Molecular modeling of hexakis(areneisonitrile)technetium(I), tricarbonyl η5 cyclopentadienyl technetium and technetium(V)-oxo complexes: MM3 parameter development and prediction of biological properties

Journal of Molecular Graphics and Modelling

Volumn 25, Issue 5, 2007, Pages 616-632

  Wolohan, Peter ^a   Reichert, David E ^a  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

MM3 parameters; P glycoprotein; QSAR; Technetium

Indexed keywords

BLOOD; COMPLEXATION; CORRELATION METHODS; GENETIC ALGORITHMS; MATHEMATICAL MODELS; MOLECULAR ORIENTATION; NITROGEN COMPOUNDS;

GLYCOPROTEINS; ISONITRILES; LIVER; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP (QSAR) MODELS;

TECHNETIUM COMPOUNDS;

GLYCOPROTEIN P; ISONITRILE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TECHNETIUM COMPLEX;

AB INITIO CALCULATION; ACCURACY; ALGORITHM; ARTICLE; AUTOMATION; BLOOD; CORRELATION ANALYSIS; CRYSTALLOGRAPHY; FORCE; KIDNEY; LIGAND BINDING; LIVER; METAL BINDING; MOLECULAR MODEL; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; TISSUE DISTRIBUTION; VALIDATION STUDY;

ALGORITHMS; ANIMALS; COMPUTER SIMULATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOTECHNETIUM COMPOUNDS; P-GLYCOPROTEIN; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RADIOPHARMACEUTICALS; TECHNETIUM COMPOUNDS; TISSUE DISTRIBUTION;

EID: 33846635401     PISSN: 10933263     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jmgm.2006.04.007     Document Type: Article

References (39)

1. Jurisson S.S., and Lydon J.D. Potential technetium small molecule radiopharmaceuticals. Chem. Rev. 99 (1999) 2205-2218
2. Liu S., and Edwards D.S. 99mTc-labeled small peptides as diagnostic radiopharmaceuticals. Chem. Rev. 99 (1999) 2235-2268
3. Reichert D.E., Lewis J.S., and Anderson C.J. Metal complexes as diagnostic tools. Coord. Chem. Rev. 184 (1999) 3-66
4. Prats E., Aisa F., Abos M.D., Villavieja L., Garcia-Lopez F., et al. Mammography and 99mTc-MIBI scintimammography in suspected breast cancer. J. Nucl. Med. 40 (1999) 296-301
5. Piwnica-Worms D., Chiu M.L., Budding M., Kronauge J.F., Kramer R.A., et al. Functional imaging of multidrug-resistant P-glycoprotein with an organotechnetium complex. Can. Res. 53 (1993) 977-984
6. Rao V.V., Chiu M.L., Kronauge J.F., and Piwnica-Worms D. Expression of recombinant human multidrug resistance P-glycoprotein in insect cells confers decreased accumulation of technetium-99m-sestamibi. J. Nucl. Med. 35 (1994) 510-515
7. Kung H.F., Kim H.J., Kung M.P., Meegalla S.K., Plossl K., et al. Imaging of dopamine transporters in humans with technetium-99m TRODAT-1. Eur. J. Nucl. Med 23 (1996) 1527-1530
8. Das M., and Mukhopadhyay K. Dopamine transporter: functional implication in neurobehavioral disorders. J. Cell Tissue Res. 5 (2005) 487-496
9. Han H., Cho C.-G., and Lansbury Jr. P.T. Technetium complexes for the quantitation of brain amyloid. Chem. Rev. 118 (1996) 4506-4507
10. Katzenellenbogen J.A., Welch M.J., and Dehdashti F. The development of estrogen and progestin radiopharmaceuticals for imaging breast cancer. Anticancer Res. 17 (1997) 1573-1576
11. Wüst F. Use of [99mTc]technetium-labeled steroids as probes for steroid hormone receptors. Methods Mol. Biol. 176 (2001) 133-143
12. DiZio J.P., Anderson C.J., Davison A., Ehrhardt G.J., Carlson K.E., et al. Technetium- and rhenium-labeled progestins: synthesis, receptor binding and in vivo distribution of an 11 beta-substituted progestin labeled with technetium-99 and rhenium-186. J. Nucl. Med. 33 (1992) 558-569
13. Hom R.K., and Katzenellenbogen J.A. Technetium-99m-labeled receptor-specific small-molecule radiopharmaceuticals: recent developments and encouraging results. Nucl. Med. Biol. 24 (1997) 485-498
14. Hansch C., Maloney P.P., Fujita T., and Muir R.M. Correlation of biological activity of phenoxyacetic acids with Hammett substituent constants and partition coefficients. Nature 194 (1962) 178-180
15. Hansch C., and Leo A. Exploring QSAR Fundamentals and Applications in Chemistry and Biology (1995), American Chemical Society, Washington, DC
16. Agarwal A., Pearson P.P., Taylor E.W., Li H.B., Dahlgren T., et al. Three-dimensional quantitative structure-activity relationships of 5-HT receptor binding data for tetrahydropyridinylindole derivatives: a comparison of the Hansch and CoMFA methods. J. Med. Chem. 36 (1993) 4006-4014
17. Hansch C., Leo A., Mekapati S.B., and Kurup A. QSAR and ADME. Bioorg. Med. Chem. 12 (2004) 3391-3400
18. Klein C., Kaiser D., Kopp S., Chiba P., and Ecker G.F. Similarity based SAR (SIBAR) as tool for early ADME profiling. J. Comput. Aided Mol. Des. 16 (2003) 785-793
19. Garg R., Kurup A., Mekapati S.B., and Hansch C. Cyclooxygenase (COX) inhibitors: a comparative QSAR study. Chem. Rev. 103 (2003) 703-731
20. Wolohan P., Yoo J., Welch M.J., and Reichert D.E. QSAR studies of copper azamacrocycles and thiosemicarbazones: MM3 parameter development and prediction of biological properties. J. Med. Chem. 48 (2005) 5561-5569
21. Allinger N.L., Yuh Y.H., and Lii J.H. Molecular mechanics. The MM3 force field for hydrocarbons. J. Am. Chem. Soc. 111 (1989) 8551-8566
22. Gundertofte K., Liljefors T., Norrby P.-O., and Pettersson I. A comparison of conformational energies calculated by several molecular mechanics methods. J. Comput. Chem. 17 (1996) 429-449
23. *) parameters for ruthenium(II)-polypyridyl complexes. Inorg. Chem. 37 (1998) 4120-4127
24. Strassner T., Busold M., and Herrmann Wolfgang A. MM3 parametrization of four- and five-coordinated rhenium complexes by a genetic algorithm-which factors influence the optimization performance?. J. Comput. Chem. 23 (2002) 282-290
25. Norrby P.-O., and Brandt P. Deriving force field parameters for coordination complexes. Coord. Chem. Rev. 212 (2001) 79-109
26. Cundari T.R., and Fu W. Genetic algorithm optimization of a molecular mechanics force field for technetium. Inorg. Chim. Acta 300-302 (2000) 113-124
27. J.W. Ponder, TINKER4.2, 2004.
28. Allen F.H., and Kennard O. 3D search and research using the Cambridge Structural Database. Chem. Des. Autom. News 8 (1993) 31-37
29. Schaftenaar G., and Noordik J.H. MOLDEN: a pre- and post-processing program for molecular and electronic structures. J. Comput. Aided Mol. Des. 14 (2000) 123-134
30. Bayly C.I., Cieplak P., Cornell W.D., and Kollman P.A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: the RESP model. J. Phys. Chem. 97 (1993) 10269-10280
31. Jaguar, 5.0 ed., Schrödinger, Inc., Portland, OR, 2004.
32. Herman L.W., Sharma V., Kronauge J.F., Barbarics E., Herman L.A., et al. Novel hexakis(areneisonitrile)technetium(I) complexes as radioligands targeted to the multidrug resistance P-glycoprotein. J. Med. Chem. 38 (1995) 2955-2963
33. Molecular Operating Environment, Chemical Computing Group Inc., Que., Canada, 1997-2004.
34. Gasteiger J., and Marsili M. Iterative partial equalization of orbital electronegativity-a rapid access to atomic charges. Tetrahedron 36 (1980) 3219-3288
35. Bernard J., Ortner K., Spingler B., Pietzsch H.-J., and Alberto R. Aqueous synthesis of derivatized cyclopentadienyl complexes of technetium and rhenium directed toward radiopharmaceutical application. Inorg. Chem. 42 (2003) 1014-1022
36. Bandoli G., Dolmella A., Porchia M., Refosco F., and Tisato F. Structural overview of technetium compounds. Coord. Chem. Rev. 214 (2001) 43-90
37. Wildman S.A., and Crippen G.M. Prediction of physicochemical parameters by atomic contributions. J. Chem. Inf. Comput. Sci. 39 (1999) 868-873
38. L.H. Hall, L.B. Kier, Molecular connectivity chi indices for database analysis and structure-property modelling, in: Topological Indices and Related Descriptors in QSAR and QSPR; Gordon & Breach Science Publishers, Amsterdam, 1999, pp. 307-360.
39. Balaban A.T. Chemical graphs. XXXIV. Five new topological indexes for the branching of tree-like graphs. Theor. Chim. Acta 53 (1979) 355-375