Comparison of Two Methods for the Estimation of Stability of Copper(II) Bis-Complexes with Aromatic Ligands Relevant to Alzheimer’s Disease

Open access

Abstract

In order to compare the density functional theory (DFT) and the method with the molecular valence connectivity index of the 3rd order (3χv) in the estimation of stability constants log β2, we used copper(II) complexes with thioflavin-based intercalation compounds designed for application in Alzheimer’s disease. Correlation of ten log β2 values calculated by DFT with 3χv yielded r=0.988 and S.E.=0.85. The correlations of indices ING, HOMA and 3χv with log β2, and the intercorrelations between the indices revealed the crucial influence of 3χv on the prediction of the stability of these complexes.

1. Kowalik-Jankowska T, Ruta-Dolejsz M, Wisniewska K, Lankiewicz L, Kozlowski H. Possible involvement of copper(II) in Alzheimer disease. Environ Health Perspect 2002;110(Suppl 5):869-70. PMID: 12426149

2. Lovell MA, Robertson JD, Teesdale WJ, Campbell JL, Markesbery WR. Copper, iron and zinc in Alzheimer’s disease senile plaques. J Neurol Sci 1998;158:47-52. doi: 10.1016/s0022-510x(98)00092-6

3. Bocca B, Forte G, Petrucci F, Pino A, Marchione F, Bomboi G, Senofonte O, Giubilei F, Alimonti A. Monitoring of chemical elements and oxidative damage in patients affected by Alzheimer’s disease. Ann Ist Super Sanita 2005;41:197-203. PMID: 16244393

4. Brewer GJ. The risks of copper toxicity contributing to cognitive decline in the aging population and to Alzheimer’s disease. J Am Coll Nutr 2009;28:238-42. PMID: 20150596

5. Brewer GJ, Newsome DA. Copper Proof: How Chronic Copper Toxicity is Causing the Epidemic of Alzheimer’s Disease and Dementia. Ann Arbor: George J. Brewer Inc; 2009.

6. Sparks D, Friedland R, Retanceska S, Schreurs BG, Shi J, Perry G, Smith MA, Sharma A, Derosa S, Ziolkowski C, Stankovic G. Trace copper levels in the drinking water, but not zinc of aluminium, infl uence CNS Alzheimer’s like pathology. J Nutr Health Aging 2006;10:247-54. PMID: 16886094

7. Waldman M, Lamb M. Dying for a Hamburger: Modern Meat Processing and the Epidemic of Alzheimer’s Diesease. New York (NY): Thomas Dunne Books, St. Martin’s Press; 2004.

8. Sinha R, Cross AJ, Graubard BI, Leitzmann MF, Schatzkin A. Meat intake and mortality: A perspective study of over half a million people. Arch Intern Med 2009;169:562-71. doi: 10.1001/archinternmed.2009.6

9. Morris MC, Evans DA, Tangney CC, Benias JL, Schneider JA, Wilson RS, Scherr PA. Dietary copper and high saturated and trans fat intakes associated with cognitive decline. Arch Neurol 2006;63:1085-8. doi: 10.1001/archneur.63.8.1085

10. Masters CL, Simms G, Weinman A, Multhaup G, McDonald BL, Beyreuther K. Amyloid plaque core protein in Alzheimer diesease and Down syndrome. Proc Natl Acad Sci USA 1985;82:4245-9. PMID: 3159021

11. Esch F, Keim PS, Beattie EC, Blacher RW, Culwell AR, Oltersdorf T, McClure D, Ward PJ. Cleavage of amyloid beta peptide during constitutive processing of its precursor. Science 1990;244:1122-4. doi: 10.1126/science.2111583

12. Otvos LJ, Szendrei GI, Lee VM, Mantsch HH. Human and rodent Alzheimer β-amyloid peptides acquire distinct conformations in membrane-mimicking solvents. Eur J Biochem 1993;211:249-57. doi: 10.1111/j.1432-1033.1993. tb19893.x

13. Hou L, Zagorski MG. NMR reveals anomalous copper(II) binding to amyloid Aβ peptide of Alzheimer’s disease. J Am Chem Soc 2006;128:9260-1. doi: 10.1021/ja046032u

14. Innocenti M, Salvietti E, Guidotti M, Casini A, Bellandi S, Foresti ML, Gabbiani C, Pozzi A, Zatta P, Messori L. Trace copper(II) and zinc(II) ions drastically modify the aggregation behavior of amyloid-β1-42: An AFM study. J Alzheimer’s Dis 2010;19:1323-9. doi: 10.3233/JAD-2010-1338

15. Huang X, Atwood CS, Hartshorn MA, Multhaup G, Goldstein LE, Scarpa RC, Cuajungco MP, Gray DN, Lim J, Moir RD, Tanzi RE, Bush AI. The Aβ peptide of Alzheimer’s disease directly produces hydrogen peroxide through metal ion reduction. Biochemirsty 1999;38:7609-16. doi: 10.1021/ bi990438f

16. Opazo C, Ruiz FH, Inestrosa NC. Amyloid-β-peptide reduces copper(II) to copper(I) independent of its aggregation state. Biol Res 2000;33:125-31. PMID: 15693279

17. Da Silva GFZ, Ming LJ. Alzheimer’s disease related copper(II)-β-amyloid peptide exhibits phenol monooxygenase and catechol oxidase activities. Angew Chem Int Ed 2005;44:5501-4. doi: 10.1002/anie.200501013

18. Ferrada E, Arancibia V, Loeb B, Norambuena E, Olea-Azar C, Huidobro-Toro JP. Stoichiometry and conditional stability constants of Cu(II) or Zn(II) clioquinol complexes; implications for Alzheimer’s and Huntington’s disease therapy. Neurotoxicology 2007;28:445-9. doi: 10.1016/j. neuro.2007.02.004

19. Lim S, Paterson BM, Fodero-Tavoletti MT, O’Keefe GJ, Cappai R, Barnham KJ, Villemagne VL, Donnelly PS. A copper radiopharmaceutical for diagnostic imaging of Alzheimer’s disease: a bis(thiosemicarbazonato)copper(II) complex that binds to amyloid-beta plaques. Chem Commun (Camb) 2010;46:5437-9. doi: 10.1039/c0cc01175d

20. Rodriguez-Rodriguez C, de Groot NS, Rimola A, Alvarez- Larena A, Lloveras V, Vidal-Gancedo J, Ventura S, Vendrell J, Sodupe M, Gonzalez-Duarte P. Design, selection, and characterization of thioflavin-based intercalation compounds with metal chelating properties for application in Alzheimer’s disease. J Am Chem Soc 2009;131:1436-51. doi: 10.1021/ja806062g.

21. Rimola A, Ali-Torres J, Rodriguez-Rodriguez C, Poater J, Matito E, Sola M, Sodupe M. Ab initio design of chelating ligands relevant to Alzheimer’s disease: Influence of metalloaromaticity. J Phys Chem A 2011;115:12659-66. doi: 10.1021/jp203465h

22. Raos N, Miličević A. Estimation of stability constants of coordination compounds using models based on topological indices. Arh Hig Rada Toksikol 2009;60:123-8. doi: 10.2478/10004-1254-60-2009-1923

23. Miličević A, Raos N. Estimation of stability constants by graph-theoretical models. Binding of amino acids to copper(II) and nickel(II) complexes of iminodiacetates and pyridyl derivatives of aspartic acid. Int J Chem Model 2008;1:395-403.

24. Miličević A, Branica G, Raos N. Irving-Williams order in the framework of connectivity index 3χv enables simultaneous prediction of stability constants of bivalent transition metal complexes. Molecules 2011;16:1103-12. doi: 10.3390/ molecules16021103

25. Miličević A, Raos N. Modeling of stability constants of mono-complexes of La3+, Ce3+, Pr3+, and Nd3+ with carboxylic acids in water-dioxane solutions by using connectivity index 3χv. Chem Phys Lett 2012;528:63-7. doi: 10.1016/j. cplett.2012.01.023

26. Herges R. Topology in chemistry: designing Mobius molecules. Chem Rev 2006;106:4820-42. doi: 10.1021/ cr0505425

27. Mauksch M, Tsogoeva SB. Demonstration of “Mobius” aromaticity in planar metallacycles. Chem Eur J 2010;16:7843-51. doi: 10.1002/chem.201000396

28. Tetko IV, Gasteiger J, Todeschini R, Mauri A, Livingstone D, Ertl P, Palyulin VA, Radchenko EV, Zefirov NS, Makarenko AS, Tanchuk VY, Prokopenko VV. Virtual computational chemistry laboratory-design and description. J Comput Aid Mol Des 2005;19:453-63. doi: 10.1007/s10822-005-8694-y

29. VCCLAB, Virtual Computational Chemistry Laboratory [displayed 30 August 2013]. Available at http://www.vcclab. org

30. NCI/CADD Group. Online SMILES Translator and Structure File Generator [displayed 30 August 2013]. Available at http://cactus.nci.nih.gov/services/translate/

31. Randić M. On history of the Randić index and emerging hostility toward chemical graph theory. MATCH Commun Math Comput Chem 2008;59:5-124.

32. Kier LB, Hall LH. Molecular connectivity VII: specifi c treatment to heteroatoms. J Pharm Sci 1976;65:1806-9. PMID: 1032667

33. Kier LB, Hall LH. Molecular Connectivity in Structure- Activity Analysis. New York (NY): John Wiley & Sons; 1986.

34. Kier LB, Hall LH. Molecular Connectivity in Chemistry and Drug Research. New York (NY): Academic Press; 1976.

35. Randić M. On characterization of molecular branching. J Am Chem Soc 1975;97:6609-15. doi: 10.1021/ ja00856a001

36. Lučić B, Trinajstić N. Comparison between the sumconnectivity index and product-connectivity index for benzenoid hydrocarbons. Chem Phys Lett 2009;475:146-8. doi: 10.1016/j.cplett.2009.05.022

37. Lučić B, Trinajstić N. Multivariate regression outperforms several robust architectures of neural networks in QSAR modeling. J Chem Inf Comput Sci 1999;39:121-32. doi: 10.1021/ci980090f

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