surface-enhanced Raman chemical imaging (SER-CI); Polymorphism; Multivariate analysis
Abstract :
[en] This study demonstrates, for the first time, the ability of surface-enhanced Raman chemical imaging (SER-CI) combined with multivariate analysis to detect low levels (0.1% (w/w)) of a polymorphic form in a pharmaceutical mixture. In the studied formulation, piroxicam was used as a model molecule to develop this approach. Piroxicam is a widely available non-steroidal anti-inflammatory drug, exhibiting an interesting case of polymorphism, with two most commonly observed forms (β and α2). In this work, the SERS spectra of piroxicam polymorphic forms β and α2 are presented. These forms showed clear spectral differences in terms of band position and intensity. From a crystallographic point of view, the difference of exaltation between both forms was correlated with a preferred orientation of crystallites of form α2 making its SERS detection difficult compared to form β. A preferred orientation of the (1k0) crystallographic planes of α2 was demonstrated in samples, not promoting an appropriate molecular orientation onto the metallic surface. Additionally, a semi-quantitative approach using SER-CI combined with chemometric tools was developed enabling to detect crystallites of form β below the detection limit of conventional Raman microscopy. The exaltation of the Raman signal in the presence of silver nanoparticles allowed a higher sensitivity and a reduction of the acquisition time by a factor of 6.
Research center :
CIRM - Centre Interdisciplinaire de Recherche sur le Médicament - ULiège
Bellur Atici, E., Karliga, B., Quantitative determination of two polymorphic forms of imatinib mesylate in a drug substance and tablet formulation by X-ray powder diffraction, differential scanning calorimetry and attenuated total reflectance Fourier transform infrared spectroscopy. J. Pharm. Biomed. Anal. 114 (2015), 330–340.
Boiret, M., Rutledge, D.N., Gorretta, N., Ginot, Y.M., Roger, J.M., Application of independent component analysis on Raman images of a pharmaceutical drug product: pure spectra determination and spatial distribution of constituents. J. Pharm. Biomed. Anal. 90 (2014), 78–84.
Boiret, M., De Juan, A., Gorretta, N., Ginot, Y.M., Roger, J.M., Distribution of a low dose compound within pharmaceutical tablet by using multivariate curve resolution on Raman hyperspectral images. J. Pharm. Biomed. Anal. 103 (2015), 35–43.
Bunaciu, A.A., Aboul-Enein, H.Y., Hoang, V.D., Vibrational spectroscopy used in polymorphic analysis. Trends Anal. Chem. 69 (2015), 14–22.
Cailletaud, J., De Bleye, C., Dumont, E., Sacré, P.Y., Netchacovitch, L., Gut, Y., Boiret, M., Ginot, Y.M., Hubert, Ph., Ziemons, E., Critical review of surface-enhanced Raman spectroscopy applications in the pharmaceutical field. J. Pharm. Biomed. Anal. 147 (2017), 458–472.
Cailletaud, J., De Bleye, C., Dumont, E., Sacré, P.Y., Gut, Y., Bultel, L., Ginot, Y.M., Hubert, Ph., Ziemons, E., Towards a spray-coating method for the detection of low-dose compounds in pharmaceutical tablets using surface-enhanced Raman chemical imaging (SER-CI). Talanta 188 (2018), 584–592.
De Bleye, C., Sacré, P.Y., Dumont, E., Netchacovitch, L., Chavez, P.F., Piel, G., Lebrun, P., Hubert, Ph., Ziemons, E., Development of a quantitative approach using surface-enhanced Raman chemical imaging: first step for the determination of an impurity in a pharmaceutical model. J. Pharm. Biomed. Anal. 90 (2014), 111–118.
Farkas, Attila, Nagy, Brigitta, Démuth, Balázs, Balogh, Attila, Pataki, Hajnalka, Nagy, Zsombor K., Marosi, György, Variable clustering and spectral angle mapper-orthogonal projection method for Raman mapping of compound detection in tablets: variable clustering for Raman mapping of compound detection in tablet. J. Chemometrics, 31(1), 2017, e2861, 10.1002/cem.2861.
Firkala, T., Farkas, A., Vajna, B., Farkas, I., Marosi, G., Investigation of drug distribution in tablets using surface enhanced Raman chemical imaging. J. Pharm. Biomed. Anal. 76 (2013), 145–151.
Firkala, T., Farkas, A., Vajna, B., Nagy, Z.K., Pokol, G., Marosi, G., Szilagyi, I.M., Quantification of low drug concentration in model formulations with multivariate analysis using surface enhanced Raman chemical imaging. J. Pharm. Biomed. Anal. 107 (2015), 318–324.
Fortunato de Carvalho Rocha, W., Sabin, G.P., Março, P.H., Poppi, R.J., Quantitative analysis of piroxicam polymorphs pharmaceutical mixtures by hyperspectral imaging and chemometrics. Chemom. Intell. Lab. Syst. 106 (2011), 198–204.
Gourvénec, S., Lamotte, C., Pestiaux, P., Massart, D.L., Use of the orthogonal projection approach (OPA) to monitor batch processes. Appl. Spectrosc. 57 (2003), 80–87.
Griffen, J., Owen, A., Burley, J., Taresco, V., Matousek, P., Rapid quantification of low level polymorph content in a solid dose form using transmission Raman spectroscopy. J. Pharm. Biomed. Anal. 128 (2016), 35–45.
Hennigan, M.C., Ryder, A.G., Quantitative polymorph contaminant analysis in tablets using Raman and near infra-red spectroscopies. J. Pharm. Biomed. Anal. 72 (2013), 163–171.
Hernandez, M., Corda, E., Garcia-Ramos, J.V., Domingo, C., Sevilla, P., SERS of the anti-inflammatory drug piroxicam adsorbed on the surface of silver or gold colloids as nanocarrier model. J. Raman Spectrosc. 47 (2016), 402–407.
Hugelier, S., Devos, O., Ruckebusch, C., On the implementation of spatial constraints in multivariate curve resolution alternating least squares for hyperspectral image analysis. J. Chemometr. 29 (2015), 557–561.
Kang, Y., Shao, Z., Wang, Q., Hu, X., Yu, D., Quantitation of polymorphic impurity in entecavir polymorphic mixtures using powder X-ray diffractometry and Raman spectroscopy. J. Pharm. Biomed. Anal. 158 (2018), 28–37.
Koivisto, M., Virjonen, T., Heikkilä, T., Lehto, V.P., Characterization of the preferred orientation of d-mannitol crystallites in tablets. J. Pharm. Biomed. Anal. 36 (2004), 559–564.
Lee, P.C., Meisel, D., Adsorption and surface-enhanced Raman of dyes on silver and gold sols. J. Phys. Chem. 86 (1982), 3391–3395.
Lipiäinen, T., Fraser-Miller, S.J., Gordon, K.C., Strachan, C.J., Direct comparison of low- and mid-frequency Raman spectroscopy for quantitative solid-state pharmaceutical analysis. J. Pharm. Biomed. Anal. 149 (2018), 343–350.
Long, D.A., 2004. Infrared and Raman characteristic group frequencies. Tables and charts George Socrates John Wiley and Sons, Ltd, Chichester, third ed., J. Raman Spectrosc. 2001, 35, pp. 905.
Paiva, E.M., da Silva, V.H., Poppi, R.J., Pereira, C.F., Rohwedder, J.J.R., Comparison of macro and micro Raman measurement for reliable quantitative analysis of pharmaceutical polymorphs. J. Pharm. Biomed. Anal. 157 (2018), 107–115.
Qiu, J.B., Li, G., Sheng, Y., Zhu, M.R., Quantification of febuxostat polymorphs using powder X-ray diffraction technique. J. Pharm. Biomed. Anal. 107 (2015), 298–303.
Quiñones, R., Iuliucci, R.J., Behnke, G., Brown, R., Shoup, D., Riedel, T.M., Plavchak, C., Lininger, B.E., Spehar, J.M., Moving towards fast characterization of polymorphic drugs by solid-state NMR spectroscopy. J. Pharm. Biomed. Anal. 148 (2018), 163–169.
Redenti, E., Zanol, M., Ventura, P., Fronza, G., Comotti, A., Taddei, P., Bertoluzza, A., Raman and solid state 13C-NMR investigation of the structure of the 1: 1 amorphous piroxicam: β-cyclodextrin inclusion compound. Biospectroscopy 5 (1999), 243–251.
Riippi, M., Tanninen, V.P., Yliruusi, J., Effect of compression force on the crystal properties of erythromycin acistrate tablets. Eur. J. Pharm. Biopharm. 50 (2000), 365–371.
Sacré, P.Y., De Bleye, C., Chavez, P.F., Netchacovitch, L., Hubert, Ph., Ziemons, E., Data processing of vibrational chemical imaging for pharmaceutical applications. J. Pharm. Biomed. Anal. 101 (2014), 123–140.
Tenho, M., Heinänen, P., Tanninen, V.P., Lehto, V.P., Does the preferred orientation of crystallites in tablets affect the intrinsic dissolution?. J. Pharm. Biomed. Anal. 43 (2007), 1315–1323.
Tinmanee, R., Larsen, S.C., Morris, K.R., Kirsch, L.E., Quantification of gabapentin polymorphs in gabapentin/excipient mixtures using solid state 13C NMR spectroscopy and X-ray powder diffraction. J. Pharm. Biomed. Anal. 146 (2017), 29–36.
Vidal, M., Amigo, J.M., Pre-processing of hyperspectral images. Essential steps before image analysis. Chemom. Intell. Lab. Syst. 117 (2012), 138–148.
Vrecer, F., Vrbinc, M., Meden, A., Characterization of piroxicam crystal modifications. Int. J. Pharm. 256 (2003), 3–15.
Zhang, X., De Juan, A., Tauler, R., Local rank-based spatial information for improvement of remote sensing hyperspectral imaging resolution. Talanta 146 (2016), 1–9.
