Computational-aided design for dopamine prodrugs based on novel chemical approach

Chemical Biology and Drug Design

Volumn 78, Issue 5, 2011, Pages 853-863

  Karaman, Rafik ^a  

^a AL QUDS UNIVERSITY   (Palestine)

Author keywords

Amide hydrolysis; DFT calculations; Dopamine; Menger's aliphatic amide; Prodrugs; Proton transfer reactions; Proximity orientation

Indexed keywords

ACETAMIDE; CARBOXYLIC ACID; DOPAMINE DERIVATIVE; HYDROCARBON; KEMP ACID AMIDE; PRODRUG; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; BLOOD BRAIN BARRIER; COMPUTER AIDED DESIGN; DECARBOXYLATION; DENSITY FUNCTIONAL THEORY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG DOSAGE FORM; DRUG HALF LIFE; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENTERIC COATED TABLET; HYDROPHILICITY; IN VITRO STUDY; LIPOPHILICITY; PARKINSON DISEASE; PH; PRIORITY JOURNAL; PROTON TRANSPORT; QUANTUM CHEMISTRY;

AMIDES; COMPUTER-AIDED DESIGN; DOPAMINE; HALF-LIFE; HUMANS; KINETICS; PRODRUGS; QUANTUM THEORY; THERMODYNAMICS;

EID: 80054112134     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01208.x     Document Type: Article

References (38)

1. De Stefano A., Sozio P., Cerasa L.S. (2008) Antiparkinson prodrugs. Molecules;13:46-68.
2. Benes F.M. (2001) Carlsson and the discovery of dopamine. Trends Pharmacol Sci;22:46-47.
3. Rooseboom M., Commandeur J.N.M., Vermeulen N.P.E. (2004) Enzyme-catalyzed activation of anticancer prodrugs. Pharmacol Rev;56:53-102.
4. Karaman R. (2008) Analysis of Menger's spatiotemporal hypothesis. Tetrahedron Lett;49:5998-6002.
5. Karaman R. (2009) Cleavage of Menger's aliphatic amide: a model for peptidase enzyme solely explained by proximity orientation in intramolecular proton transfer. J Mol Struct (THEOCHEM);910:27-33.
6. Karaman R. (2010) The efficiency of proton transfer in Kirby's enzyme model, a computational approach. Tetrahedron Lett;51:2130-2135.
7. Karaman R., Pascal R. (2010) A computational analysis of intramolecularity in proton transfer reactions. Org Bimol Chem;8:5174-5178.
8. Karaman R., Hallak H. (2010) Anti-malarial pro-drugs - a computational aided design. Chem Biol Drug Des;76:350-360.
9. Karaman R. (2010) A general equation correlating intramolecular rates with attack parameters: distance and angle. Tetrahedron Lett;51:5185-5190.
10. Karaman R. (2010) Prodrugs of aza nucleosides based on proton transfer reactions. J Comput Mol Des;24:961-970.
11. Karaman R. (2011) Analyzing the efficiency of proton transfer to carbon in Kirby's enzyme model- a computational approach. Tetrahedron Lett;52:699-704.
12. Kirby A.J. (1997) Efficiency of proton transfer catalysis in models and enzymes. Acc Chem Res;30:290-296.
13. Brown C.J., Kirby A.J. (1997) Efficiency of proton transfer catalysis. Intramolecular general acid catalysis of the hydrolysis of dialkyl acetals of benzaldehyde. J Chem Soc Perkin Trans;2:1081-1093.
14. Craze G.-A., Kirby A.J. (1974) The role of carboxy-group in intramolecular catalysis of acetal hydrolysis. The hydrolysis of substituted 2-methoxymethoxybenzoic acids. J Chem Soc Perkin Trans;2:61-66.
15. Barber S.E., Dean K.E.S., Kirby A. (1999) A mechanism for efficient proton-transfer catalysis. Intramolecular general acid catalysis of the hydrolysis of 1-arylethyl ethers of salicylic acid. Can J Chem;77:792-801.
16. Asaad N., Davies J.E., Hodgson D.R.W., Kirby A.J. (2005) The search for efficient intramolecular proton transfer from carbon: the kinetically silent intramolecular general base-catalyzed elimination reaction of o-phenyl 8-dimethylamino-1-naphthaldoximes. J Phys Org Chem;18:101-109.
17. Kirby A.J., Parkinson A. (1994) Most efficient intramolecular general acid catalysis of acetal hydrolysis by the carboxy group. J Chem Soc Chem Commun;1994:707-708.
18. Kirby A.J., Lima M.F., de Silva D., Roussev C.D., Nome F. (2006) Efficient intramolecular general acid catalysis of nucleophilic attack on a phosphodiester. J Am Chem Soc;128:16944-16952.
19. Hartwell E., Hodgson D.R.W., Kirby A.J. (2000) Exploring the limits of efficiency of proton-transfer catalysis in models and enzymes. J Am Chem Soc;122:9326-9327.
20. Menger F.M. (1985) on the source of intramolecular and enzymatic reactivity. Acc Chem Res;18:128-134.
21. Menger F.M., Chow J.F., Kaiserman H., Vasquez P.C. (1983) Directionality of proton transfer in solution: three systems of known angularity. J Am Chem Soc;105:4996-5002.
22. Menger F.M. (1983) Directionality of organic reactions in solution. Tetrahedron;39:1013-1040.
23. Menger F.M., Ladika M. (1988) Fast hydrolysis of an aliphatic amide at neutral pH and ambient temperature. A peptidase model. J Am Chem Soc;110:6794-6796.
24. Menger F.M., Galloway A.L., Musaev D.G. (2003) Relationship between rate and distance. Chem Commun;9:2370-2371.
25. Menger F.M. (2005) An alternative view of enzyme catalysis. Pure Appl Chem;77:1873-1886.
26. Kirby A.J., Williams N.H. (1994) Efficient intramolecular general acid catalysis of enol ether hydrolysis. Hydrogen-bonding stabilization of the transition state for proton transfer to carbon. J Chem Soc, Perkin Trans;2:643-648.
27. Kirby A.J., Williams N.H. (1991) Efficient intramolecular general acid catalysis of vinyl ether hydrolysis by the neighboring carboxylic acid group. J Chem Soc Chem Commun;1991:1643-1644.
28. Curran T.P., Borysenko C.W., Abelleira S.M., Messier R.J. (1994) Intramolecular acylolysis of amide derivatives of Kemp's triacid: strain effects and reaction rates. J Org Chem;59:3522-3529.
29. Gerschler J.J., Wier K.A., Hansen D.E. (2007) Amide bond cleavage: acceleration due to a 1, 3-diaxial interaction with a carboxylic acid. J Org Chem;72:654-657.
30. Dougan M.L., Chin J.L., Solt K., Hansen D.E. (2004) Rapid cleavage of cyclic tertiary amides of Kemp's triacid: effects of ring structure. Med Chem Lett;14:4153-4156.
31. Burker U., Allinger N.L. (1982) Molecular Mechanics. Washington, DC: American Chemical Society.
32. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. (1985) AM1: a new general purpose quantum mechanical molecular model. J Am Chem Soc;107:3902-3909.
33. Murrell J.N., Laidler K.J. (1968) Symmetries of activated complexes. Trans Faraday Soc;64:371-377.
34. Muller K. (1980) Reaction paths on multidimensional energy hypersurfaces. Angew Chem Int Ed Engl;19:1-13.
35. Cancès M., Mennucci B., Tomasi J. (1997) A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. J Chem Phys;107:3032-3041.
36. Mennucci B., Tomasi J. (1997) Coninuum solvation models: a new approach to the problem of solute's charge distribution and cavity boundaries. J Chem Phys;106:5151.
37. Mennucci B., Cancès E., Tomasi J. (1997) Evaluation of solvent effects in isotropic and anisotropic dielectrics and in ionic solutions with a unified integral equation method: theoretical bases, computational implementation, and numerical applications. J Phys Chem B;101:10506-10517.
38. Tomasi J., Mennucci B., Cancès E. (1999) The IEF version of the PCM solvation method: an overview of a new method addressed to study molecular solutes at the QM ab initio level. J Mol Struct (THEOCHEM);464:211-226.