nav emailalert searchbtn searchbox tablepage yinyongbenwen piczone journalimg journalInfo journalinfonormal searchdiv searchzone qikanlogo popupnotification paper paperNew
2024, 04, v.44 12-22
生物正交反应在microRNAs诊疗中的应用研究
基金项目(Foundation): 重庆市教委科学技术研究项目(青年)(KJQN202201168)
邮箱(Email): tangyaqin@cqut.edu.cn;
DOI:
发布时间: 2024-12-15
出版时间: 2024-12-15
移动端阅读
摘要:

miRNA作为一种非编码小分子RNA,在转录后调控基因表达中起着重要作用,其异常表达可诱发多种疾病。大量研究表明,miRNAs的异常表达是由于多种肿瘤类型的基因突变导致,产生的miRNAs也可通过相关基因的调节,进一步促进肿瘤的发展。因此,基于miRNAs的研究是近年的研究热点;其中,靶向miRNAs的诊疗研究对于肿瘤的治疗和研究具有重要意义。此外,近年来,生物正交反应由于其反应的专属性、高效性以及温和性在miRNAs诊疗中取得了重要进展。因此,该文详细总结了生物正交反应的类型、反应机理以及反应条件;在此基础上,进一步讨论了生物正交反应在miRNAs诊疗中的应用,以期为后续miRNAs诊疗研究提供理论和技术支持。

Abstract:

MiRNAs, as a small non-coding molecule, play a crucial role in the post-transcriptional regulation of gene expression, and their abnormal expression can lead to many diseases. Numerous studies have demonstrated that gene mutations in various types of tumors can lead to the abnormal expression of miRNAs, which can then be further enhanced by the regulation of related genes to further facilitate tumor progression. Therefore, miRNArelated research has become a popular topic in recent years, especially in terms of diagnosis and treatment. In addition, biorthogonal reactions have made great progress in the diagnosis and treatment of miRNAs due to their specificity, efficiency, and gentleness. This review provides a comprehensive summary of the types, reaction mechanisms, and reaction conditions of biological orthogonal reactions. Furthermore, it discusses the application of biorthogonal reactions in the diagnosis and treatment of miRNAs, in order to provide theoretical and technical support for future miRNA diagnosis and treatment research.

参考文献

[1]李达秀,向云.MicroRNA高灵敏检测及成像方法的研究进展[J].化学传感器,2019,39(04):1-13.

[2]Calin G A,Croce C,M.MicroRNA signatures in human cancers[J].Nat.Rev.Cancer.,2006,611:857-866.

[3]Li L,Chen J G,Chen X,et al.Serum miRNAs as predictive and preventive biomarker for pre-clinical hepatocellular carcinoma[J].Cancer Lett.,2016,:234-240.

[4]Agard N J,Prescher J A,Bertozzi C R.A Strain-Promoted[3+2] Azide-Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems[J].J.Am.Chem.Soc.,2004,12646:15046-15047.

[5]Battigelli A,Almeida B,Shukla A.Recent Advances in Bioorthogonal Click Chemistry for Biomedical Applications[J].Bioconjug.Chem.,2022,3 3(2):263-271.

[6]Mattay J,Dittmar M,Rentmeister A.Chemoenzymatic strategies for RNA modification and labeling[J]. Curr.Opin.Chem.Biol.,2021,63:46-56.

[7]Wu D,Yang K,Zhang Z K,et al.Metal-free bioorthogonal click chemistry in cancer theranostics[J].Chem.Soc.Rev.,2022,514:1336-1376.

[8]Sletten E M,Bertozzi C R.Bioorthogonal Chemistry:Fishing for Selectivity in a Sea of Functionality[J].Angew.Chem.Int.Ed.Engl.,2009,48(38):6974-98.

[9]Yang M,Jalloh A S,Wei W,et al.Biocompatible click chemistry enabled compartment-specific pH measurement inside E.coli[J].Nat.Commun.,2014,5:4981.

[10]Rondon A,Degoul F.Antibody Pretargeting Based on Bioorthogonal Click Chemistry for Cancer Imaging and Targeted Radionuclide Therapy[J].Bioconjug.Chem.,2020,31(2):159-173.

[11]Lee D E,Na J H,Lee S,et al.Facile method to radiolabel glycol chitosan nanoparticles with 64Cu via copper-free click chemistry for MicroPET imaging[J].Mol.Pharm.,2013,10(6):2190-8.

[12]Bosch S M V D,Rossin R,Verkerk P R,et al.Evaluation of strained alkynes for Cu-free click reaction in live mice[J].Nucl.Med.Biol.,2013,40(3):415-423.

[13]Au K M,Tripathy A,Lin C P,et al.Bespoke Pretargeted Nanoradioimmunotherapy for the Tre atment of Non-Hodgkin Lymphoma[J].ACS.Nano.,2018,12(2):1544-1563.

[14]Ning X H,Temming R P,Dommerholt J,et al.Protein Modification by Strain-Promoted Alkyne-Nitrone Cycloaddition[J].Angew.Chem.Int.Ed.Engl.,2010,49(17):3065-8.

[15]Mckay C S,Blake J A,Cheng J,et al.Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes for labeling human cancer cells[J].Chem.Commun.(Camb).,2011,47(36):10040-2.

[16]Blackman M L,Royzen M,Fox J M.Tetrazine Ligation:Fast Bio conjugation Based on Inverse-Electron-Demand Diels-Alder Reactivity[J].J.Am.Chem.Soc.,2008,130(41):13518-13519.

[17]Selvaraj R,Fox J M.An efficient and mild oxidant for the synthesis of s-tetrazines[J].Tetrahedron Lett.,2014,55(34):4795-4797.

[18]Taylor M T,Blackman M L,Dmitrenko O,et al.Design and synthesis of highly reactive dienophiles for the tetrazine-trans-cyclooctene ligation[J].J.Am.Chem.Soc.,2011,133(25):9646-9649.

[19]Oliveira B L,Guo Z,Bernardes G.J.L.Inverse electron demand Diels-Alder reactions in chemical biology[J].Chem.Soc.Rev.,46(16):4895-4950.

[20]Nakahara H,Hagimori M,et al.Inverse electrondemand diels-alder reactions of tetrazine and norbornene at the air-water interface[J].Colloids Surf.B.,2022,211:112333.

[21]Maggi A,Ruivo E,Fissers J,et al.Development of a novel antibo dy-tetrazine conjugate for bioorthogonal pretargeting[J].Org.Biomol.Chem.,2016,14(31):7544-51.016,1431

[22]Selvaraj R,Fox J M.Trans-Cyclooctene-a stable,voracious die nophile for bioorthogonal labeling[J].Curr.Opin.Chem.Biol.,2013,17(5):753-60.

[23]Yu Z P,Pan Y C,Wang Z Y,et al.Genetically Encoded Cyclopropene Directs Rapid,Photo clickChemistry-Mediated Protein Labeling in Mammalian Cells[J].Angew.Chem.Int.Ed.Engl.,2012,51(42):10600-4.

[24]Lang K,Davis L,Wallace S,et al.Genetic encoding of bicyclononynes and trans-cyclooctenes for site-specific protein labeling in vitro and in live mammalian cells via rapid fluorogenic diels-alder reactions[J].J.Am.Chem.Soc.,2012,134(25):10317-20.

[25]Maggi A,Ruivo E,Fissers J,et al.Development of a novel antibody-tetrazine conjugate for bioorthogonal pretargeting[J].Org.Biomol.Chem.,2016,14(31):7544-51.

[26]Yarema K.J,Mahal L.K,Bruehl R.E,et al.Metabolic delivery of ketone groups to sialic acid residues.Application To cell surface gly coform engineering[J].J.Biol.Chem.,1998,273(47):31168.

[27]Tenno M,Ohtsubo K,Hagen F.K,et al.Initiation of Protein O Glycosylation by the Polypeptide GalNAcT-1in Vascular Biology and Humoral Immunity[J].Mol.Cell.Biol.,2007,27(24):8783-8796.

[28]Nilsson B.L,Kiessling L.L,Raines R.T.Staudinger Ligation:A Peptide from a Thioester and Azide[J].Org.Lett., 2000,2(13):1939-1941.

[29]Hymbaugh Bergman S J,Comstock L R.N-mustard analogs of S-adenosyl-L-methionine as biochemical probes of protein arginine methylation[J].Bioorg.Med.Chem.,2015,23(15):5050-5055.

[30]Igata Y,Saito-Tarashima N,Matsumoto D,et al.A'catch and release'strategy towards HPLCfree purification of synthetic oligonucleotides by a combination of the strain-promoted alkyne-azide cycloaddition and the photocleavage[J].Bioorg.Med.Chem.,2017,25(21):5962-5967.

[31]Saxon E,Armstrong J I,Bertozzi C.R.A"Traceless"Staudinger Ligation for the Chemoselective Synthesis of Amide Bonds[J].Org.Lett.,2000,2(14):2141-2143.

[32]Soellner M B,Nilsson B L,Raines R.T.Reaction mechanism and kinetics of the traceless Staudinger ligation[J].J.Am.Chem.Soc.,2006,128(27):8820-8.

[33]Bednarek C,Wehl I,Jung N,et al.The Staudinger Ligation.Chemical reviews[J].Chem.Rev.,2020,120(10):4301-4354.

[34]Alonso-de Castro S,Ruggiero E,et al.Riboflavin as a bio orthogonal photocatalyst for the activation of a PtIV prodrug[J].Chem.Sci.2017,8(6):4619-4625.

[35]Yu Z P,Pan Y C,Wang Z Y,et al.Genetically Encoded Cyclopropene Directs Rapid,Photoclick-ChemistryMediated Protein Labeling in Mammalian Cells[J].Angew.Chem.Int.Ed.Engl.,2012,51(42):10600-4.

[36]Dong J J,Krasnova L,Finn M.G,et al.Sulfur(Ⅵ)Fluoride Exchange(SuFEx):Another Good Reaction for Click Chemistry[J].Angew.Chem.Int.Ed.Engl.,2014,53(36):9430-48.

[37]邓祥熙,赵聪慧,薛倩,等.生物正交点击化学在生物成像中的应用[J].化学传感器,2022,4202:19-31.

[38]Zeng Y,Ramya T.N.C,Dirksen A,et al.Highefficiency labeling of sialylated glycoproteins on living cells[J].Nat.Methods.,2009,6(3):207-9.

[39]Hou Z.F,Wang Y,Wan C,et al.Sulfonium Triggered Alkyne-Azide Click Cycloaddition[J].Org.Lett.,2022,24(7):1448-1453.

[40]Tavakoli S,Liu Y.F,Potts J.L,et al.Click chemistrybased amplification and detection of endogenous RNA and DNA molecules in situ using clampFISH probes[J].Methods.Enzymol.,2020,641:459-476.

[41]Gubu A,Su W,Zhao X,et al.Circular Antisense Oligonucleotides for Specific RNase-H-Mediated microRNA Inhibition with Reduced Off-Target Effects and Nonspecific Immunostimulation[J].J.Med.Chem.,2021,64(21):16046-16055.

[42]Chen,Ming,Wang,et al.Tension promoted circular probe for highly selective microRNA detection and imaging[J].Bio sens.Bioelectron.,2016,85:151-156.

[43]Tang Y Q,Wang T T,He X,et al.Highly sensitive and selective miRNA detection based on closed ring probe and multiple signal amplification[J].Chem.Commun.(Camb).,2016,52(96):13905-13908.

[44]Gupta M,Levine S.R,Spitale R C.Probing Nascent RNA with Metabolic Incorporation of Modified Nucleosides[J].Acc.Chem.Res.,2022,55(18):2647-2659.

[45]Plenz M,Meyer M F,Grumm F,et al.Impact of Lossy Compression Techniques on the Impedance Determination[J].Energies.,2020,13(14):1-12.

[46]Hall D G,Rybak T,Verde let T.Multicomponent Hetero-[4+2] Cycloaddition/Allylboration Reaction:From Natural Product Synthesis to Drug Discovery[J].Acc.Chem.Res.,2016,49(11):2489-2500.

[47]Loehr M.O,Luedtke N W.A Kinetic and Fluorogenic Enhancement Strategy for Labeling of Nucleic Acids[J].Angew.Chem.Int.Ed.Engl.,2022,61(22):202112931.

[48]Lorenz D A,Garner A L.A click chemistry-based microRNA maturation assay optimized for high-throughput screening[J].Chem.Commun.(Camb).,2016,52(53):8267-70.

[49]Liu L,Zhang D,Johnson M,et al.Light-activated tetrazines enable live-cell spatiotemporal control of bioorthogonal reactions[J].Nat.Chem.,2022,14(9):1078-1085.

[50]Gorska K,Winssinger N.Rapid miRNA imaging in cells using fluorogenic templated Staudinger reaction between PNA-based probes[J].Methods.Mol.Biol.,2014,1050:179-92.

[51]Morihiro K,Ankenbruck N,Lukasak B,et al.Small Molecule Release and Activation through DNA Computing[J].J.Am.Chem.Soc.,2017,139(39):13909-13915.

[52]Krell K,Wagenknecht H.A.Fluorogenic and Bioorthogonal Modification of RNA Using Photoclick Chemistry[J].Biomolecules.,2020,10(3):480.

[53]Nainar S,Kubota M,Mcnitt C,et al.Temporal Labeling of Nascent RNA Using Photoclick Chemistry in Live Cells.[J].J.Am.Chem.Soc.,2017,139(24):8090-8093.

[54]Huang L,Chen Y,Chen L,et al.Photo-clickable micro RNA for in situ fluorescence labeling and imaging of micro RNA in living cells.[J].Chem.Comm.(Camb).,2017,53(4 8):6452-6455.

基本信息:

中图分类号:R313;O657.3

引用信息:

[1]钟敏,周子为,李达秀,等.生物正交反应在microRNAs诊疗中的应用研究[J].化学传感器,2024,44(04):12-22.

基金信息:

重庆市教委科学技术研究项目(青年)(KJQN202201168)

发布时间:

2024-12-15

出版时间:

2024-12-15

引用

GB/T 7714-2015 格式引文
MLA格式引文
APA格式引文