoveries Ther. 2012, 6, 238.
[62] Chaicham, A.; Sahasithiwat, S.; Tuntulani, T.; Tomapatanaget, B. Chem. Commun. 2013, 49, 9287.
[63] Jun, E. J.; Liu, H.; Choi, J. Y.; Lee, J. Y.; Yoon, J. Sens. Actuators, B 2013, 176, 611.
[64] Ptak, T.; M?ynarz, P.; Dobosz, A.; Rydzewska, A.; Prokopowicz, M. J. Mol. Struct. 2013, 1040, 59.
[65] Liu, S.; Y. Shi, F.; Zhao, X.; Chen, L.; Su, X. Biosens. Bioelectron. 2013, 47, 379.
[66] Ma, Y.; Zhao, Y.; Zhang, F. Sens. Actuators, B 2017, 241, 735.
[67] Yang, Z. R.; Wang, M. M.; Wang, X. S. Anal. Chem. 2017, 89, 1930.
[68] Xu, Z.; Kim, S. K.; Han, S. J.; Lee, C.; Kociok-Kohn, G.; James, T. D.; Yoon, J. Eur. J. Org. Chem. 2009, 18, 3058.
[69] Swamy, K. M. K.; Lee, Y. J.; Lee, H. N.; Chun, J.; Kim, Y.; Kim, S. J.; Yoon, J. J. Org. Chem. 2006, 71, 8626.
[70] Wu, X.; Chen, X. X.; Song, B. N.; Huang, Y. J.; Ouyang, W. J.; Li, Z.; Jiang, Y. B. Chem. Commun. 2014, 50, 13987.
[71] Solís-Delgado, L. E.; Ochoa-Terán, A.; Yatsimirsky, A. K. Anal. Lett. 2016, 49, 2301.
[72] Mohammadpour, Z.; Safavi, A.; Omidvar, A.; Mohajeri, A.; Mobaraki, N.; Shamsipur, M. J. Fluorine Chem. 2016, 190, 12.
[73] Guan, R.; Chen, H.; Cao, F.; Cao, D.; Deng, Y. Inorg. Chem. Commun. 2013, 38, 112.
[74] Jose, D. A.; Elstner, M.; Schiller, A. Chem.-Eur. J. 2013, 19, 14451.
[75] Yoon, J. W.; Jeong, H.; Lee, M. H. Bull. Korean Chem. Soc. 2017, 38, 329.
[76] KyungáKwon, S.; NaáLee, H. Chem. Commun. 2008, 45, 5915.
[77] Chen, X.; Li, H.; Jin, L. Tetrahedron Lett. 2014, 55, 2537.
[78] Higashi, A.; Kishikawa, N.; Ohyama, K. Tetrahedron Lett. 2017, 58, 2774.
[79] Rhee, S. G. Science 2006, 312, 1882.
[80] Lin, M. T.; Beal, M. F. Nature 2006, 443, 787.
[81] Dai, H.; Lü, W.; Zuo, X.; Zhu, Q.; Pan, C.; Niu, X.; Chen, X. Biosens. Bioelectron. 2017, 95, 131.
[82] Reverte, M.; Vaissiere, A.; Boisguerin, P. ACS Sens. 2016, 1, 970.
[83] Chen, Z.; Tian, Z.; Kallio, K. J. Am. Chem. Soc. 2016, 138, 4900.
[84] Rios, N.; Piacenza, L.; Trujillo, M. Free Radical Biol. Med. 2016, 101, 284.
[85] Du, Ý, L.; Ni, N.; Li, M.; Wang, B. Tetrahedron Lett. 2010, 51, 1152.
[86] Du, L.; Li, M.; Zheng, S.; Wang, B. Tetrahedron Lett. 2008, 49, 3045.
[87] Li, J.; Sun, Q.; Mao, Y. J. Electroanal. Chem. 2017, 794, 1.
[88] Wu, S.; Guo, H.; Wang, L. Sens. Actuators, B 2017, 245, 11.
[89] Dervisevic, M.; Çevik, E.; ?enel, M. J. Electroanal. Chem. 2016, 776, 18.
[90] Silva-Carrillo, C.; Reynoso-Soto, E. A.; Paraguay-Delgado, F. J. Electroanal. Chem. 2017, 164, B86.
[91] Guo, S.; Chen, J.; Cai, B. Y. Mater. Chem. Front. 2017, 1, 61.
[92] Wang, W.; Kong, L.; Zhu, J. J. Colloid Interface Sci. 2017, 498, 1.
[93] Jiang, G.; Zhu, W.; Shen, X. Microchim. Acta 2017, 1, 1.
[94] Cheng, T.; Zhu, S.; Zhu, B. J. Sep. Sci. 2016, 39, 1347.
[95] Na, W.; Liu, H.; Wang, M. Microchim. Acta 2017, 184, 1463.
[96] Gu, S.; Ma, K.; Kong, J. Int. J. Electrochem. Sci. 2017, 12, 5092.
[97] Abellán-Llobregat, A.; Jeerapan, I.; Bandodkar, A. Biosens. Bioelectron. 2017, 91, 885.
[98] Wu, S.; Guo, H. Wang, L. Sens. Actuators, B 2017, 245, 11.
[99] Takahashi, S.; Suzuki, I.; Nishiyama, T. Bumseki Kagaku 2016, 65, 751.
[100] Zhou, Y.; Dong, H.; Liu, L. Biosens. Bioelectron. 2015, 64, 442.
[101] Gao, P.; Wang, Z.; Yang, L. Electrochim. Acta 2015, 151, 370.
[102] Wang, Q.; Kaminska, I.; Niedziolka-Jonsson, J. Biosens. Bioelectron. 2013, 50, 331.
[103] Thearle, R. A.; Latiff, N. M.; Sofer, Z. Electroanalysis 2017, 29, 45.
[104] Zhou, X.; Gao, X.; Song, F. Appl. Surf. Sci. 2017, 423, 810.
[105] Lawrence, K.; Nishimura, T.; Haffenden, P.; Mitchels, J. M.; Sakurai, K.; Fossey, J. S. Marken, F. New J. Chem. 2013, 37, 1883.
[106] Suzuki, J.; Shida, N.; Inagi, S. Electroanalysis 2016, 28, 2797.
[107] Yin, H.; Zhou, Y.; Yang, Z. Sens. Actuators, B 2015, 221, 1.
[108] Wang, C.; Zholudov, Y. T.; Nsabimana, A., Xu, G.; Li, J. Anal. Chim. Acta 2016, 937, 39.
[109] Wang, C.; Wang, Q.; Zhong, M.; Kan, X. Analyst 2016, 141, 5792.
[110] Zhong, M.; Teng, Y.; Pang, S.; Yan, L.; Kan, X. Biosens. Bioelectron. 2015, 64, 212.
[111] Ooyama, Y.; Uenaka, K.; Matsugasako, A.; Harima, Y.; Ohshita, J. RSC Adv. 2013, 3, 23255.
[112] Zheng, J.; Zhang, M.; Guo, X.; Wang, J.; Xu, J. Sens. Actuators, B 2017, 250, 8.
[113] Sun, X.; Zhai, W.; Fossey, J. S.; James, T. D. Chem. Commun. 2016, 52, 3456.
[114] Wang, X.; Yuan, Z. F.; Fan, J.; Karch, K. R.; Ball, L. E.; Denu, J. M.; Garcia, B. A. Mol. Cell. Proteomics 2016, 15, 2462.
[115] Abdellaoui, S.; Corgier, B. C.; Mandon, C. A.; Doumèche, B.; Marquette, C. A.; Blum, L. J. Electroanalysis 2013, 25, 671.
[116] Nübel, G.; Sorgenfrei, F. A.; Jäschke, A. Methods 2017, 117, 14.
[117] Geninatti, C. S.; Alberti, D.; Szabo, I.; Aime, S.; Djanashvili, K. Angew. Chem. 2013, 52, 1161.
[118] Wang, W.; Yin, R.; Zhang, M.; Yu, R.; Hao, C.; Zhang, L.; Jiang, T. J. Med. Chem. 2017, 60, 2840.
[119] Munusamy, S. K.; Thirumoorthy, K.; Muralidharan, V. P. Sens. Actuators, B 2017, 244, 175.
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