Synthesis and biological activity of new iodoacetamide derivatives on mutants of squalene-hopene cyclase

Lipids

Volumn 40, Issue 7, 2005, Pages 729-735

  Ceruti, Maurizio ^a   Balliano, Gianni ^a   Rocco, Flavio ^a   Lenhart, Alexander ^b,d   Schulz, Georg E ^b   Castelli, Francesco ^c   Milla, Paola ^a  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF FREIBURG   (Germany)

^c UNIVERSITY OF CATANIA   (Italy)

^d ABBOTT GMBH AND CO KG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYMES; LIPIDS; MUTAGENESIS; SYNTHESIS (CHEMICAL);

IODOACETAMIDE DERIVATIVES; MOIETY; SQUALENE-HOPENE CYCLASE; THIOL-REACTING MOLECULES;

DERIVATIVES;

HOPENE CYCLASE; IODOACETAMIDE; LANOSTEROL; N DODECYLIODOACETAMIDE; N SQUALENYLIODOACETAMIDE; SQUALENE DERIVATIVE; UNCLASSIFIED DRUG;

ALICYCLOBACILLUS ACIDOCALDARIUS; ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; ENZYME ACTIVE SITE; ENZYME ASSAY; ENZYME INHIBITION; ESCHERICHIA COLI; MUTANT; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

BACILLUS; INTRAMOLECULAR TRANSFERASES; IODOACETAMIDE; MAGNETIC RESONANCE SPECTROSCOPY; MUTATION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

ALICYCLOBACILLUS ACIDOCALDARIUS;

EID: 24644435482     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-005-1436-7     Document Type: Article

References (40)

1. Abe, I., Rohmer, M., and Prestwich, G.D. (1993) Enzymatic Cyclization of Squalene and Oxidosqualene to Sterols and Triterpenes, Chem. Rev. 93, 2189-2206.
2. Wendt, K.U., Schulz, G.E., Corey, E.J., and Liu, D.R. (2000) Enzyme Mechanisms for Polycyclic Triterpene Formation, Angew. Chem. Int. Ed. Engl. 39, 2812-2833.
3. Corey, E.J., Virgil, S.C., Cheng, H., Hunter Baker, C., Matsuda, S.P.T., Singh, V., and Sarshar, S. (1995) New Insights Regarding the Cyclization Pathway for Sterol Biosynthesis from (S)-2,3-Oxidosqualene, J. Am. Chem. Soc. 117, 11819-11820.
4. 13C NMR, Crystallographic Observations, and Molecular Mechanics Calculations, J. Am. Chem. Soc. 120, 5970-5980.
5. Cattel, L., Ceruti, M., Viola, F., Delprino, L., Balliano, G., Duriatti, A., and Bouvier-Navé, P. (1986) The Squalene-2,3-epoxide Cyclase as a Model for the Development of New Drugs, Lipids 21, 31-38.
6. Ceruti, M., Balliano, G., Viola, F., Cattel, L., Gerst, N., and Schuber, F. (1987) Synthesis and Biological Activity of Azasqualenes, Bis-azasqualenes and Derivatives, Eur. J. Med. Chem. 22, 199-208.
7. Ceruti, M., Balliano, G., Viola, F., Grosa, G., Rocco, F., and Cattel, L. (1992) 2,3-Epoxy-10-aza-10,11-dihydrosqualene, a High-Energy Intermediate Analogue Inhibitor of 2,3-Oxidosqualene Cyclase, J. Med. Chem. 35, 3050-3058.
8. Taton, M., Benveniste, P., Rahier, A., Johnson, W.S., Liu, H.-T., and Sudhakar, A.R. (1992) Inhibition of 2,3-Oxidosqualene Cyclases, Biochemistry 31, 7892-7898.
9. Stach, D., Zheng, Y.F., Perez, A.L., Oehlschlager, A.C., Abe, I., Prestwich, G.D., and Hartman, P.G. (1997) Synthesis and Inhibition Studies of Sulfur-Substituted Squalene Oxide Analogues as Mechanism-Based Inhibitors of 2,3-Oxidosqualene Lanosterol Cyclase, J. Med. Chem. 40, 201-209.
10. Abe, I., Liu, W., Oehlschlager, A.C., and Prestwich, G.D. (1996) Mechanism-Based Active Site Modification of Oxidosqualene Cyclase by Tritium-Labeled 18-Thia-2,3-oxidosqualene, J. Am. Chem. Soc. 118, 9180-9181.
11. Rocco, F., Oliaro Bosso, S., Viola, F., Milla, P., Roma, G., Grossi, G., and Ceruti, M. (2003) Conjugated Methyl Sulfide and Phenyl Sulfide Derivatives of Oxidosqualene as Inhibitors of Oxidosqualene and Squalene-Hopene Cyclases, Lipids 38, 201-207.
12. Abad, J.L., Guardiola, M., Casas, J., Sanchez-Baeza, F., and Messeguer, A. (1996) 2,3;18,19-Dioxidosqualene Stereoisomers: Characterization and Activity as Inhibitors of Purified Pig Liver 2,3-Oxidosqualene-Lanosterol Cyclase, J. Org. Chem. 61, 7603-7607.
13. Xiao, X., and Prestwich, G.D. (1991) 29-Methylidene-2,3-oxidosqualene: A Potent Mechanism-Based Inactivator of Oxidosqualene Cyclase, J. Am. Chem. Soc. 113, 9673-9674.
14. Abe, I., Bai, M., Xiao, X.-Y., and Prestwich, G.D. (1992) Affinity Labeling of Vertebrate Oxidosqualene Cyclases with a Tritiated Suicide Substrate, Biochem. Biophys. Res. Commun. 187, 32-38.
15. Corey, E.J., Cheng, H., Hunter Baker, C., Matsuda, S.P.T., Li, D., and Song, X. (1997) Studies on the Substrate Binding Segments and Catalytic Action of Lanosterol Synthase. Affinity Labeling with Carbocations Derived from Mechanism-Based Analogs of 2,3-Oxidosqualene and Site-Directed Mutagenesis Probes, J. Am. Chem. Soc. 119, 1289-1296.
16. Ceruti, M., Rocco, F., Viola, F., Balliano, G., Milla, P., Arpicco, S., and Cattel, L. (1998) 29-Methylidene-2,3-oxidosqualene Derivatives as Stereospecific Mechanism-Based Inhibitors of Liver and Yeast Oxidosqualene Cyclase, J. Med. Chem. 41, 540-554.
17. Ganem, B., Dong, Y.H., Zheng, Y.F., and Prestwich, G.D. (1999) Amidrazone and Amidoxime Inhibitors of Squalene Hopene Cyclase, J. Org. Chem. 64, 5441-5446.
18. Viola, F., Ceruti, M., Cattel, L., Milla, P., Poralla, K., and Balliano, G. (2000) Rationally Designed Inhibitors as Tools for Comparing the Mechanism of Squalene-Hopene Cyclase with Oxidosqualene Cyclase, Lipids 35, 297-303.
19. Ceruti, M., Balliano, G., Rocco, F., Milla, P., Arpicco, S., Cattel, L., and Viola, F. (2001) Vinyl Sulfide Derivatives of Truncated Oxidosqualene as Selective Inhibitors of Oxidosqualene and Squalene-Hopene Cyclases, Lipids 36, 629-636.
20. Wendt, K.U., Poralla, K., and Schulz, G.E. (1997) Structure and Function of Squalene Cyclase, Science 277, 1811-1815.
21. Wendt, K.U., Feil, C., Lenhart, A., Poralla, K., and Schulz, G.E. (1997) Crystallization and Preliminary X-ray Crystallographic Analysis of Squalene-Hopene Cyclase from Alicyclobacillus acidocaldarius, Protein Sci. 6, 722-724.
22. Thoma, R., Schulz-Gasch, T., D'Arcy, B., Benz, J., Aebi, J., Dehmlow, H., Hennig, M., Stihle, M., and Ruf, A. (2004) Insight into Steroid Scaffold Formation from the Structure of Human Oxidosqualene Cyclase, Nature 432, 118-122.
23. Reinert, D.J., Balliano, G., and Schulz, G.E. (2004) Conversion of Squalene to the Pentacarbocyclic Hopene, Chem. Biol. 11, 121-126.
24. Milla, P., Lenhart, A., Grosa, G., Viola, F., Weihofen, W.A., Schulz, G.E., and Balliano, G. (2002) Thiol-Modifying Inhibitors for Understanding Squalene Cyclase Function, Eur. J. Biochem. 269, 2108-2116.
25. 3H]-2,3- Oxidosqualene, J. Labelled Comp. Radiopharm. 34, 577-585.
26. Van Esch, J.H., Hoffmann, M.A.M., and Nolle, R.J.M. (1995) Reduction of Nicotinamides, Flavins, and Manganese Porphyrins by Formate, Catalyzed by Membrane-Bound Rhodium Complexes, J. Org. Chem. 60, 1599-1610.
27. 2SH, Langmuir 11, 4371-4382.
28. Viaud, M.C., and Rollin, P. (1990) Zinc Azide Mediated Mitsunobu Substitution. An Expedient Method for the One-Pot Azidation of Alcohols, Synthesis, 130-132.
29. Grosa, G., Viola, F., Ceruti, M., Brusa, P., Delprino, L., Dosio, F., and Cattel, L. (1994) Synthesis and Biological Activity of a Squalenoid Maleimide and Other Classes of Squalene Derivatives as Irreversible Inhibitors of 2,3-Oxidosqualene Cyclase, Eur. J. Med. Chem. 29, 17-23.
30. Field, R.B., Holmlund, C.E., and Whittaker, N.F. (1979) The Effects of the Hypocholesteremic Compound 3β-(2,2-dimethyl-aminoethoxy)-Androst-5-en- 17-one on the Sterol and Steryl Ester Composition of Saccharomyces cerevisiae, Lipids 14, 741-747.
31. Popjak, G. (1969) Enzymes of Sterol Biosynthesis in Liver and Intermediates of Sterol Biosynthesis, in Methods in Enzymology Vol. 15, pp. 393-454, Elsevier, New York.
32. Balliano, G., Viola, F., Ceruti, M., and Cattel, L. (1992) Characterization and Partial Purification of Squalene-2,3-oxide Cyclase from Saccharomyces cerevisiae, Arch. Biochem. Biophys. 293, 122-129.
33. Sambrook, J., Frisch, E.F., and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual, 2nd edn., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
34. Dang, T.Y., and Prestwich, G.D. (2000) Site-Directed Mutagenesis of Squalene-Hopene Cyclase: Altered Substrate Specificity and Product Distribution, Chem. Biol. 7, 643-649.
35. Lindsey, S., and Harwood, H.J. (1995) Inhibition of Mammalian Squalene Synthetase Activity by Zaragozic Acid A Is a Result of Competitive Inhibition Followed by Mechanism-Based Irreversible Inactivation, J. Biol. Chem. 16, 9083-9096.
36. Ceruti, M., Viola, F., Dosio, F., Cattel, L., Bouvier-Navé, P., and Ugliengo, P. (1988) Stereospecific Synthesis of Squalenoid Epoxide Vinyl Ethers as Inhibitors of 2,3-Oxidosqualene Cyclase, J. Chem. Soc., Perkin Trans. 1, 461-469.
37. 2+-ATPase of Rabbit Skeletal-Muscle Sarcoplasmic-Reticulum- Identification of Sites Labeled with Aryl-Isothiocyanates and Thiol-Directed Conformational Probes, Biochim. Biophys. Acta 1203, 60-70.
38. Wan, L., Chen, Y.H., and Chang, T.W. (2003) Improving Pharmacokinetic Properties of Adrenocorticotropin by Site-Specific Lipid Modification, J. Pharm. Sci. 92, 1882-1892.
39. Feil, C., Süssmuth, R., Jung, G., and Poralla, K. (1996) Site-Directed Mutagenesis of Putative Active-Site Residues in Squalene-Hopene Cyclase, Eur. J. Biochem. 242, 51-55.
40. Seckler, B., and Poralla, K. (1986) Characterization and Partial Purification of Squalene-Hopene Cyclase from Bacillus acidocaldarius, Biochim. Biophys. Acta 881, 356-363.