磺胺类抗生素在水环境中的光化学行为
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摘要
磺胺类抗生素(SAs)是水环境中广泛存在的一类新型污染物,因其具有"准"持久性和潜在的生态风险而备受关注.表层水体中,SAs具有多种解离形态,表现为"复合"的光化学行为,从而影响其环境归趋及生态风险.本文总结了水环境中SAs光化学行为研究的最新进展,介绍了该类污染物的直接、间接和自敏化光解动力学,讨论了p H和溶解性物质对其光解动力学的影响机制,评述了其光化学转化路径及羟基自由基氧化机理,简述了该类抗生素的光催化降解和光致毒性效应.最后,对SAs的光化学行为研究进行了展望.
Sulfonamide antibiotics( SAs) are emerging pollutants that are ubiquitous in the aquatic environment. They have recently been received increasing concerns due to their pseudo-persistence and potential ecological risks. SAs exist in different dissociation forms in sunlit natural waters,and show "multivariate "photochemical behavior,which can further affect their fates and risks. The paper reviews the current progress on the environmental photochemical behavior of SAs. Their direct,indirect and self-sensitized photodegradation kinetics are introduced. The effects of p H and aqueous dissolved matter on the photodegradation kinetics are highlighted,and the transformation pathways and oxidation mechanisms of hydroxyl radical are summarized for SAs. Furthermore,the photocatalytic degradation and photoinduced toxicities of SAs are discussed. Finally,the research prospects about the photochemical behavior are proposed for antibiotics,especially for SAs.
Sulfonamide antibiotics( SAs) are emerging pollutants that are ubiquitous in the aquatic environment. They have recently been received increasing concerns due to their pseudo-persistence and potential ecological risks. SAs exist in different dissociation forms in sunlit natural waters,and show "multivariate "photochemical behavior,which can further affect their fates and risks. The paper reviews the current progress on the environmental photochemical behavior of SAs. Their direct,indirect and self-sensitized photodegradation kinetics are introduced. The effects of p H and aqueous dissolved matter on the photodegradation kinetics are highlighted,and the transformation pathways and oxidation mechanisms of hydroxyl radical are summarized for SAs. Furthermore,the photocatalytic degradation and photoinduced toxicities of SAs are discussed. Finally,the research prospects about the photochemical behavior are proposed for antibiotics,especially for SAs.
引文
[1]JIANG L,HU X L,XU T,et al.Prevalence of antibiotic resistance genes and their relationship with antibiotics in the Huangpu River and the drinking water sources,Shanghai,China[J].Science of the Total Environment,2013,458-460:267-272.
[2]LUO Y,MAO D Q,RYSE M,et al.Trends in antibiotic resistance genes occurrence in the Haihe River,China[J].Environmental Science&Technology,2010,44(19):7220-7225.
[3]王丹,隋倩,赵文涛,等.中国地表水环境中药物和个人护理品的研究进展[J].科学通报,2014,59(9):743-751.WANG D,SUI Q,ZHAO W T,et al.Pharmaceutical and personal care products in the surface water of China:A review[J].Chinese Science Bulletin,2014,59(9):743-751(in Chinese).
[4]葛林科,张思玉,谢晴,等.抗生素在水环境中的光化学行为[J].中国科学:化学,2010,40(2):124-135.GE L K,ZHANG S Y,XIE Q,et al.Progress in studies on aqueous environmental photochemical behavior of antibiotics[J].Scientia Sinica Chimica,2010,40(2):124-135(in Chinese).
[5]HOMEM V,SANTOS L.Degradation and removal methods of antibiotics from aqueous matrices-A review[J].Journal of Environmental Management,2011,92:2304-2347.
[6]VERLICCHI P,AUKIDY M A,ZAMBELLO E.Occurrence of pharmaceutical compounds in urban wastewater:Removal,mass load and environmental risk after a secondary treatment-A review[J].Science of the Total Environment,2012,429:123-155.
[7]LEUNG H W,MINH T B,MURPHY M B,et al.Distribution,fate and risk assessment of antibiotics in sewage treatment plants in Hong Kong,South China[J].Environment International,2012,42:1-9.
[8]GAO L H,SHI Y L,LI W H,et al.Occurrence of antibiotics in eight sewage treatment plants in Beijing,China[J].Chemosphere,2012,86:655-671.
[9]贾瑷,胡建英,孙建仙,等.环境中的医药品与个人护理品[J].化学进展,2009,21(2/3):389-399.JIA A,HU J Y,SUN J X,et al.Pharmaceuticals and personal care products(PPCPs)in Environment[J].Progress in Chemistry,2009,21(2/3):389-399(in Chinese).
[10]LIU J L,WONG M H.Pharmaceuticals and personal care products(PPCPs):A review on environmental contamination in China[J].Environment International,2013,59:208-224.
[11]YANG C C,HUANG C L,CHENG T C,et al.Inhibitory effect of salinity on the photocatalytic degradation of three sulfonamide antibiotics[J].International Biodeterioration&Biodegradation,2015,102:116-125.
[12]MA Y P,LI M,WU M M,et al.Occurrences and regional distributions of 20 antibiotics in water bodies during groundwater recharge[J].Science of the Total Environment,2015,518-519:498-506.
[13]葛林科,任红蕾,鲁建江,等.我国环境中新兴污染物抗生素及其抗性基因的分布特征[J].环境化学,2015,34(5):875-883.GE L K,REN H L,LU J J,et al.Occurrence of antibiotics and corresponding resistance genes in the environment of China[J].Environmental Chemistry,2015,34(5):875-883(in Chinese).
[14]杨常青,王龙星,侯晓虹,等.大辽河水系河水中16种抗生素的污染水平分析[J].色谱,2012,30(8):756-762.YANG C Q,WANG L X,HOU X H,et al.Analysis of pollution levels of 16 antibiotics in the river water of Daliao River water system[J].Chinese Journal of Chromatography,2012,30(8):756-762(in Chinese).
[15]ZHANG R J,TANG J H,LI J,et al.Antibiotics in the offshore waters of the Bohai Sea and the Yellow Sea in China:Occurrence,distribution and ecological risks[J].Environmental Pollution,2013,174:71-77.
[16]NA G S,GU J,GE L K,et al.Detection of 36 antibiotics in coastal waters using high performance liquid chromatography-tandem mass spectrometry[J].Chinese Journal of Oceanology and Limnology,2011,29(5):1093-1102.
[17]WEI R C,GE F,HUANG S Y,et al.Occurrence of veterinary antibiotics in animal wastewater and surface water around farms in Jiangsu Province,China[J].Chemosphere,2011,82(10):1408-1414.
[18]NA G S,FANG X D,CAI Y Q,et al.Occurrence,distribution,and bioaccumulation of antibiotics in coastal environment of Dalian,China[J].Marine Pollution Bulletin,2013,69(1-2):233-237.
[19]JIANG L,HU X L,YIN D Q,et al.Occurrence,distribution and seasonal variation of antibiotics in the Huangpu River,Shanghai,China[J].Chemosphere,2011,82:822-828.
[20]CHEN K,ZHOU J L.Occurrence and behavior of antibiotics in water and sediments from the Huangpu River,Shanghai,China[J].Chemosphere,2014,95:604-612.
[21]LI W H,SHI Y L,GAO L H,et al.Occurrence of antibiotics in water,sediments,aquatic plants,and animals from Baiyangdian Lake in North China[J].Chemosphere,2012,89:1307-1315.
[22]ZHENG Q,ZHANG R J,WANG Y H,et al.Occurrence and distribution of antibiotics in the Beibu Gulf,China:Impacts of river discharge and aquaculture activities[J].Marine Environmental Research,2012,78:26-33.
[23]LUO Y,XU L,RYSE M,et al.Occurrence and transport of tetracycline,sulfonamide,quinolone,and macrolide antibiotics in the Haihe River Basin,China[J].Environmental Science&Technology,2011,45(5):1827-1833.
[24]XU W H,ZHANG G,ZOU S C,et al.Determination of selected antibiotics in the Victoria Harbour and the Pearl River,South China using high-performance liquid chromatography-electrospray ionization tandem mass spectrometry[J].Environmental Pollution,2007,145:672-679.
[25]ZOU S C,XU W H,ZHANG R J,et al.Occurrence and distribution of antibiotics in coastal water of the Bohai Bay,China:Impacts of river discharge and aquaculture activities[J].Environmental Pollution,2011,159(10):2913-2920.
[26]LIANG X M,CHEN B W,NIE X P,et al.The distribution and partitioning of common antibiotics in water and sediment of the Pearl River Estuary,South China[J].Chemosphere,2013,92(11):1410-1416.
[27]ZHANG R J,ZHANG G,ZHENG Q,et al.Occurrence and risks of antibiotics in the Laizhou Bay,China:Impacts of river discharge[J].Ecotoxicology and Environmental Safety,2012,80:208-215.
[28]LEI X N,LU J J,LIU Z L,et al.Concentration and distribution of antibiotics in water-sediment system of Bosten Lake,Xinjiang[J].Environmental Science and Pollution Research,2015,22(3):1670-1678.
[29]葛林科,李凯,杨凯,等.UV-vis光照下唑类抗菌药氟康唑的光化学反应类型[J].环境科学,2013,34(8):3132-3136.GE L K,LI K,YANG K,et al.Photochemical reaction types of the azole fungicide fluconazole under UV-vis irradiation[J].Environmental Science,2013,34(8):3132-3136(in Chinese).
[30]CHALLIS J K,CARLSON J C,FRIESEN K J,et al.Aquatic photochemistry of the sulfonamide antibiotic sulfapyridine[J].Journal of Photochemistry and Photobiology A:Chemistry,2013,262:14-21.
[31]GALAN M J G,CRUZ M S D,BARCELO D.Kinetic studies and characterization of photolytic products of sulfamethazine,sulfapyridine and their acetylated metabolites in water under simulated solar irradiation[J].Water Research,2012,46:711-722.
[32]LIAN J F,QIANG Z M,LI M K.UV photolysis kinetics of sulfonamides in aqueous solution based on optimized fluence quantification[J].Water Research,2015,75:43-50.
[33]LI Y J,WEI X X,CHEN J W.Photodegradation mechanism of sulfonamides with excited triplet state dissolved organic matter:A case of sulfadiazine with 4-carboxybenzophenone as a proxy[J].Journal of Hazardous Materials,2015,290:9-15.
[34]BOREEN A L,ARNOLD X A,MCNEILL K.Photochemical fate of sulfa drugs in the aquatic environment:Sulfa drugs containing fivemembered heterocyclic groups[J].Environmental Science&Technology,2004,38(14):3933-3940.
[35]BOREEN A L,ARNOLD W A,MCNEILL K.Triplet-sensitized photodegradation of sulfa drugs containing six-membered heterocyclic groups:Identification of an SO2extrusion photoproduct[J].Environmental Science&Technology,2005,39(10):3630-3638.
[36]陈景文,全燮.环境化学[M].大连:大连理工大学出版社,2009:103-116.CHEN J W,QUAN X.Environmental Chemistry[M].Dalian:Dalian University of Technology Press,2009:103-116(in Chinese).
[37]BONVIN F,OMLIN J,RUTLER R,et al.Direct photolysis of human metabolites of the antibiotic sulfamethoxazole:Evidence for abiotic back-transformation[J].Environmental Science&Technology,2013,47(13):6746-6755.
[38]NIU J,ZHANG L,LI Y,et al.Effects of environmental factors on sulfamethoxazole photodegradation under simulated sunlight irradiation:Kinetics and mechanism[J].Journal of Environmental Sciences,2013,25(6):1098-1106.
[39]XU J,HAO Z,GUO C,et al.Photodegradation of sulfapyridine under simulated sunlight irradiation:Kinetics,mechanism and toxicity evolvement[J].Chemosphere,2014,99:186-191.
[40]TORNIAINEN K,TAMMILEHTO S,ULVI V.The effect of p H,buffer type and drug concentration on the photodegradation of ciprofloxacin[J].International Journal of Pharmaceutics,1996,132(1-2):53-61.
[41]WEI X X,CHEN J W,XIE Q,et al.Distinct photolytic mechanisms and products for different dissociation species of ciprofloxacin[J].Environmental Science&Technology,2013,47(9):4284-4290.
[42]GE L K,CHEN J W,WEI X X,et al.Aquatic photochemistry of fluoroquinolone antibiotics:Kinetics,pathways,and multivariate effects of main water constituents[J].Environmental Science&Technology,2010,44(7):2400-2405.
[43]葛林科,陈景文,张思玉,等.水中氟喹诺酮类抗生素加替沙星的光降解[J].科学通报,2010,55(11):996-1001.GE L K,CHEN J W,ZHANG S Y,et al.Photodegradation of fluoroquinolone antibiotic gatifloxacin in aqueous solutions[J].Chinese Science Bulletin,2010,55(11):996-1001(in Chinese).
[44]WERNER J J,ARNOLD W A,MCNEILL K.Water hardness as a photochemical parameter:Tetracycline photolysis as a function of calcium concentration,magnesium concentration,and p H[J].Environmental Science&Technology,2006,40(23):7236-7241.
[45]NIU J F,LI Y,WANG W L.Light-source-dependent role of nitrate and humic acid in tetracycline photolysis:Kinetics and mechanism[J].Chemosphere,2013,92(11):1423-1429.
[46]LI Y,NIU J F,SHANG E X,et al.Synergistic photogeneration of reactive oxygen species by dissolved organic matter and C60in aqueous phase[J].Environmental Science&Technology,2015,49(2):965-973.
[47]LI K,ZHANG P,GE L K,et al.Concentration-dependent photodegradation kinetics and hydroxyl-radical oxidation of phenicol antibiotics[J].Chemosphere,2014,111:278-282.
[48]LIU H,ZHAO H,QUAN X,et al.Formation of chlorinated intermediate from bisphenol A in surface saline water under simulated solar light irradiation[J].Environmental Science&Technology,2009,43(20):7712-7717.
[49]ZHANG R,SUN P,BOYER T H,et al.Degradation of pharmaceuticals and metabolite in synthetic human urine by UV,UV/H2O2and UV/PDS[J].Environmental Science&Technology,2015,49(5):3056-3066.
[50]MILL T.Predicting photoreaction rates in surface waters[J].Chemosphere,1999,38(6):1379-1390.
[51]COOPER W J,ZIKA R G,PETASNE R G,et al.Sunlight-induced photochemistry of humic substances in natural waters:Major reactive species[J].Advances in Chemistry,2009,219(1):333-362.
[52]PAUL T,MACHESKY M L,STRATHMANN T J.Surface complexation of the zwitterionic fluoroquinolone antibiotic ofloxacin to nanoanatase TiO 2photocatalyst surfaces[J].Environmental Science&Technology,2012,46(21):11896-11904.
[53]NEAFSEY K,ZENG X,LEMLEY A T.Degradation of sulfonamides in aqueous solution by membrane anodic Fenton treatment[J].Journal of Agricultural and Food Chemistry,2010,58(2):1068-1076.
[54]ZHANG J.Degradation mechanism of sulfa drugs based on theoretical prediction and experimental examination in TiO 2suspension[J].Research on Chemical Intermediates,2014,40(3):1089-1102.
[55]CHEN Y,LI H,WANG Z,et al.Photoproducts of tetracycline and oxytetracycline involving self-sensitized oxidation in aqueous solutions:Effects of Ca2+and Mg2+[J].Journal of Environmental Sciences,2011,23(10):1634-1639.
[56]BAEZA C,KNAPPE D R U.Transformation kinetics of biochemically active compounds in low-pressure UV Photolysis and UV/H2O2advanced oxidation processes[J].Water Research,2011,45:4531-4543.
[57]SAGI G,CSAY T,SZABO L,et al.Analytical approaches to the OH radical induced degradation ofsulfonamide antibiotics in dilute aqueous solutions[J].Journal of Pharmaceutical and Biomedical Analysis,2015,106:52-60.
[58]GE L K,NA G S,ZHANG S Y,et al.New insights into the aquatic photochemistry of fluoroquinolone antibiotics:Direct photodegradation,hydroxyl-radical oxidation,and antibacterial activity changes[J].Science of the Total Environment,2015,527-528:12-17.
[59]孙兴霞,许毓.水中磺胺类抗生素的光降解及富里酸对其光降解的影响[J].中国科学技术大学学报,2013,43(8):654-660.SUN X X,XU Y.Photodegradation of sulfa antibiotics and the impact of fulvic acids on it in water[J].Journal of University of Science and Technology of China,2013,43(8):654-660(in Chinese).
[60]黄春年,李学德,花日茂.磺胺二甲嘧啶在水溶液中的光化学降解[J].环境污染与防治,2011,33(12):59-64.HUANG C N,LI X D,HUA R M.Photochemical degradation of sulfamethazine in aqueous solution[J].Environmental Pollution and Control,2011,33(12):59-64(in Chinese).
[61]马艳,高乃云,张东.UV-C辐照降解水中磺胺类药物[J].净水技术,2014,33(3):75-78.MA Y,GAO N Y,ZHANG D.Degradation of Sulfonamides by UV-C Irradiation in Water Treatment[J].Water Purification Technology,2014,33(3):75-78(in Chinese).
[62]XU J,HAO Z N,GUO C S,et al.Photodegradation of sulfapyridine under simulated sunlight irradiation:Kinetics,mechanism and toxicity evolvement[J].Chemosphere,2014,99:186-191.
[63]QIANG Z,ADAMS C.Potentiometric determination of acid dissociation constants(p Ka)for human and veterinary antibiotics[J].Water Research,2004,38(12):2874-2890.
[64]GUERARD J J,CHIN Y P,MASH H,et al.Photochemical fate of sulfadimethoxine in aquaculture waters[J].Environmental Science&Technology,2009,43(22):8587-8592.
[65]WENK J,VON GUNTEN U,CANONICA S.Effect of dissolved organic matter on the transformation of contaminants induced by excited triplet states and the hydroxyl radical[J].Environmental Science&Technology,2011,45(4):1334-1340.
[66]赵家兴,陈景文,张思玉,等.Mg2+配位作用对磺胺嘧啶结构及吸收光谱影响的计算模拟及验证[J].环境化学,2011,30(12):1975-1982.ZHAO J X,CHEN J W,ZHANG S Y,et al.Computational simulation and validation of Mg2+complexation effects on the structure and absorption spectra of sulfadiazine[J].Environmental Chemistry,2011,30(12):1975-1982(in Chinese).
[67]ZHOU D N,HUANG W Y,WU F,et al.Photodegradation of chloromycetin in aqueous solutions:kinetics and influencing factors[J].Reaction Kinetics Mechanisms and Catalysis,2010,100(1):45-53.
[68]BEATE F,ANDREAS V,FELIX M,et al.Copper redox transformation and complexation by reduced and oxidized soil humic acid.1.X-ray absorption spectroscopy study[J].Environmental Science&Technology,2013,47(19):10903-10911.
[69]李英杰,尉小旋,乔显亮,等.溶解性有机质及Cu(II)配位对磺胺二甲基嘧啶光转化的影响[J].科学通报,2015,60(30):2900-2906.LI Y J,WEI X X,QIAO X L,et al.Effects of dissolved organic matter and coordination with Cu(II)on the phototransformation of sulfamethazine in aqueous solutions[J].Chinese Science Bulletin,2015,60(30):2900-2906(in Chinese).
[70]路莹,鲁楠,赵雅辉,等.磺胺甲唑在磷钨酸/二氧化钛复合膜上的光催化降解[J].环境化学,2014,33(4):649-655.LU Y,LU N,ZHAO Y H,et al.Photocatalytic degradation sulfamethoxazole of using H3PW12O40/TiO 2composite film[J].Environmental Chemistry,2014,33(4):649-655(in Chinese).
[71]BATISTA A P S,PIRES F C C,TEIXEIRA A C S C.The role of reactive oxygen species in sulfamethazine degradationusing UV-based technologies and products identification[J].Journal of Photochemistry and Photobiology A:Chemistry,2014,290:77-85.
[72]POMELLI C S,CHIAPPE C,LAPI A.Accelerating effect of imidazolium ionic liquids on the singlet oxygen promoted oxidation of thioethers:A theoretical study[J].Journal of Photochemistry and Photobiology A:Chemistry,2012,240(15):59-65.
[73]CZAPLICKA M.Photo-degradation of chlorophenols in the aqueous solution[J].Journal of Hazardous Materials,2006,134(1-3):45-59.
[74]BATISTA A P S,PIRES F C C,TEIXEIRA A C S C.Photochemical degradation of sulfadiazine,sulfamerazine andsulfamethazine:Relevance of concentration and heterocyclicaromatic groups to degradation kinetics[J].Journal of Photochemistry and Photobiology A:Chemistry,2014,286:40-46.
[75]焦晓微,赵丹,罗一,等.磺胺甲唑在羟基自由基作用下降解机理的密度泛函研究[J].安全与环境学报,2013,13(2):40-45.JIAO X W,ZHAO D,LUO Y,et al.Density functional studies of the reaction mechanism of sulfamethoxazole with hydroxyl radical[J].Journal of Safety and Environment,2013,13(2):40-45(in Chinese).
[76]CALZA P,MEDANA C,PAZZI M,et al.Photocatalytic transformations of sulphonamides on titanium dioxide[J].Applied Catalysis BEnvironmental,2004,53(1):63-69.
[77]梁凤颜,尹平河,赵玲,等.水体中微污染磺胺嘧啶光催化降解行为[J].生态环境学报,2009,18(4):1227-1230.LIANG F Y,YIN P H,ZHAO L,et al.Photocatalytic degradation of trace sulfadiazine in water[J].Ecology and Environmental Sciences,2009,18(4):1227-1230(in Chinese).
[78]ABELLN M N,BAYARRI B,GIMENEZ J,et al.Photocatalytic degradation of sulfamethoxazole in aqueous suspension of TiO 2[J].Applied Catalysis B:Environmental,2007,74:233-241.
[79]XU L,WANG G,MA F,et al.Photocatalytic degradation of an aqueous sulfamethoxazole over the metallic silver and Keggin unit codoped titania nanocomposites[J].Applied Surface Science,2012,258:7039-7046.
[80]DLUGOSZ M,ZMUDZKI P,KWIECIEN A,et al.Photocatalytic degradation of sulfamethoxazole in aqueous solution using a floating TiO 2-expanded perlite photocatalyst[J].Journal of Hazardous Materials,2015,298:146-153.
[81]JUNG J,KIM Y,KIM J,et al.Environmental levels of ultraviolet light potentiate the toxicity of sulfonamide antibiotics in Daphnia magna[J].Ecotoxicology,2008,17(1):37-45.
[82]TROVA G,NOGUEIRA R F P,AGUERA A,et al.Photodegradation of sulfamethoxazole in various aqueous media:Persistence,toxicity and photoproducts assessment[J].Chemosphere,2009,77(10):1292-1298.
[83]ZESSEL K,MOHRING S,HAMSCHER G,et al.Biocompatibility and antibacterial activity of photolytic products of sulfonamides[J].Chemosphere,2014,100:167-174.
[84]CHIRON S,MINERO C,VIONE D.Photodegradation processes of the antiepileptic drug carbamazepine,relevant to estuarine waters[J].Environmental Science&Technology,2006,40(19):5977-5983.
[85]SANKODA K,KURIBAYASHI T,NOMIYAMA K,et al.Occurrence and source of chlorinated polycyclic aromatic hydrocarbons(Cl-PAHs)in Tidal Flats of the Ariake Bay,Japan[J].Environmental Science&Technology,2013,47(13):7037-7044.
[86]胡学锋,吴蕾,骆永明.苯胺在含富里酸/Fe(Ⅲ)高盐水体中的光氯化[J].环境化学,2014,33(4):611-616.HU X F,WU L,LUO Y M.Photochlorination of aniline in Fe(Ⅲ)/fulvic acid-containing saline water under simulated light irradiation[J].Environmental Chemistry,2014,33(4):611-616(in Chinese).
[87]DODD M C,SHAH A D,VON GUNTEN U,et al.Interactions of fluoroquinolone antibacterial agents with aqueous chlorine:Reaction kinetics,mechanisms,and transformation pathways[J].Environmental Science&Technology,2005,39(18):7065-7076.
[88]EDHLUND B L,ARNOLD W A,MCNEILL K.Aquatic photochemistry of nitrofuran antibiotics[J].Environmental Science&Technology,2006,40(17):5422-5427.
[89]任红蕾,张蓬,李凯,等.水中氟喹诺酮类抗生素光降解过程中抑菌活性的变化[J].环境化学,2014,33(5):753-759.REN H L,ZHANG P,LI K,et al.Changes in antibacterial activity of fluoroquinolone antibiotics due to photodegradation[J].Environmental Chemistry,2014,33(5):753-759(in Chinese).
[90]PAUL T,DODD M C,STRATHMANN T J.Photolytic and photocatalytic decomposition of aqueous ciprofloxacin:Transformation products and residual antibacterial activity[J].Water Research,2010,44(10):3121-3132.
[91]STURINI M,SPELTINI A,MARASCHI F,et al.Photodegradation of fluoroquinolones in surface water and antimicrobial activity of the photoproducts[J].Water Research,2012,46(17):5575-5582.
[2]LUO Y,MAO D Q,RYSE M,et al.Trends in antibiotic resistance genes occurrence in the Haihe River,China[J].Environmental Science&Technology,2010,44(19):7220-7225.
[3]王丹,隋倩,赵文涛,等.中国地表水环境中药物和个人护理品的研究进展[J].科学通报,2014,59(9):743-751.WANG D,SUI Q,ZHAO W T,et al.Pharmaceutical and personal care products in the surface water of China:A review[J].Chinese Science Bulletin,2014,59(9):743-751(in Chinese).
[4]葛林科,张思玉,谢晴,等.抗生素在水环境中的光化学行为[J].中国科学:化学,2010,40(2):124-135.GE L K,ZHANG S Y,XIE Q,et al.Progress in studies on aqueous environmental photochemical behavior of antibiotics[J].Scientia Sinica Chimica,2010,40(2):124-135(in Chinese).
[5]HOMEM V,SANTOS L.Degradation and removal methods of antibiotics from aqueous matrices-A review[J].Journal of Environmental Management,2011,92:2304-2347.
[6]VERLICCHI P,AUKIDY M A,ZAMBELLO E.Occurrence of pharmaceutical compounds in urban wastewater:Removal,mass load and environmental risk after a secondary treatment-A review[J].Science of the Total Environment,2012,429:123-155.
[7]LEUNG H W,MINH T B,MURPHY M B,et al.Distribution,fate and risk assessment of antibiotics in sewage treatment plants in Hong Kong,South China[J].Environment International,2012,42:1-9.
[8]GAO L H,SHI Y L,LI W H,et al.Occurrence of antibiotics in eight sewage treatment plants in Beijing,China[J].Chemosphere,2012,86:655-671.
[9]贾瑷,胡建英,孙建仙,等.环境中的医药品与个人护理品[J].化学进展,2009,21(2/3):389-399.JIA A,HU J Y,SUN J X,et al.Pharmaceuticals and personal care products(PPCPs)in Environment[J].Progress in Chemistry,2009,21(2/3):389-399(in Chinese).
[10]LIU J L,WONG M H.Pharmaceuticals and personal care products(PPCPs):A review on environmental contamination in China[J].Environment International,2013,59:208-224.
[11]YANG C C,HUANG C L,CHENG T C,et al.Inhibitory effect of salinity on the photocatalytic degradation of three sulfonamide antibiotics[J].International Biodeterioration&Biodegradation,2015,102:116-125.
[12]MA Y P,LI M,WU M M,et al.Occurrences and regional distributions of 20 antibiotics in water bodies during groundwater recharge[J].Science of the Total Environment,2015,518-519:498-506.
[13]葛林科,任红蕾,鲁建江,等.我国环境中新兴污染物抗生素及其抗性基因的分布特征[J].环境化学,2015,34(5):875-883.GE L K,REN H L,LU J J,et al.Occurrence of antibiotics and corresponding resistance genes in the environment of China[J].Environmental Chemistry,2015,34(5):875-883(in Chinese).
[14]杨常青,王龙星,侯晓虹,等.大辽河水系河水中16种抗生素的污染水平分析[J].色谱,2012,30(8):756-762.YANG C Q,WANG L X,HOU X H,et al.Analysis of pollution levels of 16 antibiotics in the river water of Daliao River water system[J].Chinese Journal of Chromatography,2012,30(8):756-762(in Chinese).
[15]ZHANG R J,TANG J H,LI J,et al.Antibiotics in the offshore waters of the Bohai Sea and the Yellow Sea in China:Occurrence,distribution and ecological risks[J].Environmental Pollution,2013,174:71-77.
[16]NA G S,GU J,GE L K,et al.Detection of 36 antibiotics in coastal waters using high performance liquid chromatography-tandem mass spectrometry[J].Chinese Journal of Oceanology and Limnology,2011,29(5):1093-1102.
[17]WEI R C,GE F,HUANG S Y,et al.Occurrence of veterinary antibiotics in animal wastewater and surface water around farms in Jiangsu Province,China[J].Chemosphere,2011,82(10):1408-1414.
[18]NA G S,FANG X D,CAI Y Q,et al.Occurrence,distribution,and bioaccumulation of antibiotics in coastal environment of Dalian,China[J].Marine Pollution Bulletin,2013,69(1-2):233-237.
[19]JIANG L,HU X L,YIN D Q,et al.Occurrence,distribution and seasonal variation of antibiotics in the Huangpu River,Shanghai,China[J].Chemosphere,2011,82:822-828.
[20]CHEN K,ZHOU J L.Occurrence and behavior of antibiotics in water and sediments from the Huangpu River,Shanghai,China[J].Chemosphere,2014,95:604-612.
[21]LI W H,SHI Y L,GAO L H,et al.Occurrence of antibiotics in water,sediments,aquatic plants,and animals from Baiyangdian Lake in North China[J].Chemosphere,2012,89:1307-1315.
[22]ZHENG Q,ZHANG R J,WANG Y H,et al.Occurrence and distribution of antibiotics in the Beibu Gulf,China:Impacts of river discharge and aquaculture activities[J].Marine Environmental Research,2012,78:26-33.
[23]LUO Y,XU L,RYSE M,et al.Occurrence and transport of tetracycline,sulfonamide,quinolone,and macrolide antibiotics in the Haihe River Basin,China[J].Environmental Science&Technology,2011,45(5):1827-1833.
[24]XU W H,ZHANG G,ZOU S C,et al.Determination of selected antibiotics in the Victoria Harbour and the Pearl River,South China using high-performance liquid chromatography-electrospray ionization tandem mass spectrometry[J].Environmental Pollution,2007,145:672-679.
[25]ZOU S C,XU W H,ZHANG R J,et al.Occurrence and distribution of antibiotics in coastal water of the Bohai Bay,China:Impacts of river discharge and aquaculture activities[J].Environmental Pollution,2011,159(10):2913-2920.
[26]LIANG X M,CHEN B W,NIE X P,et al.The distribution and partitioning of common antibiotics in water and sediment of the Pearl River Estuary,South China[J].Chemosphere,2013,92(11):1410-1416.
[27]ZHANG R J,ZHANG G,ZHENG Q,et al.Occurrence and risks of antibiotics in the Laizhou Bay,China:Impacts of river discharge[J].Ecotoxicology and Environmental Safety,2012,80:208-215.
[28]LEI X N,LU J J,LIU Z L,et al.Concentration and distribution of antibiotics in water-sediment system of Bosten Lake,Xinjiang[J].Environmental Science and Pollution Research,2015,22(3):1670-1678.
[29]葛林科,李凯,杨凯,等.UV-vis光照下唑类抗菌药氟康唑的光化学反应类型[J].环境科学,2013,34(8):3132-3136.GE L K,LI K,YANG K,et al.Photochemical reaction types of the azole fungicide fluconazole under UV-vis irradiation[J].Environmental Science,2013,34(8):3132-3136(in Chinese).
[30]CHALLIS J K,CARLSON J C,FRIESEN K J,et al.Aquatic photochemistry of the sulfonamide antibiotic sulfapyridine[J].Journal of Photochemistry and Photobiology A:Chemistry,2013,262:14-21.
[31]GALAN M J G,CRUZ M S D,BARCELO D.Kinetic studies and characterization of photolytic products of sulfamethazine,sulfapyridine and their acetylated metabolites in water under simulated solar irradiation[J].Water Research,2012,46:711-722.
[32]LIAN J F,QIANG Z M,LI M K.UV photolysis kinetics of sulfonamides in aqueous solution based on optimized fluence quantification[J].Water Research,2015,75:43-50.
[33]LI Y J,WEI X X,CHEN J W.Photodegradation mechanism of sulfonamides with excited triplet state dissolved organic matter:A case of sulfadiazine with 4-carboxybenzophenone as a proxy[J].Journal of Hazardous Materials,2015,290:9-15.
[34]BOREEN A L,ARNOLD X A,MCNEILL K.Photochemical fate of sulfa drugs in the aquatic environment:Sulfa drugs containing fivemembered heterocyclic groups[J].Environmental Science&Technology,2004,38(14):3933-3940.
[35]BOREEN A L,ARNOLD W A,MCNEILL K.Triplet-sensitized photodegradation of sulfa drugs containing six-membered heterocyclic groups:Identification of an SO2extrusion photoproduct[J].Environmental Science&Technology,2005,39(10):3630-3638.
[36]陈景文,全燮.环境化学[M].大连:大连理工大学出版社,2009:103-116.CHEN J W,QUAN X.Environmental Chemistry[M].Dalian:Dalian University of Technology Press,2009:103-116(in Chinese).
[37]BONVIN F,OMLIN J,RUTLER R,et al.Direct photolysis of human metabolites of the antibiotic sulfamethoxazole:Evidence for abiotic back-transformation[J].Environmental Science&Technology,2013,47(13):6746-6755.
[38]NIU J,ZHANG L,LI Y,et al.Effects of environmental factors on sulfamethoxazole photodegradation under simulated sunlight irradiation:Kinetics and mechanism[J].Journal of Environmental Sciences,2013,25(6):1098-1106.
[39]XU J,HAO Z,GUO C,et al.Photodegradation of sulfapyridine under simulated sunlight irradiation:Kinetics,mechanism and toxicity evolvement[J].Chemosphere,2014,99:186-191.
[40]TORNIAINEN K,TAMMILEHTO S,ULVI V.The effect of p H,buffer type and drug concentration on the photodegradation of ciprofloxacin[J].International Journal of Pharmaceutics,1996,132(1-2):53-61.
[41]WEI X X,CHEN J W,XIE Q,et al.Distinct photolytic mechanisms and products for different dissociation species of ciprofloxacin[J].Environmental Science&Technology,2013,47(9):4284-4290.
[42]GE L K,CHEN J W,WEI X X,et al.Aquatic photochemistry of fluoroquinolone antibiotics:Kinetics,pathways,and multivariate effects of main water constituents[J].Environmental Science&Technology,2010,44(7):2400-2405.
[43]葛林科,陈景文,张思玉,等.水中氟喹诺酮类抗生素加替沙星的光降解[J].科学通报,2010,55(11):996-1001.GE L K,CHEN J W,ZHANG S Y,et al.Photodegradation of fluoroquinolone antibiotic gatifloxacin in aqueous solutions[J].Chinese Science Bulletin,2010,55(11):996-1001(in Chinese).
[44]WERNER J J,ARNOLD W A,MCNEILL K.Water hardness as a photochemical parameter:Tetracycline photolysis as a function of calcium concentration,magnesium concentration,and p H[J].Environmental Science&Technology,2006,40(23):7236-7241.
[45]NIU J F,LI Y,WANG W L.Light-source-dependent role of nitrate and humic acid in tetracycline photolysis:Kinetics and mechanism[J].Chemosphere,2013,92(11):1423-1429.
[46]LI Y,NIU J F,SHANG E X,et al.Synergistic photogeneration of reactive oxygen species by dissolved organic matter and C60in aqueous phase[J].Environmental Science&Technology,2015,49(2):965-973.
[47]LI K,ZHANG P,GE L K,et al.Concentration-dependent photodegradation kinetics and hydroxyl-radical oxidation of phenicol antibiotics[J].Chemosphere,2014,111:278-282.
[48]LIU H,ZHAO H,QUAN X,et al.Formation of chlorinated intermediate from bisphenol A in surface saline water under simulated solar light irradiation[J].Environmental Science&Technology,2009,43(20):7712-7717.
[49]ZHANG R,SUN P,BOYER T H,et al.Degradation of pharmaceuticals and metabolite in synthetic human urine by UV,UV/H2O2and UV/PDS[J].Environmental Science&Technology,2015,49(5):3056-3066.
[50]MILL T.Predicting photoreaction rates in surface waters[J].Chemosphere,1999,38(6):1379-1390.
[51]COOPER W J,ZIKA R G,PETASNE R G,et al.Sunlight-induced photochemistry of humic substances in natural waters:Major reactive species[J].Advances in Chemistry,2009,219(1):333-362.
[52]PAUL T,MACHESKY M L,STRATHMANN T J.Surface complexation of the zwitterionic fluoroquinolone antibiotic ofloxacin to nanoanatase TiO 2photocatalyst surfaces[J].Environmental Science&Technology,2012,46(21):11896-11904.
[53]NEAFSEY K,ZENG X,LEMLEY A T.Degradation of sulfonamides in aqueous solution by membrane anodic Fenton treatment[J].Journal of Agricultural and Food Chemistry,2010,58(2):1068-1076.
[54]ZHANG J.Degradation mechanism of sulfa drugs based on theoretical prediction and experimental examination in TiO 2suspension[J].Research on Chemical Intermediates,2014,40(3):1089-1102.
[55]CHEN Y,LI H,WANG Z,et al.Photoproducts of tetracycline and oxytetracycline involving self-sensitized oxidation in aqueous solutions:Effects of Ca2+and Mg2+[J].Journal of Environmental Sciences,2011,23(10):1634-1639.
[56]BAEZA C,KNAPPE D R U.Transformation kinetics of biochemically active compounds in low-pressure UV Photolysis and UV/H2O2advanced oxidation processes[J].Water Research,2011,45:4531-4543.
[57]SAGI G,CSAY T,SZABO L,et al.Analytical approaches to the OH radical induced degradation ofsulfonamide antibiotics in dilute aqueous solutions[J].Journal of Pharmaceutical and Biomedical Analysis,2015,106:52-60.
[58]GE L K,NA G S,ZHANG S Y,et al.New insights into the aquatic photochemistry of fluoroquinolone antibiotics:Direct photodegradation,hydroxyl-radical oxidation,and antibacterial activity changes[J].Science of the Total Environment,2015,527-528:12-17.
[59]孙兴霞,许毓.水中磺胺类抗生素的光降解及富里酸对其光降解的影响[J].中国科学技术大学学报,2013,43(8):654-660.SUN X X,XU Y.Photodegradation of sulfa antibiotics and the impact of fulvic acids on it in water[J].Journal of University of Science and Technology of China,2013,43(8):654-660(in Chinese).
[60]黄春年,李学德,花日茂.磺胺二甲嘧啶在水溶液中的光化学降解[J].环境污染与防治,2011,33(12):59-64.HUANG C N,LI X D,HUA R M.Photochemical degradation of sulfamethazine in aqueous solution[J].Environmental Pollution and Control,2011,33(12):59-64(in Chinese).
[61]马艳,高乃云,张东.UV-C辐照降解水中磺胺类药物[J].净水技术,2014,33(3):75-78.MA Y,GAO N Y,ZHANG D.Degradation of Sulfonamides by UV-C Irradiation in Water Treatment[J].Water Purification Technology,2014,33(3):75-78(in Chinese).
[62]XU J,HAO Z N,GUO C S,et al.Photodegradation of sulfapyridine under simulated sunlight irradiation:Kinetics,mechanism and toxicity evolvement[J].Chemosphere,2014,99:186-191.
[63]QIANG Z,ADAMS C.Potentiometric determination of acid dissociation constants(p Ka)for human and veterinary antibiotics[J].Water Research,2004,38(12):2874-2890.
[64]GUERARD J J,CHIN Y P,MASH H,et al.Photochemical fate of sulfadimethoxine in aquaculture waters[J].Environmental Science&Technology,2009,43(22):8587-8592.
[65]WENK J,VON GUNTEN U,CANONICA S.Effect of dissolved organic matter on the transformation of contaminants induced by excited triplet states and the hydroxyl radical[J].Environmental Science&Technology,2011,45(4):1334-1340.
[66]赵家兴,陈景文,张思玉,等.Mg2+配位作用对磺胺嘧啶结构及吸收光谱影响的计算模拟及验证[J].环境化学,2011,30(12):1975-1982.ZHAO J X,CHEN J W,ZHANG S Y,et al.Computational simulation and validation of Mg2+complexation effects on the structure and absorption spectra of sulfadiazine[J].Environmental Chemistry,2011,30(12):1975-1982(in Chinese).
[67]ZHOU D N,HUANG W Y,WU F,et al.Photodegradation of chloromycetin in aqueous solutions:kinetics and influencing factors[J].Reaction Kinetics Mechanisms and Catalysis,2010,100(1):45-53.
[68]BEATE F,ANDREAS V,FELIX M,et al.Copper redox transformation and complexation by reduced and oxidized soil humic acid.1.X-ray absorption spectroscopy study[J].Environmental Science&Technology,2013,47(19):10903-10911.
[69]李英杰,尉小旋,乔显亮,等.溶解性有机质及Cu(II)配位对磺胺二甲基嘧啶光转化的影响[J].科学通报,2015,60(30):2900-2906.LI Y J,WEI X X,QIAO X L,et al.Effects of dissolved organic matter and coordination with Cu(II)on the phototransformation of sulfamethazine in aqueous solutions[J].Chinese Science Bulletin,2015,60(30):2900-2906(in Chinese).
[70]路莹,鲁楠,赵雅辉,等.磺胺甲唑在磷钨酸/二氧化钛复合膜上的光催化降解[J].环境化学,2014,33(4):649-655.LU Y,LU N,ZHAO Y H,et al.Photocatalytic degradation sulfamethoxazole of using H3PW12O40/TiO 2composite film[J].Environmental Chemistry,2014,33(4):649-655(in Chinese).
[71]BATISTA A P S,PIRES F C C,TEIXEIRA A C S C.The role of reactive oxygen species in sulfamethazine degradationusing UV-based technologies and products identification[J].Journal of Photochemistry and Photobiology A:Chemistry,2014,290:77-85.
[72]POMELLI C S,CHIAPPE C,LAPI A.Accelerating effect of imidazolium ionic liquids on the singlet oxygen promoted oxidation of thioethers:A theoretical study[J].Journal of Photochemistry and Photobiology A:Chemistry,2012,240(15):59-65.
[73]CZAPLICKA M.Photo-degradation of chlorophenols in the aqueous solution[J].Journal of Hazardous Materials,2006,134(1-3):45-59.
[74]BATISTA A P S,PIRES F C C,TEIXEIRA A C S C.Photochemical degradation of sulfadiazine,sulfamerazine andsulfamethazine:Relevance of concentration and heterocyclicaromatic groups to degradation kinetics[J].Journal of Photochemistry and Photobiology A:Chemistry,2014,286:40-46.
[75]焦晓微,赵丹,罗一,等.磺胺甲唑在羟基自由基作用下降解机理的密度泛函研究[J].安全与环境学报,2013,13(2):40-45.JIAO X W,ZHAO D,LUO Y,et al.Density functional studies of the reaction mechanism of sulfamethoxazole with hydroxyl radical[J].Journal of Safety and Environment,2013,13(2):40-45(in Chinese).
[76]CALZA P,MEDANA C,PAZZI M,et al.Photocatalytic transformations of sulphonamides on titanium dioxide[J].Applied Catalysis BEnvironmental,2004,53(1):63-69.
[77]梁凤颜,尹平河,赵玲,等.水体中微污染磺胺嘧啶光催化降解行为[J].生态环境学报,2009,18(4):1227-1230.LIANG F Y,YIN P H,ZHAO L,et al.Photocatalytic degradation of trace sulfadiazine in water[J].Ecology and Environmental Sciences,2009,18(4):1227-1230(in Chinese).
[78]ABELLN M N,BAYARRI B,GIMENEZ J,et al.Photocatalytic degradation of sulfamethoxazole in aqueous suspension of TiO 2[J].Applied Catalysis B:Environmental,2007,74:233-241.
[79]XU L,WANG G,MA F,et al.Photocatalytic degradation of an aqueous sulfamethoxazole over the metallic silver and Keggin unit codoped titania nanocomposites[J].Applied Surface Science,2012,258:7039-7046.
[80]DLUGOSZ M,ZMUDZKI P,KWIECIEN A,et al.Photocatalytic degradation of sulfamethoxazole in aqueous solution using a floating TiO 2-expanded perlite photocatalyst[J].Journal of Hazardous Materials,2015,298:146-153.
[81]JUNG J,KIM Y,KIM J,et al.Environmental levels of ultraviolet light potentiate the toxicity of sulfonamide antibiotics in Daphnia magna[J].Ecotoxicology,2008,17(1):37-45.
[82]TROVA G,NOGUEIRA R F P,AGUERA A,et al.Photodegradation of sulfamethoxazole in various aqueous media:Persistence,toxicity and photoproducts assessment[J].Chemosphere,2009,77(10):1292-1298.
[83]ZESSEL K,MOHRING S,HAMSCHER G,et al.Biocompatibility and antibacterial activity of photolytic products of sulfonamides[J].Chemosphere,2014,100:167-174.
[84]CHIRON S,MINERO C,VIONE D.Photodegradation processes of the antiepileptic drug carbamazepine,relevant to estuarine waters[J].Environmental Science&Technology,2006,40(19):5977-5983.
[85]SANKODA K,KURIBAYASHI T,NOMIYAMA K,et al.Occurrence and source of chlorinated polycyclic aromatic hydrocarbons(Cl-PAHs)in Tidal Flats of the Ariake Bay,Japan[J].Environmental Science&Technology,2013,47(13):7037-7044.
[86]胡学锋,吴蕾,骆永明.苯胺在含富里酸/Fe(Ⅲ)高盐水体中的光氯化[J].环境化学,2014,33(4):611-616.HU X F,WU L,LUO Y M.Photochlorination of aniline in Fe(Ⅲ)/fulvic acid-containing saline water under simulated light irradiation[J].Environmental Chemistry,2014,33(4):611-616(in Chinese).
[87]DODD M C,SHAH A D,VON GUNTEN U,et al.Interactions of fluoroquinolone antibacterial agents with aqueous chlorine:Reaction kinetics,mechanisms,and transformation pathways[J].Environmental Science&Technology,2005,39(18):7065-7076.
[88]EDHLUND B L,ARNOLD W A,MCNEILL K.Aquatic photochemistry of nitrofuran antibiotics[J].Environmental Science&Technology,2006,40(17):5422-5427.
[89]任红蕾,张蓬,李凯,等.水中氟喹诺酮类抗生素光降解过程中抑菌活性的变化[J].环境化学,2014,33(5):753-759.REN H L,ZHANG P,LI K,et al.Changes in antibacterial activity of fluoroquinolone antibiotics due to photodegradation[J].Environmental Chemistry,2014,33(5):753-759(in Chinese).
[90]PAUL T,DODD M C,STRATHMANN T J.Photolytic and photocatalytic decomposition of aqueous ciprofloxacin:Transformation products and residual antibacterial activity[J].Water Research,2010,44(10):3121-3132.
[91]STURINI M,SPELTINI A,MARASCHI F,et al.Photodegradation of fluoroquinolones in surface water and antimicrobial activity of the photoproducts[J].Water Research,2012,46(17):5575-5582.