Research Progress on Biosensing and Drug Delivery Mediated by the Staudinger Ligation

doi:10.13560/j.cnki.biotech.bull.1985.2018-0096

Abstract

Abstract: The Staudinger ligation is a type of metal-free catalyzed click reaction between organic azide and phosphine under the mild conditions like at room temperature and in the water solution. Due to its bio-orthogonality and no potential cytotoxicity,Staudinger ligation is now widely used in the surface functionalization of materials,synthesis and labelling of various biological macromolecules. At the same time,there is great development space for applying Staudinger ligation in the synthesis and delivery of drugs and biosensors. In this review,the Staudinger ligation is described in detail involving the reaction mechanism,the factors influencing the reaction kinetics,the yield of the ligation and the reaction process,and the biomarker technology mediated by the ligation. On these bases,the biosensing applications mediated by the Staudinger ligation are discussed,including fluorescent biosensors targeting nucleic acids and small molecules,the applications of cell imaging technology in nucleic acid and glycan,and the applications in drug synthesis and delivery. At last,the future development trend of the Staudinger ligation is forecasted and the application prospects in the biosensing are presented.

Key words: Staudinger ligation, click chemistry, biosensing, drug delivery, cell imaging

ZHANG Yang-zi, ZHU Long-jiao, SHAO Xiang-Li, XU Wen-tao. Research Progress on Biosensing and Drug Delivery Mediated by the Staudinger Ligation[J]. Biotechnology Bulletin, 2019, 35(1): 187-198.

References

[1] Kolb HC, Finn MG, Sharpless KB.Click chemistry:diverse chemical function from a few good reactions[J]. Chembiochem, 2001, 40(11):2005-2021.
[2] Lahann J.Click chemistry for biotechnology and materials science[M]. Chichester:John Wiley & Sons, 2009.
[3] Nwe K, Brechbiel MW.Growing applications of “click chemistry” for bioconjugation in contemporary biomedical research[J]. Cancer Biotherapy and Radiopharmaceuticals, 2009, 24(3):289-302.
[4] Turner APF, Karube I, Wilson GS, et al.Biosensors:fundamentals and applications[M]. Oxford, New York:Oxford University Press, 1987.
[5] van Berkel SS, van Eldijk MB, van Hest J. Staudinger Ligation as a method for bioconjugation[J]. Angewandte Chemie International Edition, 2011, 50(38):8806-8827.
[6] Köhn M, Breinbauer R.The Staudinger ligation—a gift to chemical biology[J]. Angewandte Chemie International Edition, 2004, 43(24):3106-3116.
[7] Saxon E, Bertozzi C R.Cell surface engineering by a modified Staudinger reaction[J]. Science, 2000, 287(5460):2007-2010.
[8] Nilsson BL, Kiessling LL, Raines RT.Staudinger ligation: a peptide from a thioester and azide[J]. Organic Letters, 2000, 2(13):1939-1941.
[9] Saxon E, Armstrong JI, Bertozzi R.A “Traceless” staudinger ligation for the chemoselective synthesis of amide bonds[J]. Organic Letters, 2000, 2(14):2141-2143.
[10] Carroll L, Evans HL, Aboagye EO, et al.Bioorthogonal chemistry for pre-targeted molecular imaging-progress and prospects[J]. Organic & Biomolecular Chemistry, 2013, 11(35):5772-5781.
[11] Schilling CI, Jung N, Biskup M, et al.Bioconjugation via azide-Staudinger ligation:an overview[J]. Chemical Society Reviews, 2011, 40(9):4840-4871.
[12] Rahim MK, Kota R, Lee S, et al.Bioorthogonal chemistries for nanomaterial conjugation and targeting[J]. Nanotechnology Reviews, 2013, 2(2):215-227.
[13] Lin FL, Hoyt HM, van Halbeek H, et al. Mechanistic investigation of the Staudinger ligation[J]. J Am Chem Soc, 2005, 127(8):2686-2695.
[14] Sundhoro M, Jeon S, Park JH, et al.Perfluoroaryl azide-staudinger reaction:a fast and bioorthogonal reaction[J]. Angewandte Chemie International Edition, 2017, 56(2017):12117-12121.
[15] Tam A, Soellner MB, Raines RT.Water-soluble phosphinothiols for traceless Staudinger ligation and integration with expressed protein ligation[J]. J Am Chem Soc, 2007, 129(37):11421-11430.
[16] Hangauer MJ, Bertozzi CR.A FRET-based fluorogenic phosphine for live-cell imaging with the staudinger ligation[J]. Angewandte Chemie, 2008, 47(13):2394-2397.
[17] Wang CCY, Seo TS, Li Z, et al.Site-specific fluorescent labeling of DNA using Staudinger ligation[J]. Bioconjug Chem, 2003, 14(3):697-701.
[18] Weisbrod S H, Marx A.A nucleoside triphosphate for site-specific labelling of DNA by the Staudinger ligation[J]. Chem Commun, 2007, 18(2007):1828-1830.
[19] Baccaro A, Weisbrod SH, Marx A.DNA conjugation by the Staudinger ligation:new thymidine analogues[J]. Synthesis, 2007, 13(2007):1949-1954.
[20] Schulz D, Rentmeister A.Current approaches for RNA Labeling in vitro and in cells based on click reactions[J]. Chembiochem, 2014, 15(16):2342-2347.
[21] Jawalekar AM, Meeuwenoord N, Cremers JSGO, et al.Conjugation of nucleosides and oligonucleotides by[3+2]cycloaddition[J]. The Journal of Organic Chemistry, 2008, 73(1):287-290.
[22] Aigner M, Hartl M, Fauster K, et al.Chemical synthesis of site-specifically 2’-Azido-modified rna and potential applications for bioconjugation and RNA interference[J]. Chembiochem, 2011, 12(1):47-51.
[23] Fauster K, Hartl M, Santner T, et al.2’-Azido RNA, a versatile tool for chemical biology:synthesis, X-ray structure, siRNA applications, click Labelling[J]. ACS Chemical Biology, 2012, 7(3):581-589.
[24] Frommer J, Hieronymus R, Selvi Arunachalam T, et al.Preparation of modified long-mer RNAs and analysis of FMN binding to the ypaA aptamer from B. subtilis[J]. RNA Biology, 2014, 11(5):609-623.
[25] Rao H, Sawant AA, Tanpure AA, et al.Posttranscriptional chemical functionalization of azide-modified oligoribonucleotides by bioorthogonal click and Staudinger reactions[J]. Chem Commun, 2012, 48(4):498-500.
[26] Pianowski Z, Gorska K, Oswald L, et al.Imaging of mRNA in Live cells using nucleic acid-templated reduction of azidorhodamine probes[J]. J Am Chem Soc, 2009, 131(18):6492-6497.
[27] Gorska K, Keklikoglou I, Tschulena U, et al.Rapid fluorescence imaging of miRNAs in human cells using templated Staudinger reaction[J]. Chemical Science, 2011, 2(10):1969-1975.
[28] Cohen AS, Dubikovskaya EA, Rush JS, et al.Real-time bioluminescence imaging of glycans on live cells[J]. J Am Chem Soc, 2010, 132(25):8563-8565.
[29] Chang PV, Prescher JA, Hangauer MJ, et al.Imaging cell surface glycans with bioorthogonal chemical reporters[J]. J Am Chem Soc, 2007, 129(27):8400-8401.
[30] De Graaf AJ, Kooijman M, Hennink WE, et al.Nonnatural amino acids for site-specific protein conjugation[J]. Bioconjug Chem, 2009, 20(7):1281-1295.
[31] Tsao ML, Tian F, Schultz PG.Selective Staudinger modification of proteins containing p-azidophenylalanine[J]. Chembiochem, 2005, 6(12):2147-2149.
[32] Vabbilisetty P, Sun XL.Liposome surface functionalization based on different anchoring lipids via Staudinger ligation[J]. Organic & Biomolecular Chemistry, 2014, 12(8):1237-1244.
[33] Abe H, Wang J, Furukawa K, et al.A reduction-triggered fluorescence probe for sensing nucleic acids[J]. Bioconjug Chem, 2008, 19(6):1219-1226.
[34] Franzini RM, Kool ET.Efficient nucleic acid detection by templated reductive quencher release[J]. J Am Chem Soc, 2009, 131(44):16021-16023.
[35] Di Pisa M, Seitz O.Nucleic acid templated reactions for chemical biology[J]. ChemMedChem, 2017, 12(12):872-882.
[36] Franzini RM, Kool ET.Improved templated fluorogenic probes enhance the analysis of closely related pathogenic bacteria by microscopy and flow cytometry[J]. Bioconjug Chem, 2011, 22(9):1869-1877.
[37] Velema WA, Kool ET.Fluorogenic templated reaction cascades for RNA detection[J]. J Am Chem Soc, 2017, 139(15):5405-5411.
[38] Yu H, Zheng J, Yang S, et al.Use of a small molecule as an initiator for interchain staudinger reaction:A new ATP sensing platform using product fluorescence[J]. Talanta, 2018, 178(2018):282-286.
[39] Peng F, Gao J, Zhang W, et al.ESIPT-based highly selective fluorescent probe for organic azides through Staudinger ligation[J]. Journal of Photochemistry and Photobiology A:Chemistry, 2017.
[40] Azoulay M, Tuffin G, Sallem W, et al.A new drug-release method using the Staudinger ligation[J]. Bioorganic & medicinal chemistry Letters, 2006, 16(12):3147-3149.
[41] Xu S, Liu Y, Tai H C, et al.Synthesis of transferrin(Tf)conjugated liposomes via Staudinger ligation[J]. International Journal of Pharmaceutics, 2011, 404(1):205-210.
[42] Gobbo P, Luo W, Cho SJ, et al.Small gold nanoparticles for interfacial Staudinger-Bertozzi ligation[J]. Organic & Biomolecular Chemistry, 2015, 13(15):4605-4612.
[43] Parkhouse SM, Garnett MC, Chan WC.Targeting of polyamidoamine-DNA nanoparticles using the Staudinger ligation:attachment of an RGD motif either before or after complexation[J]. Bioorganic & Medicinal Chemistry, 2008, 16(13):6641-6650.
[44] Galán T, Prieto-Simón B, ALvira M, et al.label-free electrochemical DNA sensor using “click”-functionalized PEDOT electrodes[J]. Biosensors and Bioelectronics, 2015, 74(2015):751-756.
[45] Zhou Y, Wang S, Zhang K, et al.Visual detection of copper(II)by azide-and alkyne-functionalized gold nanoparticles using click chemistry[J]. Angewandte Chemie, 2008, 120(39):7564-7566.
[46] Palla M, Kumar S, Li Z, et al.Click chemistry based biomolecular conjugation monitoring using surface-enhanced Raman spectroscopy mapping[C]. 2016 IEEE SENSORS, 2016.
[47] Zhu K, Zhang Y, He S, et al.Quantification of proteins by functionalized gold nanoparticles using click chemistry[J]. Anal Chem, 2012, 84(10):4267-4270.
[48] Qi H, Ling C, Huang R, et al.Functionalization of single-walled carbon nanotubes with protein by click chemistry as sensing platform for sensitized electrochemical immunoassay[J]. Electrochimica Acta, 2012, 63(2012):76-82.
[49] Fratila RM, Navascuez M, Idiago-López J, et al.Covalent immobilisation of magnetic nanoparticles on surfaces via strain-promoted azide-alkyne click chemistry[J]. New Journal of Chemistry, 2017, 41(19):10835-10840.