Inhibition of Diamine Oxidases and Polyamine Oxidases by Diamine-based Compounds

Overview

Journal J Neural Transm (Vienna)

Specialties Neurology
Physiology

Date 2007 Mar 27

PMID 17385064

Citations 2

Authors

M Sebela

M Tylichova

P Pec

Affiliations

Soon will be listed here.

Abstract

This review reports on inhibitors of copper-containing amine oxidases and flavoprotein polyamine oxidases, which are structurally based on diamines. In the introduction, basic characteristics and classification of amine oxidases are described together with the significance of their synthetic inhibitors. The following text is divided into several chapters, which deal with diaminoketones, aza-diamines, unsaturated diamine analogs and diamines with heterocyclic substituents. Then it continues with diamine- and agmatine-based inhibitors of polyamine oxidases. Each chapter gives detailed information on the inhibition mode, potency and structural relationships. The conclusion points out possible roles of mechanism-based inhibitors of amine oxidases in physiological and medicinal research.

Citing Articles

The Neuroprotective Effects of Agmatine on Parkinson's Disease: Focus on Oxidative Stress, Inflammation and Molecular Mechanisms.

Zamanian M, Nazifi M, Khachatryan L, Taheri N, Sadeghi Ivraghi M, Menon S Inflammation. 2024; .

PMID: 39225914 DOI: 10.1007/s10753-024-02139-7.

Amine oxidase copper-containing 1 (AOC1) is a downstream target gene of the Wilms tumor protein, WT1, during kidney development.

Kirschner K, Braun J, Jacobi C, Rudigier L, Persson A, Scholz H J Biol Chem. 2014; 289(35):24452-62.

PMID: 25037221 PMC: 4148871. DOI: 10.1074/jbc.M114.564336.

References

MACHOLAN L, Rozprimova L, Sedlackova E . 1,4-diamino-2-butanon (2-ketoputrescine) as strong and short acting competitive inhibitor of diamine oxidase. Biochim Biophys Acta. 1967; 132(2):505-7. DOI: 10.1016/0005-2744(67)90169-6. View

Hu R, Pegg A . Rapid induction of apoptosis by deregulated uptake of polyamine analogues. Biochem J. 1998; 328 ( Pt 1):307-16. PMC: 1218922. DOI: 10.1042/bj3280307. View

Sebela M, Radova A, Angelini R, Tavladoraki P, Frebort I I, Pec P . FAD-containing polyamine oxidases: a timely challenge for researchers in biochemistry and physiology of plants. Plant Sci. 2001; 160(2):197-207. DOI: 10.1016/s0168-9452(00)00380-0. View

Ha H, Woster P, Yager J, Casero Jr R . The role of polyamine catabolism in polyamine analogue-induced programmed cell death. Proc Natl Acad Sci U S A. 1997; 94(21):11557-62. PMC: 23536. DOI: 10.1073/pnas.94.21.11557. View

Binda C, Coda A, Angelini R, Federico R, Ascenzi P, Mattevi A . A 30-angstrom-long U-shaped catalytic tunnel in the crystal structure of polyamine oxidase. Structure. 1999; 7(3):265-76. DOI: 10.1016/s0969-2126(99)80037-9. View

Frebort I, Sebela M, Svendsen I, Hirota S, Endo M, Yamauchi O . Molecular mode of interaction of plant amine oxidase with the mechanism-based inhibitor 2-butyne-1,4-diamine. Eur J Biochem. 2000; 267(5):1423-33. DOI: 10.1046/j.1432-1327.2000.01132.x. View

Sebela M, Lamplot Z, Petrivalsky M, Kopecny D, Lemr K, Frebort I . Recent news related to substrates and inhibitors of plant amine oxidases. Biochim Biophys Acta. 2003; 1647(1-2):355-60. DOI: 10.1016/s1570-9639(03)00094-3. View

Cona A, Rea G, Angelini R, Federico R, Tavladoraki P . Functions of amine oxidases in plant development and defence. Trends Plant Sci. 2006; 11(2):80-8. DOI: 10.1016/j.tplants.2005.12.009. View

Lamplot Z, Sebela M, Malon M, Lenobel R, Lemr K, Havlis J . 1,5-diamino-2-pentyne is both a substrate and inactivator of plant copper amine oxidases. Eur J Biochem. 2004; 271(23-24):4696-708. DOI: 10.1111/j.1432-1033.2004.04434.x. View

10.

Bellelli A, Cavallo S, Nicolini L, Cervelli M, Bianchi M, Mariottini P . Mouse spermine oxidase: a model of the catalytic cycle and its inhibition by N,N1-bis(2,3-butadienyl)-1,4-butanediamine. Biochem Biophys Res Commun. 2004; 322(1):1-8. DOI: 10.1016/j.bbrc.2004.07.074. View

11.

Bianchi M, Polticelli F, Ascenzi P, Botta M, Federico R, Mariottini P . Inhibition of polyamine and spermine oxidases by polyamine analogues. FEBS J. 2006; 273(6):1115-23. DOI: 10.1111/j.1742-4658.2006.05137.x. View

12.

Lamplot Z, Sebela M, Frycak P, Longu S, Padiglia A, Medda R . Reactions of plant copper/topaquinone amine oxidases with N6-aminoalkyl derivatives of adenine. J Enzyme Inhib Med Chem. 2005; 20(2):143-51. DOI: 10.1080/14756360400021866. View

13.

Pec P, Frebort I . 1,4-Diamino-2-butyne as the mechanism-based pea diamine oxidase inhibitor. Eur J Biochem. 1992; 209(2):661-5. DOI: 10.1111/j.1432-1033.1992.tb17333.x. View

14.

Stranska J, Sebela M, Tarkowski P, Rehulka P, Chmelik J, Popa I . Inhibition of plant amine oxidases by a novel series of diamine derivatives. Biochimie. 2006; 89(1):135-44. DOI: 10.1016/j.biochi.2006.08.001. View

15.

Ascenzi P, Fasano M, Marino M, Venturini G, Federico R . Agmatine oxidation by copper amine oxidase. Eur J Biochem. 2002; 269(3):884-92. DOI: 10.1046/j.0014-2956.2002.02718.x. View

16.

Pec P, Frebort I . Some amines as inhibitors of pea diamine oxidase. J Enzyme Inhib. 1992; 5(4):323-9. DOI: 10.3109/14756369109069074. View

17.

MACHOLAN L . Substrate-like inhibitors of diamine oxidase: some relations between the structure of aliphatic aminoketones and their inhibitory effect. Arch Biochem Biophys. 1969; 134(2):302-7. DOI: 10.1016/0003-9861(69)90288-4. View

18.

Binda C, Angelini R, Federico R, Ascenzi P, Mattevi A . Structural bases for inhibitor binding and catalysis in polyamine oxidase. Biochemistry. 2001; 40(9):2766-76. DOI: 10.1021/bi002751j. View

19.

Cona A, Manetti F, Leone R, Corelli F, Tavladoraki P, Polticelli F . Molecular basis for the binding of competitive inhibitors of maize polyamine oxidase. Biochemistry. 2004; 43(12):3426-35. DOI: 10.1021/bi036152z. View

20.

MACHOLAN L . 3-Hydroxycadaverine, a new substrate for diamine oxidase. Enzymologia. 1972; 42(4):303-15. View