Recent Progress on Fluorescent Probes for the Detection of Methylglyoxal

doi:10.6023/cjoc202403003

Abstract

Methylglyoxal (MGO), as a highly active carbonyl compound, plays an important role in physiological and patho- logical processes. As a glycosylation agent, MGO can react with proteins, DNAs and lipids to form advanced glycation end products (AGEs), which leads to protein dysfunctions and cell death, and then causes a series of diseases, such as cardiovascular disease, inflammation, diabetes and so on. Therefore, it is important to develop an efficient, rapid and in situ method for detecting intracellular MGO. Fluorescent probes have been widely used in the detection of MGO in biological systems due to their advantages of good selectivity, high sensitivity and non-invasiveness. In this review, the research progress on fluorescence probes of MGO is summarized and the design concept, recognition mechanism and biological application are emphasized in recent years. Finally, the prospect to design and applications of fluorescence probes for MGO is also discussed.

Key words: methylglyoxal, active carbonyl compounds, advanced glycation end products, fluorescent probes

Cite this article

Yaping Wang, Yanling Fan, Yongqi Ren, Yulin Xu. Recent Progress on Fluorescent Probes for the Detection of Methylglyoxal[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3299-3308.

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Fig. & Tab. 16

Scheme 1. Structures of probes 1~3 and its responding reactions towards methylglyoxal

Scheme 2. Structure of probe 4 and its reaction mechanism of methylglyoxal

Scheme 3. Structures of probes 5 and 6 and its responding reactions towards methylglyoxal

Scheme 4. Structure of probe 7 and its responding reactions towards formaldehyde, methylglyoxal and oxalaldehyde

Scheme 5. Structure of probe 8 and its reaction mechanism of methylglyoxal

Scheme 6. Structure of probe 9 and its reaction mechanism of methylglyoxal

Scheme 7. Structure of probe 10 and its strategy for detection of methylglyoxal

Scheme 8. Structure of probe 11 and its responding reactions towards methylglyoxal

Scheme 9. Structure of probe 13

Scheme 10. Structure of probe 15 and its strategy for detection of methylglyoxal

Scheme 11. Structure of probe 16 and its responding reactions towards methylglyoxal

Scheme 12. Structures of probes 17 and 18 and its reaction mechanism of glyoxals

Scheme 13. Structure of probe 19 and its responding reactions towards glyoxals

Scheme 14. Structure of probe 20 and its responding reactions towards glyoxals

Scheme 15. Structure of probe 21 and its responding reactions towards methylglyoxal

Scheme 16. Structure of probe 22 and its responding reactions towards methylglyoxal

References 34

[1]	Kalapos M. P. Toxicol. Lett. 1999, 110, 145. doi: 10.1016/s0378-4274(99)00160-5 pmid: 10597025
[2]	Falone S.; D'Alessandro A.; Mirabilio A.; Petruccelli G.; Cacchio M.; Ilio C. D.; Loreto S. D.; Amicarelli F. PLoS One 2012, 7, e31401.
[3]	Jia X.-M.; Olson D. J. H.; Ross A. R. S.; Wu L.-Y. FASEB J. 2006, 20, 1555.
[4]	Gao Y.; Wang Y. Biochemistry 2006, 45, 15654.
[5]	Cantero A.; Portero-Otin M.; Ayala V.; Auge N.; Sanson M.; Elbaz M.; Thiers J.; Pamplona R.; Salvayre R.; Negre-Salvayre A. FASEB J. 2007, 21, 3096.
[6]	Rabbani N.; Thornalley; P. J. Amino Acids 2012, 42, 1133. doi: 10.1007/s00726-010-0783-0 pmid: 20963454
[7]	Biswas A.; Wang B.; Miyagi M.; Nagaraj R.H. Biochem. J. 2008, 409, 771. pmid: 17941823
[8]	Matafome P.; Sena C.; Seica R. Endocrine 2013, 43, 472. doi: 10.1007/s12020-012-9795-8 pmid: 22983866
[9]	(a) Matafome P.; Santos-Silva D.; Crisóstomo J.; Rodrigues T.; Rodrigues L.; Sena C.; Pereira P.; Seica R.; Arch. Physiol. Biochem. 2012, 118, 58. doi: 10.3109/13813455.2012.658065 pmid: 11270668
	(b) Dhar A.; Dhar I.; Desai K. M.; Wu L.-Y. Br. J. Pharmacol. 2010, 161, 843. pmid: 11270668
	(c) Singh R.; Barden A.; Mori T.; Beilin L. Diabetologia 2001, 44, 129. doi: 10.1007/s001250051591 pmid: 11270668
	(d) Du J.; Suzuki H.; Nagase F.; Akhand A. A.; Nakashima I. Free Radic. Biol. Med. 2001, 31, 469. pmid: 11270668
[10]	(a) Chen Y.; Hu A.; Yang L.-Y.; Li Z.-Y.; Yan K. Chin. J. Org. Chem. 2017, 37, 1939 (in Chinese). pmid: 19185865
	(陈燚, 胡奥晗, 杨凌毅, 李早英, 严琨, 有机化学, 2017, 37, 1939.) doi: 10.6023/cjoc201703040 pmid: 19185865
	(b) Rabbani N.; Thornalley P. J. Biochem. Soc. Trans. 2014, 42, 425. pmid: 19185865
	(c) Kilhovd B. K.; Juutilainen A.; Lehto S.; Rnnemaa T.; Torjesen P. A.; Hanssen K. F.; Laakso M. Atherosclerosis 2009, 205, 590. doi: 10.1016/j.atherosclerosis.2008.12.041 pmid: 19185865
[11]	Brouwers O.; Niessen P. M.; Haenen G.; Miyata T.; Brownlee M.; Stehouwer C. D.; Mey J. G. D.; Schalkwijk C.G. Diabetologia 2010, 53, 989. doi: 10.1007/s00125-010-1677-0 pmid: 20186387
[12]	(a) Mclellan A. C.; Phillips S. A.; Thornalley P. J. Anal. Biochem. 1992, 206, 17. pmid: 15369718
	(b) Chaplen F. W. R.; Fahl W. E.; Cameron D. C. Anal. Biochem. 1996, 238, 171. doi: 10.1006/abio.1996.0271 pmid: 15369718
	(c) Nemet I.; Varga-Defterdarovi L.; Turk Z. Clin. Biochem. 2004, 37, 875. pmid: 15369718
[13]	Wild R.; Ooi L.; Velandai S. G. M. Anal. Bioanal. Chem. 2012, 403, 2577.
[14]	(a) Li Y.-T.; Zhao X.-J.; Jiang Y.-R.; Yang B.-Q. New J. Chem. 2018, 42, 19478.
	(b) Zhou L.; Chen Y.; Shao B.; Cheng J.; Li X. Front. Chem. Sci. Eng. 2022, 16, 34. doi: 10.1007/s11705-021-2050-1
	(c) Yang X.; Lu X.; Wang J.; Zhang Z.; Du X.; Zhang J.; Wang J. J. Agric. Food Chem. 2022, 70, 3047.
[15]	(a) Li J.-J.; Ban L.-F.; Tang L.-J. Chin. J. Org. Chem. 2021, 41, 241 (in Chinese).
	(李娇娇, 班立夫, 汤立军, 有机化学, 2021, 41, 241.) doi: 10.6023/cjoc202006023
	(b) Hou J.; Qian M.; Zhao H.; Li Y.; Liao Y.; Han G.; Xu Z.; Wang F.; Song Y.; Liu Y. Anal. Chim. Acta 2018, 1024, 169.
	(c) Wei Y.; Wang X.; Shi W.; Chen R.; Zheng L.; Wang Z.; Chen K.; Gao L. Eur. J. Med. Chem. 2021, 226, 113828.
[16]	(a) Liu X.; Li N.; Li M.; Chen H.; Zheng K. Coord. Chem. Rev. 2020, 404, 213109.1.
	(b) Wei C.; Zhang P.-Z.; Li X.-L. Chin. J. Org. Chem. 2019, 39, 3375 (in Chinese).
	(魏超, 张平竹, 李小六, 有机化学, 2019, 39, 3375.) doi: 10.6023/cjoc201906029
	(c) Chen E.-Q.; Tang Y.-H.; Wang L.; Ren J.-B.; Lin W.-Y. Chin. J. Org. Chem. 2021, 41, 1200 (in Chinese).
	(陈恩庆, 唐永和, 王蕾, 任江波, 林伟英, 有机化学, 2021, 41, 1200.) doi: 10.6023/cjoc202009016
[17]	Wang T.; Jr E. F. D.; Fitzgerald K. J.; Spiegel D. A. J. Am. Chem. Soc. 2013, 135, 12429.
[18]	Tang T.; Zhou Y.-M.; Chen Y.-Q.; Li M.-J.; Feng Y.; Wang C.-C.; Wang S.-R.; Zhou X. Anal. Methods, 2015, 7, 2386.
[19]	Zhang W.-Z.; Zhang F.-Y.; Wang Y.-L.; Song B.; Zhang R.; Yuan J. L. Inorg. Chem. 2017, 56, 1309.
[20]	Liu C.; Jiao X.-J.; He S.; Zhao L.-C.; Zeng X.-S. Dyes Pigm. 2017, 138, 23.
[21]	Yang M.-W.; Fan J.-L.; Zhang J.-W.; Du J.-J.; Peng X.-J. Chem. Sci. 2018, 9, 6758.
[22]	Gao S.-Y.; Tang Y.-H.; Lin W.-Y. J. Fluoresc. 2019, 29, 155.
[23]	Ding C.-Y.; Wang F.-Y.; Dang Y.-J.; Xu Zh.-A.; Li L.-L.; Lai Y.; Yu H.-J.; Luo Y.; Huang R.-M.; Zhang A.; Zhang W. Anal. Chem. 2019, 91, 15577.
[24]	Dang Y.-J.; Wang F.-Y.; Li L.-L.; Lai Y.; Xu Z.-A.; Xiong Z.; Zhang A.; Tian Y.; Ding C.-Y.; Zhang W. Chem. Commun. 2020, 56, 707.
[25]	Liu J.; Li M.; Dang Y.-J.; Lou H.-M.; Xu Z.-A.; Zhang W. Biosens. Bioelectron. 2022 204, 114068.
[26]	(a) Dang Y.-J.; Lai Y.; Chen F.-P.; Sun O.; Ding C.-Y.; Zhang W.; Xu Z.-A. Anal. Chem. 2022, 94, 1076.
	(b) Dang Y.-J. Ph.D. Dissertation, East China Normal University, Shanghai, 2021 (in Chinese).
	(党⼀菁, 博士论文, 华东师范大学, 上海, 2021.)
[27]	Wang H.-L.; Xu Y.-L.; Rao L.; Yang C.-T.; Yuan H.; Gao T.-J.; Chen X.; Sun H.-Y.; Xian M.; Liu C.-R.; Liu C.-L. Anal. Chem. 2019, 91, 5646. doi: 10.1021/acs.analchem.8b05426
[28]	Xu H.; Liu Q.-Q.; Song X.-D.; Wang C.; Wang X.-R.; Ma S.-N.; Wang X.-L.; Feng Y.; Meng X.-M.; Liu X.-G.; Wang W.; Lou K.-Y. Anal. Chem. 2020, 92, 13829.
[29]	Wang W.-L.; Chen J.-W.; Ma H.-J.; Xing W.-J.; Lv N.; Zhang B.-N.; Xu H.; Wang W.; Lou K.-Y. Chem. Commun. 2021, 57, 8166.
[30]	Chen J.-W.; Lin Y.-N.; Xing W.-J.; Zhang X.-C.; Xu H.; Wang W.; Lou K.-Y. RSC Adv. 2022, 12, 9473.
[31]	Wang Z.-M.; Bian Y.-Y.; Liu C.; He S.; Zhao L.-C.; Zeng X.-S. Chem. Commun. 2022, 58, 6453.
[32]	Xu H.; Liu X.-R.; Cai Z.-H.; Zheng J.-F.; Wang Y.-W.; Peng Y. Org. Biomol. Chem. 2022, 20, 4782.
[33]	Zhang Y.; Li W.; Chen X.-Q.; Xiong S.-Q.; Bian Y.-N.; Yuan L.; Gao X.-Y.; Su D.-D. Anal. Chem. 2023, 95, 2579. doi: 10.1021/acs.analchem.2c05476 pmid: 36642958
[34]	Ma Y.; Shang J.-H.; Liu L.-H.; Li M.-H.; Xu X.-Y.; Cao H.; Xu L.; Sun W.; Song G.-S.; Zhang X.-B. J. Am. Chem. Soc. 2023, 145, 17881.

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