乏氧激活荧光探针设计、合成及应用研究进展
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摘要
介绍了肿瘤细胞的乏氧情况以及常规的肿瘤细胞乏氧检测手段,然后分别从荧光探针的设计构成、荧光探针的识别机理以及荧光探针的应用等方面对乏氧激活荧光探针进行了描述和总结,概述了构成荧光探针的常用荧光团,并详细探讨了构成荧光探针的乏氧靶向基团及其应用,重点介绍了硝基类和偶氮类两类乏氧感应基团,为新型荧光探针的设计合成提供了指引思路,提供了一种更高效、精准的肿瘤细胞的乏氧检测方法。
This article describes the hypoxic microenvironment of tumor cells and conventional methods for detecting hypoxia in tumor cells. The hypoxia-activated fluorescent probes were described in detail from the design, identification mechanism and application of fluorescent probes. The common fluorophores constituting fluorescent probes are summarized, and the hypoxic targeting groups constituting the fluorescent probes and their applications are discussed in detail. This paper focuses on two types of hypoxic sensing groups, nitro and azo.These provide guidelines for the design and synthesis of novel fluorescent probes, providing a more efficient and accurate method for detecting tumor hypoxic cells.
This article describes the hypoxic microenvironment of tumor cells and conventional methods for detecting hypoxia in tumor cells. The hypoxia-activated fluorescent probes were described in detail from the design, identification mechanism and application of fluorescent probes. The common fluorophores constituting fluorescent probes are summarized, and the hypoxic targeting groups constituting the fluorescent probes and their applications are discussed in detail. This paper focuses on two types of hypoxic sensing groups, nitro and azo.These provide guidelines for the design and synthesis of novel fluorescent probes, providing a more efficient and accurate method for detecting tumor hypoxic cells.
引文
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[13]Sun W,Chu T.In vivo click reaction between Tc-99m-labeled azadibenzocyclooctyne-MAMA and 2-nitroimidazole-azide for tumor hypoxia targeting[J].Bioorganic&Medicinal Chemistry Letters,2015,25(20):4453-4456.
[14]Kurihara R,Ikemura Y,Tanabe K.Preparation of alkyne-labeled 2-nitroimidazoles for identification of tumor hypoxia by Raman spectroscopy.[J].Bioorganic&Medicinal Chemistry Letters,2016,26(20):4892-4894.
[15]Romieu A,Chevalier A,Renard P Y.Azo-based fluorogenic probes for biosensing and bioimaging:Recent advances and upcoming challenges[J].Chemistry-An Asian Journal,2017,12(16):2008-2028.
[16]Sun L,Li G,Chen X,et al.Azo-based iridium(Ⅲ)complexes as multicolor phosphorescent probes to detect hypoxia in 3Dmulticellular tumor spheroids[J].Scientific Reports,2015,5(8):14837.
[17]Yi-Xian Y.Interaction between DNA and chiral dinuclear Ru(Ⅱ)complexes[J].Chinese Journal of Inorganic Chemistry,2008,24(8):1265-1271.
[18]None.Graphical abstract:Chem Eur J 26/2016[J].Chemistry-A European Journal,2016,22(26):8710-8720.
[19]Okkelman I A,Foley T,Papkovsky D B,et al.Multi-parametric imaging of hypoxia and cell cycle in intestinal organoid culture[J].Advances in Experimental Medicine and Biology,2017,1035(21):85-103.
[20]Dmitriev R I,Kondrashina A V,Koren K,et al.Small molecule phosphorescent probes for O2 imaging in 3D tissue models[J].Biomaterials Science,2014,2(6):853-866.
[2]Stoyanova R,Huang K,Sandler K,et al.Mapping tumor hypoxia in vivo using pattern recognition of dynamic contrast-enhanced MRI data[J].Translational Oncology,2012,5(6):437-447.
[3]Lee C T,Boss M K,Dewhirst M W.Imaging tumor hypoxia to advance radiation oncology[J].Antioxid Redox Sign,2014,21(2):313-337.
[4]Nan Y,Zhou Q,Zhao W,et al.In vivo imaging of hypoxia generation stimulated by testosterone using a micelle-based near-infrared fluorescent probe[J].Sensors and Actuators B:Chemical,2019,288(1):543-551.
[5]Belli C,Trapani D,Viale G,et al.Targeting the microenvironment in solid tumors[J].Cancer Treatment Reviews,2018,65(18):22-32.
[6]Sharma A,Arambula J F,Koo S,et al.Hypoxia-targeted drug delivery[J].Chemical Society Reviews,2019,48(suppl 5):771-813.
[7]李扬.氧化还原过程检测用荧光探针的设计、合成与性能研究[D].上海:华东理工大学,2014.
[8]Guo T,Cui L,Shen J,et al.A highly sensitive long-wavelength fluorescence probe for nitroreductase and hypoxia:Selective detection and quantification[J].Chemical Communications,2013,49(92):10820.
[9]Nakata E,Yukimachi Y,Kariyazono H.Design of a bioreductively-activated fluorescent pH probe for tumor hypoxia imaging[J].Bioorg Med Chem,2009,17(19):6952-6958.
[10]Li Z,Li X,Gao X,et al.Nitroreductase detection and hypoxic tumor cell imaging by a designed sensitive and selective fluorescent probe,7-[(5-nitrofuran-2-yl)methoxy]-3H-phenoxazin-3-one[J].Analytical Chemistry,2013,85(8):3926-3932.
[11]杨怡君,丁劲松.硝基咪唑类在肿瘤乏氧显像剂中的作用和研究进展[J].药学学报,2016,51(8):1227-1232.
[12]Micka?l Bourgeois,Rajerison H,Fran?ois Guerard,et al.Contribution of[164Cu]-ATSM PET in molecular imaging of tumour hypoxia compared to classical[18F]-MISO-A selected review[J].Nuclear Medicine Review.Central&Eastern Europe:journal of Bulgarian,Czech,Macedonian,Polish,Romanian,Russian,Slovak,Yugoslav societies of nuclear medicine and Ukrainian Society of Radiology,2011,14(2):90-95.
[13]Sun W,Chu T.In vivo click reaction between Tc-99m-labeled azadibenzocyclooctyne-MAMA and 2-nitroimidazole-azide for tumor hypoxia targeting[J].Bioorganic&Medicinal Chemistry Letters,2015,25(20):4453-4456.
[14]Kurihara R,Ikemura Y,Tanabe K.Preparation of alkyne-labeled 2-nitroimidazoles for identification of tumor hypoxia by Raman spectroscopy.[J].Bioorganic&Medicinal Chemistry Letters,2016,26(20):4892-4894.
[15]Romieu A,Chevalier A,Renard P Y.Azo-based fluorogenic probes for biosensing and bioimaging:Recent advances and upcoming challenges[J].Chemistry-An Asian Journal,2017,12(16):2008-2028.
[16]Sun L,Li G,Chen X,et al.Azo-based iridium(Ⅲ)complexes as multicolor phosphorescent probes to detect hypoxia in 3Dmulticellular tumor spheroids[J].Scientific Reports,2015,5(8):14837.
[17]Yi-Xian Y.Interaction between DNA and chiral dinuclear Ru(Ⅱ)complexes[J].Chinese Journal of Inorganic Chemistry,2008,24(8):1265-1271.
[18]None.Graphical abstract:Chem Eur J 26/2016[J].Chemistry-A European Journal,2016,22(26):8710-8720.
[19]Okkelman I A,Foley T,Papkovsky D B,et al.Multi-parametric imaging of hypoxia and cell cycle in intestinal organoid culture[J].Advances in Experimental Medicine and Biology,2017,1035(21):85-103.
[20]Dmitriev R I,Kondrashina A V,Koren K,et al.Small molecule phosphorescent probes for O2 imaging in 3D tissue models[J].Biomaterials Science,2014,2(6):853-866.