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RESEARCH ARTICLE

Surfactant toxicity to Artemia franciscana and the influence of humic acid and chemical composition

Rachel D. Deese A , Madeline R. LeBlanc A and Robert L. Cook A B
+ Author Affiliations
- Author Affiliations

A Choppin Hall 307, Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.

B Corresponding author. Email: rlcook@lsu.edu

Environmental Chemistry 13(3) 507-516 https://doi.org/10.1071/EN15108
Submitted: 28 May 2015  Accepted: 31 August 2015   Published: 23 November 2015

Environmental context. Surfactants, a pollutant class routinely introduced into aquatic environments, can be toxic to a variety of species. It is thus important to understand how surfactants’ toxicity is influenced by their interactions with other environmental constituents, including natural organic matter. We report the changes in toxicity of three surfactants to brine shrimp in the presence of unmodified and chemically modified humic acids.

Abstract. Surfactants can be extremely toxic to aquatic species and are introduced to the environment in a variety of ways. It is thus important to understand how other environmental constituents, in this case humic acids (HAs), may alter the toxicity of anthropogenic surfactants. Hatching and mortality assays of Artemia Franciscana were performed for three different toxic surfactants: Triton X-100 (Tx-100, non-ionic), cetylpyridinium chloride (CPC, cationic) and sodium dodecyl sulfate (SDS, anionic). HAs of varying composition and concentrations were added to the assays to determine the toxicity mitigating ability of the HAs. Tx-100 had a significant toxic effect on Artemia mortality rates and HAs from terrestrial sources were able to mitigate the toxicity, but an aquatic HA did not. CPC and SDS limited hatching success of the Artemia and, as HAs were added, the hatching percentages increased for all HA sources, indicating toxicity mitigation. In order to determine which functional groups within HAs were responsible for the interaction with the surfactants, the HAs were chemically modified by: (i) bleaching to reduce aromatics, (ii) Soxhlet extraction to reduce lipids and (iii) acid hydrolysis to reduce O- and N-alkyl groups. Although most of the modified HAs had some toxicity mitigating ability for each of the surfactants, there were two notable differences: (1) the lipid-extracted HA did not reduce the toxicity of Tx-100 and (2) the bleached HA had a lower toxicity mitigating ability for CPC than the other modified HAs.


References

[1]  F. J. Stevenson, Humus Chemistry: Genesis, Composition, Reactions, 2nd edn 1994 (Wiley: New York).

[2]  R. Sutton, G. Sposito, Molecular structure in soil humic substances: the new view. Environ. Sci. Technol. 2005, 39, 9009.
Molecular structure in soil humic substances: the new view.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtFGmtb7L&md5=588b30f3885c96509557a4e1b71f93caCAS | 16382919PubMed |

[3]  B. Vigneault, A. Percot, M. Lafleur, P. G. C. Campbell, Permeability changes in model and phytoplankton membranes in the presence of aquatic humic substances. Environ. Sci. Technol. 2000, 34, 3907.
Permeability changes in model and phytoplankton membranes in the presence of aquatic humic substances.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXlsVSls7k%3D&md5=714ab6019291a81c7fad82a40b5a1d75CAS |

[4]  P. G. C. Campbell, M. R. Twiss, K. J. Wilkinson, Accumulation of natural organic matter on the surfaces of living cells: implications for the interaction of toxic solutes with aquatic biota. Can. J. Fish. Aquat. Sci. 1997, 54, 2543.
Accumulation of natural organic matter on the surfaces of living cells: implications for the interaction of toxic solutes with aquatic biota.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXhsVGqtrk%3D&md5=631f8dccbdacacfa579d5bc272645c90CAS |

[5]  L. M. Ojwang’, R. L. Cook, Environmental conditions that influence the ability of humic acids to induce permeability in model biomembranes. Environ. Sci. Technol. 2013, 47, 8280.
Environmental conditions that influence the ability of humic acids to induce permeability in model biomembranes.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVWhtbjJ&md5=f4749fcd994ee785b0d6f562df327693CAS | 23805776PubMed |

[6]  E. Tipping, Cation Binding by Humic Substances 2002, pp. 37–45 (Cambridge University Press: Cambridge, UK).

[7]  N. M. Elayan, W. D. Treleaven, R. L. Cook, Monitoring the effect of three humic acids on a model membrane system using 31P NMR. Environ. Sci. Technol. 2008, 42, 1531.
Monitoring the effect of three humic acids on a model membrane system using 31P NMR.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsVWjtLo%3D&md5=ecea0ec74ac3aec37fdfc17bbb40ad33CAS | 18441799PubMed |

[8]  M. R. Twiss, L. Granier, P. Lafrance, P. G. C. Campbell, Bioaccumulation of 2,2′,5,5′-tetrachlorobiphenyl and pyrene by picoplankton (Synechococcus leopoliensis, Cyanophyceae): Influence of variable humic acid concentrations and pH. Environ. Toxicol. Chem. 1999, 18, 2063.
| 1:CAS:528:DyaK1MXls1Sqs7c%3D&md5=9503eb0ffa5b3280bce170b3614ea096CAS |

[9]  B. Vigneault, P. G. C. Campbell, Uptake of cadmium by freshwater green algae: effects of pH and aquatic humic substances. J. Phycol. 2005, 41, 55.
Uptake of cadmium by freshwater green algae: effects of pH and aquatic humic substances.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXisVeqtLs%3D&md5=855cfc999a07aeebcde302f2bfc5b066CAS |

[10]  L. Parent, M. R. Twiss, P. G. C. Campbell, Influences of natural dissolved organic matter on the interaction of aluminum with the microalga Chlorella: a test of the free-ion model of trace metal toxicity. Environ. Sci. Technol. 1996, 30, 1713.
Influences of natural dissolved organic matter on the interaction of aluminum with the microalga Chlorella: a test of the free-ion model of trace metal toxicity.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XhvVKnsr4%3D&md5=2603ebdc7a293882be31a26129b6229eCAS |

[11]  K. J. Wilkinson, P. M. Bertsch, C. H. Jagoe, P. G. C. Campbell, Surface complexation of aluminum on isolated fish gill cells. Environ. Sci. Technol. 1993, 27, 1132.
Surface complexation of aluminum on isolated fish gill cells.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXit1Oks7o%3D&md5=8d9f3e23df767ef83c0aa5330660d88cCAS |

[12]  J. F. McCarthy, B. D. Jimenez, T. Barbee, Effect of dissolved humic material on accumulation of polycyclic aromatic hydrocarbons: Structure-activity relationships. Aquat. Toxicol. 1985, 7, 15.
Effect of dissolved humic material on accumulation of polycyclic aromatic hydrocarbons: Structure-activity relationships.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XhvVOl&md5=2902bd1250cb7a605448d44c80da0a0fCAS |

[13]  M. Stalmans, E. Matthijs, N. De Oude, Fate and effect of detergent chemicals in the marine and estuarine environment. Water Sci. Technol. 1991, 24, 115.
| 1:CAS:528:DyaK38XptV2msg%3D%3D&md5=769749164bc002b2c3267c3e1192977fCAS |

[14]  H. Rogers, Sources, behaviour and fate of organic cotaminants during sewage treatment and in sewage sludges. Sci. Total Environ. 1996, 185, 3.
Sources, behaviour and fate of organic cotaminants during sewage treatment and in sewage sludges.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XjtFWiu7c%3D&md5=c36599e1befe91f65c539aee71f0c910CAS | 8643958PubMed |

[15]  C. N. Mulligan, R. N. Yong, B. F. Gibbs, Surfactant-enhanced remediation of contaminated soil: a review. Eng. Geol. 2001, 60, 371.
Surfactant-enhanced remediation of contaminated soil: a review.Crossref | GoogleScholarGoogle Scholar |

[16]  M. Czarnota, P. Thomas, Using Surfactants, Wetting Agents, and Adjuvants in the Greenhouse. Document number B 1319 2013 (Cooperative Extension, The University of Georgia) Available at http://extension.uga.edu/publications/ [Verified 22 September 2015].

[17]  H.-Y. Song, Y.-H. Kim, S.-J. Seok, H.-W. Gil, J.-O. Yang, E.-Y. Lee, S.-Y. Hong, Cellular toxicity of surfactants used as herbicide additives. J. Korean Med. Sci. 2012, 27, 3.
Cellular toxicity of surfactants used as herbicide additives.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XisVSms7s%3D&md5=1fb852bc180bd8171284f23e9ec733ecCAS | 22219606PubMed |

[18]  U. Zoller, Handbook of Detergents: Environmental Impact 2004 (CRC Press: Boca Raton, FL).

[19]  S. A. Ostroumov, Biological Effects of Surfactants 2006 (CRC Press: Boca Raton, FL).

[20]  G.-G. Ying, Fate, behavior and effects of surfactants and their degradation products in the environment. Environ. Int. 2006, 32, 417.
Fate, behavior and effects of surfactants and their degradation products in the environment.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XitVCktb8%3D&md5=695b2d015ad87c973daa6e91f26de86dCAS | 16125241PubMed |

[21]  Y. Chen, M. Geurts, S. B. Sjollema, N. I. Kramer, J. L. Hermens, S. T. Droge, Acute toxicity of the cationic surfactant C12-Benzalkonium in different bioassays: how test design affects bioavailability and effect concentrations. Environ. Toxicol. Chem. 2014, 33, 606.
Acute toxicity of the cationic surfactant C12-Benzalkonium in different bioassays: how test design affects bioavailability and effect concentrations.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXisV2ls7g%3D&md5=5dc335ad1cf7d625aa7444076cd8a72fCAS | 24273010PubMed |

[22]  Ž. Pavlić, Ž. Vidaković-Cifrek, D. Puntarić, Toxicity of surfactants to green microalgae Pseudokirchneriella subcapitata and Scenedesmus subspicatus and to marine diatoms Phaeodactylum tricornutum and Skeletonema costatum. Chemosphere 2005, 61, 1061.
Toxicity of surfactants to green microalgae Pseudokirchneriella subcapitata and Scenedesmus subspicatus and to marine diatoms Phaeodactylum tricornutum and Skeletonema costatum.Crossref | GoogleScholarGoogle Scholar | 16263376PubMed |

[23]  P. Abel, Toxicity of synthetic detergents to fish and aquatic invertebrates. J. Fish Biol. 1974, 6, 279.
Toxicity of synthetic detergents to fish and aquatic invertebrates.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2cXlsVKns7k%3D&md5=62ec464046926adce63ed9452da0046cCAS |

[24]  T. Cserháti, E. Forgaces, G. Oros, Biological activity and environmental impact of anionic surfactants. Environ. Int. 2002, 28, 337.
Biological activity and environmental impact of anionic surfactants.Crossref | GoogleScholarGoogle Scholar | 12437283PubMed |

[25]  M. Lewis, V. Wee, Aquatic safety assessment for cationic surfactants. Environ. Toxicol. Chem. 1983, 2, 105.
Aquatic safety assessment for cationic surfactants.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXktFSnu7c%3D&md5=5533dadf5cce6f09f245e119b5157dcbCAS |

[26]  R. Singh, N. Gupta, S. Singh, R. Suman, K. Annie, Toxicity of ionic and non-ionic surfactants to six microbes found in Agra, India. Bull. Environ. Contam. Toxicol. 2002, 69, 265.
Toxicity of ionic and non-ionic surfactants to six microbes found in Agra, India.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xmt1Wju78%3D&md5=f07b8e3e2512d08e23f16f22e922e979CAS | 12107704PubMed |

[27]  M. Ishiguro, W. Tan, L. K. Koopal, Binding of cationic surfactants to humic substances. Colloid Surface A. 2007, 306, 29.
Binding of cationic surfactants to humic substances.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXovFertr4%3D&md5=e1fe42ccdfb104f69ac297d446f82b21CAS |

[28]  L. K. Koopal, T. P. Goloub, T. A. Davis, Binding of ionic surfactants to purified humic acid. J. Colloid Interface Sci. 2004, 275, 360.
Binding of ionic surfactants to purified humic acid.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXksFKit7Y%3D&md5=1f1f65cadcb01fd3b8736703fba27358CAS | 15178260PubMed |

[29]  W. H. Otto, D. J. Britten, C. K. Larive, NMR diffusion analysis of surfactant-humic substance interactions. J. Colloid Interface Sci. 2003, 261, 508.
NMR diffusion analysis of surfactant-humic substance interactions.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjtl2ru78%3D&md5=3928427dcf27502eac77e92355511630CAS | 16256562PubMed |

[30]  S. J. Traina, D. C. Mcavoy, D. J. Versteeg, Association of linear alkylbenzenesulfonates with dissolved humic substances and its effect on bioavailability. Environ. Sci. Technol. 1996, 30, 1300.
Association of linear alkylbenzenesulfonates with dissolved humic substances and its effect on bioavailability.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xht1yks7s%3D&md5=520d8cd2b7f785c4bc69afb2aface9ebCAS |

[31]  M. Luckey, Membrane Structural Biology: with Biochemical and Biophysical Foundations 2008 (Cambridge University Press: New York).

[32]  W. Tan, L. K. Koopal, W. Norde, Interaction between humic acid and lysozyme, studied by dynamic light scattering and isothermal titration calorimetry. Environ. Sci. Technol. 2009, 43, 591.
Interaction between humic acid and lysozyme, studied by dynamic light scattering and isothermal titration calorimetry.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXnt1Sq&md5=5a8dd491be41525c9d5f931462c35f12CAS | 19244988PubMed |

[33]  H. Lippold, U. Gottschalch, H. Kupsch, Joint influence of surfactants and humic matter on PAH solubility. Are mixed micelles formed? Chemosphere 2008, 70, 1979.
Joint influence of surfactants and humic matter on PAH solubility. Are mixed micelles formed?Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhvVWguro%3D&md5=3e321258b8cd2dee737be3db562b8958CAS | 17980402PubMed |

[34]  M. Keiluweit, M. Kleber, Molecular-level interactions in soils and sediments: the role of aromatic pi-systems. Environ. Sci. Technol. 2009, 43, 3421.
Molecular-level interactions in soils and sediments: the role of aromatic pi-systems.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXktF2gs7c%3D&md5=241426ca2ea4052e18a276b8d4f99d83CAS | 19544834PubMed |

[35]  J. J. Pignatello, Interaction of anthropogenic organic chemicals with organic matter in natural particles. IUPAC Series on Biophysico-chemical Processes in Environmental Systems, Volume 3 Biophysico-Chemical Processes of Anthropogenic Organic Compounds in Environmental System. 3 (Eds B. Xing, N. Senesi, P. M. Huang) 2011, pp. 3–50 (Wiley: New York).

[36]  K. A. Thorn, D. W. Folan, P. MacCarthy, Characterization of the International Humic Substances Society Standard and Reference Fulvic and Humic Acids by Solution State 13C and 1H NMR. Document number 89-4196 1989, (Department of the Interior: Denver, CO, USA).

[37]  C. W. Coleman, A. L. Waldroup, Cetylpyridinium Chloride: Claim for Exception 1999, (Food and Drug Administration, Little Rock, AR)

[38]  Triton X-100: Technical Data sheet. 2010 (The Dow Chemical Company). Available at http://www.dow.com/markets-and-solutions/products/TRITON/TRITONX100 [Verified 16 September 2015].

[39]  Screening Information Dataset Initial Assessment Profile: Sodium Dodecyl Sulfate. CAS number 151-2135-3 1995 (Organization of Economic Cooperation and Development). Available at http://webnet.oecd.org/HPV/UI/Search.aspx [Verified 16 September 2015].

[40]  B. S. Nunes, F. D. Carvalho, L. M. Guilhermino, G. V. Stappen, Use of the genus Artemia in ecotoxicity testing. Environ. Pollut. 2006, 144, 453.
Use of the genus Artemia in ecotoxicity testing.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XpslSltL4%3D&md5=e81eec2e1d714b42a178bcc27e81d55dCAS | 16677747PubMed |

[41]  T. H. MacRae, A. S. Pandey, Effects of metals on early life stages of the brine shrimp, Artemia: a developmental toxicity assay. Arch. Environ. Contam. Toxicol. 1991, 20, 247.
Effects of metals on early life stages of the brine shrimp, Artemia: a developmental toxicity assay.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXps1Ckuw%3D%3D&md5=b5ae992913ad0bc8d32d14ce0fc8666eCAS | 2015000PubMed |

[42]  C. Arulvasu, S. M. Jennifer, D. Prabhu, D. Chandhirasekar, Toxicity effect of silver nanoparticles in brine shrimp Artemia. Scientific World J. 2014, 2014, 256919.
Toxicity effect of silver nanoparticles in brine shrimp Artemia.Crossref | GoogleScholarGoogle Scholar |

[43]  L. Manfra, F. Savorelli, M. Pisapia, E. Magaletti, A. M. Cicero, Long-term lethal toxicity test with the crustacean Artemia franciscana. J. Vis. Exp. 2012, 62, 3790.
| 22525984PubMed |

[44]  G. Almendros, Effects of different chemical modifications on peat humic acid and their bearing on some agrobiological characteristics of soil. Commun Soil Sci Plan. 1994, 25, 2711.
Effects of different chemical modifications on peat humic acid and their bearing on some agrobiological characteristics of soil.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXlsFKntbg%3D&md5=9ff095cf855b68c5ee5391501a590f3bCAS |

[45]  G. Chilom, A. S. Bruns, J. A. Rice, Aggregation of humic acid in solution: Contributions of different fractions. Org. Geochem. 2009, 40, 455.
Aggregation of humic acid in solution: Contributions of different fractions.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjsVCjsL0%3D&md5=bbad64d3742a33de37d6209959157779CAS |

[46]  L. E. Wise, M. Murphy, A. d’Addieco, Chlorite holocellulose, its fractionation and bearing on summative wood analysis and on studies on the hemicelluloses. Paper Trade Journal 1946, 122, 35.
| 1:CAS:528:DyaH28XnsFWi&md5=c4cf14311d33fbf96ca48d49b2877be7CAS |

[47]  Methods for Measuring the Acute Toxicity of Effluents and Receiving Waters to Freshwater and Marine Organisms, Appendix A, Park B: Distribution, Life Cycle, Taxonomy, and Culture Methods: Brine Shrimp (Artemia salina) 2002 (Environmental Protection Agency). Available at http://water.epa.gov/scitech/methods/cwa/wet/ [Verified 16 September 2015].

[48]  P. Sorgeloos, C. R.-V. D. Wielen, G. Persoone, The use of Artemia nauplii for toxicity tests - a critical analysis. Ecotoxicol. Environ. Saf. 1978, 2, 249.
The use of Artemia nauplii for toxicity tests - a critical analysis.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1MXktVSrtbw%3D&md5=10a1659341561ccd51aecc2802705fa5CAS | 751788PubMed |

[49]  R. S. Matthews, Artemia salina as a test organism for measuring superoxide-mediated toxicity. Free Radic. Biol. Med. 1995, 18, 919.
Artemia salina as a test organism for measuring superoxide-mediated toxicity.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXkslSkurY%3D&md5=6b924017e332ecb3440ee75ae86faabbCAS | 7797101PubMed |

[50]  A. L. Rodd, M. A. Creighton, C. A. Vaslet, J. R. Rangel-Mendez, R. H. Hurt, A. B. Kane, Effects of surface-engineered nanoparticle-based dispersants for marine oil spills on the model organism Artemia franciscana. Environ. Sci. Technol. 2014, 48, 6419.
Effects of surface-engineered nanoparticle-based dispersants for marine oil spills on the model organism Artemia franciscana.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXnvVSnsb0%3D&md5=7f37adab4f8d9a4d3659c22b96e8d410CAS | 24823274PubMed |

[51]  B. Xing, W. B. McGill, M. J. Dudas, Cross-correlation of polarity curves to predict partition coefficients of nonionic organic contaminants. Environ. Sci. Technol. 1994, 28, 1929.
Cross-correlation of polarity curves to predict partition coefficients of nonionic organic contaminants.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXls12gsrk%3D&md5=17e5ea890f15caf6123b617ba4da1077CAS | 22175935PubMed |

[52]  G. Chilom, J. A. Rice, Structural organization of humic acid in the solid state. Langmuir 2009, 25, 9012.
Structural organization of humic acid in the solid state.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXlt1GqsrY%3D&md5=d01f16ef40a6ed4f646e9711a0d0ba10CAS | 19408899PubMed |

[53]  P. J. Mitchell, M. J. Simpson, High affinity sorption domains in soil are blocked by polar soil organic matter components. Environ. Sci. Technol. 2013, 47, 412.
High affinity sorption domains in soil are blocked by polar soil organic matter components.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhslKhsL3F&md5=0f82ff26443c465398561cf00d7bcab4CAS | 23206246PubMed |

[54]  C. Lattao, J. Birdwell, J. J. Wang, R. L. Cook, Studying organic matter molecular assemblage within a whole organic soil by nuclear magnetic resonance. J. Environ. Qual. 2008, 37, 1501.
Studying organic matter molecular assemblage within a whole organic soil by nuclear magnetic resonance.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXos1eksLY%3D&md5=b3643533612f3b119227b3774db53fc5CAS | 18574182PubMed |

[55]  Y.-P. Chin, G. R. Aiken, K. M. Danielsen, Binding of pyrene to aquatic and commercial humic substances: The role of molecular weight and aromaticity. Environ. Sci. Technol. 1997, 31, 1630.
Binding of pyrene to aquatic and commercial humic substances: The role of molecular weight and aromaticity.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXislSlt7w%3D&md5=b92a5bd3432c0d55d5658820e4539204CAS |

[56]  Y. Laor, W. J. Farmer, Y. Aochi, P. F. Strom, Phenanthrene binding and sorption to dissolved and to mineral-associated humic acid. Water Res. 1998, 32, 1923.
Phenanthrene binding and sorption to dissolved and to mineral-associated humic acid.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXks1SmsLk%3D&md5=c1307831ee14d8e838cdc9c39ef25948CAS |

[57]  J. L. Bonin, M. J. Simpson, Variation in phenanthrene sorption coefficients with soil organic matter fractionation: the result of structure or conformation? Environ. Sci. Technol. 2007, 41, 153.
Variation in phenanthrene sorption coefficients with soil organic matter fractionation: the result of structure or conformation?Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtlCit7nL&md5=4a0a286e9a5146bee47340d9ebf9f978CAS | 17265941PubMed |