Research Progress of Biosensing Mediated by the Thiol-ene Click Reaction

doi:10.13560/j.cnki.biotech.bull.1985.2021-0329

Abstract

Abstract:

The thiol-ene click reaction is a metal-free catalytic click reaction,which is currently being widely used in molecular labelling,new material synthesis and material surface functionalization. This article describes the reaction mechanism of the thiol-ene click reaction,the factors affecting the reaction,and the biomarker technology mediated by the reaction. On this basis,the article discusses the applications of the sulfhydryl-ene click reaction in biosensing,cell imaging,and biofunctionalization of nanomaterials. Finally,the paper predicts future development direction and application prospects of the thiol-ene click reaction.

Key words: thiol-ene click reaction, biosensing, cell imaging, functionalization

ZHENG Shu-juan, TONG Tao, XU Wen-tao, HUANG Kun-lun. Research Progress of Biosensing Mediated by the Thiol-ene Click Reaction[J]. Biotechnology Bulletin, 2021, 37(12): 243-251.

Figures/Tables 3

References 42

[1]	Kolb HC, Finn MG, Sharpless KB. Click chemistry:diverse chemical function from a few good reactions[J]. Angew Chem Int Ed Engl, 2001, 40(11):2004-2021. doi: 10.1002/(ISSN)1521-3773 URL
[2]	Nwe K, Brechbiel MW. Growing applications of “click chemistry” for bioconjugation in contemporary biomedical research[J]. Cancer Biother Radiopharm, 2009, 24(3):289-302. doi: 10.1089/cbr.2008.0626 URL
[3]	Lowe AB. Thiol-ene “click” reactions and recent applications in polymer and materials synjournal[J]. Polym Chem, 2010, 1(1):17-36. doi: 10.1039/B9PY00216B URL
[4]	Sumerlin BS, Vogt AP. Macromolecular engineering through click chemistry and other efficient transformations[J]. Macromolecules, 2010, 43(1):1-13. doi: 10.1021/ma901447e URL
[5]	Cramer NB, Reddy SK, O’Brien AK, et al. Thiol-ene photopolymerization mechanism and rate limiting step changes for various vinyl functional group chemistries[J]. Macromolecules, 2003, 36(21):7964-7969. doi: 10.1021/ma034667s URL
[6]	Guo JS, Huang YB, Jing XB, et al. Synjournal and characterization of functional poly(γ-benzyl-l-glutamate)(PBLG)as a hydrophobic precursor[J]. Polymer, 2009, 50(13):2847-2855. doi: 10.1016/j.polymer.2009.04.016 URL
[7]	Escorihuela J, Bañuls MJ, Grijalvo S, et al. Direct covalent attachment of DNA microarrays by rapid thiol-ene “click” chemistry[J]. Bioconjug Chem, 2014, 25(3):618-627. doi: 10.1021/bc500033d URL
[8]	Escorihuela J, Bañuls MJ, Puchades R, et al. DNA microarrays on silicon surfaces through thiol-ene chemistry[J]. Chem Commun Camb Engl, 2012, 48(15):2116-2118.
[9]	Bañuls MJ, Jiménez-Meneses P, Meyer A, et al. Improved performance of DNA microarray multiplex hybridization using probes anchored at several points by thiol-ene or thiol-yne coupling chemistry[J]. Bioconjug Chem, 2017, 28(2):496-506. doi: 10.1021/acs.bioconjchem.6b00624 URL
[10]	Chu Q, Liu Y, Jiang S, et al. A novel adsorbent based on aptamer prepared via “thiol-ene” click for specific recognition of phthalic acid esters[J]. Anal Chim Acta, 2021, 1146:109-117.
[11]	Madaan N, Terry A, Harb J, et al. Thiol-ene-thiol photofunctionalization of thiolated monolayers with polybutadiene and functional thiols, including thiolated DNA[J]. J Phys Chem C, 2011, 115(46):22931-22938. doi: 10.1021/jp206134g URL
[12]	Wang Z, Zhao JC, Lian HZ, et al. Aptamer-based organic-silica hybrid affinity monolith prepared via “thiol-ene” click reaction for extraction of thrombin[J]. Talanta, 2015, 138:52-58. doi: 10.1016/j.talanta.2015.02.009 URL
[13]	Jonkheijm P, Weinrich D, Köhn M, et al. Photochemical surface patterning by the thiol-ene reaction[J]. Angew Chem, 2008, 120(23):4493-4496. doi: 10.1002/(ISSN)1521-3757 URL
[14]	Wittrock S, Becker T, Kunz H. Synthetic vaccines of tumor-associated glycopeptide antigens by immune-compatible thioether linkage to bovine serum albumin[J]. Angew Chem Int Ed, 2007, 46(27):5226-5230. doi: 10.1002/(ISSN)1521-3773 URL
[15]	Heidecke CD, Lindhorst TK. Iterative synjournal of spacered glycodendrons as oligomannoside mimetics and evaluation of their antiadhesive properties[J]. Chemistry, 2007, 13(32):9056-9067.
[16]	Ortiz RA, Garcia Valdéz AE, Martinez Aguilar MG, et al. An effective method to prepare sucrose polymers by Thiol-Ene photopolymerization[J]. Carbohydr Polym, 2009, 78(2):282-286. doi: 10.1016/j.carbpol.2009.03.045 URL
[17]	Wang YQ, Huang D, Wang X, et al. Fabrication of zwitterionic and pH-responsive polyacetal dendrimers for anticancer drug delivery[J]. Biomater Sci, 2019, 7(8):3238-3248. doi: 10.1039/C9BM00606K URL
[18]	Norberg O, Lee IH, Aastrup T, et al. Photogenerated lectin sensors produced by thiol-ene/yne photo-click chemistry in aqueous solution[J]. Biosens Bioelectron, 2012, 34(1):51-56. doi: 10.1016/j.bios.2012.01.001 pmid: 22341757
[19]	Chen G, Amajjahe S, Stenzel MH. Synjournal of thiol-linked neoglycopolymers and thermo-responsive glycomicelles as potential drug carrier[J]. Chem Commun:Camb, 2009(10):1198-1200.
[20]	Fiore M, Marra A, Dondoni A. Photoinduced thiol-ene coupling as a click ligation tool for thiodisaccharide synjournal[J]. J Org Chem, 2009, 74(11):4422-4425. doi: 10.1021/jo900514w URL
[21]	Yan Y, Fu J, Wang T, et al. Controlled release of silyl ether camptothecin from thiol-ene click chemistry-functionalized mesoporous silica nanoparticles[J]. Acta Biomater, 2017, 51:471-478. doi: 10.1016/j.actbio.2017.01.062 URL
[22]	Ding H, Li B, Jiang Y, et al. pH-responsive UV crosslinkable chitosan hydrogel via “thiol-ene” click chemistry for active modulating opposite drug release behaviors[J]. Carbohydr Polym, 2021, 251:117101. doi: 10.1016/j.carbpol.2020.117101 URL
[23]	Su X, Kuang L, Battle C, et al. Mild two-step method to construct DNA-conjugated silicon nanoparticles:scaffolds for the detection of microRNA-21[J]. Bioconjug Chem, 2014, 25(10):1739-1743. doi: 10.1021/bc5004026 URL
[24]	González-Lucas D, Bañuls MJ, García-Rupérez J, et al. Covalent attachment of biotinylated molecular beacons via thiol-ene coupling. A study on conformational changes upon hybridization and streptavidin binding[J]. Microchimica Acta, 2017, 184(9):3231-3238. doi: 10.1007/s00604-017-2310-4 URL
[25]	Guo WJ, Vilaplana L, Hansson J, et al. Immunoassays on thiol-ene synthetic paper generate a superior fluorescence signal[J]. Biosens Bioelectron, 2020, 163:112279. doi: 10.1016/j.bios.2020.112279 URL
[26]	Rong YW, Ali S, Ouyang Q, et al. A turn-on upconversion fluorescence sensor for acrylamide in potato chips based on fluorescence resonance energy transfer and thiol-ene Michael addition[J]. Food Chem, 2021, 351:129215. doi: 10.1016/j.foodchem.2021.129215 URL
[27]	Ma YH, Fu S, Tan YX, et al. Design and synjournal of highly fluorescent and stable fullerene nanoparticles as probes for folic acid detection and targeted cancer cell imaging[J]. Nanotechnology, 2021, 32(19):195501. doi: 10.1088/1361-6528/abdf02 URL
[28]	Liu Y, Yu Y, Lam JW, et al. Simple biosensor with high selectivity and sensitivity:thiol-specific biomolecular probing and intracellular imaging by AIE fluorogen on a TLC plate through a thiol-ene click mechanism[J]. Chemistry, 2010, 16(28):8433-8438.
[29]	Oyman Eyrilmez G, Doran S, Murtezi E, et al. Selective cell adhesion and biosensing applications of bio-active block copolymers prepared by CuAAC/thiol-ene double click reactions[J]. Macromol Biosci, 2015, 15(9):1233-1241. doi: 10.1002/mabi.201500099 pmid: 25974890
[30]	Hynes WF, Doty NJ, Zarembinski TI, et al. Micropatterning of 3D microenvironments for living biosensor applications[J]. Biosensors:Basel, 2014, 4(1):28-44.
[31]	Li YL, Bao L, Zhou QL, et al. Functionalized graphene obtained via thiol-ene click reactions as an efficient electrochemical sensor[J]. ChemistrySelect, 2017, 2(29):9284-9290. doi: 10.1002/slct.201700659 URL
[32]	Zeng K, Guo ML, Zhang YJ, et al. Thiol-ene click chemistry for the fabrication of Ru(bpy)₃₂+-based solid-state electrochemiluminescence sensor[J]. Electrochem Commun, 2011, 13(12):1353-1356.
[33]	Melnik E, Muellner P, Bethge O, et al. Streptavidin binding as a model to characterize thiol-ene chemistry-based polyamine surfaces for reversible photonic protein biosensing[J]. Chem Commun:Camb, 2014, 50(19):2424-2427. doi: 10.1039/c3cc48640k URL
[34]	Hao HY, Huang JJ, Liu P, et al. Rapid buildup arrays with orthogonal biochemistry gradients via light-induced thiol-ene “click” chemistry for high-throughput screening of peptide combinations[J]. Acs Appl Mater Inter, 2020, 12(18):20243-20252. doi: 10.1021/acsami.0c03199 URL
[35]	Buhl M, Vonhören B, Ravoo BJ. Immobilization of enzymes via microcontact printing and thiol-ene click chemistry[J]. Bioconjug Chem, 2015, 26(6):1017-1020. doi: 10.1021/acs.bioconjchem.5b00282 URL
[36]	Colak B, Di Cio S, Gautrot JE. Biofunctionalized patterned polymer brushes via thiol-ene coupling for the control of cell adhesion and the formation of cell arrays[J]. Biomacromolecules, 2018, 19(5):1445-1455. doi: 10.1021/acs.biomac.7b01436 URL
[37]	Huang HY, Liu MY, Tuo X, et al. One-step fabrication of PEGylated fluorescent nanodiamonds through the thiol-ene click reaction and their potential for biological imaging[J]. Appl Surf Sci, 2018, 439:1143-1151. doi: 10.1016/j.apsusc.2017.12.233 URL
[38]	Ruizendaal L, Pujari SP, Gevaerts V, et al. Biofunctional silicon nanoparticles by means of thiol-ene click chemistry[J]. Chem Asian J, 2011, 6(10):2776-2786. doi: 10.1002/asia.v6.10 URL
[39]	Campos MA, Paulusse JM, Zuilhof H. Functional monolayers on oxide-free silicon surfaces via thiol-ene click chemistry[J]. Chem Commun:Camb, 2010, 46(30):5512-5514. doi: 10.1039/c0cc01264e URL
[40]	Robidillo CJT, Aghajamali M, Faramus A, et al. Interfacing enzymes with silicon nanocrystals through the thiol-ene reaction[J]. Nanoscale, 2018, 10(39):18706-18719. doi: 10.1039/C8NR05368E URL
[41]	Muhsir P, Çakmakçi E, Demir S, et al. Amine functional magnetic nanoparticles via waterborne thiol-ene suspension photopolymerization for antibody immobilization[J]. Colloids Surf B:Biointerfaces, 2018, 170:122-128. doi: 10.1016/j.colsurfb.2018.05.062 URL
[42]	Yaşar M, Yöntem FD, Kahraman MV, et al. Polymeric nanoparticles for selective protein recognition by using thiol-ene miniemulsion photopolymerization[J]. J Biomater Sci Polym Ed, 2020, 31(16):2044-2059. doi: 10.1080/09205063.2020.1793705 URL

功能基团 Functional group	Rp ∝[SH]^x[C=C]^y
功能基团 Functional group	x	y	Rp max
丙烯酸酯Acrylate	0.4	0.6	2.1
烯丙基醚 Allylether	1	0	1.0
乙烯基醚 Vinylether	0.5	0.5	4.8
降冰片烯 Norbornene	0.5	0.5	6.0
乙烯基硅氮烷Vinylsilazane	0	1	3.3

功能基团 Functional group	Rp ∝[SH]^x[C=C]^y
功能基团 Functional group	x	y	Rp max
丙烯酸酯Acrylate	0.4	0.6	2.1
烯丙基醚 Allylether	1	0	1.0
乙烯基醚 Vinylether	0.5	0.5	4.8
降冰片烯 Norbornene	0.5	0.5	6.0
乙烯基硅氮烷Vinylsilazane	0	1	3.3