Stereoselective binding of benzodiazepines and related compounds on calmodulin-sepharose
Corresponding Author
Ilona Fitos
Central Research Institute for Chemistry, The Hungarian Academy of Sciences, Budapest, Hungary
Central Research Institute for Chemistry, The Hungarian Academy of Sciences, P.O. Box 17, H-1525 Budapest, HungarySearch for more papers by this authorJüalia Visy
Central Research Institute for Chemistry, The Hungarian Academy of Sciences, Budapest, Hungary
Search for more papers by this authorJulianna Kardos
Central Research Institute for Chemistry, The Hungarian Academy of Sciences, Budapest, Hungary
Search for more papers by this authorMiklóas Simonyi
Central Research Institute for Chemistry, The Hungarian Academy of Sciences, Budapest, Hungary
Search for more papers by this authorCorresponding Author
Ilona Fitos
Central Research Institute for Chemistry, The Hungarian Academy of Sciences, Budapest, Hungary
Central Research Institute for Chemistry, The Hungarian Academy of Sciences, P.O. Box 17, H-1525 Budapest, HungarySearch for more papers by this authorJüalia Visy
Central Research Institute for Chemistry, The Hungarian Academy of Sciences, Budapest, Hungary
Search for more papers by this authorJulianna Kardos
Central Research Institute for Chemistry, The Hungarian Academy of Sciences, Budapest, Hungary
Search for more papers by this authorMiklóas Simonyi
Central Research Institute for Chemistry, The Hungarian Academy of Sciences, Budapest, Hungary
Search for more papers by this authorAbstract
A method has been presented to evaluate the Ca2+-dependent binding affinity of ligands to calmodulin (CaM) from their chromatographic retentions obtained on a CaM-Sepharose column. Enantiomers of benzodiazepines and related compounds could be separated. Among chiral calcium antagonists, verapamil showed stereoselectivity of binding. © 1995 Wiley-Liss, Inc.
Literature Cited
- 1 Babu, Y. S., Bugg, C. E., Cook, W. J. Structure of calmodulin refined at 2.2 Å resolution. J. Mol. Biol. 204: 191–204, 1988.
- 2 Cheung, W. Y. Calmodulin plays a pivotal role in cellular regulation. Science 207: 19–27, 1980.
- 3 Weiss, B., Prozialeck, W. C., Wallace, T. L. Interaction of drugs with calmodulin. Biochem. Pharmacol. 31: 2217–2226, 1982.
- 4 Ogita, K., Suzuki, T., Pingping, Z., Yoneda, Y. Inhibition by calmodulin antagonists of [3H]MK-801 binding in brain synaptic membranes. J. Neurochem. 59: 1008–1016, 1992.
- 5 Bouhoute, A., Leclercq, G. Estradiol derivatives bearing the side-chain of tamoxifen antagonize the association between the estrogen receptor and calmodulin. Biochem. Pharmacol. 47: 748–751, 1994.
- 6 Prozialeck, W. C., Weiss, B. Inhibition of calmodulin by phenothiazines and related drugs: structure–activity relationships. J. Pharmacol. Exp. Ther. 222: 509–516, 1982.
- 7 Hidaka, H., Asano, M., Tanaka, T. Activity-structure relationship of calmodulin antagonists. Naphthalene-sulfonamide derivatives. Mol. Pharmacol. 20: 571–578, 1981.
- 8 Barrera, G., Screpanti, I., Paradisi, L., Parola, M., Ferretti, C., Vacca, A., Farina, A., Dianzani, M. U., Frati, L., Gulino, A. Structure-activity relationships of calmodulin antagonism by tryphenylethylene antiestrogens. Biochem. Pharmacol. 35: 2984–2986, 1986.
- 9 DeLorenzo, P. J., Burdette, S., Holderness, J. Benzodiazepine inhibition of the calcium-calmodulin protein kinase system in brain membrane. Science 213: 546–549, 1981.
- 10 Reid, D. G., MacLachlan, L. K., Robinson, S. P., Camilleri, P., Dyke, C. A., Thorpe, C. J. Calmodulin discriminates between the two enantiomers of the receptor-operated calcium channel blocker SK&F 96365: a study using 1H-NMR and chiral HPLC. Chirality 2: 229–232, 1990.
- 11 Fitos, I., Tegyey, Z., Simonyi, M., Sjöholm, I., Larsson, T., Lagercrantz, C. Stereoselective binding of 3-acetoxy-, and 3-hydroxy-1,4-benzodiazepine-2-ones to human serum albumin. Biochem. Pharmacol. 35: 263–269, 1986.
- 12 Fitos, I., Visy, J., Magyar, A., Kajtár, J., Simonyi, M. Stereoselective effect of warfarin and bilirubin on the binding of 5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2 one enantiomers to human serum albumin. Chirality 2: 161–166, 1990.
- 13 LaPorte, D. C., Wierman, B. M., Storm, D. R. Calcium-induced exposure of a hydrophobic surface on calmodulin. Biochemistry 19: 3814–3819, 1980.
- 14 Lagercrantz, C., Larsson, T., Karlsson, H. Binding of some fatty acids and drugs to immobilized bovine serum albumin studied by column affinity chromatography. Anal. Biochem. 99: 352–364, 1979.
- 15 Marshak, D. R., Lukas, T. J., Watterson, D. M. Drug-protein interactions: binding of chlorpromazine to calmodulin, calmodulin fragments, and related calcium binding proteins. Biochemistry 24: 144–150, 1985.
- 16 Levin, R. M., Weiss, B. Selective binding of antipsychotics and other psychoactive agents to the calcium-dependent activator of cyclic nucleotide phosphodiesterase. J. Pharmacol. Exp. Ther. 208: 454–459, 1979.
- 17 Morgan, P. F., Patel, J., Marangos, P. J. Characterization of [3H]Ro 5–4864 binding to calmodulin using a rapid filtration technique. Biochem. Pharmacol. 36: 4257–4262, 1987.
- 18 Chiesi, M., Schwaller, R., Eichenberger, K. Structural dependency of the inhibitory action of benzodiazepines and related compounds on the mitochondrial Na+–Ca2+ exchanger. Biochem. Pharmacol. 37: 4399–4403, 1988.
- 19 Heitmann, W., Liepmann, H., Mätzel, U., Zeugner, H., Fuchs, A. M., Krähling, H., Ruhland, M., Mol, F., Tulp, M. Th.M. 1,4-Benzodiazepines and 1,5-benzodiazocines XI. Synthesis and biological activity. Eur. J. Med. Chem. 23: 249–256, 1988.
- 20 Simonyi, M., Fitos, I. Stereoselective binding of a 2,3-benzodiazepine to human serum albumin. Effect of conformation on tofizopam binding. Biochem. Pharmacol. 32: 1917–1920, 1983.
- 21 Kwon, Y.-W., Triggle, D. J. Chiral aspects of drug action at ion channels: a commentary on the stereoselectivity of drug actions at voltage-gated ion channels with particular reference to verapamil actions at the Ca2+ channel. Chirality 3: 393–404, 1991.
- 22 Chu, Y.-Q., Wainer, I. W. Determination of the enantiomers of verapamil and norverapamil in serum using coupled achiral-chiral high-performance liquid chromatography. J. Chromatogr. 497: 191–200, 1989.
- 23 Johnson, J. D., Wittenauer, L. A. A fluorescent calmodulin that reports the binding of hydrophobic inhibitory ligands. Biochem. J. 211: 473–479, 1983.
- 24 Movsesian, M. A., Swain, A. L., Adelstein, R. S. Inhibition of turkey gizzard myosin light chain kinase activity by dihydropyridine calcium antagonists. Biochem. Pharmacol. 33: 3759–3764, 1984.