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Pattern recognition methods in the study of thermal decomposition of α-amino acids

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Abstract

There are many examples in the literature of a strict relation between the pathways of decomposition of a drug substance and chemical structure of its molecule. For this reason, a study has now been performed on the relation between thermal decomposition of α-amino acids and their chemical structure. To achieve this goal, a group of a dozen or so compounds was chosen at random, and the results obtained using the DTA, TG and DTG analyses of their thermal decomposition were interpreted by highly advanced multivariate methods, principal component analysis and cluster analysis. By this statistical analysis, the influence of specific functional groups on thermal decomposition of α-amino acids was determined. It has been found that first two principal components explain together more than 75 % of variance, and in an exceptional case, about 90 %. The third stage of decomposition was that at which the thermoanalytical data were best correlated with chemical constitution of a compound. It has also been recognized that a better discrimination among the analysed compounds was obtained for the DTA data set. The results can be useful for identification of a relation between the pathway of degradation of a drug substance and chemical structure of its molecule, and for predicting chemical stability of the compounds studied.

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References

  1. Carstensen JT. Drug stability: principles and practices. New York: Marcel Dekker, Inc.; 1995.

    Google Scholar 

  2. Yoshioka S, Stella VJ. Stability of drugs and dosage forms. New York: Kluwer Academic, Plenum Publisher; 2000.

    Google Scholar 

  3. ICH Topics Q1A (R2). Note for guidance on stability testing: stability testing of new drug substances and products. CPMP/ICH/2736/99: August 2003.

  4. Craig DQM, Reading M, editors. Thermal analysis of pharmaceuticals. Boca Raton: CRC Press; 2007.

    Google Scholar 

  5. Glass BD, Cs Novak, Brown ME. The thermal and photostability of solid pharmaceuticals: a review. J Therm Anal Calorim. 2004;77:1013–36.

    Article  CAS  Google Scholar 

  6. Beezer AE, Gaisford S, Hills AK, Willson RJ, Mitchell JC. Pharmaceutical microcalorimetry: applications to long-term stability studies. Int J Pharm. 1999;179:159–65.

    Article  CAS  Google Scholar 

  7. Simon P, Veverka M, Okuliar J. New screening method for the determination of stability of pharmaceuticals. Int J Pharm. 2004;270:21–6.

    Article  CAS  Google Scholar 

  8. Waterman KC, Adami RC. Accelerated aging: prediction of chemical stability of pharmaceuticals. Int J Pharm. 2005;293:101–25.

    Article  CAS  Google Scholar 

  9. Tita B, Marian E, Tita D, Vlase G, Doca N, Vlase T. Comparative kinetic study of decomposition of some diazepine derivatives under isothermal and non-isothermal conditions. J Therm Anal Calorim. 2008;94:447–52.

    Article  CAS  Google Scholar 

  10. Li X, Wu Y, Gu D, Gan F. Thermal decomposition kinetics of nickel(II) and cobalt(II) azo barbituric acid complexes. Thermochim Acta. 2009;493:85–9.

    Article  CAS  Google Scholar 

  11. Bannach G, Arcaro R, Ferroni DC, Siqueira AB, Treu-Filho O, Ionashiro M, Schnitzler E. Thermoanalytical study of some anti-inflammatory analgesic agents. J Therm Anal Calorim. 2010;102:163–70.

    Article  CAS  Google Scholar 

  12. Rodante F, Vecchio S, Tomassetti M. Multi-step decomposition processes for some antibiotics: a kinetic study. Thermochim Acta. 2002;394:7–18.

    Article  CAS  Google Scholar 

  13. Macedo RO, Gomes do Nascimento T, Soares Aragao CF, Barreto Gomes AP. Application of thermal analysis in the characterization of anti-hypertensive drugs. J Therm Anal Calorim. 2000;59:657–61.

    Article  CAS  Google Scholar 

  14. Arslan H, Dondas HA. Thermal behaviour of some spiro benzodiazepine derivatives. Thermochim Acta. 2000;354:107–15.

    Article  CAS  Google Scholar 

  15. Wesolowski M, Kosecka E, Erecinska J, Kobylczyk K. The influence of chemical structure of sulfonamides on the course of their thermal decomposition. J Therm Anal Calorim. 2003;74:465–76.

    Article  CAS  Google Scholar 

  16. Wesolowski M, Szynkaruk P. Thermal decomposition of methylxanthines: interpretation of the results by PCA. J Therm Anal Calorim. 2008;93:739–46.

    Article  CAS  Google Scholar 

  17. Szynkaruk P, Wesolowski M, Samson-Rosa M. Principal component analysis of thermal decomposition of magnesium salts used as drugs. J Therm Anal Calorim. 2010;101:505–12.

    Article  CAS  Google Scholar 

  18. Trotta F, Zanetti M, Camino G. Thermal degradation of cyclodextrins. Polym Degrad Stab. 2000;69:373–9.

    Article  CAS  Google Scholar 

  19. Lizarraga E, Zabaleta C, Palop JA. Thermal stability and decomposition of pharmaceutical compounds. J Therm Anal Calorim. 2007;89:783–92.

    Article  CAS  Google Scholar 

  20. Otto M. Chemometrics: statistics and computer application in analytical chemistry. New York: Wiley-VCH; 2007.

    Google Scholar 

  21. Hill T, Lewicki P. Statistics, methods and applications: a comprehensive reference for science, industry, and data mining. Tulsa: StatSoft, Inc.; 2007.

    Google Scholar 

  22. Physicochemical guide-book. 2nd ed. Warsaw: WNT; 1974.

  23. Aldrich, Handbook of fine chemicals and laboratory equipment. St. Louis: Sigma-Aldrich Co; 2000–2001.

  24. Lancaster synthesis. Mühlheim am Main: GmbH; 1999–2000.

  25. Grunenberg D, Bougeard D, Schrader B. DSC-investigations of 22 crystalline neutral aliphatic amino acids in the temperature range 233 to 423 K. Thermochim Acta. 1984;77:59–66.

    Article  CAS  Google Scholar 

  26. Bougeard D. Phase transition and vibrational spectra of l-leucine. Ber Bunsenges Phys Chem. 1983;87:279–83.

    CAS  Google Scholar 

Download references

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Correspondence to Marek Wesolowski.

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Wesolowski, M., Erecinska, J. Pattern recognition methods in the study of thermal decomposition of α-amino acids. J Therm Anal Calorim 109, 585–593 (2012). https://doi.org/10.1007/s10973-012-2550-9

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