Density functional theory studies on a non-covalent interaction system: hydrogen-bonded dimers of zoledronate
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A computational study was carried out to characterize the hydrogen-bonded dimers of Zoledronate (ZOL), which is used widely in treating skeletal diseases. The stable conformations, hydrogen bonding interactions, IR spectra, thermodynamic properties, and electronic characteristics of nine possible ZOL dimers were studied using density functional theory (DFT) at the B3LYP/6–311++G** level. The stability of dimers was determined according to the analyses of total electronic energies and hydrogen bonding interactions. The results showed that both the number and intensity of hydrogen bonds played an important role in determining the stability order of dimers, and the hydrogen bonding interactions in dimers resulted in a red shift of hydroxyl vibration with a corresponding increase in intensity. The calculated thermodynamic properties illustrated that the dimerization process can take place spontaneously at room temperature. Natural bond orbital and atoms in molecules analyses revealed that the nature of hydrogen bonding interactions was attributed to the interactions from lone pair orbital n(A) to the antibonding orbital σ*(D-H), and the interactions were closed-shell interactions in hydrogen-bonded dimers of ZOL.
KeywordsZoledronate dimer Hydrogen bonding interaction Stability Thermodynamic property DFT
This work was supported by the Natural Science Foundation of Jiangsu Province (BK20181128), 333 Project of Jiangsu Province (BRA2016518), Jiangsu Provincial Medical Youth Talent (QNRC2016626, QNRC2016629), Wuxi Municipal Commission of Health and Family Planning (Q201748), and Jiangsu Institute of Nuclear Medicine (QN201706).
- 4.Russell RG, Xia Z, Dunford JE, Oppermann U, Kwaasi A, Hulley PA, Kavanagh KL, Triffitt JT, Lundy MW, Phipps RJ, Barnett BL, Coxon FP, Rogers MJ, Watts NB, Ebetino FH (2007) Bisphosphonates: an update on mechanisms of action and how these relate to clinical efficacy. Ann N Y Acad Sci 1117:209–257CrossRefGoogle Scholar
- 10.Hosking D, Lyles K, Brown JP, Fraser WD, Miller P, Curiel MD, Devogelaer JP, Hooper M, Su G, Zelenakas K, Pak J, Fashola T, Saidi Y, Eriksen EF, Reid IR (2007) Long-term control of bone turnover in Paget's disease with zoledronic acid and risedronate. J Bone Miner Res 22:142–148CrossRefGoogle Scholar
- 12.Coleman R, de Boer R, Eidtmann H, Llombart A, Davidson N, Neven P, von Minckwitz G, Sleeboom HP, Forbes J, Barrios C, Frassoldati A, Campbell I, Paija O, Martin N, Modi A, Bundred N (2013) Zoledronic acid (zoledronate) for postmenopausal women with early breast cancer receiving adjuvant letrozole (ZO-FAST study): final 60-month results. Ann Oncol 24:398–405CrossRefGoogle Scholar
- 14.Dieli F, Vermijlen D, Fulfaro F, Caccamo N, Meraviglia S, Cicero G, Roberts A, Buccheri S, D'Asaro M, Gebbia N, Salerno A, Eberl M, Hayday AC (2007) Targeting human γδ T cells with zoledronate and interleukin-2 for immunotherapy of hormone-refractory prostate cancer. Cancer Res 67:7450–7457CrossRefGoogle Scholar
- 23.Mammino L, Kabanda MM (2011) Interplay of intramolecular hydrogen bonds, OH orientations, and symmetry factors in the stabilization of polyhydroxybenzenes. Int J Quantum Chem 111:3701–3716Google Scholar
- 25.Hobza P, Müller-Dethlefs K (2010) Non-covalent interactions: theory and experiment. Royal Society of Chemistry, LondonGoogle Scholar
- 29.Chen LP (2013) Synthesis, characterization and antitumor activity of metal complexes based on zoledronate and its derivative. Master Thesis. Jiangnan University, WuxiGoogle Scholar
- 32.Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Nakatsuji H, Caricato M, Li X, Hratchian HP, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima R, Honda Y, Kilao O, Nakai H, Verven T, Montgomery Jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroveror VN, Kobayashi R, Normand J, Ragavachari K, Rendell A, Burant JC, Tomasi SJ, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Strattmann RE, Yazyev O, Austin AJ, Cammi R, Ochetrski JW, Martin RL, Morokuma K, Zakrazawski VG, Votn GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09 revision a.02. Gaussian Inc., Wallingford CTGoogle Scholar
- 35.Glendening ED, Badenhoop JK, Reed AE, Carpenter JE, Weinhold F (1955) NBO 3.1. Theoretical Chemistry Institute, University of Wisconsin, MadisonGoogle Scholar
- 39.Dennington RD, Ketith TA, Millam JM (2008) Gaussian Inc., Wallingford, CTGoogle Scholar