Characteristics of hydrogen bond formation between sugar and polymer in freeze-dried mixtures under different rehumidification conditions and its impact on the glass transition temperature

Koreyoshi Imamura, Yoko Asaimo, Yoshinobu Maruyama, Tohru Yokoyama, Mayo Nomura, Seiji Ogawa, Kazuhiro Nakanishi

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The characteristics of hydrogen bond formation between trehalose and polyvinylpyrrolidone (PVP) in amorphous mixtures at different hydration states were quantitatively investigated. Amorphous trehalose-PVP mixtures were prepared by freeze-drying and equilibrated at different relative humidities (RH). Infrared (IR) spectra of the trehalose-PVP mixtures were obtained by Fourier transform IR spectroscopy, (FTIR) and the IR band corresponding to C=O groups of PVP was deconvolved into the component bands responsible for C=O groups that were free and restricted by hydrogen bonds, to estimate the degree of the trehalose-PVP interactions. The FTIR analysis indicated that approximately 80% of the C=O groups of PVP formed hydrogen bonds with trehalose in the presence of more than 3 g of trehalose per gramme of PVP, independent of the RH. IR analysis of the O-H stretching vibration of the sugar demonstrated that the presence of PVP lead to an increase in the free hydroxyl groups of trehalose that did not form hydrogen bonds at RH 0%. On the other hand, the water sorption behavior of the trehalose-PVP mixtures suggested that rehumidification diminished the effect of PVP on increasing the free OH groups. Thus a peculiar relationship may exist between Tg, RH and the composition of the mixture: The presence of PVP increased Tg at RHs 0 and above 23% but decreased Tg at 11%.

Original languageEnglish
Pages (from-to)1301-1312
Number of pages12
JournalJournal of Pharmaceutical Sciences
Volume97
Issue number3
DOIs
Publication statusPublished - Mar 2008

Fingerprint

Povidone
Transition Temperature
Sugars
Glass
Trehalose
Hydrogen
Hydrogen bonds
Polymers
Humidity
Atmospheric humidity
Infrared radiation
Glass transition temperature
Freeze Drying
Fourier Analysis
Fourier Transform Infrared Spectroscopy
Vibration
Hydration
Hydroxyl Radical
Stretching
Sorption

Keywords

  • Amorphous
  • Excipients
  • Freeze-drying
  • FTIR
  • Glass transition
  • Polymers

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Molecular Medicine
  • Pharmacology

Cite this

Characteristics of hydrogen bond formation between sugar and polymer in freeze-dried mixtures under different rehumidification conditions and its impact on the glass transition temperature. / Imamura, Koreyoshi; Asaimo, Yoko; Maruyama, Yoshinobu; Yokoyama, Tohru; Nomura, Mayo; Ogawa, Seiji; Nakanishi, Kazuhiro.

In: Journal of Pharmaceutical Sciences, Vol. 97, No. 3, 03.2008, p. 1301-1312.

Research output: Contribution to journalArticle

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abstract = "The characteristics of hydrogen bond formation between trehalose and polyvinylpyrrolidone (PVP) in amorphous mixtures at different hydration states were quantitatively investigated. Amorphous trehalose-PVP mixtures were prepared by freeze-drying and equilibrated at different relative humidities (RH). Infrared (IR) spectra of the trehalose-PVP mixtures were obtained by Fourier transform IR spectroscopy, (FTIR) and the IR band corresponding to C=O groups of PVP was deconvolved into the component bands responsible for C=O groups that were free and restricted by hydrogen bonds, to estimate the degree of the trehalose-PVP interactions. The FTIR analysis indicated that approximately 80{\%} of the C=O groups of PVP formed hydrogen bonds with trehalose in the presence of more than 3 g of trehalose per gramme of PVP, independent of the RH. IR analysis of the O-H stretching vibration of the sugar demonstrated that the presence of PVP lead to an increase in the free hydroxyl groups of trehalose that did not form hydrogen bonds at RH 0{\%}. On the other hand, the water sorption behavior of the trehalose-PVP mixtures suggested that rehumidification diminished the effect of PVP on increasing the free OH groups. Thus a peculiar relationship may exist between Tg, RH and the composition of the mixture: The presence of PVP increased Tg at RHs 0 and above 23{\%} but decreased Tg at 11{\%}.",
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AB - The characteristics of hydrogen bond formation between trehalose and polyvinylpyrrolidone (PVP) in amorphous mixtures at different hydration states were quantitatively investigated. Amorphous trehalose-PVP mixtures were prepared by freeze-drying and equilibrated at different relative humidities (RH). Infrared (IR) spectra of the trehalose-PVP mixtures were obtained by Fourier transform IR spectroscopy, (FTIR) and the IR band corresponding to C=O groups of PVP was deconvolved into the component bands responsible for C=O groups that were free and restricted by hydrogen bonds, to estimate the degree of the trehalose-PVP interactions. The FTIR analysis indicated that approximately 80% of the C=O groups of PVP formed hydrogen bonds with trehalose in the presence of more than 3 g of trehalose per gramme of PVP, independent of the RH. IR analysis of the O-H stretching vibration of the sugar demonstrated that the presence of PVP lead to an increase in the free hydroxyl groups of trehalose that did not form hydrogen bonds at RH 0%. On the other hand, the water sorption behavior of the trehalose-PVP mixtures suggested that rehumidification diminished the effect of PVP on increasing the free OH groups. Thus a peculiar relationship may exist between Tg, RH and the composition of the mixture: The presence of PVP increased Tg at RHs 0 and above 23% but decreased Tg at 11%.

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