Reactions of aminoguanidine with a-dicarbonyl compounds studied by electrospray ionization mass spectrometry

European Journal of Mass Spectrometry

Volumn 18, Issue 4, 2012, Pages 385-397

  Saraiva, Marco A ^a,b   Borges, Carlos M ^a   Florêncio, M Helena ^a  

^a UNIVERSITY OF LISBON   (Portugal)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

A dicarbonyls; Aminoguanidine; Aminotriazines; Electrospray ionization mass spectrometry

Indexed keywords

AMINES; MASS SPECTROMETRY;

AMINOGUANIDINE; AMINOTRIAZINES; BIOCHEMICAL PROCESS; DICARBONYL COMPOUNDS; DICARBONYLS; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; INFORMATION CONCERNING; PHARMACOLOGICAL PROPERTIES;

ELECTROSPRAY IONIZATION;

AMINOGUANIDINE; CARBON; GUANIDINE DERIVATIVE; TRIAZINE DERIVATIVE;

ARTICLE; BINDING SITE; CHEMISTRY; DRUG SCREENING; ELECTROSPRAY MASS SPECTROMETRY; METHODOLOGY;

BINDING SITES; CARBON; DRUG EVALUATION, PRECLINICAL; GUANIDINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TRIAZINES;

EID: 84866406182     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.1191     Document Type: Article

References (27)

1. M. Brownlee, H. Vlassara, A.Kooney, P. Ulrich and A. Cerami, "Aminoguanidine prevents diabetes-induced arterial wall protein cross-linking", Science 232, 1629 (1986). doi: 10.1126/science.3487117
2. I. Mišur and Z. Turk, "Substituted guanidine compounds as inhibitors of nonenzymatic glycation in vitro", Croat. Chem. Acta. 74, 455 (2001).
3. S. Rahbar and J.L. Figarola, "Inhibitors and breakers of advanced glycation endproducts (AGEs): a review", Curr. Med. Chem. - Imun. Endoc. Metab. Agents 2, 135 (2002). doi: 10.2174/1568013023358889
4. V.M. Monnier, "Intervention against the Maillard reaction in vivo", Arch. Biochem. Biophys. 419, 1 (2003). doi: 10.1016/j.abb.2003.08. 014
5. P.J. Thornalley, "Use of aminoguanidine (Pimagedine) to prevent the formation of advanced glycation endproduct", Arch. Biochem. Biophys. 419, 31 (2003). doi: 10.1016/j.abb.2003.08.013
6. P.V. Bharatam, P. Iqbal, A. Maldi and R. Tiwari, "Electron delocalization in aminoguanidine: a computational study", J. Phys. Chem. A 108, 10509 (2004). doi: 10.1021/jp049366e
7. E. Lieber and G.B.L. Smith, "The chemistry of aminoguanidine and related substances", Chem. Rev. 25, 213 (1939). doi: 10.1021/cr60081a003
8. P. Ou and S.P. Wolf, "Aminoguanidine: a drug proposed for prophylaxis in diabetes inhibits catalase and generates hydrogen peroxyde in vitro", Biochem. Pharmacol. 46, 1139 (1993). doi: 10.1016/0006-2952(93) 90461-5
9. A. Philis-Tsimikis, S. Parthasarathy, S. Picard, W. Palinski and J. Witztum, "Aminoguanidine has both pro-oxidant and antioxidant activity toward LDL", Arterioscler. Thromb. Vasc. Biol. 15, 367 (1995). doi: 10.1161/01.ATV.15.3.367
10. J.T. Skamarauskas, A.G. McKay and J.V. Hunt, "Aminoguanidine and its pro-oxidant effects on an experimental model of protein glycation", Free Rad. Biol. Med. 21, 801 (1996). doi: 10.1016/0891-5849(96)00183-9
11. Y. Nohara, T. Usui, T. Kinoshita and M. Watanabe, "Generation of superoxide anions during the reaction of guanidino compounds with methylglyoxal", Chem. Pharm. Bull. 50, 179 (2002). doi: 10.1248/cpb.50.179
12. D.L. Price, P.M. Rhett, S.R. Thorpe and J.W.Baynes, "Chelating activity of advanced glycation end-products inhibitors", J. Biol. Chem. 276, 48967 (2001). doi: 10.1074/jbc.M108196200
13. L.S. Santos, L. Knaack and J.O. Metzger, "Investigation of chemical reactions in solution using API-MS", Int. J. Mass Spectrom. 246, 84 (2005) (and references therein). doi: 10.1016/j.ijms.2005.08.016
14. M.N. Eberlin, "Electrospray ionization mass spectrometry: a major tool to investigate reaction mechanism in both solution and the gas phase", Eur. J. Mass Spectrom. 13, 19 (2007). doi : 10.1255/ejms.837
15. M.A. Saraiva, C.M. Borges and M.H. Florêncio, "Behaviour of 4-(-2-hydroxyethyl)-1-piperazineethanesulfonic acid under electrospray ionisation mass spectrometry conditions," Eur. J. Mass Spectrom. 16, 199 (2010). doi: 10.1255/ejms.1061
16. J.G. Erickson, "3-Amino-as-triazines", J. Am. Chem. Soc. 74, 4706 (1952). doi: 10.1021/ja01138a506
17. T.W. Lo, T. Selwood and P.J. Thornalley, "Reaction of methylglyoxal with aminoguanidine under physiological conditions and prevention of methylglyoxal binding to plasma proteins", Biochem. Pharmacol. 48, 1865 (1994). doi: 10.1016/0006-2952(94)90584-3
18. T.L. Constantopoulos, G.S. Jackson and C.G. Enke, "Effects of salt concentration on analyte response using electrospray ionization mass spectrometry", J. Am. Soc. Mass Spectrom. 10, 625 (1999). doi: 10.1016/S1044-0305(99)00031-8
19. M.A. Saraiva, C.M. Borges and M.H. Florêncio, "Reactions of a modified lysine with aldehydic and ketonic dicarbonyl compounds: an electrospray mass spectrometry structure activity study", J. Mass Spectrom. 41, 216 (2006). doi: 10.1002/jms.980
20. M.A. Saraiva, C.M. Borge and M.H. Florêncio, "Non-enzymatic model glycation reactions - a comprehensive study of the reactivity of a modified arginine with aldehydic and diketonic dicarbonyl compounds by electrospray mass spectrometry", J. Mass Spectrom. 41, 755 (2006). doi: 10.1002/jms.1031
21. M.A. Saraiva, C.M. Borge and M.H. Florêncio, "Towards the control and inhibition of glycation - the role of the guanidine reaction center with aldehydic and diketonic dicarbonyls. A mass spectrometry study. J. Mass Spectrom. 41, 1346 (2006). doi: 10.1002/jms.1109
22. J. Sunner, G. Nicol and P. Kebarle, "Factors determining relative sensitivity of analytes in positive mode atmospheric pressure ionization mass spectrometry", Anal. Chem. 60, 1300 (1988). doi: 10.1021/ac00164a012
23. P.J. Thornalley, A. Yurek-George and O.K. Argirov, "Kinetics and mechanism of the reaction of aminoguanidine with the a-oxoaldehydes glyoxal, methylglyoxal, and 3-deoxyglucosone under physiological conditions", Biochem. Pharmacol. 60, 55 (2000). doi: 10.1016/S0006-2952(00)00287-2
24. J Limanto, R.A. Desmond, D.R. Gauthier, Jr, P.N. Devine, R.A. Reamer and R.P. Volante, "A regioselective approach to 5-substituted-3-amino-1,2,4- triazines", Org. Lett. 5, 2271 (2003). doi: 10.1021/ol034602+
25. E. Garnier, J. Guillard, E. Pasquinet, F. Suzenet, D. Poullain, C. Jarry, J.-M. Léger, B. Lebret and G. Guillaumet, "Highly diastereoselective synthesis of C(6)-functionalized dihydroimidazotriazines", Org. Lett. 5, 4595 (2003). doi: 10.1021/ol035743e
26. H. Neunhoeffer, in Comprehensive heterocyclic chemistry II, Chapter 6.11, Ed by A.R. Katrizky, C.W. Rees and E.F.V. Scriven. Pergamon Press, Oxford, UK, pp. 507-573 (1996).
27. P.V. Bernhardt and E.J. Hayes, "Aminotriazines as locking fragments in macrocyclic synthesis", Inorg. Chem. 37, 4214 (1998). doi: 10.1021/ic980243g