Chromatographic separation and biological evaluation of benzimidazole derivative enantiomers as inhibitors of leukotriene biosynthesis

Journal of Pharmaceutical and Biomedical Analysis

Volumn 89, Issue , 2014, Pages 88-92

  Sardella, Roccaldo ^a   Levent, Serkan ^b   Ianni, Federica ^a   Çalişkan, Burcu ^b   Gerstmeier, Jana ^c   Pergola, Carlo ^c   Werz, Oliver ^c   Banoglu, Erden ^b   Natalini, Benedetto ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

^b GAZI UNIVERSITY   (Turkey)

^c FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

5 Lipoxygenase activating protein; Benzimidazole; Chromatographic enantioisolation; FLAP; Polysaccharide based stationary phases

Indexed keywords

ALCOHOL; AMYLOSE; ARACHIDONATE 5 LIPOXYGENASE ACTIVATING PROTEIN INHIBITOR; BENZIMIDAZOLE DERIVATIVE; DIETHYLAMINE; HEXANE; LEUKOTRIENE;

ARTICLE; BIOASSAY; CHIRAL CHROMATOGRAPHY; CHIRALITY; ELUTION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; ISOLATION PROCEDURE; ISOMER; LIPOGENESIS; PRIORITY JOURNAL; PROCESS OPTIMIZATION; QUANTITATIVE ANALYSIS; SCREENING;

5-LIPOXYGENASE-ACTIVATING PROTEIN; BENZIMIDAZOLE; CHROMATOGRAPHIC ENANTIOISOLATION; FLAP; POLYSACCHARIDE-BASED STATIONARY PHASES;

AMYLOSE; BENZIMIDAZOLES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG CONTAMINATION; HEXANES; HUMANS; LEUKOTRIENE ANTAGONISTS; LEUKOTRIENES; NEUTROPHILS;

EID: 84888110033     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2013.10.039     Document Type: Article

References (22)

1. Haeggström J.Z., Funk C.D. Lipoxygenase and leukotriene pathways: biochemistry, biology, and roles in disease. Chem. Rev. 2011, 111:5866-5898.
2. Radmark O., Werz O., Steinhilber D., Samuelsson B. 5-Lipoxygenase: regulation of expression and enzyme activity. Trends Biochem. Sci. 2007, 32:332-341.
3. Mancini J.A., Abramovitz M., Cox M.E., Wong E., Charleson S., Perrier H., Wang Z., Prasit P., Vickers P.J. 5-Lipoxygenase-activating protein is an arachidonate binding protein. FEBS Lett. 1993, 318:277-281.
4. Evans J.F., Ferguson A.D., Mosley R.T., Hutchinson J.H. What's all the FLAP about? 5-Lipoxygenase-activating protein inhibitors for inflammatory diseases. Trends Pharmacol. Sci. 2008, 29:72-78.
5. Hutchinson J.H., Li Y., Arruda J.M., Baccei C., Bain G., Chapman C., Correa L., Darlington J., King C.D., Lee C., Lorrain D., Prodanovich P., Rong H., Santini A., Stock N., Prasit P., Evans J.F. 5-Lipoxygenase-activating protein inhibitors: development of 3-[3-tert-butylsulfanyl-1-[4-(6-methoxy-pyridin-3-yl)-benzyl]-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid (AM103). J. Med. Chem. 2009, 52:5803-5815.
6. Stock N., Baccei C., Bain G., Broadhead A., Chapman C., Darlington J., King C., Lee C., Li Y., Lorrain D.S., Prodanovich P., Rong H., Santini A., Zunic J., Evans J.F., Hutchinson J.H., Prasit P. 5-Lipoxygenase-activating protein inhibitors. Part 2: 3-{5-((S)-1-acetyl-2,3-dihydro-1H-indol-2-ylmethoxy)-3-tert-butylsulfanyl-1-[4-(5-methoxy-pyrimidin-2-yl)-benzyl]-1H-indol-2-yl}-2,2-dimethyl-propionic acid (AM679)-a potent FLAP inhibitor. Bioorg. Med. Chem. Lett. 2010, 20:213-217.
7. Stock N., Baccei C., Bain G., Chapman C., Correa L., Darlington J., King C., Lee C., Lorrain D.S., Prodanovich P., Santini A., Schaab K., Evans J.F., Hutchinson J.H., Prasit P. 5-Lipoxygenase-activating protein inhibitors. Part 3: 3-{3-tert-Butylsulfanyl-1-[4-(5-methoxy-pyrimidin-2-yl)-benzyl]-5-(5-methyl-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid (AM643)-a potent FLAP inhibitor suitable for topical administration. Bioorg. Med. Chem. Lett. 2010, 20:4598-4601.
8. Stock N.S., Bain G., Zunic J., Li Y., Ziff J., Roppe J., Santini A., Darlington J., Prodanovich P., King C.D., Baccei C., Lee C., Rong H., Chapman C., Broadhead A., Lorrain D., Correa L., Hutchinson J.H., Evans J.F., Prasit P. 5-Lipoxygenase-activating protein (FLAP) inhibitors. Part 4: development of 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5-(5-methylpyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethylpropionic acid (AM803), a potent, oral, once daily FLAP inhibitor. J. Mater. Chem. 2011, 54:8013-8029.
9. Banoglu E., Çalişkan B., Luderer S., Eren G., Özkan Y., Altenhofen W., Weinigel C., Barz D., Gerstmeier J., Pergola C., Werz O. Identification of novel benzimidazole derivatives as inhibitors of leukotriene biosynthesis by virtual screening targeting 5-lipoxygenase-activating protein. Bioorg. Med. Chem. 2012, 20:3728-3741.
10. Francotte E.R. Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers. J. Chromatogr. A 2001, 906:379-397.
11. Cox G.B. Preparative Enantioselective Chromatography 2005, Wiley-Blackwell.
12. Pirkle W.H., Koscho M.E. Predictable chromatographic separations of enantiomers: aryl allenic acids and their derivatives. J. Chromatogr. A 1997, 761:65-70.
13. Pergola C., Dodt G., Rossi A., Neunhoeffer E., Lawrenz B., Northoff H., Samuelsson B., Radmark O., Sautebin L., Werz O. ERK-mediated regulation of leukotriene biosynthesis by androgens: a molecular basis for gender differences in inflammation and asthma. Proc. Natl. Acad. Sci. U. S. A. 2008, 105:19881-19886.
14. Chankvetadze B., Yashima E., Okamoto Y. Chloromethylphenylcarbamate derivatives of cellulose as chiral stationary phases for high-performance liquid chromatography. J. Chromatogr. A 1994, 670:39-49.
15. Chankvetadze B., Yashima E., Okamoto Y. Dimethyl-, dichloro- and chloromethylphenylcarbamates of amylose as chiral stationary phases for high-performance liquid chromatography. J. Chromatogr. A 1995, 694:101-109.
16. Natalini B., Sardella R., Ianni F., García-Rubiño M.E., Conejo-García A., Núñez M.C., Gallo M.A., Campos J.M. Chromatographic enantioresolution of six purine derivatives endowed with anti-human breast cancer activity. Chromatographia 2013, 76:475-482.
17. Ye Y.K., Stringham R.W. Effect of mobile phase amine additives on enantioselectivity for phenylalanine analogs. J. Chromatogr. A 2001, 927:53-60.
18. Ye Y.K., Stringham R.W. The effect of acidic and basic additives on the enantioseparation of basic drugs using polysaccharide-based chiral stationary phases. Chirality 2006, 18:519-530.
19. Natalini B., Sardella R., Massari S., Ianni F., Tabarrini O., Cecchetti V. Synthesis and chromatographic enantioresolution of anti-HIV quinolone derivatives. Talanta 2011, 85:1392-1397.
20. Maier N.M., Lindner W. Stereoselective chromatography methods for drug analysis. Chirality in Drug Research 2006, 189-260. Wiley, Weinheim. E. Francotte, W. Lindner (Eds.).
21. Wang T., Wenslow R.M. Effect of alcohol mobile-phase modifiers on the structure and chiral selectivity of amylase tris(3,5-dimethylphenylcarbamate) chiral stationary phase. J. Chromatogr. A 2003, 1015:99-110.
22. Wenslow R.M., Wang T. Solid-state NMR characterization of amylase tris(3,5-dimethylphenylcarbamate) chiral stationary-phase structure as a function of mobile-phase composition. Anal. Chem. 2001, 73:4190-4195.