Curve-fitting FTIR studies of loratadine/hydroxypropyl-β-cyclodextrin inclusion complex induced by co-grinding process

Shan Yang Lin, Cheng Hung Hsu, Ming Thau Sheu

Research output: Contribution to journalArticle

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Abstract

The formation steps of inclusion complex caused by co-grinding loratadine (LOR) and hydroxypropyl-β-cyclodextrin (HP-β-CD) with a molar ratio of 1:1 or 1:2 were quantitatively investigated by Fourier transform infrared (FTIR) spectroscopy with curve-fitting analysis and differential scanning calorimetry (DSC). The phase solubility study and the co-evaporated solid products of the mixture of LOR and HP-β-CD were also examined. The result indicates that the aqueous solubility of LOR was linearly increased with the increase of HP-β-CD concentrations, in which the phase solubility diagram was classified as AL type. The higher apparent stability constant (2.22×104M-1) reveals that the inclusion complex formed between LOR and HP-β-CD was quite stable. The endothermic peak at 134.6°C for the melting point of LOR gradually disappeared from DSC curves of LOR/HP-β-CD coground mixtures by increasing the cogrinding time, as the disappearance of the co-evaporated solid products. The disappearance of this endothermic peak from LOR/HP-β-CD coground mixture or the co-evaporated solid products was due to the inclusion complex formation between LOR and HP-β-CD after cogrinding process or evaporation. Moreover, IR peaks at 1676cm-1 down-shifted from 1703cm-1 (CO stretching) and at 1235cm-1 upper-shifted from 1227cm-1 (C-O stretching) related to LOR in the inclusion complex were observed with the increase of cogrinding time, but the peak at 1646cm-1 due to O-H stretching of HP-β-CD was shifted to 1640cm-1. The IR spectrum of 15min-coground mixture was the same as the IR spectrum of the co-evaporated solid product, strongly indicating that the grinding process could cause the inclusion complex formation between LOR and HP-β-CD. Three components (1700, 1676, and 1640cm-1) and their compositions were certainly obtained in the 1740-1600cm-1 region of FTIR spectra for the LOR/HP-β-CD coground mixture and the co-evaporated solid products by curve-fitting analysis. The component of 1700cm-1 detected was due to the un-included LOR in the inclusion complex. This implies that FTIR spectroscopy with curve-fitting analysis might be useful for discriminating the components and compositions in the inclusion complex.

Original languageEnglish
Pages (from-to)799-803
Number of pages5
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume53
Issue number3
DOIs
Publication statusPublished - Nov 2010

Fingerprint

Loratadine
Cyclodextrins
Curve fitting
Fourier Analysis
Fourier transforms
Infrared radiation
Solubility
Stretching
Differential Scanning Calorimetry
Fourier Transform Infrared Spectroscopy
Differential scanning calorimetry
Carbon Monoxide
Chemical analysis
Freezing
Melting point

Keywords

  • Co-grinding
  • Curve-fitting
  • DSC
  • FTIR
  • Hydroxypropyl-β-cyclodextrin
  • Inclusion complex
  • Loratadine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Spectroscopy
  • Clinical Biochemistry

Cite this

Curve-fitting FTIR studies of loratadine/hydroxypropyl-β-cyclodextrin inclusion complex induced by co-grinding process. / Lin, Shan Yang; Hsu, Cheng Hung; Sheu, Ming Thau.

In: Journal of Pharmaceutical and Biomedical Analysis, Vol. 53, No. 3, 11.2010, p. 799-803.

Research output: Contribution to journalArticle

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N2 - The formation steps of inclusion complex caused by co-grinding loratadine (LOR) and hydroxypropyl-β-cyclodextrin (HP-β-CD) with a molar ratio of 1:1 or 1:2 were quantitatively investigated by Fourier transform infrared (FTIR) spectroscopy with curve-fitting analysis and differential scanning calorimetry (DSC). The phase solubility study and the co-evaporated solid products of the mixture of LOR and HP-β-CD were also examined. The result indicates that the aqueous solubility of LOR was linearly increased with the increase of HP-β-CD concentrations, in which the phase solubility diagram was classified as AL type. The higher apparent stability constant (2.22×104M-1) reveals that the inclusion complex formed between LOR and HP-β-CD was quite stable. The endothermic peak at 134.6°C for the melting point of LOR gradually disappeared from DSC curves of LOR/HP-β-CD coground mixtures by increasing the cogrinding time, as the disappearance of the co-evaporated solid products. The disappearance of this endothermic peak from LOR/HP-β-CD coground mixture or the co-evaporated solid products was due to the inclusion complex formation between LOR and HP-β-CD after cogrinding process or evaporation. Moreover, IR peaks at 1676cm-1 down-shifted from 1703cm-1 (CO stretching) and at 1235cm-1 upper-shifted from 1227cm-1 (C-O stretching) related to LOR in the inclusion complex were observed with the increase of cogrinding time, but the peak at 1646cm-1 due to O-H stretching of HP-β-CD was shifted to 1640cm-1. The IR spectrum of 15min-coground mixture was the same as the IR spectrum of the co-evaporated solid product, strongly indicating that the grinding process could cause the inclusion complex formation between LOR and HP-β-CD. Three components (1700, 1676, and 1640cm-1) and their compositions were certainly obtained in the 1740-1600cm-1 region of FTIR spectra for the LOR/HP-β-CD coground mixture and the co-evaporated solid products by curve-fitting analysis. The component of 1700cm-1 detected was due to the un-included LOR in the inclusion complex. This implies that FTIR spectroscopy with curve-fitting analysis might be useful for discriminating the components and compositions in the inclusion complex.

AB - The formation steps of inclusion complex caused by co-grinding loratadine (LOR) and hydroxypropyl-β-cyclodextrin (HP-β-CD) with a molar ratio of 1:1 or 1:2 were quantitatively investigated by Fourier transform infrared (FTIR) spectroscopy with curve-fitting analysis and differential scanning calorimetry (DSC). The phase solubility study and the co-evaporated solid products of the mixture of LOR and HP-β-CD were also examined. The result indicates that the aqueous solubility of LOR was linearly increased with the increase of HP-β-CD concentrations, in which the phase solubility diagram was classified as AL type. The higher apparent stability constant (2.22×104M-1) reveals that the inclusion complex formed between LOR and HP-β-CD was quite stable. The endothermic peak at 134.6°C for the melting point of LOR gradually disappeared from DSC curves of LOR/HP-β-CD coground mixtures by increasing the cogrinding time, as the disappearance of the co-evaporated solid products. The disappearance of this endothermic peak from LOR/HP-β-CD coground mixture or the co-evaporated solid products was due to the inclusion complex formation between LOR and HP-β-CD after cogrinding process or evaporation. Moreover, IR peaks at 1676cm-1 down-shifted from 1703cm-1 (CO stretching) and at 1235cm-1 upper-shifted from 1227cm-1 (C-O stretching) related to LOR in the inclusion complex were observed with the increase of cogrinding time, but the peak at 1646cm-1 due to O-H stretching of HP-β-CD was shifted to 1640cm-1. The IR spectrum of 15min-coground mixture was the same as the IR spectrum of the co-evaporated solid product, strongly indicating that the grinding process could cause the inclusion complex formation between LOR and HP-β-CD. Three components (1700, 1676, and 1640cm-1) and their compositions were certainly obtained in the 1740-1600cm-1 region of FTIR spectra for the LOR/HP-β-CD coground mixture and the co-evaporated solid products by curve-fitting analysis. The component of 1700cm-1 detected was due to the un-included LOR in the inclusion complex. This implies that FTIR spectroscopy with curve-fitting analysis might be useful for discriminating the components and compositions in the inclusion complex.

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