留言板

尊敬的读者、作者、审稿人, 关于本刊的投稿、审稿、编辑和出版的任何问题, 您可以本页添加留言。我们将尽快给您答复。谢谢您的支持!

姓名
邮箱
手机号码
标题
留言内容
验证码

光交联技术的生物应用研究进展

孙瑞 高银佳 史海斌

孙瑞, 高银佳, 史海斌. 光交联技术的生物应用研究进展[J]. 中国光学(中英文), 2018, 11(3): 444-458. doi: 10.3788/CO.20181103.0444
引用本文: 孙瑞, 高银佳, 史海斌. 光交联技术的生物应用研究进展[J]. 中国光学(中英文), 2018, 11(3): 444-458. doi: 10.3788/CO.20181103.0444
SUN Rui, GAO Yin-jia, SHI Hai-bin. Advances in biological application of photo-crosslinking technique[J]. Chinese Optics, 2018, 11(3): 444-458. doi: 10.3788/CO.20181103.0444
Citation: SUN Rui, GAO Yin-jia, SHI Hai-bin. Advances in biological application of photo-crosslinking technique[J]. Chinese Optics, 2018, 11(3): 444-458. doi: 10.3788/CO.20181103.0444

光交联技术的生物应用研究进展

基金项目: 

国家重点研发计划 2016YFC0101200

国家自然科学基金 21572153

江苏省高校自然科学研究重大项目 15KJA310004

苏州市科技计划 SYG201520

详细信息
    作者简介:

    孙瑞(1992—),男,江苏徐州人,硕士研究生,2015年于南京工业大学获得学士学位,主要从事光响应型分子探针构建及在肿瘤诊疗方面的应用基础研究。E-mail:20154220015@stu.suda.edu.cn

    史海斌(1978—),男,山西长治人,教授,博士(新加坡国立大学),博士后(美国斯坦福大学)。主要从事分子影像探针的构建及生物医学应用研究。E-mail:hbshi@stu.suda.edu.cn

  • 中图分类号: O621.37

Advances in biological application of photo-crosslinking technique

Funds: 

National Program on Key Basic Research Projects of China 2016YFC0101200

National Natural Science Foundation of China 21572153

Major projects of Natural Science Research in Universities in Jiangsu Province 15KJA310004

Science and Technology Plan of Suzhou City SYG201520

More Information
  • 摘要: 光交联反应作为一种快速、简单和时空可控的交联工具广泛地应用于化学、生物、医学和材料等不同研究领域。本文详细介绍了常用的小分子光交联基团的结构、分类及反应机理,重点综述了光交联技术在生物医学领域的应用研究,并对其应用前景进行了展望。目前大多光交联基团仅对紫外和可见光具有敏感性,紫外和可见光穿透力弱、组织吸收强和散射等问题严重限制了该技术在生物体内的应用研究。因此,进一步研究光交联技术在生物体系的应用和开发长波长光(如近红外或远红外光)介导的新交联技术对于药物研发和疾病诊疗具有重要的科学意义。

     

  • 图 1  光交联反应基团分类[12]

    Figure 1.  Commonly used photolabeling reactive species[12]

    图 2  光交联探针标记蛋白质示意图

    Figure 2.  Schematic diagram of protein labeling by photo-crosslinking probes

    图 3  3种光交联分子探针:3a[25]、3b[26]和3c[28]

    Figure 3.  Three kinds of photo-crosslinking probes:3a[25], 3b[26]and 3c[28]

    图 4  (a) 光交联分子探针G的分子结构;(b)筛选分析和确定G15和G16的IC50值;(c)寄生感染血红细胞与抑制剂G15和G16共孵育后细胞成像图片[29]

    Figure 4.  (a)Structure of the probe G. (b)In situ screening assay and determination of the IC50 values of G15 and G16. (c)Representative images of parasite-infected RBCs treated with G15 and G16[29]

    图 5  (a) 利用光交联分子探针研究达沙替尼和星形孢菌素的靶标蛋白示意图;(b)光交联分子探针DA-1和DA-2的分子结构[31];(c)光交联分子探针STS-1的分子结构[32]

    Figure 5.  (a)Overall strategy of proteome profiling of potential cellular targets of dasatinib and staurosporine using photo-crosslinking probes. Structure of the probe(b) DA-1, DA-2[31] and (c)STS-1[32]

    图 6  利用光交联技术和生物正交反应标记蛋白质示意图[33-35]

    Figure 6.  Photo-crosslinking probe labeling strategies using photo-crosslinkers and bioorthogonal handles[33-35]

    图 7  3种光交联底物类似物:ManNDAz, SiaDAz[39]和pBpa[41]

    Figure 7.  Three types of photo-crosslinking substrate analogue:ManNDAz, SiaDAz[39] and pBpa[41]

    图 8  光交联分子探针DiZSek标记策略[43]

    Figure 8.  Scheme of bait and prey protein via DiZSek[43]

    图 9  (a) 光交联DNA分子探针构建及其蛋白标记[46];(b)光交联核苷类似物DBN标记[47]

    Figure 9.  (a)Development of DNA probe with diazirine and the diazirine-modified DNA to bind proreins[46]; (b)Diazirine-based nucleoside analogue(DBN, B) can form a DNA interstrand cross-link upon UV irradiation[47]

    图 10  (a) 利用3-三氟甲基-3-苯基二吖丙啶功能化修饰碳纳米管[54]和(b)金刚石[55];(c)光交联磷盐分子构建疏水性涂料[56]

    Figure 10.  (a)Functionalization of carbon nanotubes[54] and (b)micro-diamond using 3-trifluoromethyl-3-phenyldiazirine[55]; (c)diazirine modified specific phosphonium salts to prepare robust hydrophobic coatings[56]

    图 11  光交联荧光分子探针标记二氧化硅纳米颗粒[58]

    Figure 11.  Schematic illustration of light-triggered fluorescent labeling of silica nanoparticles[58]

    图 12  (a) 光诱导金纳米颗粒自组装;(b)老鼠肿瘤部位光声成像及对应光声信号值;(c)光热治疗图片[62]

    Figure 12.  (a)Schematic illustration of light-triggered assembly of gold nanoparticles; (b)photoacustic imaging and quantifed photoacustic signal and (c)photothermal therapy of the tumorous sites of mice[62]

  • [1] 刑其毅, 徐瑞秋, 裴伟伟, 等.基础有机化学(第三版, 下册)[M].北京:高等教育出版社, 2005:712-746.

    XING Q Y, WU R Q, PEI W W, et al.. Basic Organic Chemistry[M]. Beijing:Higher Education Press, 2005:712-746.(in Chinese)
    [2] SINGH A, THORNTON E R, WESTHEIMER F H. The photolysis of diazoactylchymotrypsin[J]. Journal of Biological Chemistry, 1962, 237(9):3006-3008.
    [3] SUMRANJIT J, CHUNG S J. Recent advances in target characterization and identification by photoaffinity probes[J]. Molecules, 2013, 18(9):10425-40451. doi: 10.3390/molecules180910425
    [4] XIA Y, PENG L. Photoactivatable lipid probes for studying biomembranes by photoaffinity labeling[J]. Chemical Reviews, 2013, 113(10):7880-7929. doi: 10.1021/cr300419p
    [5] HATANAKA Y. Development and leading-edge application of innovative photoaffinity labeling[J]. Chemical & Pharmaceutical Bulletin, 2015, 46(1):1-12.
    [6] DAS J. Aliphatic diazirines as photoaffinity probes for proteins:recent developments[J]. Chemical Reviews, 2011, 111(8):4405-4417. doi: 10.1021/cr1002722
    [7] ITO Y. Photoimmobilization for microarrays[J]. Biotechnology Progress, 2006, 22(4):924-932. doi: 10.1021/bp060143a
    [8] ZHAO C W, ZHANG Z D, YANG W T. A remote photochemical reaction for surface modification of polymeric substrate[J]. Journal of Polymer Science Part A-polymer Chemistry, 2012, 50(18):3698-3702. doi: 10.1002/pola.v50.18
    [9] LAWRENCE E J, WILDGOOSE G G, ALDOUS L, et al.. 3-aryl-3-(trifluoromethyl)diazirines as versatile photoactivated "linker" molecules for the improved covalent modification of graphitic and carbon nanotube surfaces[J]. Chemistry of Materials, 2011, 23(16):3740-3751. doi: 10.1021/cm201461w
    [10] 孟想, 杨蕊竹, 刘东旭, 等.紫外固化型聚合物水凝胶的周期图案形成及其调控[J].中国光学, 2012, 5(4):436-443. http://www.chineseoptics.net.cn/CN/abstract/abstract8772.shtml

    MENG X, YANG R ZH, LIU D X, et al.. Formation and adjustment of cycle pattern of UV-curable polymeric hydeogel[J]. Chinese Optics, 2012, 5(4):436-443.(in Chinese) http://www.chineseoptics.net.cn/CN/abstract/abstract8772.shtml
    [11] 刘东旭, 夏虹, 孙允陆, 等.飞秒激光直写生物凝胶模板原位合成纳米粒子[J].中国光学, 2014, 7(4):608-615. http://www.chineseoptics.net.cn/CN/abstract/abstract9150.shtml

    LIU D X, XIA H, SUN Y L, et al.. Femtosecond laser direct writing bio-gel template for in situ synthesis of nanoparticles[J]. Chinese Optics, 2014, 7(4):608-615.(in Chinese) http://www.chineseoptics.net.cn/CN/abstract/abstract9150.shtml
    [12] FLEMING S A. Chemical reagents in photoaffinity labeling[J]. Tetrahedron, 1995, 51(46):12479-12520. doi: 10.1016/0040-4020(95)00598-3
    [13] BORDEN W T, GRITSAN N P, HADAD C M, et al.. The interplay of theory and experiment in the study of phenylnitrene[J]. Accounts of Chemical Research, 2000, 33(11):765-771. doi: 10.1021/ar990030a
    [14] PLATZ M S. Comparison of phenylcarbene and phenyinitrene[J]. Accounts of Chemical Research, 1995, 28(12):487-492. doi: 10.1021/ar00060a004
    [15] BLENCOWE A, HAYES W. Development and application of diazirine in biological and synthetic macromolecular systems[J]. Soft Matter, 2005, 1(3):178-205. doi: 10.1039/b501989c
    [16] AMBROZ H B, KEMP T J. Aryl cation-new light on old intermediates[J]. Chemical Society Reviews, 1979, 8(3):353-365. doi: 10.1039/cs9790800353
    [17] KOTZYBA-HIBERT F, KAPFER I, GOELDNER M. Recent trends in photoaffinity labeling[J]. Angewandte Chemie International Edition, 1995, 34(12):1296-1312. doi: 10.1002/(ISSN)1521-3773
    [18] DORMAN G, PRESTWICH G D. Benzophenone photophores in biochemistry[J]. Biochemistry, 1994, 33(19):5661-5673. doi: 10.1021/bi00185a001
    [19] DORMAN G, PRESTWICH G D, ELLIOTT J T, et al.. Benzophenone photoprobes for phosphoinositides, peptides and drugs[J]. Photochem Photobiol, 1997, 65(22):222-234.
    [20] AGARWAL S, BELL C M, ROTHBART S B, et al.. AMP-activated Protein Kinase(AMPK) Control of mTORC1 Is p53-and TSC2-independent in pemetrexed-treated carcinoma cells[J]. Journal of Biological Chemistry, 2015, 290(46):27473-27486. doi: 10.1074/jbc.M115.665133
    [21] BRODIE N I, MAKEPEACE K A T, PETROTCHENKO E V, et al.. Isotopically-coded short-range hetero-bifunctional photo-reactive crosslinkers for studying protein structure[J]. Journal of Proteomics, 2015, 118:12-20. doi: 10.1016/j.jprot.2014.08.012
    [22] YABE T, HOSODA-YABE R, SAKAI H, et al.. Development of a photoreactive probe-based system for detecting heparin[J]. Analytical Biochemistry, 2015, 472:1-6. doi: 10.1016/j.ab.2014.11.007
    [23] GUO H J, LI Z Q. Developments of bioorthogonal handle-containing photo-crosslinkers for photoaffinity labeling[J]. Med. Chem. Commun., 2017, 8(8):1585-1591. doi: 10.1039/C7MD00217C
    [24] FUNG S K, ZOU T T, CAO B, et al.. Cyclometalated gold(Ⅲ) complexes containing N-Heterocyclic carbene ligands engage multiple anti-cancer molecular targets[J]. Angewandte Chemie International Edition, 2017, 56(14):3892-3896. doi: 10.1002/anie.201612583
    [25] SCHWANSTECHER M, LÖSER S, CHUDZIAK F, et al.. Identification of a 38-kDa high affinity sulfonylurea-binding peptide in insulin-secreting cells and cerebral cortex[J]. Journal of Biological Chemistry, 1994, 269(27):17768-17771. http://cn.bing.com/academic/profile?id=cf1479bf74421fb56fa1e457e02a6b59&encoded=0&v=paper_preview&mkt=zh-cn
    [26] FRICK W, BAUERSCH FER A, BAUER J, et al.. Synthesis of a biotin-tagged photoaffinity probe of 2-azetidinone cholesterol absorption inhibitors[J]. Bioorganic & Medicinal Chemistry, 2003, 11(8):1639-1642. http://cn.bing.com/academic/profile?id=6952531eeab909814cc395b1535c79ac&encoded=0&v=paper_preview&mkt=zh-cn
    [27] ROTH M, CHEN W Y. Sorting out functions of sirtuins in cancer[J]. Oncogene, 2014, 33(13):1609-1620. doi: 10.1038/onc.2013.120
    [28] SEIFERT T, MALO M, LENGQVIST J, et al.. Identification of the binding site of chroman-4-one-based sirtuin 2-selective inhibitors using photoaffinity labeling in combination with tandem mass spectrometry[J]. Journal of Medicinal Chemistry, 2016, 59(23):10794-10799. doi: 10.1021/acs.jmedchem.6b01117
    [29] LIU K, SHI H B, XIAO H G, et al.. Functional profiling, identification and inhibition of plasmepsins in intraerythrocytic malaria parasites[J]. Angewandte Chemie International Edition, 2009, 48(44):8293-8297. doi: 10.1002/anie.200903747
    [30] SHI H B, LIU K, XU A, et al.. Small molecule microarray-facilitated screening of affinity-based probes(AfBPs) for γ-secretase[J]. Chemical Communications, 2009, 33(33):5030-5032. http://cn.bing.com/academic/profile?id=a3de8353cfadaba8314c03dd01b9bdf5&encoded=0&v=paper_preview&mkt=zh-cn
    [31] SHI H B, ZHANG C J, CHEN G Y, et al.. Cell-based proteome profiling of potential dasatinib targets by use of affinity-based probes[J]. Journal of the American Chemical Society, 2012, 134(6):3001-3014. doi: 10.1021/ja208518u
    [32] SHI H B, CHENG X M, YAO S Q, et al.. Proteome profiling reveals potential cellular targets of staurosporine using a clickable cell-permeable probe[J]. Chemical Communications, 2011, 47(40):11306-11308. doi: 10.1039/c1cc14824a
    [33] LI Z Q, HAO P L, LI L, et al.. Design and synthesis of minimalist terminal alkyne-containing diazirine photo-crosslinkers and their incorporation into kinase inhibitors for cell-and tissue-based proteome profiling[J]. Angewandte Chemie International Edition, 2013, 52(33):8551-8556. doi: 10.1002/anie.201300683
    [34] LI Z Q, WANG D Y, LI L, et al.. "Minimalist" cyclopropene-containing photo-cross-linkers suitable for live-cell imaging and affinity-based protein labeling[J]. Journal of the American Chemical Society, 2014, 136(28):9990-9998. doi: 10.1021/ja502780z
    [35] LI Z Q, QIAN L H, YAO S Q, et al.. Tetrazole photoclick chemistry:reinvestigating its suitability as a bioorthogonal reaction and potential applications[J]. Angewandte Chemie International Edition, 2016, 55(6):2002-2006. doi: 10.1002/anie.201508104
    [36] YU S H, BOYCE M, WANDS A M, et al.. Metabolic labeling enables selective photocrosslinking of O-GlcNAc-modified proteins to their binding partners[J]. Proceedings of the National Academy of Sciences of the United States of America, 2012, 109(13):4834-4839. doi: 10.1073/pnas.1114356109
    [37] KRISHNAMURTHY M, DUGAN A, NWOKOYE A, et al.. Caught in the act:covalent crosslinking captures activator-coactivator interactions in vivo[J]. ACS Chemical Biology, 2016, 6(12):1321-1326. http://cn.bing.com/academic/profile?id=31b2f23a05790eebfbae77e5e0ad513b&encoded=0&v=paper_preview&mkt=zh-cn
    [38] SONG C X, HE C. Bioorthogonal labeling of 5-hydroxymethylcytosine in genomic DNA and diazirine-based DNA photo-cross-linking probes[J]. Accounts of Chemical Research, 2011, 44(9):709-717. doi: 10.1021/ar2000502
    [39] AND Y T, KOHLER J J. Photoactivatable crosslinking sugars for capturing glycoprotein interactions[J]. Journal of the American Chemical Society, 2008, 130(11):3278-3279. doi: 10.1021/ja7109772
    [40] BOND M R, WHITMAN C M, KOHLER J J. Metabolically incorporated photocrosslinking sialic acid covalently captures a ganglioside-protein complex[J]. Molecular Biosystems, 2010, 6(10):1796-1799. doi: 10.1039/c0mb00069h
    [41] YU D, WOWOR A J, COLE J L, et al.. Defining the Escherichia coli SecA dimer interface residues through in vivo site-specific photo-cross-linking[J]. Journal of Bacteriology, 2013, 195(12):2817-2825. doi: 10.1128/JB.02269-12
    [42] ZHANG M, LIN S, SONG X, et al.. A genetically incorporated crosslinker reveals chaperone cooperation in acid resistance[J]. Nature Chemical Biology, 2011, 7(10):671-677. doi: 10.1038/nchembio.644
    [43] LIN S, HE D, LONG T, et al.. Genetically encoded cleavable protein photo-cross-linker[J]. Journal of the American Chemical Society, 2014, 136(34):11860-11863. doi: 10.1021/ja504371w
    [44] YANG Y, SONG H P, HE D, et al.. Genetically encoded protein photocrosslinker with a transferable mass spectrometry-identifiable label[J]. Nature Communications, 2016, DOI: 10.1038/ncomms12299.
    [45] YAN H, ZHONG G, X U G, et al.. Sodium taurocholate cotransporting polypeptide is a functional receptor for human hepatitis B and D virus[J]. Elife, 2012, 1(1):e00049-e00049. http://cn.bing.com/academic/profile?id=305aba0d2c29d37474fb444fc26914bc&encoded=0&v=paper_preview&mkt=zh-cn
    [46] SHIGDEL U K, ZHANG J L, HE C. Diazirine-based DNA photo-cross-linking probes for the study of protein DNA interactions[J]. Angewandte Chemie International Edition, 2008, 47(1):90-93. doi: 10.1002/(ISSN)1521-3773
    [47] QIU Z H, LU L H, JIAN X, HE C. A diazirine-based nucleoside analogue for efficient DNA interstrand photocross-linking[J]. Journal of the American Chemical Society, 2008, 130(44):14398-14399. doi: 10.1021/ja805445j
    [48] NAKAMOTO K, UENO Y. Diazirine-containing RNA photo-cross-linking probes for capturing microRNA targets[J]. The Journal of Organic Chemistry, 2014, 79(6):2463-2472. doi: 10.1021/jo402738t
    [49] YAN M D, REN J. Covalent immobilization of ultrathin polymer films by thermal activation of perfluorophenyl azide[J]. Chemistry of Materials, 2004, 16(9):1627-1632. doi: 10.1021/cm034921v
    [50] LIU L, ENGELHARD M H, YAN M D. Surface and interface control on photochemically initiated immobilization[J]. Journal of the American Chemical Society, 2006, 128(43):14067-14072. doi: 10.1021/ja062802l
    [51] LIU L H, YAN M D. Functionalization of pristine graphene with perfluorophenyl azides[J]. Journal of Materials Chemistry, 2011, 21(10):3273-3276. doi: 10.1039/c0jm02765k
    [52] PARK J, JAYAWARDENA S N, CHEN X, et al.. A general method for the fabrication of grapheme-nanoparticle hybrid material[J]. Chemical Communications, 2015, 51(14):2882-2885. doi: 10.1039/C4CC07936A
    [53] ISMAILI H, LEE S, WORKENTIN M S. Diazirine-modified gold nanoparticle:template for efficient photoinduced interfacial carbene insertion reactions[J]. Langmuir, 2010, 26(18):14958-14964. doi: 10.1021/la102621h
    [54] ISMAILI H, LAGUGNE-LABARTHET F, WORKENTIN M S. Covalently assembled gold nanoparticle-carbon nanotube hybrids via a photoinitiated carbene addition reaction[J]. Chemistry of Materials, 2011, 23(6):1519-1525. doi: 10.1021/cm103284g
    [55] ISMAILI H, WORKENTIN M S. Covalent diamond gold nanojewel hybrids via photochemically generated carbenes[J]. Chemical Communications, 2011, 47(27):7788-7790. doi: 10.1039/c1cc12125a
    [56] GHIASSIAN S, ISMAILI H, LUBBOCK BRETT D W, et al.. Photoinduced carbene generation from diazirine modified task specific phosphonium salts to prepare robust hydrophobic coatings[J]. Langmuir, 2012, 28(33):12326-12333. doi: 10.1021/la301975u
    [57] GHIASSIAN S, BIESINGER M C, WORKENTIN M S. Synthesis of small water-soluble diazirine-functionalized gold nanoparticles and their photochemical modification[J]. Canadian Journal of Chemistry, 2015, 93(1):98-105. doi: 10.1139/cjc-2014-0287
    [58] SUN R, YIN L, ZHANG S H, et al.. Simple light-triggered fluorescent labeling of silica nanoparticles for cellular imaging applications[J]. Chemistry-A European Journal, 2017, 23(56):13893-13896. doi: 10.1002/chem.201703653
    [59] BAN Q F, BAI T, DUAN X, et al.. Noninvasive photothermal cancer therapy nanoplatforms via integrating nanomaterials and functional polymers[J]. Biomaterials Science, 2017, 5(2):190-210. doi: 10.1039/C6BM00600K
    [60] MIESZAWSKA A J, MULDER W J M, FAYAD Z A, et al.. Multifunctional gold nanoparticles for diagnosis and therapy of disease[J]. Molecular Pharmaceutics, 2013, 10(3):831-847. doi: 10.1021/mp3005885
    [61] 李欣远, 纪穆为, 王虹智, 等.近红外光热转换纳米晶研究进展[J].中国光学, 2017, 10(5):541-554. http://www.chineseoptics.net.cn/CN/abstract/abstract9545.shtml

    LI X Y, JI M W, WANG H ZH, et al.. Research progress of near-infrared photothermal conversion nanocrystals[J]. Chinese Optics, 2017, 10(5):541-554.(in Chinese) http://www.chineseoptics.net.cn/CN/abstract/abstract9545.shtml
    [62] CHENG X J, SUN R, YIN L, et al.. Light-triggered assembly of gold nanoparticles for photothermal therapy and photoacoustic imaging of tumors in vivo[J]. Advanced Materials, 2017, DOI: 10.1002/adma.201604894.
    [63] COYNE C P, JONES T, BEAR R. Synthesis of a covalent epirubicin-(C3-amide)-anti-HER2/neu immunochemotherapeutic utilizing a UV-photoactivated anthracycline intermediate[J]. Cancer Biotherapy and Radiopharmaceuticals, 2012, 27(1):41-55. doi: 10.1089/cbr.2011.1097
  • 加载中
图(12)
计量
  • 文章访问数:  8409
  • HTML全文浏览量:  3555
  • PDF下载量:  977
  • 被引次数: 0
出版历程
  • 收稿日期:  2018-01-19
  • 修回日期:  2018-02-13
  • 刊出日期:  2018-06-01

目录

    /

    返回文章
    返回