Screening for low aquatic bioaccumulation (1): Lipinski's ‘Rule of 5’ and molecular size

References

• European Commission, REGULATION (EC) No 1907/2006 OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 18 December 2006 concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH), establishing a European Chemicals Agency, amending Directive 1999/45/EC and repealing Council Regulation (EEC) No 793/93 and Commission Regulation (EC) No 1488/94 as well as Council Directive 76/769/EEC and Commission Directives 91/155/EEC, 93/67/EEC, 93/105/EC and 2000/21/EC, Brussels, Belgium, 2006
   Google Scholar
• OECD . 1996 . Guidelines for testing of chemicals. 305. Bioconcentration: Flow-through fish test , France : Paris .
   Google Scholar
• Arnot , JA and Gobas , FAPC . 2003 . A generic QSAR for assessing the bioaccumulation potential of organic chemicals in aquatic food webs . QSAR Combi. Sci. , 22 : 337 – 345 .
   Google Scholar
• Sijm , DTHM , Rikken , MGJ , Rorije , E , Traas , TP , McLachlan , MS and Peijnenburg , WJGM . 2007 . “ Transport, accumulation and transformation processes ” . In Risk Assessment of Chemicals: An Introduction, , 2nd , Edited by: van Leeuwen , CJ and Vermeire , TG . 73 – 158 . Dordrecht : Springer .
   Google Scholar
• Gobas , FAPC , de Wolf , W , Burkhard , LP , Verbruggen , EMJ and Plotzke , K . 2009 . Revisiting bioaccumulation criteria for POPs and PBT assessments . Integr. Environ. Assess. Manag. , 5 : 624 – 637 .
   PubMedGoogle Scholar
• ILSI HESI/JRC/SETAC-EU, Workshop on Bioaccumulation Assessments, Dutch Congress Centre, The Hague, The Netherlands, May 5–6, 2006
   Google Scholar
• Nichols , JW , Bonnell , M , Dimitrov , S , Escher , BI , Han , X and Kramer , NI . 2009 . Bioaccumulation assessment using predictive approaches . Integr. Environ. Assess. Manag. , 5 : 577 – 597 .
   PubMedGoogle Scholar
• Pavan , M , Netzeva , TI and Worth , AP . 2008 . Review of literature-based quantitative structure-activity relationship models for bioconcentration . QSAR Combi. Sci. , 27 : 21 – 31 .
   Google Scholar
• Dearden , JC . 2004 . “ QSAR modeling of bioaccumulation ” . In Predicting Chemical Toxicity and Fate , Edited by: Cronin , MTD and Livingstone , DJ . 333 – 355 . Boca Raton , FL : CRC Press .
   Google Scholar
• Nendza , M . 1998 . Structure–Activity Relationships in Environmental Sciences , London : Chapman & Hall .
   Google Scholar
• Nendza , M and Müller , M . 2007 . Literature study: Effects of molecular size and lipid solubility on bioaccumulation potential , Dessau , , Germany : Umweltbundesamt .
   Google Scholar
• Arijs , K , Versonnen , B , Jeliazkova , N , Comber , M , Verdonck , F , Iaccino , F and Vangheluwe , M . Validation of bioaccumulation threshold criteria. Poster at SETAC Europe 17th Annual Meeting, Porto, 2007
   Google Scholar
• Dimitrov , S , Dimitrova , N , Parkerton , T , Comber , M , Bonnell , M and Mekenyan , OG . 2005 . Base-line model for identifying the bioaccumulation potential of chemicals . SAR QSAR Environ. Res. , 16 : 531 – 554 .
   PubMed Web of Science ®Google Scholar
• Anliker , R , Moser , P and Poppinger , D . 1988 . Bioaccumulation of dyestuffs and organic pigments in fish: Relationships to hydrophobicity and steric factors . Chemosphere, , 17 : 1631 – 1644 .
   Web of Science ®Google Scholar
• Dimitrov , S , Dimitrova , N , Walker , JD , Veith , GD and Mekenyan , OG . 2002 . Predicting bioconcentration factors of highly hydrophobic chemicals. Effects of molecular size . Pure Appl. Chem. , 74 : 1823 – 1830 .
   Web of Science ®Google Scholar
• European Communities, Technical guidance document on risk assessment in support of Commission Directive 93/67/EEC on risk assessment for new notified substances, Commission Regulation (EC) No 1488/94 on risk assessment for existing substances, Directive 98/8/EC of the European Parliament and of the Council concerning the placing of biocidal products on the market, Joint Research Centre, Ispra, Italy, 2003
   Google Scholar
• Opperhuizen , A , van der Velde , EW , Gobas , FAPC , Liem , DAK , van der Steen , JMD and Hutzinger , O . 1985 . Relationship between bioconcentration in fish and steric factors of hydrophobic chemicals . Chemosphere , 14 : 1871 – 1896 .
   Web of Science ®Google Scholar
• Opperhuizen , A , Damen , HWJ , Asyee , GM , van der Steen , JMD and Hutzinger , O . 1987 . Uptake and elimination by fish of polydimethylsiloxanes (silicones) after dietary and aqueous exposure . Toxicol. Environ. Chem. , 13 : 265 – 285 .
   Web of Science ®Google Scholar
• Beek , B . 1991 . “ Welcome address and introduction ” . In Bioaccumulation in Aquatic Systems , Edited by: Nagel , R and Loskill , R . 1 – 5 . Weinheim : VCH .
   Google Scholar
• Environment Canada, Environmental categorization for persistence, bioaccumulation and inherent toxicity of substances on the domestic substances list using QSARs, 2000
   Google Scholar
• Comber , M , Robertson , S and Sijm , DTHM . Discussion paper for the TC NES subgroup on PBTs ACHS/06/11A, 2006, Available at http://www.defra.gov.uk/environment/chemicals/achs/060606/agenda.htm
   Google Scholar
• Sakuratani , Y , Noguchi , Y , Kobayashi , K , Yamada , J and Nishihara , T . 2008 . Molecular size as a limiting characteristic for bioconcentration in fish . J. Environ. Biol. , 29 : 89 – 92 .
   PubMed Web of Science ®Google Scholar
• ECHA, Guidance on information requirements and chemical safety assessment Chapter R.11: PBT assessment, 2008, Available at http://echa.europa.eu/reach_en.asp
   Google Scholar
• Connell , DW and Hawker , DW . 1988 . Use of polynominal expressions to describe the bioconcentration of hydrophobic chemicals by fish . Ecotox. Environ. Saf. , 16 : 242 – 257 .
   PubMed Web of Science ®Google Scholar
• Nendza , M . 1991 . “ QSARs of bioconcentration: validity assessment of log Pow/log BCF correlations ” . In Bioaccumulation in Aquatic Systems , Edited by: Nagel , R and Loskill , R . 43 – 66 . Weinheim : VCH .
   Google Scholar
• Gobas , FAPC , Moore , MM , Hermens , JLM and Arnot. , JA . 2006 . Bioaccumulation reality check , Vol. 7 , 40 – 41 . SETAC Globe .
   Google Scholar
• Jonker , M and van der Haijden , S . 2007 . Bioconcentration factor hydrophobicity cut-off: An artificial phenomenon reconstructed . Environ. Sci. Technol. , 41 : 7363 – 7369 .
   PubMed Web of Science ®Google Scholar
• Hawker , DW and Connell , DW . 1989 . A simple water/octanol partition system for bioconcentration investigations . Environ. Sci. Technol. , 23 : 961 – 965 .
   Web of Science ®Google Scholar
• Lipinski , CA , Lombardo , F , Dominy , BW and Feeney , PJ . 1997 . Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings . Adv. Drug Deliv. Rev. , 23 : 3 – 25 .
   Web of Science ®Google Scholar
• Escher , BI and Weisbrod , A . 2006 . The ‘A' in ADME: Beyond Kow? . SETAC Globe, , 7 ( 2 ) : 45 – 46 .
   Google Scholar
• EURAS, CEFIC LRI Goldstandard Database, 2007, Available at http://ambit.sourceforge.net/euras/
   Google Scholar
• European Trade Union Confederation, Priority list for REACH authorisation, 2009, Available at http://www.etuc.org/a/6022
   Google Scholar
• State of Washington, Department of Ecology, Chapter 173-333 WAC: Persistent bioaccumulative toxins, 2006, Available at www.ecy.wa.gov/pubs/wac173333.pdf
   Google Scholar
• ECHA, Candidate list of Substances of Very High Concern for Authorisation, 2009. Available at http://echa.europa.eu/chem_data/candidate_list_table_en.asp
   Google Scholar
• EPA , US . PBT chemicals which are subject to reporting under the EPCRA section 313, 2009, Available at http://www.epa.gov/tri/trichemicals/pbt%20chemicals/pbt_chem_list.htm
   Google Scholar
• ChemSec, The International Chemical Secretariat, SIN List 1.0., Brussels, Belgium, 2009, Available at http://www.chemsec.org/list/download/
   Google Scholar
• ESIS, European Chemical Substances Information System/PBT List, 2009, Available at http://ecb.jrc.it/esis/index.php?PGM=pbt
   Google Scholar
• EPA , US . 2009 . PBT Profiler Washington , DC Available at http://www.epa.gov/oppt/sf/tools/pbtprofiler.htm
   Google Scholar
• Nendza , M , Aldenberg , T , Benfenati , E , Benigni , R , Cronin , M , Escher , S , Fernandez , A , Gabbert , S , Giralt , F , Hewitt , M , Hrovat , M , Jeram , S , Kroese , D , Madden , J , Mangelsdorf , I , Rallo , R , Roncaglioni , A , Rorije , E , Segner , H , Simon-Hettich , B and Vermeire. , T . 2010 . Data quality assessment for in silico methods: A survey of approaches and needs, in In Silico Toxicology: Principles and applications, M. Cronin and J. Madden eds Royal Society of Chemistry, Cambridge, UK (in press)
   Google Scholar
• EPA , US . EPI Suite v 3.12. Washington, DC, 2005, Available at http://www.epa.gov/opptintr/exposure/docs/episuite.htm
   Google Scholar
• Dimitrov , S , Dimitrova , N , Walker , J , Veith , GD and Mekenyan , OG . 2003 . Bioconcentration potential predictions based on molecular attributes - an early warning approach for chemicals found in humans, birds, fish and wildlife . QSAR Combi. Sci. , 22 : 58 – 68 .
   Google Scholar
• Schüürmann , G . 1990 . QSAR analysis of the acute fish toxicity of organic phosphorothionates using theoretically derived molecular descriptors . Environ. Toxicol. Chem. , 9 : 417 – 428 .
   Web of Science ®Google Scholar
• Opperhuizen , A . 1991 . “ Bioconcentration and biomagnification: Is a distinction necessary? ” . In Bioaccumulation in Aquatic Systems , Edited by: Nagel , R and Loskill , R . 67 – 80 . Weinheim : VCH .
   Google Scholar
• Hardy , R , MacKie , PR , Whittle , KJ and McIntyre , AD . 1974 . Discrimination in the assimilation of n-alkanes in fish . Nature , 252 : 577 – 578 .
   PubMed Web of Science ®Google Scholar
• Tolls , J , Haller , M , Labee , H , Verweij , M and Sijm , DTHM . 2000 . Experimental determination of bioconcentration of the nonionic surfactant alcohol ethoxylate . Environ. Toxicol. Chem. , 19 : 646 – 653 .
   Web of Science ®Google Scholar
• Seydel , JK and Wiese , M . 2002 . Drug–Membrane Interactions, Analysis, Drug Distribution, Modeling , Weinheim : Wiley-VCH .
   Google Scholar
• Avdeef , A . 2003 . Absorption and Drug Development , Hoboken , NJ : John Wiley & Sons .
   Google Scholar
• Duffy , JC . 2004 . “ Prediction of pharmacokinetic parameters in drug design and toxicology ” . In Predicting Chemical Toxicity and Fate , Edited by: Cronin , MTD and Livingstone , DJ . 229 – 261 . Boca Raton : CRC Press .
   Google Scholar
• Escher , BI and Schwarzenbach , RP . 1996 . Partitioning of substituted phenols in liposome–water, biomembrane–water and octanol–water systems . Environ. Sci. Technol. , 30 : 260 – 270 .
   Web of Science ®Google Scholar
• Schaper , KJ , Zhang , H and Raevsky , OA . 2001 . pH-dependent partitioning of acidic and basic drugs into liposomes - a quantitative structure-activity relationship analysis . Quant. Struct. Act. Relat. , 20 : 46 – 54 .
   Google Scholar
• Kwon , JH , Katz , LE and Liljestrand , HM . 2006 . Use of a parallel artificial membrane system to evaluate passive absorption and elimination in small fish . Environ. Toxicol. Chem. , 25 : 3083 – 3092 .
   PubMed Web of Science ®Google Scholar
• Escher , BI , Berger , C , Bramaz , N , Kwon , JH , Richter , M , Tsinman , O and Avdeef , A . 2008 . Membrane-water partitioning, membrane permeability, and baseline toxicity of the parasiticides ivermectin, albendazole, and morantel . Environ. Toxicol. Chem. , 27 : 909 – 918 .
   PubMed Web of Science ®Google Scholar
• Kwon , JH and Escher , BI . 2008 . A modified parallel artificial membrane permeability assay for evaluating bioconcentration of highly hydrophobic chemicals in fish . Environ. Sci. Technol. , 42 : 1787 – 1793 .
   PubMed Web of Science ®Google Scholar
• Pauletti , GM , Ökamu , FW and Borchardt , RT . 1997 . Effect of size and charge on passive diffusion of peptides across caco-2 cell monolayers via the paracellular pathway . Pharm. Res. , 14 : 164 – 168 .
   PubMed Web of Science ®Google Scholar
• Pärt , P . 1990 . The perfused fish gill preparation in studies of the bioavailability of chemicals . Ecotox. Environ. Saf. , 19 : 106 – 115 .
   PubMed Web of Science ®Google Scholar
• Pärt , P , Saarikoski , J , Tuurala , H and Havaste , K . 1992 . The absorption of hydrophobic chemicals across perfused rainbow trout gills: Methodological aspects . Ecotox. Environ. Saf. , 24 : 275 – 286 .
   PubMed Web of Science ®Google Scholar
• Wood , CM and Pärt , P . 1997 . Cultured branchial epithelia from freshwater fish gills . J. Exp. Biol., , 200 : 1047 – 1059 .
   PubMed Web of Science ®Google Scholar
• Gobas , FAPC , Opperhuizen , A and Hutzinger , O . 1986 . Bioconcentration of hydrophobic organic chemicals in fish: Relationship with membrane permeation . Environ. Toxicol. Chem. , 5 : 637 – 646 .
   Web of Science ®Google Scholar
• Gobas , FAPC and Mackay , D . 1987 . Dynamics of hydrophobic organic chemical bioconcentration in fish . Environ. Toxicol. Chem. , 6 : 495 – 504 .
   Web of Science ®Google Scholar
• European Commission . 2007 . Reference preliminary technical guidance document Chapter PBT and vPvB assessment - Draft , Belgium : Brussels .
   Google Scholar