Synthesis and biological evaluation of guanidino compounds endowed with subnanomolar affinity as competitive inhibitors of maize polyamine oxidase

Journal of Medicinal Chemistry

Volumn 52, Issue 15, 2009, Pages 4774-4785

  Manetti, Fabrizio ^a   Cona, Alessandra ^b   Angeli, Lucilla ^a   Mugnaini, Claudia ^a   Raffi, Francesco ^a   Capone, Caterina ^b   Dreassi, Elena ^a   Zizzari, Alessandra Tania ^a   Tisi, Alessandra ^b   Federico, Rodolfo ^b   Botta, Maurizio ^a  

^a UNIVERSITY OF SIENA   (Italy)

^b ROMA TRE UNIVERSITY   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AGMATINE; AGMATINE DERIVATIVE; GUANIDINE DERIVATIVE; IMINOCTADINE; POLYAMINE OXIDASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; COMPETITIVE INHIBITION; ENZYME INHIBITION; MAIZE; NONHUMAN; SYNTHESIS;

AGMATINE; BINDING SITES; BINDING, COMPETITIVE; ENZYME INHIBITORS; GUANIDINES; OXIDOREDUCTASES ACTING ON CH-NH GROUP DONORS; STRUCTURE-ACTIVITY RELATIONSHIP; ZEA MAYS;

EID: 68549120960     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900371z     Document Type: Article

References (42)

1. Wallace, H. M.; Fraser, A. V.; Hughes, A. A perspective of polyamine metabolism. Biochem. J. 2003, 376, 1-14.
2. Seiler, N. Catabolism of polyamines. Amino Acids 2004, 26, 217-233.
3. Cona, A.; Rea, G.; Angelini, R.; Federico, R.; Tavladoraki, P. Functions of amine oxidases in plant development and defence. Trends Plant Sci. 2006, 11, 80-88.
4. Federico, R.; Alisi, C.; Forlani, F. Properties of the polyamine oxidase from the cell wall of maize seedlings. Phytochemistry 1989, 28, 45-46.
5. Cervelli, M.; Cona, A.; Angelini, R.; Polticelli, F.; Federico, R.; Mariottini, P. A barley polyamine oxidase isoform with distinct structural features and subcellular localization. Eur. J. Biochem. 2001, 268, 3816-3830.
6. Maiale, S. J.; Marina, M.; Sánchez, D. H.; Pieckenstain, F. L.; Ruiz, A. O. In vitro and in vivo inhibition of plant polyamine oxidase activity by polyamine analogues. Phytochemistry 2008, 69, 2552-2558.
7. Wu, T.; Yankovskaya, V.; McIntire, W. S. Cloning, sequencing, and heterologous expression of the murine peroxisomal flavoprotein, N1-acetylated polyamine oxidase. J. Biol. Chem. 2003, 278, 20514-20525.
8. Vujcic, S.; Diegelman, P.; Bacchi, C. J.; Kramer, D. L.; Porter, C. W. Identification and characterization of a novel flavin-containing spermine oxidase of mammalian cell origin. Biochem. J. 2002, 367, 665-675.
9. Landry, J.; Sternglanz, R. Yeast Fms1 is a FAD-utilizing polyamine oxidase. Biochem. Biophys. Res. Commun. 2003, 303, 771-776.
10. Tavladoraki, P.; Rossi, M. N.; Saccuti, G.; Perez-Amador, M. A.; Polticelli, F.; Angelini, R.; Federico, R. Heterologous expression and biochemical characterization of a polyamine oxidase from Arabidopsis involved in polyamine back conversion. Plant Physiol. 2006, 141, 1519-1532.
11. Moschou, P. N.; Sanmartin, M.; Andriopoulou, A. H.; Rojo, E.; Sanchez-Serrano, J. J.; Roubelakis-Angelakis, K. A. Bridging the gap between plant and mammalian polyamine catabolism: a novel peroxisomal polyamine oxidase responsible for a full back-conversion pathway in Arabidopsis. Plant Physiol. 2008, 147, 1845-1857.
12. Seiler, N. Pharmacological aspects of cytotoxic polyamine analogs and derivatives for cancer therapy. Pharmacol. Ther. 2005, 107, 99-119.
13. Ha, H. C.; Woster, P. M.; Yage, J. D.; Casero, R. A. The role of polyamine catabolism in polyamine analogue-induced programmed cell death. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 11557-11562.
14. Hu, R. H.; Pegg, A. E. Rapid induction of apoptosis by deregulated uptake of polyamine analogues. Biochem. J. 1997, 328, 307-316.
15. Devereux, W.; Wang, Y.; Stewart, T. M.; Hacker, A.; Smith, R.; Frydmann, B.; Valasinas, A. L.; Reddy, V. K.; Marton, L. J.; Ward, T. D.; Woster, P. M.; Casero, R. A. Induction of the PAOh1/SMO polyamine oxidase by polyamine analogues in human lung carcinoma cells. Cancer Chemother. Pharmacol. 2003, 52, 383-390.
16. Chaturvedi, R.; Cheng, Y.; Asim, M.; Bussière, F. I.; Xu, H.; Gobert, A. P.; Hacker, A.; Casero, R. A. Jr.; Wilson, K. T. Induction of polyamine oxidase 1 by Helicobacter pylori causes macrophage apoptosis by hydrogen peroxide release and mitochondrial membrane depolarization. J. Biol. Chem. 2004, 279, 40161-40173.
17. Xu, H.; Chaturvedi, R.; Cheng, Y.; Bussière, F. I.; Asim, M.; Yao, M. D.; Potosky, D.; Meltzer, S. J.; Rhee, J. G.; Kim, S. S.; Moss, S. F.; Hacker, A.; Wang, Y.; Casero, R. A. Jr.; Wilson, K. T. Spermine oxidation induced by Helicobacter pylori results in apoptosis and DNA damage: implications for gastric carcinogenesis. Cancer Res. 2004, 64, 8521-8525.
18. Babbar, N.; Casero, R. A. Jr. Tumor necrosis factor-R increases reactive oxygen species by inducing spermine oxidase in human lung epithelial cells: a potential mechanism for inflammation-induced carcinogenesis. Cancer Res. 2006, 66, 11125-11130.
19. Yoda, H.; Hiroi, Y.; Sano, H. Polyamine oxidase is one of the key elements for oxidative burst to induce programmed cell death in tobacco cultured cells. Plant Physiol. 2006, 142, 193-206.
20. Wood, P. L.; Khan, M. A.; Kulow, S. R.; Mahmood, S. A.; Moskal, J. R. Neurotoxocity of reactive aldehydes: the concept of "aldehyde load" as demonstrated by neuroprotection with hydroxylamines. Brain Res. 2006, 1095, 190-199.
21. Binda, C.; Coda, A.; Angelini, R.; Federico, R.; Ascenzi, P.; Mattevi, A. A 30 A° long U-shaped catalytic tunnel in the crystal structure of polyamine oxidase. Structure 1999, 7, 265-276.
22. Binda, C.; Angelini, R.; Federico, R.; Ascenzi, P.; Mattevi, A. Structural bases for inhibition binding and catalysis in polyamine oxidase. Biochemistry 2001, 40, 2766-2776.
23. Cervelli, M.; Polticelli, F.; Federico, R.; Mariottini, P. Heterologous expression and characterization of mouse spermine oxidase. J. Biol. Chem. 2003, 278, 5271-5276.
24. Bianchi, M.; Polticelli, F.; Ascenzi, P.; Botta, M.; Federico, R.; Mariottini, P.; Cona, A. Inhibition of polyamine and spermine oxidases by polyamine analogues. FEBS J. 2006, 273, 1115-1123.
25. Cona, A.; Manetti, F.; Leone, R.; Corelli, F.; Tavladoraki, P.; Polticelli, F.; Botta, M. Molecular basis for the binding of competitive inhibitors of maize polyamine oxidase. Biochemistry 2004, 43, 3426-3435.
26. Stránská, J.; Šebela, M.; Tarkowski, P.; Řehulka, P.; ChmelÍk, J.; Popa, I.; Peč, P. Inhibition of plant amine oxidase by a novel series of diamine derivatives. Biochimie 2007, 89, 135-144.
27. Federico, R.; Leone, L.; Botta, M.; Binda, C.; Angelini, R.; Venturini, G.; Ascenzi, P. Inhibitor of pig liver and Zea mays L. polyamine oxidase: a comparative study. J. Enzyme Inhib. 2001, 13, 465-471.
28. Corelli, F.; Federico, R.; Cona, A.; Venturini, G.; Schenone, S.; Botta, M. Solution and solid-phase synthesis of aminoalkylguanidines inhibiting polyamine oxidase and nitric oxide synthase. Med. Chem. Res. 2002, 11, 309-321.
29. Dreassi, E.; Zizzari, A. T.; D'Arezzo, S.; Visca, P.; Botta, M. Analysis of guazatine mixture by LC and LC-MSand antimycotic activity determination of principal components. J. Pharm. Biomed. Anal. 2007, 43, 1499-1506.
30. Artiss, J. D.; Entwistle, W. M. The application of a sensitive uricase-peroxidase couple reaction to a centrifugal fast analyser for the determination of uric acid. Clin. Chim. Acta 1981, 116, 301-309.
31. Dixon, M. The determination of enzyme inhibitor constants. Biochem. J. 1953, 55, 170-171.
32. QikProp, version 3.0; Schrodinger, LLC: New York, 2007.
33. Artursson, P.; Karlsson, J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem. Biophys. Res. Commun. 1991, 175, 880-885.
34. Casero, R. A. Jr.; Mank, A. R.; Xiao, L.; Smith, J.; Bergeron, R. J.; Celano, P. Steady-state messenger RNA and activity correlates with sensitivity to N1,N12-bis(ethyl)spermine in human cell lines representing the major forms of lung cancer. Cancer Res. 1992, 52, 5359-5363.
35. Huang, Q.; Liu, Q.; Hao, Q. Crystal structures of Fms1 and its complex with spermine reveal substrate specificity. J. Mol. Biol. 2005, 348, 951-959.
36. GRID, version 22; Molecular Discovery, Ltd.: Marsh Road, Pinner, Middlesex, U.K.
37. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
38. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithmand an empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
39. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. An integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comput. Chem. 1990, 11, 440-467.
40. Maestro, version 7.5; Schroedinger: New York, 2006.
41. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. AM1: a new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
42. Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J. Am. Chem. Soc. 1996, 118, 11225-11236.