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Original Articles

Evaluating π-π-Interactions as a Method for Isolation of Polycyclic Aromatic Hydrocarbons from Solution

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Pages 643-655 | Received 17 Feb 2012, Accepted 16 May 2012, Published online: 13 Nov 2012

REFERENCES

  • Hunter , C. A. , Lawson , K. R. , Perkins , J. and Urch , C. J. 2001 . Aromatic Interactions . J. Chem. Soc.Perkin Trans. , 2 : 651 – 69 .
  • Tewari , A. K. and Dubey , R. 2008 . Emerging Trends in Molecular Recognition: Utility of Weak Aromatic Interactions . Bioorg. Med. Chem. , 16 : 126 – 43 .
  • Meyer , E. A. , Castellano , R. K. and Diederich , F. 2003 . Interactions with Aromatic Rings in Chemical and Biological Recognition . Angew. Chem. Int. Ed. , 42 : 1210 – 50 .
  • Salonen , L. M. , Ellermann , M. and Diederich , F. 2011 . Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures . Angew. Chem. Int. Ed. , 50 : 4808 – 42 .
  • Burley , S. K. and Petsko , G. A. 1985 . Aromatic-Aromatic Interaction: A Mechanism of Protein Structure Stabilization . Science , 229 : 23 – 8 .
  • Burley , S. K. and Petsko , G. A. 1988 . Weakly Polar Interactions in Proteins . Adv. Prot. Chem. , 39 : 125 – 89 .
  • Kryger , G. , Silman , I. and Sussman , J. L. 1998 . Three-Dimensional Structure of a Complex of E2020 with Acetylcholinesterase from Torpedo Californica . J. Physiol. , 92 : 191 – 4 .
  • Kryger , G. , Silman , I. and Sussman , J. L. 1999 . Structure of Acetylcholinesterase Complexed with E2020 (Aricept (R)): Implications for the Design of New Anti-Alzheimer Drugs . Structure , 7 : 297 – 307 .
  • Steullet , V. and Dixon , D. W. 1999 . Self-Stacking of Naphthalene bis(dicarboximide)s Probed by NMR . J. Chem. Soc., Perkin Trans. , 2 : 1547 – 58 .
  • Aas , E. , Baussant , T. , Balk , L. , Liewenborg , B and Andersen , O. K. 2000 . PAH Metabolites in Bile, Cytochrome P4501A and DNA Adducts as Environmental Risk Parameters for Chronic Oil Exposure: A Laboratory Experiment with Atlantic Cod . Aquat. Toxicol. , 51 : 241 – 58 .
  • Durell , G. , Utvik , T. R. , Johnsen , S. , Frost , T. and Neff , J. 2006 . Oil Well Produced Water Discharges to the North Sea. Part I: Comparison of Deployed Mussels (Mytilus edulis), Semi-Permeable Membrane Devices, and the DREAM Model Predictions to Estimate the Dispersion of Polycyclic Aromatic Hydrocarbons . Mar. Environ. Res. , 62 : 194 – 223 .
  • Jonsson , G. , Beyer , J. , Wells , D. and Ariese , F. 2003 . The Application of HPLC-F and GC-MS to the Analysis of Selected Hydroxyl Polycyclic Hydrocarbons in Two Certified Fish Bile Reference Materials . J. Environ. Monit. , 5 : 513 – 20 .
  • Christou , M. , Savas , U. , Schroeder , S. , Shen , X. , Thompson , T. , Gould , M. N. and Jefcoate , C. R. 1995 . Cytochromes CYP1A1 and CYP1B1 in the Rat Mammary-Gland-Cell-Specific Expression and Regulation by Polycyclic Aromatic Hydrocarbons and Hormones . Mol. Cell Endocrinol. , 115 : 41 – 50 .
  • Marston , C. P. , Pereira , C. , Ferguson , J. , Fischer , K. , Hedstrom , O. , Dashwood , W.-M. and Baird , W. M. 2001 . Effect of a Complex Environmental Mixture from Coal Tar Containing Polycyclic Aromatic Hydrocarbons (PAH) on The Tumor Initiation, PAH-DNA Binding and Metabolic Activation of Carcinogenic PAH in Mouse Epidermis . Carcinogenesis , 22 : 1077 – 86 .
  • Poster , D. L. , Schantz , M. M. , Sander , L. C. and Wise , S. A. 2006 . Analysis of Polycyclic Aromatic Hydrocarbons (PAPs) in Environmental Samples: A Critical Review of Gas Chromatographic (GC) Methods . Anal. Bioanal. Chem. , 386 : 859 – 81 .
  • Kouzayha , A. , Al Iskandarani , M. , Hokh , S. , Rabaa , A. R. , Budzinski , H. and Jaber , F. 2011 . Optimization of a Solid-Phase Extraction Method using Centrifugation for the Determination of 16 Polycyclic Aromatic Hydrocarbons in Water . J. Agric. Food Chem. , 59 : 7592 – 600 .
  • Ma , J. , Xiao , R. , Li , J. , Yu , J. , Zhang , Y. and Chen , L. 2010 . Determination of 16 Polycyclic Aromatic Hydrocarbons in Environmental Water Samples by Solid-Phase Extraction using Multi-Walled Carbon Nanotubes as Adsorbent Coupled with Gas Chromatography-Mass Spectrometry . J. Chromatogr. A , 1217 : 5462 – 9 .
  • Sijbesma , R. P. , Kentgens , A. P. M. and Nolte , R. J. M. 1991 . Binding of Dihydroxybenzenes in a Synthetic Molecular Clip. Effect of Hydrogen Bonding and Pi-Stacking . J. Org. Chem. , 56 : 3199 – 201 .
  • Sijbesma , R. P. , Kentgens , A. P. M. , Lutz , E. T. G. , Van der Maas , J. H. and Nolte , R. J. 1993 . Binding Features of Molecular Clips Derived from Diphenylglycoluril . J. Amer. Chem. Soc. , 115 : 8999 – 9005 .
  • Gieling , G. T. W. , Sceeren , H. W. , Israel , R. and Nolte , R. J. M. 1996 . Synthesis and Physical Properties Of Novel Guanidine Containing Molecular Clips. Strong Host-Guest Binding and Formation of a Lyotropic Liquid Crystalline Phase . Chem. Commun. , : 241 – 3 .
  • Reek , J. N. H. , Priem , A. H. , Engelkapm , H. , Rowan , A. E. , Elemans , J. A. A.W. and Nolte , R. J. M. 1997 . Binding Features of Molecular Clips. Separation of the Effects of Hydrogen Bonding and Pi-Pi Interations . J. Amer. Chem. Soc. , 119 : 9956 – 64 .
  • Rezaei-Seresht , E. and Hokmabadi , F. 2010 . First immobilization of a Glycoluril-Derived Molecular Clip on Merrifield Resin: Facile Separation of Dihydroxybenzenes by Affinity Chromatography . Tetrahedron Lett , 51 : 2473 – 6 .
  • Li , L. , Sun , Y. , Wang , S. , Qiu , M. and “ , A. Wu. 2010 . New Fluorescent Probes based on Supramolecular Diastereomers for the Detection of 2-nitrophenol . Talanta , 81 : 1643 – 9 .
  • Jørgensen , K. B. and Joensen , M. 2008 . Photochemical Synthesis of Chrysenols . Polycycl. Arom. Comp. , 28 : 362 – 72 .
  • Albericlo , F. , Kneib-Cordonier , N. , Bianclana , S. , Gera , L. , Masada , R. I. , Hudson , D. and Barany , G. 1990 . Preparation and Application of the 5-(4-(9-fluorenylmethyloxycarbonyl)aminomethyl-3,5-dimethoxy)-valeric Acid (PAL) Handle for Solid-Phase Synthesis of C-Terminal Peptide Amides under Mild Conditions . J. Org. Chem. , 55 : 3730 – 43 .
  • TentaGel is the trademark of Rapp Polymer GmbH . (http://www.rapp-polymere.com/preise/tent_s_d.htm)
  • Sydnes , M. O. , Hayashi , Y. , Sharma , V. K. , Hamada , T. , Bacha , U. , Barrila , J. , Freire , E. and Kiso , Y. 2006 . Synthesis of Glutamic Acid and Glutamine Peptides Possessing a Trifluoromethyl Ketone Group as SARS-CoV 3CL Protease Inhibitors . Tetrahedron , 62 : 8601 – 9 .
  • Andrade-Eiroa , A. , Leroy , V. , Dagaut , P. and Bedjanian , Y. 2010 . Determination of Polycyclic Aromatic Hydrocarbons in Kerosene and Bio-kerosene Soot . Chemosphere , 78 : 1342 – 9 .
  • Titato , G. M. and Lanças , F. M. 2005 . Comparison between Different Extraction (LLE and SPE) and Determination (HPLC and Capillary-LC) Techniques in the Analysis of Selected PAHs in Water Samples . J. Liq. Chromatogr. Relat. Technol. , 28 : 3045 – 56 .

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