CONFORMATIONAL LANDSCAPE AND UV-VIS SPECTRUM OF S-BISOPROLOL
Keywords:
bisoprolol; conformational landscape.Abstract
The conformational changes of bisoprolol (BISO) are crucial for understanding its interaction with the receptor and the mechanism of action. Therefore, here we investigated the free energy conformational landscape of the free bisoprolol base, aiming at describing the 3D structures and energetic stability of its conformers. Twenty-three unique conformers, within an energy window of 2.44 kcal×mol-1 were identified by conformational search in gas-phase, at B3LYP/6-31+G theoretical level of theory. Among these, the 10 most stable were further refined in water at the same level of theory. The most stable conformers in gas-phase exhibit an S-shape structure. The most stable conformer was used to compute the absorption spectrum of bisoprolol.
References
Prichard BN (1987) Bisoprolol: a new beta-adrenoceptor blocking drug. Eur Heart J. Suppl M: 121-129.
Lancaster SG, Sorkin EM (1988) Bisoprolol. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in hypertension and angina pectoris. Drugs. 36(3):256-285.
Wellstein A, Palm D, Belz GG (1986) Affinity and selectivity of β-adrenoceptor antagonists in vitro. J Cardiovasc Pharmacol 8 (Suppl. 11): 36–40.
Wellstein A, Palm D, Belz GG, Leopold G, Bühring KU, Pabst J. (1986) Concentration kinetics of propranolol, bisoprolol and atenolol in humans assessed with chemical detection and a subtype selective adrenoceptor, J Cardiovasc Pharmacol 8 (Suppl 11): 41-45.
Morris T, Kaumann AJ (1984) Different steric characteristics of b1- and b2-adrenoceptors. Naunyn-Schmiedebergs Arch. Pharmacol., 327, 176-179.
Wahlund G, Nerme V, Abrahamsson T, Sjöquist PO (1990) The beta 1- and beta 2-adrenoceptor affinity and beta 1-blocking potency of S- and R-metoprolol. Br J Pharmacol 99(3): 592-596.
Nathanson JA (1988) Stereospecificity of beta adrenergic antagonists: R-enantiomers show increased selectivity for b2 receptors in ciliary process. J. Pharmacol. Exp. Ther. 245: 94-101.
Brodde OE (1986) Bisoprolol (EMD 33512), a highly selective b1-adrenoceptor antagonist: in vitro and in vivo studies. J. Cardiovasc. Pharmacol. 8: 29-35
Kaumann AJ, Lemoine H (1985) Direct labelling of myocardial b1-adrenoceptors - comparison of binding affinity of 3H-(-)- bisoprolol with its blocking potency. Naunyn-Schmiedeberg's Arch. Pharmacol. 331: 27-39.
Soloviev DV, Matarrese M, Moresco RM, Todde S, Bonasera TA, Sudati F, Simonelli P, Magni F, Colombo D, Carpinelli A, Kienle MG, Fazio F. (2001) Asymmetric synthesis and preliminary evaluation of (R)- and (S)-[11C]bisoprolol, a putative beta1-selective adrenoceptor radioligand. Neurochem Int. 38(2):169-180.
Vislous OO, Bevz NYu, Georgiyants VA, Zhivora NV (2014) Development of the "dissolution” test for bisoprolol tablets News Pharm. 1(77):49-53.
Kumbhar ST, Shinde PP, Shinde DB, Solankar PB (2013) Visible Spectrophotometric Method For Estimation Of Bisoprolol From Its Bulk And Tablet Formulation. Asian J Pharm Clin Res 6(4):103-105
Wedian F, Lataifeh A (2013) Application of the Bivariate Calibration for Simultaneous Determinations of Hydrochlorothiazide/Enalapril Maleate and Hydrochlorothiazide/ Bisoprolol Fumarate in Drug Tablets. Int J Chem. 5(2):29-37
Kakde RB, Kotak VH, Barsagade AG, Chaudhary NK, Kale DL (2008) Spectrophotometric Method for Simultaneous Estimation of Amlodipine Besylate and Bisoprolol Fumarate in Pharmaceutical Preparations. Research J. Pharm. and Tech. 1(4):513-515
Shi Y, Xia Z, Zhang J, Best R, Wu C, Ponder JW, Ren P (2013) Polarizable atomic multipole-based AMOEBA force field for proteins. J Chem Theory Comput 9:4046–4063.
Halgren TA (1996) Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J Comput Chem 17:490–519.
Halgren TA (1996) Merckmolecular force field. II.MMFF94 van der Waals and electrostatic parameters for intermolecular interactions. J Comput Chem 17:520–552.
Halgren TA (1996) Merck molecular force field. III. molecular geometries and vibrational frequencies for MMFF94. J Comput Chem 17:553–586.
Halgren TA (1996) Merck molecular force field. IV. Conformational energies and geometries for MMFF94. J Comput Chem 17:587–615.
Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652.
Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789.
Vosko SH, Wilk L, Nusair M (1980) Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis. Can J Phys 58:1200–1211.
Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ (1994) Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 98:11623–11627.
Hehre WJ, Ditchfield R, Pople JA (1972) Self—consistent molecular orbital methods. XII. further extensions of gaussian—type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys 56:2257–2261.
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2010) GAUSSIAN 09 C.01. Wallingford, Gaussian Inc.
Willoughby PH, Jansma MJ, Hoye TR (2014) A guide to small molecule structure assignment through computation of (1H and 13C) NMR chemical shifts. Nat Protoc 9:643–660.
Macrae CF, Edgington PR,McCabe P, Pidcock E, Shields GP, Taylor R, Rowler M, van de Streek J (2006) Mercury: visualization and analysis of crystal structures. J Appl Crystallogr 39:453–457.
Molegro Molecular Viewer, version 2.5. Molegro ApS; Aarhus, Denmark: 2012.
Dewar MJS, Thiel W (1977) Ground-States of Molecules. 38. The MNDO Method: Approximations and Parameters, J. Am. Chem. Soc. 99: 4899-4907.
Dewar MJS, Zoebisch EG, Healy EF, (1985) AM1: A New General Purpose Quantum Mechanical Molecular Model, J. Am. Chem. Soc. 107: 3902-3909.
Warne T, Serrano-Vega MJ, Baker JG, Moukhametzianov R, Edwards PC, Henderson R, Leslie AG, Tate CG, Schertler GF (2008) Structure of a beta1 adrenergic G-protein-coupled receptor. Nature 454:486–491.
Moukhametzianov R, Warne T, Edwards PC, Serrano-Vega MJ, Leslie AG, Tate CG, Schertler GF (2011) Two distinct conformations of helix 6 observed in antagonist- bound structures of a beta1 adrenergic receptor. Proc Natl Acad Sci USA 108:8228–8232.
Warne T, Edwards PC, Leslie AG, Tate CG (2012) Crystal structures of a stabilized beta1 adrenoceptor bound to the biased agonists bucindolol and carvedilol. Structure 20: 841–849.
Warne T, Moukhametzianov R, Baker JG, Nehme´ R, Edwards PC, Leslie AG, Schertler GF, and Tate CG (2011) The structural basis for agonist and partial agonist action on a beta1 adrenergic receptor. Nature 469:241–244.
Rasmussen SG, Devree BT, Zou Y, Kruse AC, Chung KY, et al. (2011) Crystal structure of the beta(2) adrenergic receptor-Gs protein complex. Nature 477: 549–555.
Kenakin T, (2002) Drug efficacy at G protein-coupled receptors, Annu. Rev. Pharmacol. Tox, 42:349-379.
Borchard U (1998) Pharmacological properties of β-adrenoceptor blocking drugs, J Clin Bas Cardiol 1: 5.
Kobilka BK, Deupi X (2007) Conformational complexity of G-protein-coupled receptors, Trends Pharmacol. Sci. 28(8): 397-406.
Bhattacharya S, Hall S, Li H, Vaidehi N (2008) Ligand-Stabilized Conformational States of Human β2 Adrenergic Receptor: Insight into G-Protein-Coupled Receptor Activation. Biophys. J. 94: 2027–2042.
Bhattacharya S, Vaidehi N (2010) Computational Mapping of the Conformational Transitions in Agonist Selective Pathways of a G-Protein Coupled Receptor. J. Amer. Chem. Soc. 132: 5205–5214.
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