双氰基二苯代乙烯型双光子荧光铅离子探针
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摘要
以4-甲基-2,5-二氰基-4'-氨基二苯代乙烯(DCS)和双[2-(2-氨基苯基硫基)乙基]胺(BSA)分别作为双光子荧光团和铅离子配体,构建了1个新型的双光子荧光Pb2+探针(DPb),并对其结构和性能进行了表征.结果表明,该探针具有分子尺寸小、双光子吸收截面大(δ_(TPA),1020 GM)、长波长发射(λmax=609 nm)、斯托克斯位移大(209 nm)、光稳定性好、水溶性适宜、细胞渗透性优良、无细胞毒性及在生理环境下对p H不依赖等优点.该探针能选择性地检测细胞与组织中的Pb2+,猝灭常数K~(TP)_(sv)=7.58×10~5L/mol.
One-photon microscopy( OPM) uses a single photon of higher energy to excite the fluorophore,while two-photon microscopy( TPM) uses two photons of lower energy as the excitation source. Therefore,TPM has such distinct advantages as improvement of penetration depth,localized two-photon excitation,reduction of photo-damage and photobleaching,small absorption coefficient of light in tissue,and lower tissue autofluorescence. These advantages make TPM more popular among biologists. Lead is a common contaminant and has inherent toxic effects on human health and environment. Pb2+ion contamination can affect a wide variety of diseases such as anemia,irritability,memory loss,and muscle paralysis. For these reasons,there is an urgent need to develop some effective two-photon fluorescence probes to detect trace amounts of Pb2+ions in live cells and tissues. A novel two-photon fluorescence probe for Pb2+derived from 4-methyl-2,5-dicyano-4'-amino stilbene as a two-photon fluorophore and bis[2-( 2-aminophenylsulfanyls) ethyl]amine as a novel Pb2+ligand was developed. The probe possessed small molecule size, large two-photon absorption cross-section( 1020 GM),noncytotoxic effect,long-wavelength emission at 609 nm,large Stokes shift( 209 nm),excellent photostability,moderate water-solubility, good cell-permeability and p H-insensitivity in the biologically relevant range. The probe was able to selectively detect Pb2+ions in live cells and living tissues without interference from other metal ions and the membrane-bound probes,and its quenching constant( KTPsv) was 7. 58×105 L/mol.
One-photon microscopy( OPM) uses a single photon of higher energy to excite the fluorophore,while two-photon microscopy( TPM) uses two photons of lower energy as the excitation source. Therefore,TPM has such distinct advantages as improvement of penetration depth,localized two-photon excitation,reduction of photo-damage and photobleaching,small absorption coefficient of light in tissue,and lower tissue autofluorescence. These advantages make TPM more popular among biologists. Lead is a common contaminant and has inherent toxic effects on human health and environment. Pb2+ion contamination can affect a wide variety of diseases such as anemia,irritability,memory loss,and muscle paralysis. For these reasons,there is an urgent need to develop some effective two-photon fluorescence probes to detect trace amounts of Pb2+ions in live cells and tissues. A novel two-photon fluorescence probe for Pb2+derived from 4-methyl-2,5-dicyano-4'-amino stilbene as a two-photon fluorophore and bis[2-( 2-aminophenylsulfanyls) ethyl]amine as a novel Pb2+ligand was developed. The probe possessed small molecule size, large two-photon absorption cross-section( 1020 GM),noncytotoxic effect,long-wavelength emission at 609 nm,large Stokes shift( 209 nm),excellent photostability,moderate water-solubility, good cell-permeability and p H-insensitivity in the biologically relevant range. The probe was able to selectively detect Pb2+ions in live cells and living tissues without interference from other metal ions and the membrane-bound probes,and its quenching constant( KTPsv) was 7. 58×105 L/mol.
引文
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[2]Jedrychowski W.,Perera F.,Jankowski J.,Rauh V.,Flak E.,Caldwell K.L.,Jones R.L.,Pac A.,Lisowska-Miszczyk I.,Int.J.Hyg.Environ.Health.,2008,211(3/4),345—351
[3]The European Parliament and the Council of the European Union,Directive on the Restriction of the Use of Certain Hazardous Substances in Electrical and Electronic Equipment,2011/65/EU
[4]Centers for Disease Control and Prevention,Morbidity and Mortality Weekly Report,2000,49(5),97—100
[5]Tahan J.E.,Granadillo V.A.,Romero R.A.,Anal.Chim.Acta,1994,295(1/2),187—197
[6]Badiei H.R.,Liu C.,Karanassios V.,Microchem.J.,2013,108,131—136
[7]Li P.C.,Jiang S.J.,Anal.Bioanal.Chem.,2006,385(6),1092—1097
[8]Bonfil Y.,Kirowa-Eisner E.,Anal.Chim.Acta,2002,457(2),285—296
[9]Lin S.Y.,Wu S.H.,Chen C.H.,Angew.Chem.Int.Ed.,2006,45(30),4948—4951
[10]Lin Y.W.,Huang C.C.,Chang H.T.,Analyst,2011,136(5),863—871
[11]Ferhan A.R.,Guo L.,Zhou X.,Chen P.,Hong S.,Kim D.H.,Anal.Chem.,2013,85(8),4094—4099
[12]Kuo S.Y.,Li H.H.,Wu P.J.,Chen C.P.,Huang Y.C.,Chan Y.H.,Anal.Chem.,2015,87(9),4765—4771
[13]Wang X.,Han B.,Gao Y.,Wang L.,Bai M.,Chem.Res.Chinese Universities,2016,32(3),325—328
[14]Nie J.,He B.,Cheng Y.M.,Yin W.,Hou C.J.,Huo D.Q.,Qian L.L.,Qin Y.N.,Fa H.B.,Chem.Res.Chinese Universities,2017,33(6),951—957
[15]Zhang B.B.,Liu X.H.,Li D.N.,Tian H.,Ma G.P.,Chang J.,Chinese Science Bulletin,2004,52(24),2846—2851(张兵波,刘旭辉,李德娜,田惠,马贵平,常津.科学通报,2004,52(24),2846—2851)
[16]Yu M.,He F.,Tang Y.,Wang S.,Li Y.,Zhu D.,Macromol.Rapid Commun.,2007,28(12),1333—1338
[17]He Q.,Miller E.V.,Wong A.P.,Chang C.J.,J.Am.Chem.Soc.,2006,128(29),9316—9317
[18]Rémi M.,Isabelle L.,Bernard V.,Chem.Eur.J.,2004,10(18),4480—4490
[19]Chen C.T.,Huang W.P.,J.Am.Chem.Soc.,2002,124(22),6246—6247
[20]Huang C.B.,Chen S.Y.,Progress in Chemistry,2017,29(10),1216—1227(黄池宝,陈绍英.化学进展,2017,29(10),1216—1227)
[21]Huang C.B.,Yi D.S.,Feng C.H.,Ren A.X.,Sun S.G.,Progress in Chemistry,2010,22(12),2408—2419(黄池宝,易道生,冯承浩,任安祥,孙世国.化学进展,2010,22(12),2408—2419)
[22]Huang C.B.,Fan J.L.,Peng X.J.,Sun S.G.,Progress in Chemistry,2007,19(11),1807—1811(黄池宝,樊江莉,彭孝军,孙世国.化学进展,2007,19(11),1807—1811)
[23]Cahalan M.D.,Parker I.,Wei S.H.,Miller M.J.,Nat.Rev.Immunol.,2002,2(11),872—880
[24]So P.T.C.,Dong C.Y.,Masters B.R.,Berland K.M.,Annu.Rev.Biomed.Eng.,2000,2(1),399—429
[25]Huang C.B.,Zhang D.H.,Zeng B.P.,Liu Q.B.,Chen H.S.,Kang S.,Chen X.Y.,Chem.J.Chinese Universities,2016,37(4),638—642(黄池宝,张道海,曾伯平,刘其斌,陈华仕,康帅,陈晓远.高等学校化学学报,2016,37(4),638—642)
[26]Diaspro A.,Robello M.,J.Photochem.Photobiol.B:Bio.,2000,55(1),1—8
[27]K9ckel R.H.,Cao J.,Zipfel W.R.,Webb W.W.,Hanson M.R.,Science,1997,276(5321),2039—2042
[28]Denk W.,Strickler J.H.,Webb W.W.,Science,1990,248(4951),73—76
[29]Cui J.Q.,Fan J.L.,Peng X.J.,Sun S.G.,Chen G.C.,Guo K.X.,Science in China Series B:Chemistry,2009,39(6),541—547
[30]Kim J.S.,Kim H.J.,Kim H.M.,Kim S.H.,Lee J.W.,Kim S.K.,Cho B.R.,J.Org.Chem.,2006,71(21),8016—8022
[31]Ahn H.C.,Yang S.K.,Kim H.M.,Li S.,Jeon S.J.,Cho B.R.,Chem.Phys.Lett.,2005,410(4—6),312—315
[32]Huang C.B.,Liang X.,Zeng Q.H.,Chen H.S.,Zeng B.P.,Yi D.S.,Chen X.Y.,Chem.J.Chinese Universities,2015,36(4),646—653(黄池宝,梁兴,曾启华,陈华仕,曾伯平,易道生,陈晓远.高等学校化学学报,2015,36(4),646—653)
[33]Huang C.B.,Chen H.S.,Zeng B.P.,Chen X.Y.,Chin.J.Anal.Chem.,2015,43(4),507—511(黄池宝,陈华仕,曾伯平,陈晓远.分析化学,2015,43(4),507—511)
[34]Huang C.B.,Pan Q.,Chen X.Y.,Zhao G.L.,Chen H.S.,Liang X.,LüG.L.,Chem.J.Chinese Universities,2017,38(10),1751—1756(黄池宝,潘淇,陈晓远,赵光练,陈华仕,梁兴,吕国岭.高等学校化学学报,2017,38(10),1751—1756)
[35]Huang C.B.,Ren A.X.,Li H.B.,Yang N.F.,Chem.J.Chinese Universities,2010,31(11),2222—2227(黄池宝,任安祥,李海渤,阳年发.高等学校化学学报,2010,31(11),2222—2227)
[36]Huang C.B.,Ren A.X.,Acta Chim.Sinica,2007,65(23),2765—2770(黄池宝,任安祥.化学学报,2007,65(23),2765—2770)