Destruction of microcystins by conventional and advanced oxidation processes: A review

Abstract Cyanobacteria blooms pose an environmental hazard because of the release of water soluble toxic compounds, called cyanotoxins. Microcystins (MCs), hepatotoxic cyclic peptide toxins, are the most widespread cyanotoxins with microcystin-LR (MC-LR) the most common and toxic variant. Health effects of MCs have resulted in the need of using efficient treatment methods for the removal of this class of toxins in water supplies. While physical treatment methods can remove MCs at full or some extent from contaminated water, their function is primary separation of the whole toxins as intact molecules and further processing is required. On the other hand, chemical oxidation processes are a promising alternative treatment option due to the potential of complete destruction of the MCs, transformation to less toxic by-products, and even complete mineralization. MCs reactivity towards different conventional oxidants is strongly affected by water quality parameters like pH, DOC and oxidant dose. Although there is a general trend for MCs oxidation (ozone > permanganate > chlorine >>> chlorine-based oxidants), the selection of the appropriate oxidant for toxin elimination during water treatment should be assessed for each particular source of water. Although advanced oxidation processes are generally more effective on MCs degradation than conventional oxidation processes, scale-up studies are needed before these methods are considered as economically-feasible and practical sustainable alternatives in water treatment facilities. In this review, recent literature concerning treatment of MCs in water by conventional and advanced oxidation processes are reviewed and discussed in terms of the degree of degradation, reaction kinetics, identity and toxicity of oxidation by-products and possible degradation pathways.

[1]  Huijuan Liu,et al.  Effects and mechanisms of pre-chlorination on Microcystis aeruginosa removal by alum coagulation: Significance of the released intracellular organic matter , 2012 .

[2]  C. Bernard,et al.  Health hazards for terrestrial vertebrates from toxic cyanobacteria in surface water ecosystems. , 2003, Veterinary research.

[3]  W. Glaze,et al.  Advanced Oxidation Processes. A Kinetic Model for the Oxidation of 1,2-Dibromo-3-chloropropane in Water by the Combination of Hydrogen Peroxide and UV Radiation , 1995 .

[4]  M. Teixeira,et al.  Comparing dissolved air flotation and conventional sedimentation to remove cyanobacterial cells of Microcystis aeruginosa: Part I: The key operating conditions , 2006 .

[5]  Daniel W. Smith,et al.  Cyanobacteria toxins and the current state of knowledge on water treatment options: a review , 2004 .

[6]  G. Codd Cyanobacterial toxins: Occurrence, properties and biological significance , 1995 .

[7]  M. Filipič,et al.  Patterns of microcystin-LR induced alteration of the expression of genes involved in response to DNA damage and apoptosis. , 2008, Toxicon : official journal of the International Society on Toxinology.

[8]  J. Białczyk,et al.  Degradation of microcystin-LR by ozone in the presence of Fenton reagent , 2008, Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering.

[9]  E. Bandala,et al.  Deactivation of Highly Resistant Microorganisms in Water Using Solar Driven Photocatalytic Processes , 2009 .

[10]  G. Shephard,et al.  Degradation of microcystin toxins in a falling film photocatalytic reactor with immobilized titanium dioxide catalyst. , 2002, Water research.

[11]  J. D. Carr,et al.  Kinetics and Product Identification of Oxidation by Ferrate(VI) of Water and Aqueous Nitrogen Containing Solutes , 2008 .

[12]  Yongfu Zhao,et al.  Degradation of microcystin by gamma irradiation , 2007 .

[13]  M. Swaminathan,et al.  Photochemical oxidation of reactive azo dye with UV–H2O2 process , 2004 .

[14]  Jia-Qian Jiang,et al.  Progress in the development and use of ferrate(VI) salt as an oxidant and coagulant for water and wastewater treatment. , 2002, Water research.

[15]  D. Dionysiou,et al.  LC/MS/MS structure elucidation of reaction intermediates formed during the TiO(2) photocatalysis of microcystin-LR. , 2008, Toxicon : official journal of the International Society on Toxinology.

[16]  Dionysios D. Dionysiou,et al.  Synthesis, structural characterization and evaluation of sol-gel-based NF-TiO2 films with visible light-photoactivation for the removal of microcystin-LR , 2010 .

[17]  B. Xiao,et al.  Kinetic study of the 2‐methyl‐3‐methoxy‐4‐phenylbutanoic acid produced by oxidation of microcystin in aqueous solutions , 2008, Environmental toxicology and chemistry.

[18]  V. Sharma,et al.  Ferrate(VI) oxidation of weak-acid dissociable cyanides. , 2008, Environmental science & technology.

[19]  H. Fenton,et al.  LXXIII.—Oxidation of tartaric acid in presence of iron , 1894 .

[20]  V. Sharma,et al.  Mechanisms of oxidation of organosulfur compounds by ferrate(VI). , 2011, Chemosphere.

[21]  Decomposition of microcystin-LR by Fenton oxidation. , 2001, Toxicon : official journal of the International Society on Toxinology.

[22]  Jussi Meriluoto,et al.  Oxidation of microcystins by permanganate: reaction kinetics and implications for water treatment. , 2007, Water research.

[23]  D. Dionysiou,et al.  Degradation of microcystin-LR toxin by Fenton and Photo-Fenton processes. , 2004, Toxicon : official journal of the International Society on Toxinology.

[24]  X. Qi,et al.  Destruction of microcystin-RR by Fenton oxidation. , 2009, Journal of hazardous materials.

[25]  Makoto Suzuki,et al.  Stability of microcystins from cyanobacteria: effect of light on decomposition and isomerization. , 1994, Environmental science & technology.

[26]  B. K. Hodnett Photocatalytic purification and treatment of water and air : by D.F. Ollis and H. Al-Ekabi (Editors), Elsevier Science Publishers BV, Amsterdam, 1993, ISBN 0-444-89855-7, xiv + 820 pp., f450.00/$257.25 , 1994 .

[27]  Panyue Zhang,et al.  Ultrasonic frequency effects on the removal of Microcystis aeruginosa. , 2006, Ultrasonics sonochemistry.

[28]  W. Carmichael The toxins of cyanobacteria. , 1994, Scientific American.

[29]  B. Xiao,et al.  Kinetics of the oxidation of MCRR by potassium permanganate. , 2005, Toxicon : official journal of the International Society on Toxinology.

[30]  G. Newcombe,et al.  Ozonation of NOM and algal toxins in four treated waters. , 2001, Water research.

[31]  A photodetoxification mechanism of the cyanobacterial hepatotoxin microcystin-LR by ultraviolet irradiation. , 1998, Chemical research in toxicology.

[32]  Tinglin Huang,et al.  Mechanism studies on chlorine and potassium permanganate degradation of microcystin-LR in water using high-performance liquid chromatography tandem mass spectrometry. , 2008, Water science and technology : a journal of the International Association on Water Pollution Research.

[33]  Wayne W. Carmichael,et al.  Inhibition of protein phosphatases by microcystis and nodularin associated with hepatotoxicity , 2005, Journal of Cancer Research and Clinical Oncology.

[34]  G. Newcombe,et al.  Water treatment options for dissolved cyanotoxins , 2004 .

[35]  F. Frimmel,et al.  Photochemical degradation of hydrophilic xenobiotics in the UVH2O2 process: Influence of nitrate on the degradation rate of EDTA, 2-amino-1-naphthalenesulfonate, diphenyl-4-sulfonate and 4,4′-diaminostilbene-2,2′-disulfonate , 1997 .

[36]  J. Meriluoto,et al.  Oxidation of microcystin-LR with chlorine and permanganate during drinking water treatment , 2008 .

[37]  G. Mascolo,et al.  Kinetic investigation on UV and UV/H2O2 degradations of pharmaceutical intermediates in aqueous solution , 2003 .

[38]  J. Qu,et al.  Degradation of microcystins in aqueous solution with in situ electrogenerated active chlorine. , 2005, Chemosphere.

[39]  K. Sivonen,et al.  Removal of cyanobacterial toxins in water treatment processes: Laboratory and pilot‐scale experiments , 1988 .

[40]  D. Dionysiou,et al.  Can we effectively degrade microcystins?--Implications on human health. , 2011, Anti-cancer agents in medicinal chemistry.

[41]  D. Dionysiou,et al.  Sources and Occurrence of Cyanotoxins Worldwide , 2010 .

[42]  Lise,et al.  LIVER FAILURE AND DEATH AFTER EXPOSURE TO MICROCYSTINS AT A HEMODIALYSIS CENTER IN BRAZIL LIVER FAILURE AND DEATH AFTER EXPOSURE TO MICROCYSTINS AT A HEMODIALYSIS CENTER IN BRAZIL , 2000 .

[43]  C. Adams,et al.  Release and Removal of Microcystins from Microcystis during Oxidative-, Physical-, and UV-Based Disinfection , 2010 .

[44]  Y. Adewuyi,et al.  Sonochemistry in environmental remediation. 2. Heterogeneous sonophotocatalytic oxidation processes for the treatment of pollutants in water. , 2005, Environmental science & technology.

[45]  G. Buxton,et al.  Critical Review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (⋅OH/⋅O− in Aqueous Solution , 1988 .

[46]  K. Oguma,et al.  Kinetics of Microcystis aeruginosa growth and intracellular microcystins release after UV irradiation. , 2009, Environmental science & technology.

[47]  A. Hiskia,et al.  Photolytic degradation of all chlorophenols with polyoxometallates and H2O2 , 2002 .

[48]  Peter K. J. Robertson,et al.  PHYSICO-CHEMICAL TREATMENT METHODS FOR THE REMOVAL OF MICROCYSTINS (CYANOBACTERIAL HEPATOTOXINS) FROM POTABLE WATERS , 1999 .

[49]  V. Sharma Oxidation of inorganic contaminants by ferrates (VI, V, and IV)--kinetics and mechanisms: a review. , 2011, Journal of environmental management.

[50]  Michael D. Burch,et al.  Destruction of cyanobacterial peptide hepatotoxins by chlorine and chloramine , 1994 .

[51]  D. Dionysiou,et al.  Intermediates and reaction pathways from the degradation of microcystin-LR with sulfate radicals. , 2010, Environmental science & technology.

[52]  M. Rosa,et al.  Evaluation of cyanobacterial cells removal and lysis by ultrafiltration , 2010 .

[53]  B. Xiao,et al.  Rapid quantification of total microcystins in cyanobacterial samples by periodate-permanganate oxidation and reversed-phase liquid chromatography. , 2009, Analytica chimica acta.

[54]  F. Al Momani,et al.  Treatment and kinetic study of cyanobacterial toxin by ozone , 2010, Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering.

[55]  T. Kull,et al.  Oxidative elimination of cyanotoxins: comparison of ozone, chlorine, chlorine dioxide and permanganate. , 2007, Water research.

[56]  K. Sivonen,et al.  The effect of water treatment processes on the removal of hepatotoxins fromMicrocystis andOscillatoria cyanobacteria: A laboratory study , 1989 .

[57]  H. Nakazawa,et al.  Stability of microcystins from cyanobacteria--IV. Effect of chlorination on decomposition. , 1997, Toxicon : official journal of the International Society on Toxinology.

[58]  J. Meriluoto,et al.  Oxidation of the cyanobacterial hepatotoxin microcystin-LR by chlorine dioxide: influence of natural organic matter. , 2006, Environmental science & technology.

[59]  R. Wood THE HEAT, FREE ENERGY AND ENTROPY OF THE FERRATE(VI) ION , 1958 .

[60]  O. Thomas,et al.  Ms identification of microcystin-LR chlorination by-products. , 2009, Chemosphere.

[61]  B. Nicholson,et al.  Destruction of Cyanobacterial Toxins By Ozone , 1998 .

[62]  Lionel Ho,et al.  Differences in the chlorine reactivity of four microcystin analogues. , 2006, Water research.

[63]  C revised by John Crittenden,et al.  Water treatment principles and design , 2012 .

[64]  Y. Adewuyi,et al.  Sonochemistry in environmental remediation. 1. Combinative and hybrid sonophotochemical oxidation processes for the treatment of pollutants in water. , 2005, Environmental science & technology.

[65]  H. Oh,et al.  Growth inhibition of Cyanobacteria by ultrasonic radiation: laboratory and enclosure studies. , 2003, Environmental science & technology.

[66]  F. Momani Degradation of cyanobacteria anatoxin-a by advanced oxidation processes , 2007 .

[67]  Huijuan Liu,et al.  Fe(VI)-assisted photocatalytic degradating of microcystin-LR using titanium dioxide , 2006 .

[68]  T J Lee,et al.  Ultrasonic Irradiation for Blue-Green Algae Bloom Control , 2001, Environmental technology.

[69]  B. Legube,et al.  Chlorination studies of free and combined amino acids , 1994 .

[70]  Jussi Meriluoto,et al.  Kinetics of reactions between chlorine and the cyanobacterial toxins microcystins. , 2005, Water research.

[71]  R. Stewart Oxidation mechanisms : applications to organic chemistry , 1964 .

[72]  M. Gamal El-Din,et al.  Degradation of Aqueous Pharmaceuticals by Ozonation and Advanced Oxidation Processes: A Review , 2006 .

[73]  Wen-quan Ruan,et al.  Detoxification and degradation of microcystin-LR and -RR by ozonation. , 2010, Chemosphere.

[74]  André M. Braun,et al.  Photochemical processes for water treatment , 1993 .

[75]  Y. Ku,et al.  Decomposition of chlorophenols in aqueous solution by UV/H2O2 process , 1996 .

[76]  V. Sharma,et al.  Removal of arsenite by Fe(VI), Fe(VI)/Fe(III), and Fe(VI)/Al(III) salts: effect of pH and anions. , 2009, Journal of hazardous materials.

[77]  J. Meriluoto,et al.  Oxidation of MC-LR and -RR with chlorine and potassium permanganate: toxicity of the reaction products. , 2008, Water research.

[78]  Y. Ueno,et al.  Detection of microcystins, a blue-green algal hepatotoxin, in drinking water sampled in Haimen and Fusui, endemic areas of primary liver cancer in China, by highly sensitive immunoassay. , 1996, Carcinogenesis.

[79]  W. Carmichael,et al.  Liver tumor promotion by the cyanobacterial cyclic peptide toxin microcystin-LR , 2005, Journal of Cancer Research and Clinical Oncology.

[80]  M. Anderson,et al.  Evaluation of the photoelectrocatalytic method for oxidizing chloride and simultaneous removal of microcystin toxins in surface waters , 2009 .

[81]  D. Dionysiou,et al.  Unveiling new degradation intermediates/pathways from the photocatalytic degradation of microcystin-LR. , 2008, Environmental science & technology.

[82]  D. Dionysiou,et al.  Impact of the morphological properties of thin TiO2 photocatalytic films on the detoxification of water contaminated with the cyanotoxin, microcystin-LR , 2009 .

[83]  G. Shaw,et al.  Toxicological aspects of treatment to remove cyanobacterial toxins from drinking water determined using the heterozygous P53 transgenic mouse model. , 2003, Toxicon : official journal of the International Society on Toxinology.

[84]  David C. Szlag,et al.  A review of cyanobacteria and cyanotoxins removal/inactivation in drinking water treatment , 2010, Analytical and bioanalytical chemistry.

[85]  M. Matsumura,et al.  In situ algal bloom control by the integration of ultrasonic radiation and jet circulation to flushing. , 2001, Environmental science & technology.

[86]  Lionel Ho,et al.  Effect of chlorination on Microcystis aeruginosa cell integrity and subsequent microcystin release and degradation. , 2007, Environmental science & technology.

[87]  J. Qu,et al.  Removal of cyanobacterial microcystin-LR by ferrate oxidation-coagulation. , 2002, Toxicon : official journal of the International Society on Toxinology.

[88]  David F. Ollis,et al.  Photocatalytic purification and treatment of water and air : proceedings of the 1st International Conference on TiO[2] Photocatalytic Purification and Treatment of Water and Air, London, Ontario, Canada, 8-13 November, 1992 , 1993 .

[89]  U. von Gunten,et al.  Reactions of chlorine with inorganic and organic compounds during water treatment-Kinetics and mechanisms: a critical review. , 2008, Water research.

[90]  Peter K. J. Robertson,et al.  Hydrogen peroxide enhanced photocatalytic oxidation of microcystin-lR using titanium dioxide , 2000 .

[91]  J. Vaitomaa,et al.  Phylogenetic evidence for the early evolution of microcystin synthesis. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[92]  M. Campinas,et al.  Removal of microcystins by PAC/UF , 2010 .

[93]  F. Dainton,et al.  The primary radical yield in water. A comparison of the photolysis and radiolysis of solutions of hydrogen peroxide , 1953 .

[94]  S. Suzuki,et al.  Stability of microcystins from cyanobacteria--II. Effect of UV light on decomposition and isomerization. , 1995, Toxicon : official journal of the International Society on Toxinology.

[95]  M. Gamal El-Din,et al.  Degradation of cyanobacteria toxin by advanced oxidation processes. , 2008, Journal of hazardous materials.

[96]  Daniel W. Smith,et al.  Kinetics of Microcystin-LR Oxidation by Ozone , 2001 .

[97]  Wayne W. Carmichael,et al.  Health Effects of Toxin-Producing Cyanobacteria: “The CyanoHABs” , 2001 .

[98]  X. Qi,et al.  Degradation of microcystin-RR by UV radiation in the presence of hydrogen peroxide. , 2005, Toxicon : official journal of the International Society on Toxinology.

[99]  W. Carmichael,et al.  Human Fatalities from Cyanobacteria: Chemical and Biological Evidence for Cyanotoxins , 2001 .

[100]  T. Teshiba,et al.  Ultrasonically induced degradation and detoxification of microcystin-LR (cyanobacterial toxin). , 2005, Environmental science & technology.

[101]  Olivier Thomas,et al.  State of the art on cyanotoxins in water and their behaviour towards chlorine. , 2010, Toxicon : official journal of the International Society on Toxinology.

[102]  K. O’Shea,et al.  Ultrasonically induced degradation of microcystin-LR and -RR: identification of products, effect of pH, formation and destruction of peroxides. , 2006, Environmental Science and Technology.

[103]  K. O’Shea,et al.  Mechanistic study and the influence of oxygen on the photosensitized transformations of microcystins (cyanotoxins). , 2007, Environmental science & technology.

[104]  L. Krienitz,et al.  Contribution of hot spring cyanobacteria to the mysterious deaths of Lesser Flamingos at Lake Bogoria, Kenya. , 2003, FEMS microbiology ecology.

[105]  V. Sharma,et al.  Mechanisms and efficiency of the simultaneous removal of metals and cyanides by using ferrate(VI): crucial roles of nanocrystalline iron(III) oxyhydroxides and metal carbonates. , 2011, Chemistry.

[106]  H. Shu,et al.  Decolorization of azo dye acid black 1 by the UV/H2O2 process and optimization of operating parameters. , 2004, Journal of hazardous materials.

[107]  W. Carmichael,et al.  Hepatotoxic microcystin diversity in cyanobacterial blooms collected in portuguese freshwaters , 1996 .

[108]  M. Filipič,et al.  Microcystin-LR induces oxidative DNA damage in human hepatoma cell line HepG2. , 2003, Toxicon : official journal of the International Society on Toxinology.

[109]  Peter K. J. Robertson,et al.  Processes influencing surface interaction and photocatalytic destruction of microcystins on titanium dioxide photocatalysts , 2003 .

[110]  M. D. Gurol,et al.  Chemical oxidation by photolytic decomposition of hydrogen peroxide. , 1995, Environmental science & technology.

[111]  K. Oguma,et al.  Effects of low or medium-pressure UV irradiation on the release of intracellular microcystin. , 2007, Water research.

[112]  V. Sharma,et al.  Ferrate(VI) enhanced photocatalytic oxidation of pollutants in aqueous TiO2 suspensions , 2010, Environmental science and pollution research international.

[113]  M. Matsumura,et al.  A novel strategy for cyanobacterial bloom control by ultrasonic irradiation. , 2002, Water Science and Technology.

[114]  M. Teixeira,et al.  Microcystins removal by nanofiltration membranes , 2005 .

[115]  Sung-Chul Kim,et al.  Photocatalytic oxidation of microcystin-LR in a fluidized bed reactor having TiO2-coated activated carbon , 2004 .

[116]  Photocatalytic degradation of cyanobacterial microcystin toxins in water. , 1998, Toxicon : official journal of the International Society on Toxinology.

[117]  C. Mclaughlin,et al.  Properties of ferrate vi in aqueous solution an alternate oxidant in wastewater treatment , 1985 .

[118]  Heng-feng Miao,et al.  The mechanisms of ozonation on cyanobacteria and its toxins removal , 2009 .

[119]  K. O’Shea,et al.  Ultrasonically induced degradation of 2-methylisoborneol and geosmin. , 2007, Water research.

[120]  J. Meriluoto,et al.  Oxidation of the cyanobacterial hepatotoxin microcystin-LR by chlorine dioxide: reaction kinetics, characterization, and toxicity of reaction products. , 2004, Environmental science & technology.

[121]  G. Klass,et al.  Decrease in toxicity of microcystins LA and LR in drinking water by ozonation. , 2006, Toxicon : official journal of the International Society on Toxinology.

[122]  D. Dionysiou,et al.  Degradation of microcystin-LR using sulfate radicals generated through photolysis, thermolysis and e− transfer mechanisms , 2010 .

[123]  Miguel Pelaez,et al.  Mesoporous nitrogen-doped TiO2 for the photocatalytic destruction of the cyanobacterial toxin microcystin-LR under visible light irradiation. , 2007, Environmental science & technology.

[124]  I. Falconer Cyanobacterial toxins of drinking water supplies : cylindrospermopsins and microcystins , 2005 .

[125]  Michael D. Johnson,et al.  Kinetics and mechanism of the reduction of ferrate by one-electron reductants , 1999 .

[126]  A. K. Ray,et al.  Ferrate(VI): green chemistry oxidant for degradation of cationic surfactant. , 2006, Chemosphere.

[127]  J. Meriluoto,et al.  Selective oxidation of key functional groups in cyanotoxins during drinking water ozonation. , 2007, Environmental science & technology.

[128]  L. Lawton,et al.  Mechanistic studies of the photocatalytic oxidation of microcystin-LR: an investigation of byproducts of the decomposition process. , 2003, Environmental science & technology.

[129]  W. J. Cooper,et al.  Radiolysis studies on the destruction of microcystin-LR in aqueous solution by hydroxyl radicals. , 2009, Environmental science & technology.

[130]  William H. Glaze,et al.  The Chemistry of Water Treatment Processes Involving Ozone, Hydrogen Peroxide and Ultraviolet Radiation , 1987 .