113
Views
4
CrossRef citations to date
0
Altmetric
Articles

Prediction of immobilised artificial membrane chromatography retention factors using theoretical molecular fragments and structural features

, , , , , & show all
Pages 661-678 | Received 30 Nov 2012, Accepted 06 Feb 2013, Published online: 03 Jun 2013

References

  • European Union, Overview of structure–activity relationships for environmental endpoints, Part 1: General outline and procedure, Report of the EU–DG–XII Project, QSAR for Predicting Fate and Effects of Chemicals in the Environment (Contract EV5V–CT92–0211) (1995).
  • Dearden , J.C. 1985 . Partitioning and lipophilicity in quantitative structure–activity relationships . Environ. Health Perspect. , 61 : 203 – 228 .
  • Organisation for Economic Cooperation and Development, OECD guidelines for the testing of chemicals, No. 117: Partition coefficient (n-octanol/water), high performance liquid chromatography (HPLC) method, Paris: Organisation for Economic Cooperation and Development (1994).
  • Organisation for Economic Cooperation and Development . 1995 . OECD guidelines for the testing of chemicals, No. 107: Partition coefficient (n-octanol/water): Shake flask method , Paris : Organisation for Economic Cooperation and Development .
  • Short , J. , Roberts , J. , Roberts , D.W. , Hodges , G. , Gutsell , S. and Ward , R.S. 2010 . Practical methods for the measurement of log P for surfactants . Ecotoxicol. Environ. Saf. , 73 : 1484 – 1489 .
  • Pidgeon , C. and Venkatarum , U.V. 1989 . Immobilized artificial membrane chromatography: Supports composed of membrane lipids . Anal. Biochem. , 76 : 36 – 47 .
  • Ward , R.S. , Davies , J. , Hodges , G. and Roberts , D.W. 2003 . Applications of immobilised artificial membrane chromatography to quaternary alkylammonium sulfobetaines and comparison of chromatographic methods for estimating the octanol–water partition coefficient . J. Chromatogr., A , 1006 : 67 – 75 .
  • Ledbetter , M.R. , Hodges , S.G. , Madden , J.C. , O’Connor , S. and Cronin , M.T.D. 2011 . A database of collated retention factors for immobilised artificial membrane HPLC and an assessment of the effects of experimental variability . Environ. Toxicol. Chem. , 30 : 2701 – 2708 .
  • Vaes , W.H.J. , Ramos , E.U. , Verhaar , H.J.M. and Hermens , J.L.M. 1998 . Acute toxicity of nonpolar versus polar narcosis: Is there a difference? . Environ. Toxicol Chem. , 17 : 1380 – 1384 .
  • Taillardat-Bertschinger , A. , Barbato , F. , Quercia , M.T. , Carrupt , P.A. , Reist , M. , La Rotonda , M.I. and Testa , B. 2002 . Structural properties governing retention mechanisms on immobilized artificial membrane (IAM) HPLC columns . Helv. Chim. Acta , 85 : 519 – 532 .
  • Testa , B. , Crivori , P. , Reist , M. and Carrupt , P. 2000 . The influence of lipophilicity on the pharmacokinetic behavior of drugs: Concepts and examples . Perspect. Drug Discov. , 19 : 179 – 211 .
  • Taillardat-Bertschinger , A. , Carrupt , P. , Barbato , F. and Testa , B. 2003 . Immobilized artificial membrane HPLC in drug research . J. Med. Chem. , 46 : 655 – 665 .
  • Ledbetter , M. , Gutsell , S. , Hodges , G. , Madden , J.C. , Rowe , P. and Cronin , M.T.D. 2012 . Robustness of an immobilised artificial membrane high-performance liquid chromatography for the determination of hydrophobicity . J. Chem. Eng. Data , 57 : 3696 – 3700 .
  • M. Ledbetter, Development of analytical methods to derive hydrophobicity parameters for use as descriptors for the prediction of the environmental and human health risk of chemicals, PhD thesis, Liverpool John Moores University, 2012.
  • Hansch , C. and Leo , A. 1979 . Substituent constants for correlation analysis in chemistry and biology , New York : Wiley–Interscience .
  • Leo , A. , Jow , P.Y.C. , Silipo , C. and Hansch , C. 1975 . Calculation of hydrophobic constant (log P) from π and f constants . J. Med. Chem. , 18 : 865 – 868 .
  • Rekker , R.F. 1977 . The Hydrophobic Fragmental Constant , New York : Elsevier .
  • Mannhold , R. , Rekker , R.F. , Dross , K. , Bijloo , G. and de Vries , G. 1998 . The lipophilic behaviour of organic compounds: 1. An updating of the hydrophobic fragmental constant approach . Quant. Struct.–Act. Rel. , 17 : 517 – 536 .
  • Roberts , D.W. 1991 . QSAR issues in aquatic toxicity of surfactants . Sci. Total Environ. , 109 ( 110 ) : 557 – 568 .
  • Hodges , G. , Roberts , D.W. , Marshall , S.J. and Dearden , J.C. 2006 . The aquatic toxicity of anionic surfactants to Daphnia magna – A comparative QSAR study of linear alkylbenzene sulophonates and ester sulphonates . Chemosphere , 63 : 1443 – 1450 .
  • Demare , S. , Roy , D. and Legerdre , J.Y. 1999 . Factors governing the retention of solutes on chromatographic immobilized artificial membranes: Application to anti-inflammatory and analgesic drugs . J. Liq. Chromatogr. Relat. Technol. , 22 : 2675 – 2688 .
  • SPSS Version 15.0.1, SPSS Inc. Software Products, Chicago, IL, 2006.
  • Estimation Programs Interface Suite for Microsoft Windows V 4.10., United States Environmental Protection Agency, Washington, DC, 2010.
  • D.D. Ebbing and S.D. Gammon, General Chemistry, 9th edition, Belmont: Houghton Mifflin, pp. 681 (2009).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.