Implementing molecular connectivity theory, a basic tool in modeling drugs

Journal of Pharmaceutical Sciences

Volumn 96, Issue 8, 2007, Pages 1856-1871

  Pogliani, Lionello ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

cis trans indices; Complete graphs; Dual indices; General graphs; Hydrogen perturbation; Molecular connectivity; Pseudoconnectivity indices; Simple graphs

Indexed keywords

ALKENE DERIVATIVE; HALIDE; HYDROGEN;

ATOM; CHEMICAL BOND; CIS TRANS ISOMERISM; CONCEPTUAL FRAMEWORK; ELECTRON; ENTHALPY; MOLECULAR CONNECTIVITY THEORY; MOLECULE; NONHUMAN; PARAMETER; QUANTUM CHEMISTRY; SHORT SURVEY;

EID: 34548011679     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.20862     Document Type: Short Survey

References (49)

1. Randić M. 1975. On characterization of molecular branching. J Am Chem Soc 97:6609-6615.
2. Kier LB, Hall LH, Murray WJ, Randić M. Molecular connectivity I: Relationship to non specific local anesthesia. J Pharm Sci 64:1971-1974.
3. Hall LH, Kier LB, Murray WJ. 1975. Molecular connectivity II: Relationship to water solubility and boiling point. J Pharm Sci 64:1974-1977.
4. Murray JM, Hall LH, Kier LB. 1975. Molecular connectivity III: Relationship to partition coefficients. J Pharm Sci 64:1978-1981.
5. Kier LB, Hall LH. 1976. Molecular connectivity VII: Specific treatment of heteroatoms. J Pharm Sci 65:1806-1809; 1981. Derivation and significance of valence molecular connectivity indices. J Pharm Sci 70:583-589.
6. Kier LB, Hall LH. 1986. Molecular connectivity in structure-activity analysis. New York: Wiley.
7. Pogliani L. 1992. Molecular connectivity model for determination of isoelectric point of amino acids. J Pharm Sci 81:334-336; 1992. Molecular connectivity: Treatment of the electronic structure of amino acids. J Pharm Sci 81:967-969.
8. Todeschini R, Consonni V. 2000, The Handbook of Molecular Descriptors. Weinheim: Wiley-VCH.
9. Trinajstić N. 1992. Chemical graph theory. 2nd ed. Boca Raton: CRC Press.
10. Devillers J, Balaban AT, editors. 1999. Topological indices and related descriptors in QSAR/QSPR. Amsterdam: Gordon and Breach.
11. Pogliani L. 2000. From molecular connectivity indices to semiempirical connectivity terms: Recent trends in graph theoretical descriptors. Chem Rev 100:3827-3858.
12. Pogliani L. 1994. On a graph theoretical characterization of cis/trans isomers. J Chem Inf Comput Sci 34:801-804.
13. Randić M. 1988. On characterization of three-dimensional structures. Int J Quant Chem: Quant Biol Symp 15:201-208.
14. Kier LB, Hall LH. 1999. Molecular structure description. The electrotopological state. New York: Academic press.
15. Pogliani L. 2000. Modeling with molecular pseudoconnectivity descriptors. A useful extension of the intrinsic I-state concept. J Phys Chem 104:9029-9045.
16. Pogliani L. 2001. How far are molecular connectivity descriptors from Is molecular pseudoconnectivity descriptors? J Chem Inf Comput Sci 41:836-847.
17. Pogliani L. 2002. Topics in molecular modeling: Dual indices, quality of modeling, and missing information, truncation. J Mol Struct (Theochem) 581:87-109.
18. Pogliani L. 2002. Algorithmically compressed data and the topological conjecture for the inner-core electrons. J Chem Inf Comput Sci 42:1028-1042.
19. Pogliani L. 2003. Complete graph conjecture for the inner-core electrons: Homogeneous index case. J Comput Chem 24:1097-1109.
20. Pogliani L. 2005. A natural graph-theoretical model for the partition and kinetic coefficients. New J Chem 29:1082-1088.
21. Pogliani L. 2005. Model of the physical properties of halides with complete graph based indices. Int J Quant Chem 102:38-52.
22. Pogliani L. 2006. The hydrogen perturbation in molecular connectivity computations. J Comput Chem 27:868-882.
23. Grassy G, Calas B, Yasri A, Lahana R, Woo J, Iyer S, Kaczorek M, Floc'h R, Buelow R. 1998. Computer-assisted rational design of immunosuppressive compounds. Nature Biotechn 16:746-752.
24. Duart MJ, Garcia-Domenech R, Gálvez J, Alemán PA, Martín-Algarra RV, Antón-Fos GM. 2006. Application of a mathematical topological pattern of antihistaminic activity for the selection of new drug candidates and pharmacology assays. J Med Chem 49:3667-3673.
25. de Julian-Ortiz JV, Garcia-Domenech R, Galvez J, Pogliani L. 2005. Predictability and Prediction of lowest observed adverse effect levels in a structurally heterogeneous set of chemical compounds. SAR QSAR Environ Res 16:263-272.
26. Duart MJ, Antón-Fos GM, Aleman PA, Gay-Roig JB, González-Rosende ME, Gálvez J, García-Domenech R. 2005. New potential antihistaminic compounds. Virtual combinatorial chemistry, computational screening, real synthesis, and pharmacological evaluation. J Med Chem 48:1260-1264.
27. de Julian-Ortiz JV, Galvez J, Muñoz-Callado C, Garcia-Domenech R, Gimeno-Cardona C. 1999. Virtual combinatorial synthesis and computational screening of new potential anti-herpes compounds. J Med Chem 42:3308-3314.
28. Estrada E, Uriarte E, Montero A, Teijeira M, Santana L, De Clerq E. 2000. A novel approach for the virtual screening and rational design of anticancer compounds. J Med Chem 43:1975-1985.
29. Estrada E. 2001. Recent advances on the role of topological indices in drug discovery research. Curr Med Chem 8:1573-1588.
30. Basak SC, Mills D, Hawkins DM, El-Masri HA. 2002. Prediction of tissue:air partition coefficients: A comparison of structure-based and property-based methods. SAR QSAR Environ Res 13:649-665.
31. Basak SC, Gute BD, Grunwald GD. 1999. Assessment of the mutagenicity of aromatic amines from theoretical structural parameters: A hierarchical approach. SAR QSAR Environ Res 10:117-129.
32. max) of halogenated methanes, ethanes, and ethylenes. Toxicol Lett 43:235-256.
33. Harary F, Read R. 1977. Proc. Graphs and Combinatorics Conference. George Washington University. Springer, New York. Cited in: Barrow JD. 2000. The Book of Nothing. Vintage Books, New York, p 155.
34. f in QSAR: Toxicity of aliphatic ethers. J Chem Inf Comput Sci 41:614-618.
35. f against descriptors of CODESSA. J Chem Inf Comput Sci 41:631-638.
36. Chang R. 1994. Chemistry. New York: McGraw-Hill.
37. Schmid R. 2003. The noble gas configuration - not the driving force but the rule of the game in chemistry. J Chem Educ 80:931-937.
38. z: How are they related to molecular mass? J Chem Educ 78:1544-1550.
39. Gillespie RJ. 2001. Electron densities, atomic charges, and ionic, covalent, and polar bonds. J Chem Educ 78:1688-1691.
40. Matta CF, Gillespie RJ. 2002. Understanding and interpreting molecular electron density distributions. J Chem Educ 79:1141-1152.
41. Pogliani L, de Julian-Ortiz JV. 2004. Plot methods in quantitative structure-property studies. Chem Phys Lett 393:327-330.
42. Besalu E, de Julian-Ortiz JV, Iglesias M, Pogliani L. 2006. An overlooked property of plot methods. J Math Chem 39:475-484.
43. Besalu E, de Julian-Ortiz JV, Pogliani L. 2006. Some plots are not that equivalent. MATCH Commun Math Comput Chem 55:281-286.
44. Yang C, Zhong C. 2003. Modified connectivity indices and their applications to QSPR study. J Chem Inf Comput Sci 43:1998-2004.
45. Pogliani L. 2006. The evolution of the valence delta in molecular connectivity theory, internet electron. J Mol Des 5:364-375.
46. Mihalić Z, Nikolić S, Trinajstić N. 1992. Comparative study of molecular descriptors derived from the distance matrix. J Chem Inf Comput Sci 32:28-37.
47. Randić M. 1991. Orthogonal molecular descriptors. New J Chem 15:517-525.
48. Randić M. 1991. Correlation of enthalpy of octanes with orthogonal connectivity indices. J Mol Struct (Theochem) 233:45-59.
49. Lučić B, Nikolić N, Trinajstić N. 1995. The structure-property models can be improved using orthogonalized descriptors. J Chem Inf Comput Sc 35:532-538.