Modeling and spectroscopic studies of bisphosphonate-bone interactions. The Raman, NMR and crystallographic investigations of Ca-HEDP complexes

Bone

Volumn 41, Issue 4, 2007, Pages 668-678

  Cukrowski, Ignacy ^a   Popović, Ljiljana ^a   Barnard, Werner ^a   Paul, Sylvia O ^b   van Rooyen, Petrus H ^a   Liles, David C ^a  

^a UNIVERSITY OF PRETORIA   (South Africa)

^b UNIVERSITY OF SOUTH AFRICA   (South Africa)

Author keywords

Bisphosphonate; Cancer; Crystal structure; Modeling; Spectroscopy

Indexed keywords

BISPHOSPHONIC ACID DERIVATIVE; CALCIUM; ETIDRONIC ACID; HYDROXYAPATITE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CALCIUM BINDING; CATTLE; CHEMICAL INTERACTION; COMPLEX FORMATION; COMPUTER PROGRAM; CONTROLLED STUDY; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; FLUORESCENCE; MOLECULAR MODEL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; RAMAN SPECTROMETRY; STRUCTURE ANALYSIS; VIBRATION; X RAY DIFFRACTION;

ANIMALS; BONE AND BONES; CALCIUM; CATTLE; ETIDRONIC ACID; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, BIOLOGICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SPECTRUM ANALYSIS, RAMAN; VIBRATION; X-RAY DIFFRACTION;

EID: 34548534318     PISSN: 87563282     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bone.2007.05.008     Document Type: Article

References (47)

1. Constantz B.R., Ison I.C., Fulmer M.T., Poser R.D., Smith S.T., Van Wagoner M., Ross J., Goldstein S.A., Jupiter J.B., and Rosenthal D.I. Skeletal repair by in situ formation of the mineral phase of bone. Science 267 (1995) 1796-1799
2. Yoshioka M., Yoshida Y., Inoue S., Lambrechts P., Vanherle G., Nomura Y., Okazaki M., Shintani H., and Van Meerbeek B. Adhesion/Decalcification mechanisms of acid interactions with human hard tissues. J. Biomed. Mater. Res. 59 (2002) 56-62
3. Penel G., Delfosse C., Descamps M., and Leroy G. Composition of bone and apatitic biomaterials as revealed by intravital raman microspectrometry. Bone 36 (2005) 893-901
4. Pasteris J.D., Wopenka B., Freeman J.J., Rogers K., Valsami-Jones E., Van der Houwen J.A.M., and Silva M.J. Lack of OH in nanocrystalline apatite as a function of degree of atomic order: implications for bone and biomaterials. Biomaterials 25 (2004) 229-238
5. Dorozhkin S.V., and Epple M. Biological and medical significance of calcium phosphates. Angew. Chem. Int. Ed. 41 (2002) 3130-3146
6. Nancollas G.H., Tang R., Phipps R.J., Henneman Z., Gulds S., Wu W., Mangood A., Russell R.G.G., and Ebetino F.H. Novel insights into actions of bisphosphonates on bone: differences in interactions with hydroxyapatite. Bone 38 (2006) 617-627
7. Lin J.H. Bisphosphonates: a review of their pharmacokinetic properties. Bone 18 (1996) 75-85
8. Hoskin P.J. Bisphosphonates and radiation therapy for palliation of metastatic bone disease. Cancer Treat. Rev. 29 (2003) 321-327
9. Zeevaart J.R., Jansen D.R., Botelho M.F., Abrunhosa A., Gomes C., Metello L., Kolar Z.I., Krijger G., Louw W.K.A., and Dormehl I.C. Comparison of the predicted in vivo behaviour of the Sn(II)-APDDMP Complex and the results as studied in a rodent model. J. Inorg. Biochem. 98 (2004) 1521-1530
10. Ogawa K., Mukai T., Arano Y., Otaka A., Ueda M., Uehara T., Magata Y., Hashimoto K., and Saji H. Rhenium-186-monoaminemonoamidedithiol-conjugated bisphosphonate derivatives for bone palliation. Nucl. Med. Biol. 33 (2006) 513-520
11. Lewington V.J. Cancer therapy using bone-seeking isotopes. Phys. Med. Biol. 41 (1996) 2027-2042
12. Papapoulos S.E. Bisphosphonate actions: physical chemistry revisited. Bone 38 (2006) 613-616
13. Fleisch H. Bisphosphonates: mechanisms of action. Endocr. Rev. 19 (1998) 80-100
14. Rogers M.J., Gordon S., Benford H.L., Coxon F.P., Luckman S.P., Monkkonen J., and Frith J.C. Cellular and molecular mechanisms of action of bisphosphonates. Skelet. Complic. Malign., Suppl. Cancer 88 (2000) 2961-2978
15. Corbridge D.E.C. Phosphorus: An Outline of its Chemistry, Biochemistry and Technology (1990), Elsevier Scientific, Amsterdam (4[10] Studies in Inorganic Chemistry)
16. mTc skeletal imaging agents. J. Am. Chem. Soc. 102 (1980) 2476-2478
17. Penel G., Leroy G., Rey C., Sombret B., Huvenne J.P., and Bres E. Infrared and Raman microspectrometry study of fluor-, fluor-hydroxy and hydroxy-apatite powders. J. Mater. Sci., Mater. Med. 8 (1997) 271-276
18. Van Haverbeke L., Desseyn H.O., and Herman M.A. Vibrational Spectra of mono- and polymethylene diphosphonic acids. B Soc. Chim. Belg. 81 (1972) 547-554
19. Mikelsons M.V., and Pinkerton T.C. Raman spectroscopic evidence for Tc-Oxo cores in Tc-HEDP complexes. Appl. Radiat. Isotopes 38 (1987) 569-570
20. Myund L.A., Bus'ko E.A., Smirnova N.I., Terekhin S.N., Dyatlova N.M., and Burkov K.A. Raman spectroscopy studies on the acid-base equilibria in 1-hydroxyethyl-1,1-diphosphonic acid solutions. Vestn Lenin U Fiz Kh - Seriya 4 3 (1987) 48-53
21. Myund L.A., Bus'ko E.A., Terekhin S.N., and Burkov K.A. Spectroscopic investigation of the deprotonation processes of 1-hydroxyethylidene-1,1-diphosphonic acid. Vestn Lenin U Fiz Kh - Seriya 4 1 (1990) 33-37
22. Myund L.A., Bus'ko E.A., Terekhin S.N., and Burkov K.A. Investigation of complexing Zn(II) with hydroxyethanediphosphonic acid in aqueous solution by Raman spectroscopy. J. Appl. Spectrosc.-Russian Ed. 50 (1989) 416-420
23. Matveeva A.G., Pasechnik M.P., Petrovskii P.V., Matveev S.V., and Pisareva S.A. Amino-substituted gem-diphosphonic acids: dissociation mechanism and the structure of species in aqueous solutions. Russ. Chem., B 49 (2000) 1045-1058
24. Bus'ko E.A., Myund L.A., Terekhin S.N., Burkov K.A., Dyatlova N.M., and Volkova N.A. State of hydroxyethylidenediphosphonic acid in aqeous solutions. Zh Neorg Khim 33 (1988) 603-607
25. Hein L.E., Grassi R.L., Roldan E.J.A., Gregori D., Varela M.E., and Piccinni E.P. Morphological studies of hydroxyapatite crystals exposed to disodium pamidronate. Medicina 57 Supplement 1 (1997) 10-16
26. Aminzadeh A. Fluoresence bands in the FT-Raman spectra of some calcium minerals. Spectrochim. Acta, A 53 (1997) 693-697
27. Uchtman V.A. Structural investigation of calcium binding molecules. II. The crystal and molecular structures of calcium dihydrogen ethane-1-hydroxy-1,1-diphosphonate dihydrate, CaC(CH3)(OH)(PO3H)2.2H2O; implications for polynuclear complex formation. J. Phys. Chem. 76 (1972) 1304-1310
28. Wada H., and Fernando Q. Interaction of methanehydroxyphosphonic acid and ethane-1,1-diphosphonic acid with alkali and alkaline earth metal ions. Anal. Chem. 44 (1972) 1640-1643
29. Grabenstetter R.J., and Cilley W.A. Polynuclear complex formation in solutions of calcium ion ands ethane-1-hydroxy-1,1-diphosphonic acid. I. Complexometric and PH titrations. J. Phys. Chem. 75 (1971) 676-682
30. Wiers B.H. Precipitation boundaries in calcium-pyrophosphate and calcium-ethane-1-hydroxy-1,1-diphosphonate systems. Inorg. Chem. 10 (1971) 2581-2584
31. Penel G., Leroy G., and Bres E. New preparation method of bone samples for Raman microspectrometry. Appl. Spectrosc. 52 (1998) 312-313
32. SMART (Version 5.054), SAINT (Version 6.45), SADABS (Version 2.10) and SHELXTS/SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA. 2001.
33. SHELXS-97 and SHELXL-97. Sheldrick, GM University of Göttingen, Germany; 1997.
34. Faruggia L.J. ORTEP-3 for Windows-a version of ORTEP-III with a graphical user interface (GUI). J. Appl. Crystallogr. 30 (1997) 565
35. Mercury (Version 1.4.2). Cambridge Crystallographic Data Centre. URL: http://www.ccdc.cam.ac.uk; 2007.
36. POV-Ray for Windows. (Version 3.6) Persistence of Vision Raytracer Pty. Ltd., Victoria, Australia. URL: http://www.povray.org; 2004.
37. Gaussian03, Revision D.01. Frisch, MJ, Trucks, GW, Schlegel, HB, Scuseria, GE, Robb, MA, Cheeseman, JR, Montgomery, JA, Vreven, T, Kudin, KN, Burant, JC, Millam, JM, Iyengar, SS, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, GA, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, JE, Hratchian, HP, Cross, JB, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, RE, Yazyev, O, Austin, AJ, Cammi, R, Pomelli, C, Ochterski, JW, Ayala, PY, Morokuma, K, Voth, GA, Salvador, P, Dannenberg, JJ, Zakrzewski, VG, Dapprich, S, Daniels, AD, Strain, MC, Farkas, O, Malick, DK, Rabuck, AD, Raghavachari, K, Foresman, JB, Ortiz, JV, Cui, Q, Baboul, AG, Clifford, S, Cioslowski, J, Stefanov, BB, Liu, G, Liashenko, A, Piskorz, P, Komamori, I, Martin, RL, Fox, DJ, Keith, T, Al-Laham, MA, Peng, CY, Nanayakkara, A, Challacombe, M, Gill, PMW, Johnson, B, Chen, W, Wong, MW, Gonzalez, C, and Pople, JA; 2004.
38. Scott A.P., and Radom L. Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Møller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors. J. Phys. Chem. 100 (1996) 16502-16513
39. Sahar N.D., Hong S.-I., and Kohn D.H. Micro- and nanostructural analyses of damage in bone. Micron 36 (2005) 617-629
40. Lin-Vien D., Colthup N.B., Fateley W.G., and Grasselli J.G. Organophosphorous compounds. The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules (1991), Academic Press Limited, London 263-276
41. Popovic L., De Waal D., and Boeyens J.C.A. Correlation between Raman wavenumbers and P-O bond lengths in crystalline inorganic phosphates. J. Raman Spectrosc. 36 (2005) 2-11
42. Zeevaart J.R., Jarvis N.V., Cukrowski I., and Jackson G.E. Blood plasma modelling of the in vivo behaviour of bisphosphonate-metal ion complexes as radiopharmaceuticals. S. Afr. J. Chem. 50 (1997) 189-194
43. Berezin K.V., Nechaev V.V., and Krivokhizhina T.V. Application of a method of linear scaling of frequencies in calculations of the normal vibrations of polyatomic molecules. Mol. Spectrosc. 94 (2003) 398-401
44. Berezin K.V., and Nechaev V.V. Comparison of theoretical methods and basis sets for ab initio and DFT calculations of the structure and frequencies of normal vibrations of polyatomic molecules. J. Appl. Spectrosc. 71 (2004) 164-172
45. Silvestre J.-P., Dao N.Q., and Leroux Y. A survey of the behaviour of the hydroxybisphosphonic function in crystallized acids, metallic salts and some related compounds. Heteroatom. Chem. 12 (2001) 73-89
46. Fiquet G., Richet P., and Montagnac G. High-temperature thermal expansion of lime, periclase, corundum and spinel. Phys. Chem. Miner. 27 (1999) 103-111
47. Casciani F.S., and Condrate Sr. R.A. The infrared and Raman spectra of several calcium hydrogen phosphates. Proc. Int. Congr. Phosphorous Compds. 2 (1980) 175-190