Molecular characterization of homo- and heterodimeric mercury(II)-bis- thiolates of some biologically relevant thiols by electrospray ionization and triple quadrupole tandem mass spectrometry

Journal of the American Society for Mass Spectrometry

Volumn 15, Issue 3, 2004, Pages 288-300

  Rubino, Federico Maria ^a   Verduci, Cinzia ^a   Giampiccolo, Rosario ^a   Pulvirenti, Salvatore ^a   Brambilla, Gabri ^a   Colombi, Antonio ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; AMINO ACIDS; AMMONIA; CHEMICAL BONDS; DIMERS; ISOMERS; MASS SPECTROMETRY; STOICHIOMETRY;

ELECTROPHILES; ELECTROSPRAY IONIZATION;

MERCURY COMPOUNDS;

2 METHYLOXAZOLINE 5 CARBOXYLIC ACID; ACETYLCYSTEINE; AMINO ACID; AMMONIA; CARBOXYLIC ACID DERIVATIVE; CYSTEINE; CYSTEINYLGLYCINE; FORMIC ACID; GAMMA GLUTAMYLCYSTEINE; GLUTATHIONE; GLUTATHIONE DISULFIDE; HOMOCYSTEINE; LIGAND; MERCURY; MERCURY DERIVATIVE; METAL ION; N ACETYLPENICILLAMINE; PENICILLAMINE; PEPTIDE DERIVATIVE; PYROGLUTAMIC ACID; SULFUR; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

MASS SPECTROMETRY;

ACETYLATION; ARTICLE; ATOM; BIOLOGY; CHEMICAL BOND; CHEMICAL STRUCTURE; DECOMPOSITION; ELECTROSPRAY MASS SPECTROMETRY; FRAGMENTATION REACTION; ISOMER; MOLECULAR INTERACTION; PROTON TRANSPORT; STOICHIOMETRY; TANDEM MASS SPECTROMETRY; THEORETICAL STUDY; TOXICITY; WATER LOSS;

ENVIRONMENTAL EXPOSURE; ENVIRONMENTAL POLLUTANTS; IONS; MERCURY COMPOUNDS; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFHYDRYL COMPOUNDS;

HOMO;

EID: 1442333543     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2003.10.013     Document Type: Article

References (26)

1. Sirois J.E., Atchinson W.D. Effect of Mercurials on Ligand- and Voltage-Gated Ion Channels A Review. Neurotoxicology. 17(1):1996;63-84.
2. Camerino D., Buratti M., Rubino F.M., Somaruga C., Bellugi V., Bordiga A., Bordini L., Maraschi R., Molinari M., Colosio C., Soleo L., Colombi A. Valutazione degli effetti neurotossici e nefrotossici conseguenti all'esposizione a lungo termine a mercurio metallico dei lavoratori addetti agli impianti Cloro-Soda. [Evaluation of Long-Term Neurotoxic and Nephrotoxic Effects in Chloralkali Workers Exposed to Metallic Mercury, in Italian]. La Medicina del Lavoro. 93:(3):2002;238-250.
3. Zalups R.K. Molecular Interactions with Mercury in the Kidney. Pharmacol. Rev. 52(1):2000;113-143.
4. Gelband H. The Science and Politics of Dental Amalgam. Int. J. Technol. Assess. Health Care. 14(1):1998;123-134.
5. Ramazzini, B. De Morbis Artificum Diatriba [On the Workers' Diseases]: Chap. 2: [Goldsmiths' diseases]; Chap 3: [On the Massagists' Diseases]; Chap 7: [On the Glassmakers' and Mirrormakers' Diseases] (1713 Edition, Padua, Italy); italian translation: Le Malattie dei Lavoratori (Cosmacini, G.) Teknos (Roma, Italy) 1995 pp. 21,27,45
6. Mazzella Di Bosco M., Gremigni D., Raddi R. Colesterolemia e lipoprotidogramma in 95 operai esposti al rischio di intossicazione cronica da mercurio [Cholesterol and Lipoproteins in 95 Mercury Exposed Workers, in Italian]. Lavoro Umano. 13:1961;315-322.
7. Frustaci A., Magnavita N., Chimenti C., Caldarulo M., Sabbioni E., Pietra R., Cellini C., Possati G.F., Maseri A. Marked Elevation of Myocardial Trace Elements in Idiopathic Dilated Cardiomiopathy Compared with Secundary Cardiac Dysfunction. J. Am. Coll. Cardiol. 33:1999;1578-1583.
8. Ballatori N., Clarckson T.W. Inorganic Mercury Secretion into Bile as a Low MW Complex. Biochem. Pharmacol. 33(7):1984;1087-1092.
9. Wei H., Qiu L., Divine K.K., Ashbaugh M.D., McIntyre L.C.Fernando, Q., Gandolfi A.J. Toxicity and Transport of Three Synthesized Mercury-Thiol- Complexes in Isolated Rabbit Renal Proximal Tubule Suspensions. Drug Chem. Toxicol. 22(2):1999;323-341.
10. Oram P.D., Fang X., Fernando Q., Letkeman P., Letkeman D. The Formation Constants of Mercury(II)-Glutathione Complexes. Chem. Res. Toxicol. 9(4):1996;709-712.
11. Fuhr B.J., Rabenstein D.L. Nuclear Magnetic Resonance Studies of the Solution Chemistry of Metal Complexes. IX. The Binding of Cadmium, Zinc, Lead, and Mercury to Glutathione. J. Am. Chem. Soc. 95(21):1973;6944-6950.
12. 2+ Ion l-Cysteine Complexes Implicated in Mercury Biochemistry. J. Am. Chem. Soc. 99(18):1997;6143-6145.
13. D'Agostino A., Colton R., Traeger J.C., Canty A.J. An Electrospray Mass Spectrometric Study of Organomercury(II) and Mercuric Interactions with Peptides Involving Cysteinyl Ligands. Eur. J. Mass Spectrom. 2:1996;273-285.
14. Canty A.J., Colton R., D'Agostino A.P., Traeger J.C. A Positive and Negative Ion Electrospray Mass Spectrometric Studies of Some Amino Acids and Glutathione, and Their Interactions with Alkali Metal Ions and Methylmercury(II). Inorg Chim. Acta. 223:1994;103-107.
15. Garzotti M., Rovatti L., Hamdan M. Investigation of Bombolithin Complexes with Mercury by Liquid Chromatography-Tandem Mass Spectrometry. Rapid Commun. Mass Spectrom. 12:1998;61-68.
16. Boysen R.I., Hearn M.T.W. Direct Characterization by Electrospray Ionization Mass Spectrometry of Mercuro-Polypeptide Complexes After Deprotection of Acetamidomethyl Groups from Protected Cysteine Residues of Synthetic Polypeptides. J. Biochem. Biophys. Methods. 45(2):2000;157-168.
17. Harrington C.F., Romeril J., Catterick T. The Speciation of Mercury and Organomercury Compounds by High Performance Liquid Chromatography-Atmospheric Pressure Ionization Mass Spectrometry. Rapid Commun. Mass Spectrom. 12:1998;911-916.
18. Mehra R.K., Miclat J., Kodati V.R., Abdullah R., Hunter T.C., Mulchandani P. Optical Spectroscopic and Reverse-Phase HPLC Analyses of Hg(II) Binding to Phytochelatins. Biochem. J. 314(Pt 1):1996;73-82.
19. Yen T.-Y., Villa J.A., DeWitt J.G. Analysis of phytochelatin-Cd complexes from plant tissue culture using nano-electrospray ionization tandem MS and capillary LC-ESI tandem MS. J. Mass Spectrom. 34:1999;930-941.
20. Büdi B., Sengupta S., DiBello P.M., Kinter M.T., Jacobsen D.W. A Facile Synthesis of Homocysteine-Cysteine Mixed Disulfide. Anal. Biochem. 291:2001;303-305.
21. Bernareggi A., Torti L., Maffei F.R., Carini M., Depta G., Casetta B., Farrell N., Spadacini S., Ceserani R., Tognella S. Characterization of Cisplatin-Glutathione Adducts by Liquid Chromatography-Mass Spectrometry. Evidence for Their Formation in Vitro but Not in Vivo After Concomitant Administration of Cisplatin and Glutathione to Rats and Cancer Patients. J. Chromatogr. B. 669:1995;247-263.
22. Singh R., Silvia Elipe M.V., Pearson P.G., Arison B.H., Wong B.K., White R., Yu X., Burgey C.S., Lin J.H., Baillie T.A. Metabolic Activation of a Pyrazinone-Containing Thrombin Inhibitor. Evidence for Novel Biotransformation Involving Pyrazinone Ring Oxidation, Rearrangement, and Covalent Binding to Proteins. Chem. Res. Toxicol. 16:2003;198-207.
23. Han I.-S., Kim C.K., Lee B.-S., Lee I. Ab Initio Studies of Three-Membered Ring Formation Through Intramolecular Nucleophilic Substitution. J. Comp. Chem. 18:1997;1773-1784.
24. Zoller, U. Three Membered Rings Containing Sulfur. IV. Thiironium Derivatives (Episulfonium Ions). In The Chemistry of Heterocyclic Compounds. Weissberger, A., Taylor, E. C., Eds.; Small Ring Heterocycles, Part 1. Aziridines, Azirines, Thiiranes, Thiirenes. (Hassner, A., Ed.) Wiley: New York, 1983; pp 450-474
25. Byrne M.P., Broomfield C.A., Stites W.E. Mustard Gas Crosslinking of Proteins Through Preferential Alkylation of Cysteines. J. Protein Chem. 15:1996;131-136.
26. Broch H., Hamza A., Vasilescu D. Quantum Molecular Modeling of the Interaction Between Guanine and Alkylating Agents 1. Sulfur Mustard. J. Biomol. Struct. Dyn. 13:1996;903-914.