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Volumn 66, Issue , 2012, Pages 100-108

Enantiomeric resolution of albendazole sulfoxide by semipreparative HPLC and in vitro study of growth inhibitory effects on human cancer cell lines

Author keywords

Albendazole sulfoxide; Apoptosis; Polysaccharide based chiral stationary phases; Semipreparative enantiomeric separation; Tumor cell lines

Indexed keywords

ALBENDAZOLE SULFONE; ALBENDAZOLE SULFOXIDE; AMYLOSE TRIS(3,5 DIMETHYLPHENYLCARBAMATE); AMYLOSE TRIS[1 PHENYLETHYLCARBAMATE]; CELLULOSE TRIS(3,5 DIMETHYLPHENYLCARBAMATE); METHANOL; POLYSACCHARIDE; UNCLASSIFIED DRUG;

EID: 84861222683     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.03.012     Document Type: Article
Times cited : (21)

References (59)
  • 1
    • 2542435938 scopus 로고    scopus 로고
    • Dose-dependent activity of albendazole against benzimidazole-resistant nematodes in sheep: relationship between pharmacokinetics and efficacy
    • Moreno L., Echevarria F., Muñoz F., Alvarez L., Sanchez Bruni S., Lanusse C. Dose-dependent activity of albendazole against benzimidazole-resistant nematodes in sheep: relationship between pharmacokinetics and efficacy. Exp. Parasitol. 2004, 106:150-157.
    • (2004) Exp. Parasitol. , vol.106 , pp. 150-157
    • Moreno, L.1    Echevarria, F.2    Muñoz, F.3    Alvarez, L.4    Sanchez Bruni, S.5    Lanusse, C.6
  • 2
    • 0038064280 scopus 로고    scopus 로고
    • Anthelmintic drug safety and drug administration in the control of soil-transmitted helminthiases in community campaigns
    • Urbani C., Albonico M. Anthelmintic drug safety and drug administration in the control of soil-transmitted helminthiases in community campaigns. Acta Trop. 2003, 86:215-221.
    • (2003) Acta Trop. , vol.86 , pp. 215-221
    • Urbani, C.1    Albonico, M.2
  • 3
    • 0034439133 scopus 로고    scopus 로고
    • Albendazole: a review of anthelmintics efficacy and safety in humans
    • Horton J. Albendazole: a review of anthelmintics efficacy and safety in humans. Parasitology 2000, 121:S113-S132.
    • (2000) Parasitology , vol.121
    • Horton, J.1
  • 4
    • 0011519273 scopus 로고    scopus 로고
    • Pharmacokinetic optimisation of the treatment of neurocysticercosis
    • Sotelo J., Jung H. Pharmacokinetic optimisation of the treatment of neurocysticercosis. Clin. Pharmacokinet. 1998, 34:503-515.
    • (1998) Clin. Pharmacokinet. , vol.34 , pp. 503-515
    • Sotelo, J.1    Jung, H.2
  • 5
    • 0028876002 scopus 로고
    • Neurocysticercosis: optimal dose treatment with albendazole
    • Cruz I., Cruz M.E., Carrasco F., Horton J. Neurocysticercosis: optimal dose treatment with albendazole. J. Neurol. Sci. 1995, 133:152-154.
    • (1995) J. Neurol. Sci. , vol.133 , pp. 152-154
    • Cruz, I.1    Cruz, M.E.2    Carrasco, F.3    Horton, J.4
  • 7
    • 84861226092 scopus 로고    scopus 로고
    • WHO, Fifty-Sixth World Health Assembly Provisional Agenda Item 14.2 A56/10 ed.
    • WHO, Fifty-Sixth World Health Assembly Provisional Agenda Item 14.2 A56/10 ed., 2003.
    • (2003)
  • 8
    • 0034035244 scopus 로고    scopus 로고
    • Relative contribution of cytochromes P-450 and flavin-containing monoxygenases to the metabolism of albendazole by human liver microsomes
    • Rawden H.C., Kokwaro G.O., Ward S.A., Edwards G. Relative contribution of cytochromes P-450 and flavin-containing monoxygenases to the metabolism of albendazole by human liver microsomes. Br. J. Clin. Pharmacol. 2000, 49:313-322.
    • (2000) Br. J. Clin. Pharmacol. , vol.49 , pp. 313-322
    • Rawden, H.C.1    Kokwaro, G.O.2    Ward, S.A.3    Edwards, G.4
  • 9
    • 0038740727 scopus 로고    scopus 로고
    • Albendazole, mebendazole and praziquantel. Review of non-clinical toxicity and pharmacokinetics
    • Dayan A.D. Albendazole, mebendazole and praziquantel. Review of non-clinical toxicity and pharmacokinetics. Acta Trop. 2003, 86:141-159.
    • (2003) Acta Trop. , vol.86 , pp. 141-159
    • Dayan, A.D.1
  • 11
    • 0028812229 scopus 로고
    • Chiral sulphoxidation of albendazole by the flavin adenine dinucleotide-containing and cytochrome P450-dependent monooxygenases from rat liver microsomes
    • Moroni P., Buronfosse T., Longin-Sauvageon C., Delatour P., Benoit E. Chiral sulphoxidation of albendazole by the flavin adenine dinucleotide-containing and cytochrome P450-dependent monooxygenases from rat liver microsomes. Drug Metab. Dispos. 1995, 23:160-165.
    • (1995) Drug Metab. Dispos. , vol.23 , pp. 160-165
    • Moroni, P.1    Buronfosse, T.2    Longin-Sauvageon, C.3    Delatour, P.4    Benoit, E.5
  • 12
    • 67649297606 scopus 로고    scopus 로고
    • Chiral toxicology: it is the same thing, only different
    • Smith S.W. Chiral toxicology: it is the same thing, only different. Toxicol. Sci. 2009, 110:4-30.
    • (2009) Toxicol. Sci. , vol.110 , pp. 4-30
    • Smith, S.W.1
  • 13
    • 0346874450 scopus 로고    scopus 로고
    • Three-dimensional pharmacology, a subject ranging from ignorance to overstatements
    • Waldeck B. Three-dimensional pharmacology, a subject ranging from ignorance to overstatements. Pharmacol. Toxicol. 2003, 93:203-210.
    • (2003) Pharmacol. Toxicol. , vol.93 , pp. 203-210
    • Waldeck, B.1
  • 14
    • 0026032166 scopus 로고
    • Comparative enantioselectivity in the sulphoxidation of albendazole in man, dogs and rats
    • Delatour P., Benoit E., Besse S., Boukraa A. Comparative enantioselectivity in the sulphoxidation of albendazole in man, dogs and rats. Xenobiotica 1991, 21:217-221.
    • (1991) Xenobiotica , vol.21 , pp. 217-221
    • Delatour, P.1    Benoit, E.2    Besse, S.3    Boukraa, A.4
  • 15
    • 0025048935 scopus 로고
    • Species differences in the generation of the chiral sulfoxide metabolite of albendazole in sheep and rats
    • Delatour P., Benoit E., Caude M., Tambute A. Species differences in the generation of the chiral sulfoxide metabolite of albendazole in sheep and rats. Chirality 1990, 2:156-160.
    • (1990) Chirality , vol.2 , pp. 156-160
    • Delatour, P.1    Benoit, E.2    Caude, M.3    Tambute, A.4
  • 16
    • 2042449741 scopus 로고    scopus 로고
    • Comparative hepatic and extrahepatic enantioselective sulfoxidation of abendazole and fenbendazole in sheep and cattle
    • Virkel G., Lifschitz A., Sallovitz J., Pis A., Lanusse C. Comparative hepatic and extrahepatic enantioselective sulfoxidation of abendazole and fenbendazole in sheep and cattle. Drug Metab. Dispos. 2004, 32:536-544.
    • (2004) Drug Metab. Dispos. , vol.32 , pp. 536-544
    • Virkel, G.1    Lifschitz, A.2    Sallovitz, J.3    Pis, A.4    Lanusse, C.5
  • 17
    • 0035090015 scopus 로고    scopus 로고
    • Comparative metabolism of albendazole and albendazole sulphoxide by different helminth parasites
    • Solana H.D., Rodriguez J.A., Lanusse C. Comparative metabolism of albendazole and albendazole sulphoxide by different helminth parasites. Parasitol. Res. 2001, 87:275-280.
    • (2001) Parasitol. Res. , vol.87 , pp. 275-280
    • Solana, H.D.1    Rodriguez, J.A.2    Lanusse, C.3
  • 18
    • 0034041915 scopus 로고    scopus 로고
    • Pharmacokinetics behaviour of albendazole sulphoxide enantiomers in male and female sheep
    • Capece B.P.S., Castells G., Pérez F., Arboix M., Cristòfol C. Pharmacokinetics behaviour of albendazole sulphoxide enantiomers in male and female sheep. Vet. Res. Commun. 2000, 24:339-348.
    • (2000) Vet. Res. Commun. , vol.24 , pp. 339-348
    • Capece, B.P.S.1    Castells, G.2    Pérez, F.3    Arboix, M.4    Cristòfol, C.5
  • 19
    • 0036381576 scopus 로고    scopus 로고
    • Effect of gender in the disposition of albendazole metabolites in humans
    • Mirfazaelian A., Dadashzadeh S., Rouini M.R. Effect of gender in the disposition of albendazole metabolites in humans. Eur. J. Clin. Pharmacol. 2002, 58:403-408.
    • (2002) Eur. J. Clin. Pharmacol. , vol.58 , pp. 403-408
    • Mirfazaelian, A.1    Dadashzadeh, S.2    Rouini, M.R.3
  • 20
    • 0026086748 scopus 로고
    • Chiral behaviour of the metabolites albendazole sulphoxide in sheep, goats and cattle
    • Delatour P., Garnier F., Benoit E., Caude I. Chiral behaviour of the metabolites albendazole sulphoxide in sheep, goats and cattle. Res. Vet. Sci. 1991, 50:134-138.
    • (1991) Res. Vet. Sci. , vol.50 , pp. 134-138
    • Delatour, P.1    Garnier, F.2    Benoit, E.3    Caude, I.4
  • 21
    • 0034929799 scopus 로고    scopus 로고
    • Albendazole sulphoxide enantiomeric ratios in plasma and target tissues after intravenous administration of ricobendazole to cattle
    • Cristofol C., Virkel G., Alvarez L., Sánchez S., Arboix M., Lanusse C. Albendazole sulphoxide enantiomeric ratios in plasma and target tissues after intravenous administration of ricobendazole to cattle. Drug Metab. Pharmacokinet. Toxicol. 2001, 24:117-124.
    • (2001) Drug Metab. Pharmacokinet. Toxicol. , vol.24 , pp. 117-124
    • Cristofol, C.1    Virkel, G.2    Alvarez, L.3    Sánchez, S.4    Arboix, M.5    Lanusse, C.6
  • 22
    • 0026779619 scopus 로고
    • Effect of repeated does of albendazole on enantiomerism of its sulfoxide metabolite in goats
    • Benoit E., Besse S., Delatour P. Effect of repeated does of albendazole on enantiomerism of its sulfoxide metabolite in goats. Am. J. Vet. Res. 1992, 53:1663-1665.
    • (1992) Am. J. Vet. Res. , vol.53 , pp. 1663-1665
    • Benoit, E.1    Besse, S.2    Delatour, P.3
  • 23
    • 17644414121 scopus 로고    scopus 로고
    • Antitumor activity of albendazole against the human colorectal cancer cell line HT-29: in vitro and in a xenograft model of pertoneal carcinomatosis
    • Pourgholami M.H., Akhter J., Wang L., Lu Y., Morris D.L. Antitumor activity of albendazole against the human colorectal cancer cell line HT-29: in vitro and in a xenograft model of pertoneal carcinomatosis. Cancer Chemother. Pharmacol. 2005, 55:425-432.
    • (2005) Cancer Chemother. Pharmacol. , vol.55 , pp. 425-432
    • Pourgholami, M.H.1    Akhter, J.2    Wang, L.3    Lu, Y.4    Morris, D.L.5
  • 24
    • 0035836793 scopus 로고    scopus 로고
    • In vitro and in vivo suppression of growth of hepatocellular carcinoma cells by albendazole
    • Pourgholami M.H., Woon L., Almajd R., Akhter J., Bowery P., Morris D.L. In vitro and in vivo suppression of growth of hepatocellular carcinoma cells by albendazole. Cancer Lett. 2001, 165:43-49.
    • (2001) Cancer Lett. , vol.165 , pp. 43-49
    • Pourgholami, M.H.1    Woon, L.2    Almajd, R.3    Akhter, J.4    Bowery, P.5    Morris, D.L.6
  • 25
    • 33645661534 scopus 로고    scopus 로고
    • Albendazole: a potent inhibitor of vascular endothelial growth factor and malignant ascites formation in OVCAR-3 tumor-bearing nude mice
    • Pourgholami M.H., Cai Z.Y., Lu Y., Wang L., Morris D.L. Albendazole: a potent inhibitor of vascular endothelial growth factor and malignant ascites formation in OVCAR-3 tumor-bearing nude mice. Clin. Cancer Res. 2006, 12:1928-1935.
    • (2006) Clin. Cancer Res. , vol.12 , pp. 1928-1935
    • Pourgholami, M.H.1    Cai, Z.Y.2    Lu, Y.3    Wang, L.4    Morris, D.L.5
  • 27
    • 0035847205 scopus 로고    scopus 로고
    • Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers
    • Francotte E.R. Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers. J. Chromatogr. A 2001, 906:379-397.
    • (2001) J. Chromatogr. A , vol.906 , pp. 379-397
    • Francotte, E.R.1
  • 30
    • 0029619335 scopus 로고
    • Chiral discrimination on polysaccharides derivatives
    • Yashima E., Okamoto Y. Chiral discrimination on polysaccharides derivatives. Bull. Chem. Soc. Jpn. 1995, 68:3289-3307.
    • (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 3289-3307
    • Yashima, E.1    Okamoto, Y.2
  • 31
    • 0035847277 scopus 로고    scopus 로고
    • Polysaccharide-based chiral stationary phases for high-performance liquid chromatographic enantioseparation
    • Yashima E. Polysaccharide-based chiral stationary phases for high-performance liquid chromatographic enantioseparation. J. Chromatogr. A 2001, 906:105-125.
    • (2001) J. Chromatogr. A , vol.906 , pp. 105-125
    • Yashima, E.1
  • 32
    • 0028331505 scopus 로고
    • Resolution by high-performance liquid chromatography using polysaccharide carbamates and benzoates as chiral stationary phases
    • Okamoto Y., Kaida Y. Resolution by high-performance liquid chromatography using polysaccharide carbamates and benzoates as chiral stationary phases. J. Chromatogr. A 1994, 666:403-419.
    • (1994) J. Chromatogr. A , vol.666 , pp. 403-419
    • Okamoto, Y.1    Kaida, Y.2
  • 33
    • 0042847063 scopus 로고    scopus 로고
    • Effects on enantioselectivity by the use of polysaccharide-based columns by multimodal elution
    • Cass Q.B., Degani A.L.G., Cassiano N.M. Effects on enantioselectivity by the use of polysaccharide-based columns by multimodal elution. J. Liquid Chromatogr. Relat. Technol. 2003, 26:2083-2101.
    • (2003) J. Liquid Chromatogr. Relat. Technol. , vol.26 , pp. 2083-2101
    • Cass, Q.B.1    Degani, A.L.G.2    Cassiano, N.M.3
  • 35
    • 0345708400 scopus 로고    scopus 로고
    • Enantiomeric determination of the plasma levels of omeprazole by direct plasma injection using high-performance liquid chromatography with achiral-chiral column-switching
    • Cass Q.B., Lima V.V., Oliveira R.V., Cassiano N.M., Degani A.L.G., Pedrazzoli J. Enantiomeric determination of the plasma levels of omeprazole by direct plasma injection using high-performance liquid chromatography with achiral-chiral column-switching. J. Chromatogr. B 2003, 798:275-281.
    • (2003) J. Chromatogr. B , vol.798 , pp. 275-281
    • Cass, Q.B.1    Lima, V.V.2    Oliveira, R.V.3    Cassiano, N.M.4    Degani, A.L.G.5    Pedrazzoli, J.6
  • 36
    • 4644255685 scopus 로고    scopus 로고
    • Determination of gossypol enantiomer ratio in cotton plants by chiral higher-performance liquid chromatography
    • Cass Q.B., Oliveira R.V., De Pietro A.C. Determination of gossypol enantiomer ratio in cotton plants by chiral higher-performance liquid chromatography. J. Agric. Food Chem. 2004, 52:5822-5827.
    • (2004) J. Agric. Food Chem. , vol.52 , pp. 5822-5827
    • Cass, Q.B.1    Oliveira, R.V.2    De Pietro, A.C.3
  • 37
    • 0036230172 scopus 로고    scopus 로고
    • Separation of multi-milligram quantities of gossypol enantiomers on polysaccharide-based stationary phases
    • Cass Q.B., Oliveira R.V. Separation of multi-milligram quantities of gossypol enantiomers on polysaccharide-based stationary phases. J. Liquid Chromatogr. Relat. Technol. 2002, 25:819-829.
    • (2002) J. Liquid Chromatogr. Relat. Technol. , vol.25 , pp. 819-829
    • Cass, Q.B.1    Oliveira, R.V.2
  • 38
    • 41549128448 scopus 로고    scopus 로고
    • Multimilligram enantioresolution of sulfoxide proton pump inhibitors by liquid chromatography on polysaccharide-based chiral stationary phase
    • Belaz K.R.A., Coimbra M., Barreiro J.C., Montanari A.C., Cass Q.B. Multimilligram enantioresolution of sulfoxide proton pump inhibitors by liquid chromatography on polysaccharide-based chiral stationary phase. J. Pharm. Biomed. Anal. 2008, 47:81-87.
    • (2008) J. Pharm. Biomed. Anal. , vol.47 , pp. 81-87
    • Belaz, K.R.A.1    Coimbra, M.2    Barreiro, J.C.3    Montanari, A.C.4    Cass, Q.B.5
  • 39
    • 33744985766 scopus 로고    scopus 로고
    • Multimilligram enantioresolution of low-solubility xanthonolignoids on polysaccharide chiral stationary phases using a solid-phase injection system
    • Sousa M.E., Tiritan M.E., Belaz K.R.A., Pedro M., Nascimento M.S.J., Cass Q.B., Pinto M.M.M. Multimilligram enantioresolution of low-solubility xanthonolignoids on polysaccharide chiral stationary phases using a solid-phase injection system. J. Chromatogr. A 2006, 1120:75-81.
    • (2006) J. Chromatogr. A , vol.1120 , pp. 75-81
    • Sousa, M.E.1    Tiritan, M.E.2    Belaz, K.R.A.3    Pedro, M.4    Nascimento, M.S.J.5    Cass, Q.B.6    Pinto, M.M.M.7
  • 40
    • 0029926459 scopus 로고    scopus 로고
    • Enantiomeric resolution of chiral sulfoxides on polysaccharides phases by HPLC
    • Matlin S.A., Tiritan M.E., Cass Q.B., Boyd D.R. Enantiomeric resolution of chiral sulfoxides on polysaccharides phases by HPLC. Chirality 1996, 8:147-152.
    • (1996) Chirality , vol.8 , pp. 147-152
    • Matlin, S.A.1    Tiritan, M.E.2    Cass, Q.B.3    Boyd, D.R.4
  • 41
    • 0035847277 scopus 로고    scopus 로고
    • Polysaccharide-based chiral stationary phases for high-performance liquid chromatography enantioseparation
    • Yashima E. Polysaccharide-based chiral stationary phases for high-performance liquid chromatography enantioseparation. J. Chromatogr. A 2001, 906:105-125.
    • (2001) J. Chromatogr. A , vol.906 , pp. 105-125
    • Yashima, E.1
  • 42
    • 0028243526 scopus 로고
    • HPLC with carbohydrate carbamate chiral phases: influence of chiral phase structure on enantioselectivity
    • Matlin S.A., Tiritan M.E., Crawford A.J., Cass Q.B., Boyd D.R. HPLC with carbohydrate carbamate chiral phases: influence of chiral phase structure on enantioselectivity. Chirality 1994, 6:135-140.
    • (1994) Chirality , vol.6 , pp. 135-140
    • Matlin, S.A.1    Tiritan, M.E.2    Crawford, A.J.3    Cass, Q.B.4    Boyd, D.R.5
  • 43
    • 0031657678 scopus 로고    scopus 로고
    • Preparative enantioseparation on polysaccharide phase using microporous silica as a support
    • Tiritan M.E., Cass Q.B., Del Alamo A., Matlin S.A., Grieb S.J. Preparative enantioseparation on polysaccharide phase using microporous silica as a support. Chirality 1998, 10:573-577.
    • (1998) Chirality , vol.10 , pp. 573-577
    • Tiritan, M.E.1    Cass, Q.B.2    Del Alamo, A.3    Matlin, S.A.4    Grieb, S.J.5
  • 44
    • 33645038629 scopus 로고    scopus 로고
    • Do the terms % ee and % de make sense as expressions of stereoisomer composition or stereoselectivity?
    • Gawley R.E. Do the terms % ee and % de make sense as expressions of stereoisomer composition or stereoselectivity?. J. Org. Chem. 2006, 71:2411-2416.
    • (2006) J. Org. Chem. , vol.71 , pp. 2411-2416
    • Gawley, R.E.1
  • 45
    • 0042020114 scopus 로고    scopus 로고
    • Use of semipreparative supercritical fluid chromatography to obtain small quantities of the albendazole sulfoxide enantiomers
    • Toribio L., Nozal M.J., Bernal J.L., Nieto E.M. Use of semipreparative supercritical fluid chromatography to obtain small quantities of the albendazole sulfoxide enantiomers. J. Chromatogr. A 2003, 1011:155-161.
    • (2003) J. Chromatogr. A , vol.1011 , pp. 155-161
    • Toribio, L.1    Nozal, M.J.2    Bernal, J.L.3    Nieto, E.M.4
  • 46
    • 34347230544 scopus 로고    scopus 로고
    • Sulforhodamine B colorimetric assay for cytotoxicity screening
    • Vichai V., Kirtikara K. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat. Protoc. 2006, 1:1112-1116.
    • (2006) Nat. Protoc. , vol.1 , pp. 1112-1116
    • Vichai, V.1    Kirtikara, K.2
  • 47
    • 83455182312 scopus 로고    scopus 로고
    • The in vitro anticancer activity of the crude extract of the sponge-associated fungus Eurotium cristatum and its secondary metabolites
    • Almeida A.P., Dethoup T., Singburaudom N., Lima R., Vasconcelos M.H., Pinto M.P., Kijjoa A. The in vitro anticancer activity of the crude extract of the sponge-associated fungus Eurotium cristatum and its secondary metabolites. J. Nat. Pharmaceut. 2010, 1:25-29.
    • (2010) J. Nat. Pharmaceut. , vol.1 , pp. 25-29
    • Almeida, A.P.1    Dethoup, T.2    Singburaudom, N.3    Lima, R.4    Vasconcelos, M.H.5    Pinto, M.P.6    Kijjoa, A.7
  • 49
    • 79955635866 scopus 로고    scopus 로고
    • Prenylated derivatives of baicalein and 3,7-dihidroxyflavone: synthesis and study of their effects on tumor cell lines growth, cell cycle and apoptosis
    • Neves M.P., Cidade H., Pinto M., Silva A.M., Gales L., Damas A.M., Lima R.T., Vasconcelos M.H., Nascimento M.S. Prenylated derivatives of baicalein and 3,7-dihidroxyflavone: synthesis and study of their effects on tumor cell lines growth, cell cycle and apoptosis. Eur. J. Med. Chem. 2011, 46:2562-2574.
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 2562-2574
    • Neves, M.P.1    Cidade, H.2    Pinto, M.3    Silva, A.M.4    Gales, L.5    Damas, A.M.6    Lima, R.T.7    Vasconcelos, M.H.8    Nascimento, M.S.9
  • 50
    • 78649335089 scopus 로고    scopus 로고
    • Efficient synthesis of 6-(hetero)arylthieno[3,2-b]pyridines by Suzuki-Miyaura coupling: evaluation of growth inhibition on human tumor cell lines, SARs and effects on the cell cycle
    • Queiroz M.J., Calhelha R.C., Vale-Silva L.A., Pinto E., Lima R.T., Vasconcelos M.H. Efficient synthesis of 6-(hetero)arylthieno[3,2-b]pyridines by Suzuki-Miyaura coupling: evaluation of growth inhibition on human tumor cell lines, SARs and effects on the cell cycle. Eur. J. Med. Chem. 2010, 45:5628-5634.
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 5628-5634
    • Queiroz, M.J.1    Calhelha, R.C.2    Vale-Silva, L.A.3    Pinto, E.4    Lima, R.T.5    Vasconcelos, M.H.6
  • 51
    • 78650510707 scopus 로고    scopus 로고
    • Synthesis and evaluation of tumor cell growth inhibition of methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates. Structure-activity relationships, effects on the cell cycle and apoptosis
    • Queiroz M.J., Calhelha R.C., Vale-Silva L.A., Pinto E., Almeida G.M., Vasconcelos M.H. Synthesis and evaluation of tumor cell growth inhibition of methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates. Structure-activity relationships, effects on the cell cycle and apoptosis. Eur. J. Med. Chem. 2011, 46:236-240.
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 236-240
    • Queiroz, M.J.1    Calhelha, R.C.2    Vale-Silva, L.A.3    Pinto, E.4    Almeida, G.M.5    Vasconcelos, M.H.6
  • 52
    • 56549116899 scopus 로고    scopus 로고
    • Chiral HPLC for efficient resolution of enantiomers
    • Okamoto Y., Ikai T. Chiral HPLC for efficient resolution of enantiomers. Chem. Soc. Rev. 2008, 37:2593-2608.
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 2593-2608
    • Okamoto, Y.1    Ikai, T.2
  • 54
    • 0037435951 scopus 로고    scopus 로고
    • Enantiomeric resolution of a series of chiral sulfoxides by high-performance liquid chromatography on polysaccharide-based columns with multimodal elution
    • Cass Q.B., Batigalhia F. Enantiomeric resolution of a series of chiral sulfoxides by high-performance liquid chromatography on polysaccharide-based columns with multimodal elution. J. Chromatogr. A 2003, 987:445-452.
    • (2003) J. Chromatogr. A , vol.987 , pp. 445-452
    • Cass, Q.B.1    Batigalhia, F.2
  • 55
    • 0035847236 scopus 로고    scopus 로고
    • Reviewing mobile phases used on Chiralcel OD through an application of data mining tools to CHIRBASE database
    • Piras P., Roussel C., Pierrot-Sanders J. Reviewing mobile phases used on Chiralcel OD through an application of data mining tools to CHIRBASE database. J. Chromatogr. A 2001, 906:443-458.
    • (2001) J. Chromatogr. A , vol.906 , pp. 443-458
    • Piras, P.1    Roussel, C.2    Pierrot-Sanders, J.3
  • 56
    • 0027315007 scopus 로고
    • Optical resolution by high-performance liquid chromatography on benzylcarbamates of cellulose and amylose
    • Kaida Y., Okamoto Y. Optical resolution by high-performance liquid chromatography on benzylcarbamates of cellulose and amylose. J. Chromatogr. 1993, 641:267-278.
    • (1993) J. Chromatogr. , vol.641 , pp. 267-278
    • Kaida, Y.1    Okamoto, Y.2
  • 58
    • 24944520887 scopus 로고    scopus 로고
    • Development and validation of HPLC methods for enantioseparation of mirtazapine enantiomers at analytical and semipreparative scale using polysaccharide chiral stationary phases
    • Zhai Z.D., Shi Y.P., Wang T. Development and validation of HPLC methods for enantioseparation of mirtazapine enantiomers at analytical and semipreparative scale using polysaccharide chiral stationary phases. Anal. Chim. Acta 2005, 550:123-129.
    • (2005) Anal. Chim. Acta , vol.550 , pp. 123-129
    • Zhai, Z.D.1    Shi, Y.P.2    Wang, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.