近红外二区荧光探针在生物成像领域的研究进展

doi:10.11944/j.issn.1000-0518.2019.02.180116

摘要/Abstract

摘要：

荧光技术具有操作简便、分辨率高且可实现实时成像等特点,已被广泛应用于生物医学检测和成像领域,其中,近红外二区荧光染料(NIR-Ⅱ,10001700 nm)由于其发射波长较长,光散射和组织自发荧光干扰较少,在生物组织成像中具有更高的时空分辨率和更深的成像深度。本文主要介绍了基于近红外二区荧光探针的设计原理及其在生物成像领域的研究现状,并对其发展作了进一步展望。

关键词: 近红外二区, 荧光成像, 纳米材料, 共轭聚合物

Abstract:

Due to simple operation, high resolution and real-time imaging,fluorescence technology has been widely used in detection and bioimaging. The second near-infrared window dyes(NIR-Ⅱ, 10001700 nm) have longer emission wavelength, less interference with light scattering and tissue autofluorescence, resulting in higher temporal and spatial resolution and deeper imaging depth in tissue imaging. In this review, we mainly introduce the designed mechanism and research progress in bioimaging based on NIR-Ⅱ dyes, and further give an outlook in the following studies.

Key words: second near-infrared, fluorescenceimaging, nanomaterials, conjugated polymer

苏哲,秦文璟,白磊,孙鹏飞,余昌敏,范曲立,李林. 近红外二区荧光探针在生物成像领域的研究进展[J]. 应用化学, 2019, 36(2): 123-136.

SU Zhe,QIN Wenjing,BAI Lei,SUN Pengfei,YU Changmin,FAN Quli,LI Lin. Research Progress on Bioimaging with the Second Near-infrared Fluorescence Probes[J]. Chinese Journal of Applied Chemistry, 2019, 36(2): 123-136.

参考文献

[1]	Guo Z,Park S,Yoon J,et al. Recent Progress in the Development of Near-infrared Fluorescent Probes for Bioimaging Applications[J]. Chem Soc Rev,2014,43(1):16-29.
[2]	Shanmugam V,Selvakumar S,Yeh C S.Near-Infrared Light-Responsive Nanomaterials in Cancer Therapeutics[J]. Chem Soc Rev,2014,43(17):6254-6287.
[3]	Sun Y,Qu C,Chen H,et al. Novel Benzo-bis(1,2,5-thiadiazole) Fluorophores for in Vivo NIR-Ⅱ Imaging of Cancer[J]. Chem Sci,2016,7(9):6203-6207.
[4]	Diao S,Hong G,Antaris A L,et al. Biological Imaging Without Autofluorescence in the Second Near-infrared Region[J]. Nano Res,2015,8(9):3027-3034.
[5]	Smith A M,Mohs A M,Nie S.Tuning the Optical and Electronic Properties of Colloidal Nanocrystals by Lattice Strain[J]. Nat Nanotechnol,2009,4(1):56-63.
[6]	Pansare V J,Hejazi S,Faenza W J,et al. Review of Long-Wavelength Optical and NIR Imaging Materials:Contrast Agents, Fluorophores, and Multifunctional Nano Carriers[J]. Chem Mater,2012,24(5):812-827.
[7]	Hong G,Diao S,Chang J,et al. Through-Skull Fluorescence Imaging of the Brain in a New Near-infrared Window[J]. Nat Photonics,2014,8(9):723-730.
[8]	Robinson J T,Hong G,Liang Y,et al. In Vivo Fluorescence Imaging in the Second Near-infrared Window with Long Circulating Carbon Nanotubes Capable of Ultrahigh Tumor Uptake[J]. J Am Chem Soc,2012,134(25):10664-10669.
[9]	Iijima S.Helical Microtubules of Graphitic Carbon[J]. Nature,1991,354(6348):56-58.
[10]	Balasubramanian K,Burghard M.Chemically Functionalized Carbon Nanotubes[J]. Small,2010,1(2):180-192.
[11]	De La Zerda A,Zavaleta C,Keren S,et al. Carbon Nanotubes as Photoacoustic Molecular Imaging Agents in Living Mice[J]. Nat Nanotechnol,2008,3(9):557-562.
[12]	Cherukuri P,Gannon C J,Leeuw T K,et al. Mammalian Pharmacokinetics of Carbon Nanotubes Using Intrinsic Near-infrared Fluorescence[J]. Proc Natl Acad Sci USA,2006,103(50):18882-18886.
[13]	Chen Z,Tabakman S M,Goodwin A P,et al. Protein Microarrays with Carbon Nanotubes as Multicolor Raman Labels[J]. Nat Biotechnol,2008,26(11):1285-1292.
[14]	Welsher K,Liu Z,Sherlock S P,et al. A Route to Brightly Fluorescent Carbon Nanotubes for Near-infrared Imaging in Mice[J]. Nat Nanotechnol,2009,4(11):773-780.
[15]	Welsher K,Sherlock S P,Dai H.Deep-Tissue Anatomical Imaging of Mice Using Carbon Nanotube Fluorophores in the Second Near-infrared Window[J]. Proc Natl Acad Sci USA,2011,108(22):8943-8948.
[16]	Schramm P,Schellinger P D,Fiebach J B,et al. Comparison of CT and CT Angiography Source Images with Diffusion-Weighted Imaging in Patients with Acute Stroke Within 6 Hours after Onset[J]. Stroke,2002,33(10):2426-2432.
[17]	Wright S N,Kochunov P,Mut F,et al. Digital Reconstruction and Morphometric Analysis of Human Brain Arterial Vasculature from Magnetic Resonance Angiography[J]. Neuroimage,2013,82:170-181.
[18]	Huang C H,Chen C C,Siow T Y,et al. High-Resolution Structural and Functional Assessments of Cerebral Microvasculature Using 3D Gas DeltaR2*-mMRA[J]. PLoS One,2013,8(11):e78186.
[19]	Flohr T G,Mccollough C H,Bruder H,et al. First Performance Evaluation of a Dual-source CT(DSCT) System[J]. EurJ Radiol,2006,16(2):256-268.
[20]	Jacoby C,Boring Y C,Beck A,et al. Dynamic Changes in Murine Vessel Geometry Assessed by High-Resolution Magnetic Resonance Angiography:A 9.4T Study[J]. J Magn Reson Imaging,2008,28(3):637-645.
[21]	Paulus M J,Gleason S S,Kennel S J,et al. High Resolution X-Ray Computed Tomography:An Emerging Tool for Small Animal Cancer Research[J]. Neoplasia,2000,2(1/2):62-70.
[22]	Frangioni J.In Vivo Near-infrared Fluorescence Imaging[J]. Curr Opin Chem Biol,2003,7(5):626-634.
[23]	Horton N G,Wang K,Kobat D,et al. In Vivo Three-Photon Microscopy of Subcortical Structures within an Intact Mouse Brain[J]. Nat Photonics,2013,7(3):205-209.
[24]	Drew P J,Shih A Y,Driscoll J D,et al. Chronic Optical Access Through a Polished and Reinforced Thinned Skull[J]. Nat Methods,2010,7(12):981-984.
[25]	Yang G,Pan F,Parkhurst C N,et al. Thinned-Skull Cranial Window Technique for Long-Term Imaging of the Cortex in Live Mice[J]. Nat Protoc,2010,5(2):201-208.
[26]	Diao S,Blackburn J L,Hong G,et al. Fluorescence Imaging in Vivo at Wavelengths Beyond 1500 nm[J]. Angew Chem Int Ed,2015,54(49):14758-14762.
[27]	Kim S,Fisher B,Eisler H J,et al. Type-Ⅱ Quantum Dots:CdTe/CdSe(Core/Shell) and CdSe/ZnTe(Core/Shell) Heterostructures[J]. J Am Chem Soc,2003,125(38):11466-11467.
[28]	Nikolai G,I Igor L R,Maria R G,et al. Labeling of Biocompatible Polymer Microcapsules with Near-Infrared Emitting Nanocrystals[J]. Nano Lett,2003,3(3):369-372.
[29]	Gaponik N,Talapin D V,Rogach A L,et al. Efficient Phase Transfer of Luminescent Thiol-Capped Nanocrystals:From Water to Nonpolar Organic Solvents[J]. Nano Lett,2002,2(8):803-806.
[30]	Xie R,Peng X.Synthetic Scheme for High-Quality InAs Nanocrystals Based on Self-focusing and One-Pot Synthesis of InAs-Based Core-Shell Nanocrystals[J]. Angew Chem Int Ed,2008,47(40):7677-7680.
[31]	Liu Z,Kumbhar A,Xu D,et al.Coreduction Colloidal Synthesis of ⅢⅤ Nanocrystals:The Case of InP[J]. Angew Chem Int Ed,2008,47(19):3540-3542.
[32]	Liu W,Greytak A B,Lee J,et al. Compact Biocompatible Quantum Dots via RAFT-Mediated Synthesis of Imidazole-Based Random Copolymer Ligand[J]. J Am Chem Soc,2010,132(2):472-483.
[33]	Hyun B R,Chen H,Rey D A,et al. Near-Infrared Fluorescence Imaging with Water-Soluble Lead Salt Quantum Dots[J]. J Phys Chem B,2007,111(20):5726-5730.
[34]	Sun H,Zhang F,Wei H,et al. The Effects of Composition and Surface Chemistry on the Toxicity of Quantum Dots[J]. J Mater Chem B,2013,1(47):6485-6494.
[35]	Reiss P,Protiere M,Li L.Core/Shell Semiconductor Nanocrystals[J]. Small,2009,5(2):154-168.
[36]	Wang C,Wang Y,Xu L,et al. Facile Aqueous-Phase Synthesis of Biocompatible and Fluorescent Ag2S Nanoclusters for Bioimaging:Tunable Photoluminescence from Red to Near Infrared[J]. Small,2012,8(20):3137-3142.
[37]	Hocaoglu I,Demir F,Birer O,et al. Emission Tunable, Cyto/Hemocompatible, Near-IR-Emitting Ag2S Quantum Dots by Aqueous Decomposition of DMSA[J]. Nanoscale,2014,6(20):11921-11931.
[38]	Chen H,Li B,Zhang M,et al. Characterization of Tumor-Targeting Ag2S Quantum Dots for Cancer Imaging and Therapy in Vivo[J]. Nanoscale,2014,6(21):12580-12590.
[39]	Gu Y,Cui R,Zhang Z,et al. Ultrasmall Near-Infrared Ag2Se Quantum Dots with Tunable Fluorescence for in Vivo Imaging[J]. J Am Chem Soc,2011,134(1):79-82.
[40]	Du Y,Bing X,Tao F,et al. Near-Infrared Photoluminescent Ag2S Quantum Dots from a Single Source Precursor[J]. J Am Chem Soc,2010,132(5):1470-1471.
[41]	Zhang Y,Hong G,Zhang Y,et al.Ag2S Quantum Dot:A Bright and Biocompatible Fluorescent Nanoprobe in the Second Near-infrared Window[J]. ACS Nano,2012,6(5):3695-3702.
[42]	Shen S,Zhang Y,Peng L,et al. Matchstick-Shaped Ag2S-ZnS Heteronanostructures Preserving both UV/Blue and Near-infrared Photoluminescence[J]. Angew Chem Int Ed,2011,50(31):7115-7118.
[43]	Hong G,Robinson J T,Zhang Y,et al. In Vivo Fluorescence Imaging with Ag2S Quantum Dots in the Second Near-infrared Region[J]. Angew Chem Int Ed,2012,51(39):9818-9821.
[44]	Dong B,Li C,Chen G,et al. Facile Synthesis of Highly Photoluminescent Ag2Se Quantum Dots as a New Fluorescent Probe in the Second Near-infrared Window for in Vivo Imaging[J]. Chem Mater,2013,25(12):2503-2509.
[45]	Chen G,Tian F,Zhang Y,et al. Tracking of Transplanted Human Mesenchymal Stem Cells in Living Mice Using Near-Infrared Ag2S Quantum Dots[J]. Adv Funct Mater,2014,24(17):2481-2488.
[46]	Tan M C,Kumar G A,Riman R E,et al. Synthesis and Optical Properties of Infrared-Emitting YF3:Nd Nanoparticles[J]. J Appl Phys,2009,106(6):063118.
[47]	Naczynski D J,Tan M C,Zevon M,et al. Rare-Earth-Doped Biological Composites as in Vivo Shortwave Infrared Reporters[J]. Nat Commun,2013,4(3):1345-1346.
[48]	Liu B,Chen X,Zou Y,et al. A Benzo[1,2-b:4,5-b]difuran- and Thieno-[3,4-b]thiophene-Based Low Bandgap Copolymer for Photovoltaic Applications[J]. Polym Chem,2013,4(3):470-476.
[49]	Li G,Shrotriya V,Huang J,et al. High-Efficiency Solution Processable Polymer Photovoltaic Cells by Self-organization of Polymer Blends[J]. Nat Mater,2005,4(11):864-868.
[50]	Kawamura Y,Yanagida S,Forrest S R.Energy transfer in Polymer Electrophosphorescent Light Emitting Devices with Single and Multiple Doped Luminescent Layers[J]. J Appl Phys,2002,92(1):87-93.
[51]	Burroughes J H,Bradley D D C,Brown A R,et al. Light-Emitting Diodes Based on Conjugated Polymers[J]. Nature,1990,347(6293):539-541.
[52]	Facchetti A.π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications[J]. Chem Mater,2011,23(3):733-758.
[53]	Ong B S,Wu Y,Liu P,et al. High-Performance Semiconducting Polythiophenes for Organic Thin-Film Transistors[J]. J Am Chem Soc,2004,126(11):3378-3379.
[54]	Hong G,Zou Y,Antaris A L,et al. Ultrafast Fluorescence Imaging in Vivo with Conjugated Polymer Fluorophores in the Second Near-infrared Window[J]. Nat Commun,2014,5:4206.
[55]	Shou K,Tang Y,Chen H,et al. Diketopyrrolopyrrole-Based Semiconducting Polymer Nanoparticles for in Vivo Second Near-infrared Window Imaging and Image-Guided Tumor Surgery[J]. Chem Sci,2018,9(12):3105-3110.
[56]	Wu J,You L,Lan L,et al. Semiconducting Polymer Nanoparticles for Centimeters-Deep Photoacoustic Imaging in the Second Near-infrared Window[J]. Adv Mater,2017,29(41):1703403.
[57]	Guo B,Sheng Z,Kenry K,et al. Biocompatible Conjugated Polymer Nanoparticles for Highly Efficient Photoacoustic Imaging of Orthotopic Brain Tumors in the Second Near-infrared Window[J]. Mater Horiz,2017,4(6):1151-1156.
[58]	Jiang Y,Upputuri P K,Xie C,et al. Broadband Absorbing Semiconducting Polymer Nanoparticles for Photoacoustic Imaging in Second Near-infrared Window[J]. Nano Lett,2017,17(8):4964-4969.
[59]	Yang Q,Ma Z,Wang H,et al. Rational Design of Molecular Fluorophores for Biological Imaging in the NIR-Ⅱ Window[J]. Adv Mater,2017,29(12):1605497.
[60]	Zhu S,Yang Q,Antaris A L,et al. Molecular Imaging of Biological Systems with a Clickable Dye in the Broad 800- to 1,700-nm Near-infrared Window[J]. Proc Natl Acad Sci USA,2017,114(5):962-967.
[61]	Qian G,Zhong Z,Luo M,et al. Simple and Efficient Near-infrared Organic Chromophores for Light-Emitting Diodes with Single Electroluminescent Emission Above 1000 nm[J]. Adv Mater,2009,21(1):111-116.
[62]	Antaris A L,Chen H,Cheng K,et al. A Small-Molecule Dye for NIR-Ⅱ Imaging[J]. Nat Mater,2015,15(2):235-242.
[63]	Antaris A L,Chen H,Diao S,et al. A High Quantum Yield Molecule-Protein Complex Fluorophore for Near-infrared Ⅱ Imaging[J]. Nat Commun,2017,8:15269.
[64]	Feng Y,Zhu S,Antaris A L,et al. Live Imaging of Follicle Stimulating Hormone Receptors in Gonads and Bones Using Near Infrared Ⅱ Fluorophore[J]. Chem Sci,2017,8(5):3703-3711.
[65]	Sun Y,Zeng X,Xiao Y,et al. Novel Dual-Function Near-infrared Ⅱ Fluorescence and PET Probe for Tumor Delineation and Image-Guided Surgery[J]. Chem Sci,2018,9(8):2092-2097.
[66]	Sun Y,Ding M,Zeng X,et al. Novel Bright-Emission Small-Molecule NIR-Ⅱ Fluorophores for in Vivo Tumor Imaging and Image-Guided Surgery[J]. Chem Sci,2017,8(5):3489-3493.
[67]	Li B N,Lu L F,Zhao M Y,et al. An Efficient 1064 nm NIR-Ⅱ Excitation Fluorescent Molecular Dye for Deep-Tissue High-Resolution Dynamic Bioimaging[J]. Angew Chem Int Ed,2018,57(25):7483-7487.
[68]	Cosco E D,Caram J R,Bruns O T,et al. Flavylium Polymethine Fluorophores for Near- and Shortwave Infrared Imaging[J]. Angew Chem Int Ed,2017,56(42):13126-13129.
[69]	Chen J R,Wong J B,Kuo P Y,et al. Synthesis and Characterization of Coumarin-Based Spiropyran Photochromic Colorants[J]. Org Lett,2008,10(21):4823-4826.
[70]	Shou K,Qu C,Sun Y,et al. Multifunctional Biomedical Imaging in Physiological and Pathological Conditions Using a NIR-Ⅱ Probe[J]. Adv Funct Mater,2017,27(23):1700995.
[71]	Tao Z,Hong G,Shinji C,et al. Biological Imaging Using Nanoparticles of Small Organic Molecules with Fluorescence Emission at Wavelengths Longer than 1000 nm[J]. Angew Chem Int Ed,2013,52(49):13002-13006.
[72]	Xu G,Yan Q,Lv X,et al. Imaging of Colorectal Cancers Using Activatable Nanoprobes with Second Near-infrared Window Emission[J]. Angew Chem Int Ed,2018,57(14):3626-3630.