Correlation between energetics of collisionally activated decompositions, interaction energy and biological potency of carbamate FAAH inhibitors [2]

Journal of Mass Spectrometry

Volumn 42, Issue 12, 2007, Pages 1624-1627

  Valitutti, Giovanni ^a   Duranti, Andrea ^b   Lodola, Alessio ^c   Mor, Marco ^c   Piersanti, Giovanni ^b   Piomelli, Daniele ^d   Rivara, Silvia ^c   Tontini, Andrea ^b   Tarzia, Giorgio ^b   Traldi, Pietro ^a  

^a CNR   (Italy)

^b UNIVERSITY OF URBINO   (Italy)

^c UNIVERSITY OF PARMA   (Italy)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID; FATTY ACID AMIDASE INHIBITOR;

CARBAMOYLATION; COLLISIONALLY ACTIVATED DISSOCIATION; DECOMPOSITION; ENERGY TRANSFER; ENZYME INACTIVATION; LETTER; MASS SPECTROMETER; MOLECULAR DOCKING; PRIORITY JOURNAL; THERMODYNAMICS;

AMIDOHYDROLASES; CARBAMATES; ENZYME INHIBITORS; MASS SPECTROMETRY; MODELS, MOLECULAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 38149033059     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1346     Document Type: Letter

References (18)

1. Wang J, Wang J, Davis M, DeMaio W, Scatina J, Talaat R. Integrated Strategies for Drug Discovery Using Mass Spectrometry. Wiley: New York, 2005; 289.
2. Orsatti L, Seraglia R, Traldi P, Diamantini G, Tarzia G, Tontini A. Electron impact ionization and fast atom bombardment mass spectrometry of some 3,3-dimethyl-1-(isoxazol-3-yl)triazenes, a new class of potential anticancer agents. Journal of Mass Spectrometry 1995; 30: 1567.
3. Tarzia G, Diamantini G, Tontini A, Favretto D, Traldi P. Correlation of the mutagenic properties of aryl- and heteroaryltriazenes with their electron ionization induced fragmentation. Rapid Communications in Mass Spectrometry 1996; 10: 1156.
4. Tarzia G, Diamantini G, Tontini A, Bedini A, Favretto D, Traldi P. Correlation of the antimetastatic properties of aryltriazenes with their electron impact ionization mass spectrometry. Rapid Communications in Mass Spectrometry 1997; 11: 1365.
5. Basso E, Duranti A, Mor M, Piomelli D, Tontini A, Tarzia G, Traldi P. Tandem mass spectrometric data-FAAH inhibitory activity relationships of some carbamic acid O-aryl esters. Journal of Mass Spectrometry 2004; 39: 1450.
6. Piomelli D, Tarzia G, Duranti A, Tontini A, Mor M, Compton TR, Dasse O, Monaghan EP, Parrot JA, Putman D. Pharmacological profile of the selective FAAH inhibitor KDS-4103 (URB597). CNS Drug Reviews 2006; 12: 21.
7. Tarzia G, Duranti A, Tontini A, Piersanti G, Mor M, Rivara S, Plazzi PV, Park C, Kathuria S, Piomelli D. Design, synthesis, and structure-activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors. Journal of Medicinal Chemistry 2003; 46: 2352.
8. Mor M, Rivara S, Lodola A, Plazzi PV, Tarzia G, Duranti A, Tontini A, Piersanti G, Kathuria S, Piomelli D. Cyclohexylcarbamic acid 3′- or 4′-substituted biphenyl-3-yl esters as fatty acid amide hydrolase inhibitors: synthesis, quantitative structure-activity relationships, and molecular modelling studies. Journal of Medicinal Chemistry 2004; 47: 4998.
9. Tarzia G, Duranti A, Gatti G, Piersanti G, Tontini A, Rivara S, Lodola A, Plazzi PV, Mor M, Kathuria S, Piomelli D. Synthesis and structure-activity relationships of FAAH inhibitors: cyclohexylcarbamic acid biphenyl esters with chemical modulation at the proximal phenyl ring. ChemMedChem 2006; 1: 130.
10. Patricelli MP, Lovato MA, Cravatt BF. Chemical and mutagenic investigations of fatty acid amide hydrolase: evidence for a family of serine hydrolases with distinct catalytic properties. Biochemistry 1999; 38: 9804.
11. McKinney MK, Cravatt BF. Evidence for distinct roles in catalysis for residues of the serine-serine-lysine catalytic triad. Journal of Biological Chemistry 2003; 278: 37 393.
12. Bush KL, Glish GL, McLuckey SA. Mass Spectrometry/Mass Spectrometry. Techniques and Applications of Tandem Mass Spectrometry. VCH: New York, 1988; 57.
13. Alexander JP, Cravatt BF. Mechanism of carbamate inactivation of FAAH: implications for the design of covalent inhibitors and in vivo functional probes for enzymes. Chemistry and Biology 2005; 12: 1179.
14. March RE, Todd JF. Quadrupole Ion Trap Mass Spectrometry, 2nd ed. Wiley: Hoboken, 2005; 136.
15. Gronowska J, Paradisi C, Traldi P, Vettori U. A study of relevant parameters in collisional-activation of ions in the ion-trap mass spectrometer. Rapid Communications in Mass Spectrometry 1990; 4: 306.
16. Moriguchi I, Hirono S, Liu Q, Nakagome I, Matsushita Y. Fuzzy adaptive least squares applied to structure-activity and structure-toxicity correlations. Chemical and Pharmaceutical Bulletin 1992; 40: 127.
17. Molecular modelling program: Sybyl Version 7.2. Tripos Inc.: 1699 South Hanley Rd., St. Louis, MO (USA), 63144.
18. Halgren TA. Merck molecular force field. I. Basis, form, scope, parametrization, and performance of MMFF94*. Journal of Computational Chemistry 1996; 17: 490.