Predictive models on photolysis and photoinduced toxicity of persistent organic chemicals

doi:10.1007/s11783-013-0547-7

Front Envir Sci Eng

2013, Vol. 7

Issue (6) : 803-814 https://doi.org/10.1007/s11783-013-0547-7

REVIEW ARTICLE

Predictive models on photolysis and photoinduced toxicity of persistent organic chemicals

Qing ZHANG(

)

National Natural Science Foundation of China, Beijing 100085, China

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Abstract

Photodegradation is a major abiotic transformation pathway of toxic chemicals in the environment, which in some cases might lead to photoinduced toxicities. The data on photodegradation kinetics and photoinduced toxicities of organic chemicals are essential for their risk assessment. However, the relevant data are only available for a limited number of chemicals, due to the difficulty and high cost of experimental determination. Quantitative structure-activity relationship (QSAR) models that relate photodegradation kinetics or photoinduced toxicity of organic chemicals with their physicochemical properties or molecular structural descriptors may enable simple and fast estimation of their photochemical behaviors. This paper reviews the QSAR models on photodegradation quantum yields and rate constants for toxic organic chemicals in different media including liquid phase, gaseous phase, surfaces of plant leaves, and QSAR models on photoinduced toxicity of organic chemicals to plants, bacteria, and aquatic invertebrates. Further prospects for QSAR model development on photodegradation kinetics and photoinduced toxicity of refractory organic chemicals are proposed.

Keywords quantitative structure-activity relationship (QSAR) models photodegradation persistent organic pollutants environmental media mechanisms

Corresponding Author(s): ZHANG Qing,Email:zhangq@nsfc.gov.cn

Issue Date: 01 December 2013

Cite this article:

Qing ZHANG. Predictive models on photolysis and photoinduced toxicity of persistent organic chemicals[J]. Front Envir Sci Eng, 2013, 7(6): 803-814.

URL:

https://academic.hep.com.cn/fese/EN/10.1007/s11783-013-0547-7
https://academic.hep.com.cn/fese/EN/Y2013/V7/I6/803

compounds	media	photolysis data	light sources	parameters	algorithms	number of compounds	Ref. No.
PAHs	methanol/water(1:1, v/v)	photolysis rate constants	500W medium pressure mercury lamp	quantum chemical descriptors	multiple linear regression (MLR) method	n = 17	[39]
	aqueous solution	direct photolysis quantum yields	450W medium pressure mercury lamp, UV light (313 nm, 366 nm, 436 nm)	quantum chemical descriptors	PLS algorithm	n = 13	[37]
	near-surface water body	photolysis half-life values	sunlight, latitude 40°N, midday and midsummer	quantum chemical descriptors	PLS algorithm	n = 13	[40]
	near-surface water body	photolysis half-life values	sunlight	quantum chemical descriptors	PLS algorithm	n = 13	[41]
	atmospheric areosols	photolysis half-life values	253.7 nm	quantum chemical descriptors	PLS algorithm	n = 11	[42]
	atmospheric areosols	photolysis half-life values	253.7 nm	quantum chemical descriptors	PLS algorithm	n = 11	[43]
	methanol/water(1:1, v/v)	photolysis rate constants	500W medium pressure mercury lamp	quantum chemical descriptors	MLR and back propagation (BP)-ANN method	n = 16	[44]
	fly ash	photolysis rate constants	simulated sunlight	quantum chemical descriptors	PLS algorithm	n = 16	[45]
PCDD/Fs	water/acetonitrile solution	direct photolysis quantum yields	313 nm from the Rayonet RPR 3000 ? lamps	quantum chemical descriptors	PLS algorithm	n = 7	[32]
	water/acetonitrile solution	direct photolysis quantum yields	rayonet RPR 3000 ? lamps	quantum chemical descriptors	PLS algorithm	n = 9	[33]
	Lemna gibba	photoinduced toxicity	simulated sunlight	photophysical descriptors	PLS algorithm	n = 16	[16]
	Daphnia magnaand Scenedesmus vacuolatus	photoinduced toxicity	sunlight	quantum chemical descriptors	MLRmethod	n = 19	[31]
	Lemna gibba	photoinduced toxicity	simulated sunlight	quantum chemical descriptors	PLS algorithm	n = 16	[46]
	Vibrio fischeri	photoinduced toxicity	simulated sunlight	quantum chemical descriptors	MLR method	n = 16	[35]
	cuticular waxes of laurel cherry (Prunus laurocerasus)	photolysis rate constants	high pressure mercury lamps and sunlight	quantum chemical descriptors	PLS algorithm	n = 9, 10	[47]
	spruce (Picea abies (L.) Karst.) needle surfaces	photolysis half-life values	sunlight	quantum chemical descriptors	PLS algorithm	n = 70	[48]
	spruce (Picea abies (L.) Karst.) needle surfaces	photolysis half-life values	sunlight	bond-energy-related descriptors	MLR method	n = 70	[49]
	spruce (Picea abies (L.) Karst.) needle surfaces	photolysis half-life values	sunlight	electrotopological state indices	PLS algorithm	n = 42	[50]
	spruce (Picea abies (L.) Karst.) needle surfaces	photolysis half-life values	sunlight	constitutional, topological, geometric, electrostatic, and quantum chemical descriptors	MLR and projection pursuit regression (PPR) methods	n = 42	[51]
	fly ash	photolysis half-life values	simulated sunlight	quantum chemical descriptors	PLS algorithm	n = 75	[52]
PCBs	pure water	photolysis half-life values	15W UV (254 nm)	quantum chemical descriptors	PLS algorithm	n = 7	[53]
	n-hexane	photolysis rate constants	500-W high-pressure mercury lamp	quantum chemical descriptors	PLS algorithm	n = 16	[54]
	n-hexane	photolysis half-life values	15W UV (254 nm)	quantum chemical descriptors	PLS algorithm	n = 22	[55]
ClPAHs and parent PAHs	cyclohexane	photolysis half-life values and quantum yields	450 W high-pressure mercury lamp (l>290 nm)	quantum chemical and geometrical descriptors	MLR method	n = 16	[56]
	particulates in urban air	photolysis half-life values	simulated sunlight	quantum chemical descriptors	PLS algorithm	n = 12	[57]
Nitronaphthalenes and Methylnitronaphthalenes	air	photolysis half-life values	black-lamp irradiation and natural sunlight	quantum chemical descriptors	PLS algorithm	n = 13	[58]
PBDEs	methanol/water (8:2, v:v), Methanol	direct photolysis rate constants and quantum yields	UV light in the sunlight region	quantum chemical descriptors	PLS algorithm	n = 9, 11, 15	[59]
	methanol/water (8:2, v:v)	direct photolysis rate constants and quantum yields	UV light in the sunlight region	quantum chemical descriptors	PLS algorithm	n = 9, 11, 15	[60]
	hexane and methanol	photolysis rate constants and quantum yields	rayonet RPR 3000 ? lamps	quantum chemical descriptors	PLS algorithm	n = 18	[61]
PBDEs, OH-PBDEs, and selected OCPs	methanol/water (8:2, v:v)	photolysis half-life values	UV light in the sunlight region	ground state based size, reactivity related descriptors, fragment based descriptors, and quantum chemical descriptors	PCA, PLS and ANN approach.	n = 30	[62]
substituted aromatic halides	water	photolysis quantum yields	eight RUL 3000 ? lamps	quantum chemical descriptors	factor analysis, MLR method	n = 45	[63]
	water	photolysis quantum yields	eight RUL 3000 ? lamps	quantum chemical descriptors	PLS algorithm	n = 45	[38]
	dilute aqueous solution (water:acetonitrile, 90:10, v/v)	photolysis quantum yields	eight RUL 3000 ? lamps (250 nm<l<350 nm)	molecular structural descriptors	MLR method	n = 13	[64]
	water	photolysis quantum yields	eight RUL 3000 ? lamps	quantum chemical descriptors	factor analysis and cluster analysis	n = 45	[65]
1,4-dihydropyridine antihypertensives	water	photodegradation rate constants	xenon lamp	theoretical molecular descriptors	PLS algorithm	n = 9	[66]

Tab.1 Established QSAR models on photolysis kinetics and photoinduced toxicity of organic pollutants in different media

name	chemical structure	media	analytical QSPR equations	main mechanistic points	Ref. No.
PAHs	…	methanol/water (1:1, v/v)	log k = 7.2071 - 0.0044DH_f - 1.0486DE_L-H - 0.0006TE	heat of reaction, outmost orbital electron, total bond energy	[44]
		methanol/water (1:1, v/v)	log k = -32.738+ 9.770DE_L-H - 0.715DE_L-H²	absolute hardness	[39]
		fly ash	log k = -1.902-1.556 × 10^-³M_w + 8.077 × 10^-⁵TE + 7.063 × 10^-⁶EE-1.524 × 10^-²DH_f-3.569 × 10^-²DE_L+H	molecular weight, total bond energy, electronic energy, heat of reaction, absolute electronegativity	[45]
chlorinated PAHs	…	particulates in urban air	log t_1/2 = -2.846+ 1.242E_LUMO+1-0.843E_L+H + 0.108DE_L-H + 6.820 × 10^-³DE_L-H²-2.152 × 10^-³a + 0.270E_HOMO-1-21.641Q_H⁺	the frontier molecular orbital energies and their combinations, the deformation of molecules, charge distribution for hydrogen	[57]
PCDD/Fs		spruce (Picea abies (L.) Karst.) needle surfaces	log t_1/2 = -0.6733+ 3.055 × 10^-³a-1.087 × 10^-⁴TE + 9.510 × 10^-⁴Mw + 6.920 × 10^-³DE_L-H² + 1.005 × 10^-¹DE_L-H	the deformation of molecules, total bond energy, molecular weight, absolute hardness	[48]
		fly ash	log t_1/2 = 1.045-7.814 × 10^-²E_LUMO-5.156 × 10^-²E_L+H-1.220 × 10^-¹DE_L-H + 1.017 × 10^-³Mw-1.637q_C^- + 4.121 × 10^-¹q_O^--8.116 × 10^-²E_HOMO	the accept electrons ability, absolute electronegativity, absolute hardness, molecular weight, electron donor ability, charge distribution for carbon and oxygen	[52]
PCBs		pure water	log t_1/2 = -3.681+ 1.284 × 10¹Q_C^--3.408 × 10^-²?H_f-7.202Q_Cl⁺-1.779E_LUMO+1 + 6.914 × 10^-¹E_HOMO-1.188 × 10¹Q_H⁺	heat of reaction, electron donor ability, charge distribution for carbon, hydrogen and chlorine	[53]
		n-hexane	log t_1/2 = 2.124 × 10^-²-1.997 × 10^-²?H_f-4.586 × 10^-⁴TE + 4.012 × 10^-³M_w-2.552 × 10^-¹μ-3.927Q_C^-	heat of reaction, the affinity for leaching, molecular weight, charge distribution for carbon, total bond energy	[55]
nitronaphthalenes and methylnitronaphthalenes		air	logt = -6.060-1.345 × 10^-²DH_f + 3.227E_LUMO + 4.573Q_N⁺-0.701Q_C^--9.050 × 10^-³CCR	heat of reaction, accept electrons ability, charge distribution for carbon and nitrogen	[58]
PBDEs		methanol	log k = -0.201+ 1.569 × 10^-³Mw-3.66 × 10^-⁴TE-3.93 × 10^-⁴EE-6.422 × 10^-¹E_LUMO-1.968 × 10^-³CCR-61.941Q_H⁺	molecular weight, total bond energy, electronic energy, accept electrons ability, charge distribution for hydrogen, core-core repulsion energy	[60]
		methanol/water (8:2, v:v)	log k = -17.616+ 1.320 × 10^-³Mw + 1.062 × 10^-²DH_f-3.08 × 10^-⁴TE-1.173 × 10^-³CCR-1.2939E_HOMO-5.066 × 10^-²DE_L-H²	molecular weight, heat of reaction, total bond energy, core-core repulsion energy, electron donor ability, absolute hardness
substituted aromatic halides		water	log F = -0.010 (± 0.004)BS + 0.665 (± 0.105)E_S + 1.031 (± 0.213)	steric effects, electronic effects	[64]

Tab.2 Selected QSPR equations on photolysis and their main mechanistic points of organic pollutants in different media

1	Zhang Q, Huang J, Yu G. Polychlorinated dibenzo-p-dioxins and dibenzofurans emissions from open burning of crop residues in China between 1997 and 2004. Environmental Pollution , 2008, 151(1): 39-46 doi: 10.1016/j.envpol.2007.03.011 pmid:17482329
2	Wang B, Huang J, Deng S B, Yang X L, Yu G. Addressing the environmental risk of persistent organic pollutants in China. Frontiers of Environmental Science & Engineering , 2012, 6(1): 2-16 doi: 10.1007/s11783-011-0370-y
3	Niu J F, Chen J W, Martens D, Henkelmann B, Quan X, Yang F L, Seidlitz H K, Schramm K W. The role of UV-B on the degradation of PCDD/Fs and PAHs sorbed on surfaces of spruce (Picea abies (L.) Karst.) needles. Science of the Total Environment , 2004, 322(1-3): 231-241 doi: 10.1016/j.scitotenv.2003.09.017 pmid:15081751
4	Meharg A A, Killham K. Environment: a pre-industrial source of dioxins and furans. Nature , 2003, 421(6926): 909-910 doi: 10.1038/421909a pmid:12606987
5	Heilmann C, Budtz-J?rgensen E, Nielsen F, Heinzow B, Weihe P, Grandjean P. Serum concentrations of antibodies against vaccine toxoids in children exposed perinatally to immunotoxicants. Environmental Health Perspectives , 2010, 118(10): 1434-1438 doi: 10.1289/ehp.1001975 pmid:20562056
6	de Boer J, Wester P G, Klamer H J, Lewis W E, Boon J P. Do flame retardants threaten ocean life? Nature , 1998, 394(6688): 28-29 doi: 10.1038/27798 pmid:9665124
7	Bunge M, Adrian L, Kraus A, Opel M, Lorenz W G, Andreesen J R, G?risch H, Lechner U. Reductive dehalogenation of chlorinated dioxins by an anaerobic bacterium. Nature , 2003, 421(6921): 357-360 doi: 10.1038/nature01237 pmid:12540897
8	Kim K, Kim K S, Son S H, Cho J, Kim Y C. Supercritical water oxidation of transformer oil contaminated with PCBs—A road to commercial plant from bench-scale facility. Journal of Supercritical Fluids , 2011, 58(1): 121-130 doi: 10.1016/j.supflu.2011.04.021
9	Granelli L, Eriksson J, Bergman ?. Sodium borohydride reduction of individual polybrominated diphenyl ethers. Chemosphere , 2012, 86(10): 1008-1012 doi: 10.1016/j.chemosphere.2011.11.037 pmid:22185792
10	Niu J F, Chen J W, Martens D, Quan X, Yang F L, Kettrup A, Schramm K W. Photolysis of polycyclic aromatic hydrocarbons adsorbed on spruce [Picea abies (L.) Karst] needles under sunlight irradiation. Environmental Pollution , 2003, 123(1): 39-45 doi: 10.1016/S0269-7491(02)00362-7 pmid:12663204
11	Lin J, Chen J W, Wang Y, Cai X Y, Wei X, Qiao X. More toxic and photoresistant products from photodegradation of fenoxaprop-p-ethyl. Journal of Agricultural and Food Chemistry , 2008, 56(17): 8226-8230 doi: 10.1021/jf801341s pmid:18683946
12	Niu J F, Yu G. Prediction of the ability of PAHs to be photocytotoxic to a cell line from the rainbow trout (Oncorhynchus mykiss) gill. Bulletin of Environmental Contamination and Toxicology , 2004, 73(4): 659-665 doi: 10.1007/s00128-004-0477-y pmid:15389330
13	Paasivirta J, Sinkkonen S. Environmentally relevant properties of all 209 polychlorinated biphenyl congeners for modeling their fate in different natural and climatic conditions. Journal of Chemical & Engineering Data , 2009, 54(4): 1189-1213 doi: 10.1021/je800501h
14	Niu J F, Chen J W, Henkelmann B, Quan X, Yang F L, Kettrup A, Schramm K W. Photodegradation of PCDD/Fs adsorbed on spruce (Picea abies (L.) Karst.) needles under sunlight irradiation. Chemosphere , 2003, 50(9): 1217-1225 doi: 10.1016/S0045-6535(02)00509-X pmid:12547335
15	Niu J F, Yu G, Liu X T. Advances in photolysis of persistent organic pollutants in water. Progress in Chemistry , 2005, 17(5): 938-948 (in Chinese)
16	Huang X D, Krylov S N, Ren L, McConkey B J, Dixon D G, Greenberg B M. Mechanistic quantitative structure–activity relationship model for the photoinduced toxicity of polycyclic aromatic hydrocarbons: II. An empirical model for the toxicity of 16 polycyclic aromatic hydrocarbons to the duckweed Lemna gibba L. G-3. Environmental Toxicology and Chemistry , 1997, 16(11): 2296-2301
17	Foote C S. Type I and type II mechanisms in photodynamic action. ACS Symposium Series , 1987, 339:22-38
18	Huang X D, Dixon D G, Greenberg B M. Impacts of UV radiation and photomodification on the toxicity of PAHs to higher plant Lemna gibba (duckweed). Environmental Toxicology and Chemistry , 1993, 12(6): 1067-1077
19	Oris J T, Giesy J P Jr. The photoenhanced toxicity of anthracene to juvenile sunfish (Lepomis spp.). Aquatic Toxicology , 1985, 6(2): 133-146 doi: 10.1016/0166-445X(85)90012-8
20	Huang X D, Dixon D G, Greenberg B M. Increased polycyclic aromatic hydrocarbon toxicity following their photomodification in natural sunlight: impacts on the duckweed Lemna gibba L. G-3. Ecotoxicology and Environmental Safety , 1995, 32(2): 194-200 doi: 10.1006/eesa.1995.1102 pmid:8575366
21	Boese B L, Lamberson J O, Swartz R C, Ozretich R J. Photoinduced toxicity of fluoranthene to seven marine benthic crustaceans. Archives of Environmental Contamination and Toxicology , 1997, 32(4): 389-393 doi: 10.1007/s002449900201 pmid:9175504
22	Diamond S A, Mount D R, Burkhard L P, Ankley G T, Makynen E A, Leonard E N. Effect of irradiance spectra on the photoinduced toxicity of three polycyclic aromatic hydrocarbons. Environmental Toxicology and Chemistry , 2000, 19(5): 1389-1396 doi: 10.1002/etc.5620190522
23	Wernersson A S, Dave G. Phototoxicity identification by solid phase extraction and photoinduced toxicity to Daphnia magna. Archives of Environmental Contamination and Toxicology , 1997, 32(3): 268-273 doi: 10.1007/s002449900184 pmid:9096075
24	Zhang Q, Huang J, Yu G. Prediction of soot-water partition coefficients for selected persistent organic pollutants from theoretical molecular descriptors. Progress in Natural Science-Materials International , 2008, 18(7): 867-872 doi: 10.1016/j.pnsc.2008.02.006
25	Yang P, Chen J W, Chen S, Yuan X, Schramm K W, Kettrup A. QSPR models for physicochemical properties of polychlorinated diphenyl ethers. Science of the Total Environment , 2003, 305(1-3): 65-76 doi: 10.1016/S0048-9697(02)00467-9 pmid:12670758
26	Tao X Q, Lu G N, Fei H L, Zhou K Q. Estimation of dissolvability of chloric and alkyl benzene derivatives using quantum chemical descriptors and partial least squares. Journal of Theoretical and Computational Chemistry , 2008, 7(5): 989-999 doi: 10.1142/S0219633608004350
27	Wang B, Yu G, Huang J. Application of QSAR/QSPR in fate evaluation and risk assessment of POPs. Progress in Chemistry , 2007, 19(10): 1612-1619 (in Chinese)
28	Wang Y N, Chen J W, Li X H, Wang B, Cai X, Huang L. Predicting rate constants of hydroxyl radical reactions with organic pollutants: algorithm, validation, applicability domain, and mechanistic interpretation. Atmospheric Environment , 2009, 43(5): 1131-1135 doi: 10.1016/j.atmosenv.2008.11.012
29	Zheng G, Huang W H, Lu X H. Prediction of n-octanol/water partition coefficients for polychlorinated dibenzo-p-dioxins using a general regression neural network. Analytical and Bioanalytical Chemistry , 2003, 376(5): 680-685 doi: 10.1007/s00216-003-1910-5 pmid: PMID:12761606
30	?krbi? B, Onjia A. Prediction of the Lee retention indices of polycyclic aromatic hydrocarbons by artificial neural network. Journal of Chromatography A , 2006, 1108(2): 279-284 doi: 10.1016/j.chroma.2006.01.080 pmid:16464457
31	Wang Y, Chen J W, Li F, Qin H, Qiao X L, Hao C. Modeling photoinduced toxicity of PAHs based on DFT-calculated descriptors. Chemosphere , 2009, 76(7): 999-1005 doi: 10.1016/j.chemosphere.2009.04.010 pmid:19427664
32	Chen J W, Quan X, Peijnenburg W J G M, Yang F L. Quantitative structure-property relationships (QSPRs) on direct photolysis quantum yields of PCDDs. Chemosphere , 2001, 43(2): 235-241 doi: 10.1016/S0045-6535(00)00141-7 pmid:11297403
33	Chen J W, Quan X, Schramm K W, Kettrup A, Yang F L. Quantitative structure-property relationships (QSPRs) on direct photolysis of PCDDs. Chemosphere , 2001, 45(2): 151-159 doi: 10.1016/S0045-6535(00)00554-3 pmid:11572607
34	Newsted J L, Giesy J P. Predictive models for photoinduced acute toxicity of polycyclic aromatic hydrocarbons to Daphnia magna, Strauss (Cladocera, Crustacea). Environmental Toxicology and Chemistry , 1987, 6(6): 445-461
35	El-Alawi Y S, Huang X D, Dixon D G, Greenberg B M. Quantitative structure-activity relationship for the photoinduced toxicity of polycyclic aromatic hydrocarbons to the luminescent bacteria Vibrio fischeri. Environmental Toxicology and Chemistry , 2002, 21(10): 2225-2232 pmid:12371502
36	Mezey P G, Zimpel Z, Warburton P, Walker P D, Irvine D G, Huang X D, Dixon D G, Greenbenrg B M. Use of quantitative shape-activity relationships to model the photoinduced toxicity of polycyclic aromatic hydrocarbons electron density shape features accurately predict toxicity. Environmental Toxicology and Chemistry , 1998, 17(7): 1207-1215
37	Chen J W, Peijnenburg W J G M, Quan X, Yang F L. Quantitative structure-property relationships for direct photolysis quantum yields of selected polycyclic aromatic hydrocarbons. Science of the Total Environment , 2000, 246(1): 11-20 doi: 10.1016/S0048-9697(99)00407-6 pmid:10682373
38	Chen J W, Peijnenburg W J G M, Quan X, Chen S, Zhao Y Z, Yang F L. The use of PLS algorithms and quantum chemical parameters derived from PM3 hamiltonian in QSPR studies on direct photolysis quantum yields of substituted aromatic halides. Chemosphere , 2000, 40(12): 1319-1326 doi: 10.1016/S0045-6535(99)00277-5 pmid:10789971
39	Chen J W, Kong L R, Zhu C M, Huang Q G, Wang L S. Correlation between photolysis rate constants of polycyclic aromatic hydrocarbons and frontier molecular orbital energy. Chemosphere , 1996, 33(6): 1143-1150 doi: 10.1016/0045-6535(96)00250-0
40	Chen J W, Peijnenburg W J G M, Quan X, Chen S, Martens D, Schramm K W, Kettrup A. Is it possible to develop a QSPR model for direct photolysis half-lives of PAHs under irradiation of sunlight? Environmental Pollution , 2001, 114(1): 137-143 doi: 10.1016/S0269-7491(00)00195-0 pmid:11444002
41	Lu G N, Dang Z, Tao X Q, Peng P A, Zhang D C. QSPR study on direct photolysis half-lives of PAHs in water surface. Journal of Theoretical and Computational Chemistry , 2005, 4(3): 811-822 doi: 10.1142/S0219633605001817
42	Lu G N, Dang Z, Tao X Q, Yang C, Yi X Y. Modeling and prediction of photolysis half-lives of polycyclic aromatic hydrocarbons in aerosols by quantum chemical descriptors. Science of the Total Environment , 2007, 373(1): 289-296 doi: 10.1016/j.scitotenv.2006.08.045 pmid:17173954
43	Chen J W, Quan X, Yan Y, Yang F L, Peijnenburg W J G M. Quantitative structure-property relationship studies on direct photolysis of selected polycyclic aromatic hydrocarbons in atmospheric aerosol. Chemosphere , 2001, 42(3): 263-270 doi: 10.1016/S0045-6535(00)00077-1 pmid:11100926
44	Zhou Z M, Li X L, Jing G H. Quantitative models for the structure and photodegradation of polycyclic aromatic hydrocarbons. Chinese Journal of Structural Chemistry , 2010, 29(2): 205-212 (In Chinese)
45	Niu J F, Sun P, Schramm K W. Photolysis of polycyclic aromatic hydrocarbons associated with fly ash particles under simulated sunlight irradiation. Journal of Photochemistry and Photobiology A: Chemistry , 2007, 186(1): 93-98 doi: 10.1016/j.jphotochem.2006.07.016
46	Krylov S N, Huang X D, Zeiler L F, Dixon D G, Greenberg B M. Mechanistic quantitative structure-activity relationship model for the photoinduced toxicity of polycyclic aromatic hydrocarbons: I. Physical model based on chemical kinetics in a two-compartment system. Environmental Toxicology and Chemistry , 1997, 16(11): 2283-2295
47	Chen J W, Quan X, Yang F L, Peijnenburg W J G M. Quantitative structure-property relationships on photodegradation of PCDD/Fs in cuticular waxes of laurel cherry (Prunus laurocerasus). Science of the Total Environment , 2001, 269(1-3): 163-170 doi: 10.1016/S0048-9697(00)00827-5 pmid:11305337
48	Niu J F, Huang L P, Chen J W, Yu G, Schramm K W. Quantitative structure-property relationships on photolysis of PCDD/Fs adsorbed to spruce (Picea abies (L.) Karst.) needle surfaces under sunlight irradiation. Chemosphere , 2005, 58(7): 917-924 doi: 10.1016/j.chemosphere.2004.09.051 pmid:15639263
49	Katritzky A R, Slavov S H, Stoyanova-Slavova I B, Karelson M. Correlation of the photolysis half-lives of polychlorinated dibenzo-p-dioxins and dibenzofurans with molecular structure. Journal of Physical Chemistry A , 2010, 114(7): 2684-2688 doi: 10.1021/jp910470e pmid:20112909
50	Wang L, Liu X H, Hou J. Prediction of photolysis half-lives of PCDFs with the electrotopological state indices. Acta Chimica Sinica , 2007, 65(3): 184-190 (in Chinese)
51	Yuan Y N, Zhang R S, Hu R J. Prediction of photolysis of PCDD/Fs adsorbed to spruce [Picea abies (L.) Karst.] needle surfaces under sunlight irradiation based on projection pursuit regression. QSAR & Combinatorial Science , 2009, 28(2): 155-162 doi: 10.1002/qsar.200860043
52	Niu J F, Chen J, Yu G, Schramm K W. Quantitative structure-property relationships on direct photolysis of PCDD/Fs on surfaces of fly ash. SAR and QSAR in Environmental Research , 2004, 15(4): 265-277 doi: 10.1080/10629360410001724932 pmid:15370417
53	Bao Y P, Huang Q Y, Wang W L, Xu J J, Jiang F, Feng C H. Application of quantum chemical descriptor in quantitative structure-property relationship for the prediction of photolysis half-life of PCBs in water. Frontiers of Environmental Science & Engineering in China , 2011, 5(4): 505-511 doi: 10.1007/s11783-011-0318-2
54	Li X, Fang L, Huang J, Yu G. Photolysis of mono- through deca-chlorinated biphenyls by ultraviolet irradiation in n-hexane and quantitative structure-property relationship analysis. Journal of Environmental Sciences-China , 2008, 20(6): 753-759 doi: 10.1016/S1001-0742(08)62123-3 pmid:18763572
55	Niu J F, Yang Z F, Shen Z Y, Wang L L. QSPRs for the prediction of photodegradation half-life of PCBs in n-hexane. SAR and QSAR in Environmental Research , 2006, 17(2): 173-182 doi: 10.1080/10659360600636170 pmid:16644556
56	Ohura T, Amagai T, Makino M. Behavior and prediction of photochemical degradation of chlorinated polycyclic aromatic hydrocarbons in cyclohexane. Chemosphere , 2008, 70(11): 2110-2117 doi: 10.1016/j.chemosphere.2007.08.064 pmid:17936329
57	Niu J F, Wang L L, Yang Z F. QSPRs on photodegradation half-lives of atmospheric chlorinated polycyclic aromatic hydrocarbons associated with particulates. Ecotoxicology and Environmental Safety , 2007, 66(2): 272-277 doi: 10.1016/j.ecoenv.2006.02.014 pmid:16618506
58	Niu J F, Yang Z F, Shen Z Y, Long X X. Estimation of photolysis lifetimes of the nitronaphthalenes and methylnitronaphthalenes. Bulletin of Environmental Contamination and Toxicology , 2005, 75(4): 813-819 doi: 10.1007/s00128-005-0823-8 pmid:16400565
59	Chen J W, Wang D G, Wang S L, Qiao X, Huang L. Quantitative structure-property relationships for direct photolysis of polybrominated diphenyl ethers. Ecotoxicology and Environmental Safety , 2007, 66(3): 348-352 doi: 10.1016/j.ecoenv.2006.01.003 pmid:16488010
60	Niu J F, Shen Z Y, Yang Z F, Long X X, Yu G. Quantitative structure-property relationships on photodegradation of polybrominated diphenyl ethers. Chemosphere , 2006, 64(4): 658-665 doi: 10.1016/j.chemosphere.2005.10.051 pmid:16343592
61	Fang L, Huang J, Yu G, Li X. Quantitative structure-property relationship studies for direct photolysis rate constants and quantum yields of polybrominated diphenyl ethers in hexane and methanol. Ecotoxicology and Environmental Safety , 2009, 72(5): 1587-1593 doi: 10.1016/j.ecoenv.2008.09.013 pmid:18995905
62	Heimstad E S, Bastos P M, Eriksson J, Bergman K, Harju M. Quantitative structure- photodegradation relationships of polybrominated diphenyl ethers, phenoxyphenols and selected organochlorines. Chemosphere , 2009, 77(7): 914-921 doi: 10.1016/j.chemosphere.2009.08.037 pmid:19762064
63	Chen J W, Peijnenburg W J G M, Wang L S. Using PM3 Hamiltonian, factor analysis and regression analysis in developing quantitative structure-property relationships for the photohydrolysis quantum yields of substituted aromatic halides. Chemosphere , 1998, 36(13): 2833-2853 doi: 10.1016/S0045-6535(97)10238-7
64	Peijnenburg W J G M, De Beer K G M, DeHaan M W A, Den Hollander H A, Stegeman M H L, Verboom H. Development of a structure-reactivity relationship for the photohydrolysis of substituted aromatic halides. Environmental Science & Technology , 1992, 26(11): 2116-2121 doi: 10.1021/es00035a007
65	Chen J W, Peijnenburg W J G M, Quan X, Zhao Y Z, Xue D M, Yang F L. The application of quantum chemical and statistical technique in developing quantitative structure-property relationships for the photohydrolysis quantum yields of substituted aromatic halides. Chemosphere , 1998, 37(6): 1169-1186 doi: 10.1016/S0045-6535(98)00112-X
66	Ioele G, De Luca M, Oliverio F, Ragno G. Prediction of photosensitivity of 1,4-dihydropyridine antihypertensives by quantitative structure-property relationship. Talanta , 2009, 79(5): 1418-1424 doi: 10.1016/j.talanta.2009.06.009 pmid:19635379
67	Zepp R G, Schlotzhauer P F. Photoreactivity of selected aromatic hydrocarbons in water. In: Jones P R, Leber P, eds. Polynuclear Aromatic Hydrocarbons . Ann Arbor: Ann Arbor Science Publishers, 1979, 141-158
68	Mill T, Mabey W R, Lan B Y, Baraze A. Photolysis of polycyclic aromatic hydrocarbons in water. Chemosphere , 1981, 10(11-12): 1281-1290 doi: 10.1016/0045-6535(81)90045-X
69	Miller J S, Olejnik D. Photolysis of polycyclic aromatic hydrocarbons in water. Water Research , 2001, 35(1): 233-243 doi: 10.1016/S0043-1354(00)00230-X pmid:11257878
70	Lehto K M, Vuorimaa E, Lemmetyinen H. Photolysis of polycyclic aromatic hydrocarbons (PAHs) in dilute aqueous solutions detected by fluorescence. Journal of Photochemistry and Photobiology A Chemistry , 2000, 136(1-2): 53-60 doi: 10.1016/S1010-6030(00)00321-X
71	Smith J H, Mabey W R, Bahonos N, Holt B R, Lee S S, Chou T W, Benberger D C, Mill T. Environmental pathways of selected chemicals in fresh water systems: Part II. Laboratory studies (Interagency Energy-Environment Research Report EPA-600/7–78–074). Athenes: Environmental Reserch Office of Research and Development, US Environmental Protection Agency , 1979
72	Tysklind M, Lundgren K, Rappe C, Eriksson L, Jonsson J, Sjostrom M, Ahlborg U G. Multivariate characterization and modeling of polychlorinated dibenzo-p-dioxins and dibenzofurans. Environmental Science & Technology , 1992, 26(5): 1023-1030 doi: 10.1021/es00029a023
73	Tysklind M, Rappe C. Photolytic transformation of polychlorinated dioxins and dibenzofurans in fly ash. Chemosphere , 1991, 23(8-10): 1365-1375 doi: 10.1016/0045-6535(91)90161-6
74	Koester C J, Hites R A. Photodegradation of polychlorinated dioxins and dibenzofurans absorbed to fly ash. Environmental Science & Technology , 1992, 26(3): 502-507 doi: 10.1021/es00027a008
75	Korfmacher W A, Natusch D F S, Taylor D R, Mamantov G, Wehry E L. Oxidative transformations of polycyclic aromatic hydrocarbons adsorbed on coal fly ash. Science , 1980, 207(4432): 763-765 doi: 7352284" target="_blank">10.1126/science. pmid:7352284 pmid:7352284
76	Korfmacher W A, Wehry E L, Mamantov G, Natusch D F S. Resistance to photochemical decomposition of polycyclic aromatic hydrocarbons vapor-adsorbed on coal fly ash. Environmental Science & Technology , 1980, 14(9): 1094-1099 doi: 10.1021/es60169a019
77	Yokley R A, Garrison A A, Wehry E L, Mamantov G. Photochemical transformation of pyrene and benzo[a]pyrene vapor-deposited on eight coal stack ashes. Environmental Science & Technology , 1986, 20(1): 86-90 doi: 10.1021/es00143a011 pmid:22300156
78	Schuler F, Schmid P, Schlatter C H. Photodegradation of polychlorinated dibenzo-p-dioxins and dibenzofuzans in cuticular waxes of laurel cherry (Prunus laurocerasus). Chemosphere , 1998, 36(1): 21-34 doi: 10.1016/S0045-6535(97)00349-4
79	McCrady J K, Maggard S P. Uptake and photodegradation of 2,3,7,8-tetrachlorodibenzo-p-dioxin sorbed to grass foliage. Environmental Science & Technology , 1993, 27(2): 343-350 doi: 10.1021/es00039a015
80	McConkey B J, Duxbury C L, Dixon D G, Greenberg B M. Toxicity of a PAH photooxidation product to the bacteria Photobacterium phosphoreum and the duckweed Lemna gibba: effects of phenanthrene and its primary photoproduct, phenanthrenequinone. Environmental Toxicology and Chemistry , 1997, 16(5): 892-899
81	Little E E, Cleveland L, Calfee R, Barron M G. Assessment of the photoenhanced toxicity of a weathered oil to the tidewater silverside. Environmental Toxicology and Chemistry , 2000, 19(4): 926-932 doi: 10.1002/etc.5620190420
82	Huovinen P S, Soimasuo M R, Oikari A O J. Photoinduced toxicity of retene to Daphnia magna under enhanced UV-B radiation. Chemosphere , 2001, 45(4-5): 683-691 doi: 10.1016/S0045-6535(01)00014-5 pmid:11680764
83	Apel K, Hirt H. Reactive oxygen species: metabolism, oxidative stress, and signal transduction. Annual Review of Plant Biology , 2004, 55(1): 373-399 doi: 10.1146/annurev.arplant.55.031903.141701 pmid:15377225
84	Richard A M. Future of toxicology—predictive toxicology: an expanded view of “chemical toxicity”. Chemical Research in Toxicology , 2006, 19(10): 1257-1262 doi: 10.1021/tx060116u pmid:17040094
85	Feng J, Lurati L, Ouyang H J, Robinson T, Wang Y Y, Yuan S L, Young S S. Predictive toxicology: benchmarking molecular descriptors and statistical methods. Journal of Chemical Information and Computer Sciences , 2003, 43(5): 1463-1470 doi: 10.1021/ci034032s pmid:14502479
86	Fielden M R, Zacharewski T R. Challenges and limitations of gene expression profiling in mechanistic and predictive toxicology. Toxicological Sciences , 2001, 60(1): 6-10 doi: 10.1093/toxsci/60.1.6 pmid:11222867
87	Benigni R, Giuliani A. Putting the predictive toxicology challenge into perspective: reflections on the results. Bioinformatics , 2003, 19(10): 1194-1200 doi: 10.1093/bioinformatics/btg099 pmid:12835261
88	Larson R A, Berenbaum M R. Environmental phototoxicity. Environmental Science & Technology , 1988, 22(4): 354-360 doi: 10.1021/es00169a001
89	Morgan D D, Warshawsky D, Atkinson T. The relationship between carcinogenic activities of polycyclic aromatic hydrocarbons and their singlet, triplet, and singlet-triplet splitting energies of phosphorescence lifetimes. Photochemistry and Photobiology , 1977, 25(1): 31-38 doi: 10.1111/j.1751-1097.1977.tb07421.x pmid:847021
90	Mekenyan O G, Ankley G T, Veith G D, Call D J. QSAR for photoinduced toxicity: I. Acute lethality of polycyclic aromatic hydrocarbons to Daphnia magna. Chemosphere , 1994, 28(3): 567-582 doi: 10.1016/0045-6535(94)90299-2
91	Kochevar I E. Mechanisms of drug photosensitization. Photochemistry and Photobiology , 1987, 45(6): 891-895 doi: 10.1111/j.1751-1097.1987.tb07899.x pmid:3306725
92	Ankley G T, Collyard S A, Monson P D, Kosian P A. Influence of UV light on the toxicity of sediments contaminated with PAHs. Environmental Toxicology and Chemistry , 1994, 13(11): 456-466 doi: 10.1002/etc.5620131110
93	PetiteJ M, Ormrod D P. Sulphur-dioxide and nitrogen-dioxide affect growth, gas-exchange and water relations of potato plants. Journal of the American Society for Horticultural Science , 1992, 117(1): 146-153
94	Sanderman G, B?ger P. Sites of herbicide inhibition at the photosynthetic apparatus. In: Staehelin L A, Arntzen C J, editors. Encyclopedia of Plant Physiology. New series, vol 19. Photosynthesis III . NewYork: Spinger, 1986, 595-602
95	Schmidt W, Neubauer C, Kolbowski J, Schreiber U, Urbach W. Comparison of effects of air pollutants (SO₂, O₃, NO₂) on intact leaves by measurements of chlorophyll fluorescence and P700 absorbance changes. Photosynthesis Research , 1990, 25(3): 241-248 doi: 10.1007/BF00033165
96	Moreland D E. Mechanisms of action of herbicides. Annual Review Plant Physiology and Plant Molecular Biology , 1980, 31: 365-385
97	Greenberg B M, Huang X D, Dixon D G. Applications of the aquatic higher-plant Lemna gibba for ecotoxicological assessment. Journal of Aquatic Ecosystem Health , 1992, 1(2): 147-155 doi: 10.1007/BF00044046
98	Hebert P D N. The population biology of Daphnia (Crustacea, Daphnidae). Biological Reviews , 1978, 53(3): 387-426 doi: 10.1111/j.1469-185X.1978.tb00860.x
99	Lampi M A, Gurska J, Huang X D, Dixon D G, Greenberg B M. A predictive quantitative structure-activity relationship model for the photoinduced toxicity of polycyclic aromatic hydrocarbons to Daphnia magna with the use of factors for photosensitization and photomodification. Environmental Toxicology and Chemistry , 2007, 26(3): 406-415 doi: 10.1897/06-295R.1 pmid:17373503

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