Abstract
The growth of atenolol, pindolol and betaxolol hydrochloride from melt was investigated by differential scanning calorimetry (DSC) and polarized light thermal microscopy (PLTM). Phase transitions occurring on cooling and subsequent reheating runs performed between −160 °C and a temperature above the respective melting points were studied by DSC. The thermal cycles were also followed by PLTM. Details about the dynamic of the crystallization front taken from microscopic observations are given. An explanation of the results on the basis of molecular supramolecular recognition is advanced.
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References
Turi A. Thermal characterization of polymorphic materials. London: Academic Press; 1981.
Mullin JW. Crystallization. Oxford: Elsevier; 2001.
Ropp RC. Solid state chemistry. Amsterdam: Elsevier; 2003.
Kim JW, Ulrich J. Prediction of degree of deformation and crystallization time of molten droplets in pastillation process. Int J Pharm. 2003;257:205–15.
Goskonda SR, Hileman GA, Upadrashta SM. Development of matrix controlled release beads by extrusion-spheronization technology using a statistical screening design. Drug Dev Ind Pharm. 1994;20:279–92.
Schaefer T, Holm P, Kristensen HG. Melt granulation in a laboratory scale high shear mixer. Drug Dev Ind Pharm. 1990;16:1249–77.
Passerini N, Albertini B, González-Rodríguez ML, Cavallari C, Rodriguez L. Preparation and characterisation of ibuprofen–poloxamer 188 granules obtained by melt granulation. Eur J Pharm Sci. 2002;15:71–8.
Nunes SCC, Eusebio ME, Leitão MLP, Redinha JS. Polymorphism of pindolol, 1-(1H-indol-4-yloxyl)-3-isopropylamino-propan-2-ol. Int J Pharm. 2004;285:13–21.
Canotilho J, Costa FS, Sousa AT, Redinha JS, Leitão MLP. Melting curves of terfenadine crystallized from different solvents. J Therm Anal Calorim. 1998;54:139–49.
Castro RAE. Antagonistas Adrenérgicos Selectivos beta 1: Estrutura do Atenolol. Ph.D. thesis, Universidade de Coimbra; 2006.
Mahrous MS, Issa AS, Ahmed NS. Oxidants for the colorimetric determination of pindolol. Talanta. 1992;39:69–72.
Stenlake JB. Foundations of molecular pharmacology, vol. 1. London: The Athlone Press of the University of London; 1979.
Kelton KF. Crystal nucleation in liquid and glasses in solid state physics. London: Academic Press; 1991.
Montserrat S, Roman F, Colomer P. Study of the crystallization and melting region of PET and PEN and their blends by TMDSC. J Therm Anal Calorim. 2003;72:657–66.
Balsara NP, Fetters LJ, Hadjichristidis N, Lohse DJ, Han CC, Graessley WW, et al. Thermodynamic interactions in model polyolefin blends obtained by small-angle neutron scattering. Macromolecules. 1992;25:6137–47.
Briber RM, Khoury F. The morphology of poly(vinylidene fluoride) crystallized from blends of poly(vinylidene fluoride) and poly(ethyl acrylate). J Polym Sci B. 1993;31:1253–72.
Hu WB, Mathot VBF. Liquid–liquid demixing in a binary polymer blend driven solely by the component-selective crystallizability. J Chem Phys. 2003;119:10953–8.
Katayama Y, Mizutani T, Utsumi W, Shimomura O, Yamakata M, Funakoshi K. A first-order liquid–liquid phase transition in phosphorus. Nature. 2000;403:170–3.
Mishima O. Liquid–liquid critical point in heavy water. Phys Rev Lett. 2000;85:334–6.
Soper AK, Ricci MA. Structures of high-density and low-density water. Phys Rev Lett. 2000;84:2881–4.
Lacks DJ. First-order amorphous–amorphous transformation in silica. Phys Rev Lett. 2000;84:4629–32.
Vanthiel M, Ree FH. High-pressure liquid–liquid phase change in carbon. Phys Rev B. 1993;48:3591–9.
Nunes SCC, Jesus AJL, Rosado MTS, Eusebio MES. Conformational study of isolated pindolol by HF, DFT and MP2 calculations. J Mol Struct (Theochem). 2007;806:231–8.
Debenedetti PG. Metastable liquids: concepts and principles. Princeton: Princeton University Press; 1996.
Desiraju GR. Supramolecular synthons in crystal engineering—a new organic synthesis. Angew Chem Int Ed Eng. 1995;34:2311–27.
Castro RAE, Canotilho J, Barbosa RM, Silva MR, Beja AM, Paixa JA, et al. Conformational isomorphism of organic crystals: racemic and homochiral Atenolol. Cryst Growth Des. 2007;7:496–500.
Castro RAE, Canotilho J, Barbosa RM, Redinha JS. Infrared spectroscopy of racemic and enantiomeric forms of atenolol. Spectrochim Acta A. 2007;67:1194–200.
Canotilho J, Castro RAE, Teixeira MHSF, Leitão MLP, Redinha JS. Infrared study of the acidic and basic forms of betaxolol. Spectrochim Acta A. 2006;64:279–86.
Canotilho J, Castro RAE, Rosado MTS, Ramos Silva M, Matos Beja A, Paixão JA, et al. The structure of betaxolol from single crystal X-ray diffraction and natural bond orbital analysis. J Mol Struct. 2008;891:437–42.
Chattopadhyay TK, Palmer RA, Mahadevan D. Molecular and absolute crystal structure of pindolol-1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]-2-propanol: a specific beta-adrenoreceptor antagonist with partial agonist activity. J Chem Crystallogr. 1995;25:195–9.
Castro RAE, Canotilho J, Nunes SCC, Eusebio ME, Redinha JS. A study of the structure of the pindolol based on infrared spectroscopy and natural bond orbital theory. Spectrochim Acta A. 2009;72:819–26.
Mairesse G, Boivin JC, Thomas DJ, Bonte JP, Lesieur D, Lespagnol C. Structure du chlorhydrate de l’[hydroxy-1-(R, S) isopropylamino-2 éthyl]-6 dihydro-2, 3 benzoxazole-1, 3 one-2, C12H16N2O3∙HCl. Acta Crystallogr C. 1984;40:1432–4.
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The coauthors would like to dedicate this manuscript to the memory of Professor M. Luísa P. Leitão for her invaluable contribution to the advance of thermal analysis in their research center.
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Canotilho, J., Castro, R.A.E., Rosado, M.T.S. et al. Thermal analysis and crystallization from melts. J Therm Anal Calorim 100, 423–429 (2010). https://doi.org/10.1007/s10973-009-0645-8
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DOI: https://doi.org/10.1007/s10973-009-0645-8