Investigation of lipophilicity of anticancer-active thioquinoline derivatives

Biomedical Chromatography

Volumn 21, Issue 2, 2007, Pages 123-131

  Bajda, Marek ^a   Boryczka, Stanisław ^b   Wietrzyk, Joanna ^c   Malawska, Barbara ^a  

^a JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

^b MEDICAL UNIVERSITY OF SILESIA   (Poland)

^c INSTITUTE OF IMMUNOLOGY AND EXPERIMENTAL THERAPY   (Poland)

Author keywords

Calculating partition coefficient logP; Immobilized artificial membrane; Reversed phase chromatography; Thioquinoline derivatives

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; COLUMN CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; THIN LAYER CHROMATOGRAPHY;

CACHE PROGRAM; CALCULATING PARTITION COEFFICIENT LOGP; IMMOBILIZED ARTIFICIAL MEMBRANES; LIPOPHILICITY; MOBILE PHASIS; PARTITION COEFFICIENT; REVERSED PHASE; REVERSED PHASE CHROMATOGRAPHY; RP-HPLC; THIOQUINOLINE DERIVATIVE;

ACETONITRILE;

ACETONITRILE; ANTINEOPLASTIC AGENT; PROPARGYLTHIOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; ARTIFICIAL MEMBRANE; CALCULATION; CONTROLLED STUDY; DRUG DETERMINATION; DRUG STRUCTURE; INTERMETHOD COMPARISON; LIPOPHILICITY; MOLECULAR WEIGHT; PREDICTION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; THIN LAYER CHROMATOGRAPHY;

EID: 33847061996     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.706     Document Type: Article

References (28)

1. Baguley BC and Finlay GJ. Derivatives of amsacrine: determinants required for high activity against Lewis lung carcinoma. Journal of the National Cancer Institute 1988; 80: 195.
2. Biagi G, Recantani M, Barbaro A and Borea P. Lipophilicity estimation of drugs. Process Control and Quality 1997; 10: 129.
3. Boryczka S, Wietrzyk J and Opolski A. Synthesis and antiproliferative activity in vitro of new propargyl thioquinolines. Pharmazie 2002a; 57: 151.
4. Boryczka S, Wietrzyk J, Nasulewicz A, Pełczyńska M and Opolski A. New propargyl thioquinolines - synthesis, antiproliferative activity in vitro and structure-activity relationships. Pharmazie 2002b; 57: 733.
5. Boryczka S, Kulig K and Malawska B. RP TLC Determination of the lipophilicity of anticancer-active propargyl thioquinolines. Journal of Planar Chromatography 2003; 16: 117.
6. Chau MD, Strafford M, Avdeef A, Valko K and Abraham M. Filtered-immobilized artificial membrane permeability assay as a model for drug absorption: comparison with Caco-2 and MDCK cells using the Abraham equation, http://www.pioinc.com/images/SLOChau01.pdf 2005.
7. oct. and HPLC capacity factor on a porous polymer gel in the study of a series of 2-benzamido-5-nitrothiazoles. Quantitative Structure-Activity Relationships 1998; 17: 1.
8. Ecker GF and Noe CR. In silico prediction models for blood-brain barrier permeation. Current Medicinal Chemistry 2004; 11: 1617.
9. Escuder-Gilabert, Martýnez-Pla J, Sagrado S, Villanueva-Camañas R and Medina-Hernández M. Biopartitioning micellar separation methods: modelling drug absorption. Journal of Chromatography B 2003; 797: 21.
10. Facchetti I, Grandi M, Cucchi P, Geroni C, Penco S and Vigevani A. Influence of lipophilicity of anthracyclines in LoVo and LoVo/Dx human cell lines. Anti-Cancer Drug Design 1991; 6: 385.
11. Faller B, Grim HP, Loeuillet-Ritzler F, Arnold S and Briand X. High-thoughput lipophilicity measurement with immobilized artificial membranes. Journal of Medicinal Chemistry 2005; 48: 2571.
12. Kaliszan R, Haber P, Baczek T and Siluk D. Gradient HPLC in the determination of drug lipophilicity and acidity. Pure and Applied Chemistry 2001; 73: 1465.
13. Kaliszan R, Nasal A and Markuszewski M. New approaches to chromatographic determination of lipophilicity of xenobiotics. Analytical and Bioanalytical Chemistry 2003; 377: 803.
14. Lab Tools. Tables for Laboratory Use. Merck, 2005.
15. Leeson PD and Davis AM. Time-related differences in the physical property profiles of oral drugs. Journal of Medicinal Chemistry 2004; 47: 6368.
16. Maliepaard M, de Mot NJ, Janssen LHM, van der Neut W, Verboom W and Reinhoudt DN. Role of lipophilicity in the in vitro antitumor activity of a series of new mitosene compounds. Anti-Cancer Drug Design 1992; 7: 415.
17. Mazerska Z, Augustin E, Dziegielewski J, Chołdy MW and Konopa J. QSAR of acridines, III. Structure-activity relationship for antitumor imidazoacridinones and intercorrelations between in vivo and in vitro tests. Anti-Cancer Drug Design 1996; 11: 73.
18. Ong S, Liu H and Pidggeon C. Immobilized-artificial-membrane chromatography: Measurements of membrane partition coefficient and predicting drug membrane partition permeability. Journal of Chromatography A 1996; 728: 113.
19. Pidgeon C, Ong S, Liu H, Qiu X, Pidgeon M, Dantzig A, Munroe J, Hornback WJ, Kasher JS, Glunz L and Szczerba T. IAM chromatography: An in vitro screen for predicting drug membrane permeability. Journal of Medicinal Chemistry 1995; 38: 590.
20. Proudfoot JR. The evolution of synthetic oral drug properties. Bioorganic and Medicinal Chemistry Letters. 2005; 15: 1087.
21. Sosnovsky G and Rao Num. In the search for new anticancer drugs XV. Various aliphatic and aromatic hydrazones containing the N, N; N′, N′-bis(1,2-ethanediyl)phosphoric diamide moiety. Cancer Letters 1985; 29: 309.
22. Sosnovsky G and Rao NUM. In the search for new anticancer drugs XVIII. Various mono- and bis-anthraquinone hydrazones containing the N, N; N′, N′-bis(1,2-ethanediyl)phosphoric diamide moiety. Cancer Letters 1986; 32: 155.
23. Taillardat-Bertschinger A. Molecular factors influencing retention on immobilized artificial membrane compared to partitioning in liposomes and n-octanol. Pharmaceutical Research 2002; 19: 6.
24. Taillardat-Bertschinger A and Carrupt P. Immobilized artificial membrane HPLC in drug research. Journal of Medicinal Chemistry 2003; 46: 635.
25. Testa B, van de Waterbeemd H, Folkers G and Guy R (eds). Pharmacokinetic Optimization in Drug Research: Biological, Physicochemical, and Computational Strategies Wiley-VCH: New York, 2001.
26. Tetko IV and Poda GI. Application of ALOGPS 2.1 to predict logD distribution coefficient for Pfizer proprietary compounds. Journal of Medicinal Chemistry 2004; 47: 5601.
27. Vieth M, Siegel MG, Higgs RE, Watson IA, Robertson DH, Savin KA, Durst GL and Hipskind PA. Characteristic physical properties and structural fragments of marketed oral drugs. Journal of Medicinal Chemistry 2004; 47: 224.
28. Waterhouse R. Determination lipophilicity and its use as predicator of blood-brain barrier penetration of molecular imaging agents. Molecular Imaging and Biology 2003; 5(6): 376.