Effect of pH on the complexation of irbesartan with β -, hydroxypropyl-β -, and γ -cyclodextrin: solubility enhancement and physicochemical characterization

Fakhri YOUSEF

Makale detayları

Effect of pH on the complexation of irbesartan with β -, hydroxypropyl-β -, and γ -cyclodextrin: solubility enhancement and physicochemical characterization

Yazarlar:

Fakhri YOUSEF

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2018 Vol.42 Issue 6, pp.1544-1558

Belge Tipi:

Makale

Yayın Tarihi:

11/2018

Belge Dili:

İngilizce

Document ID (Org No.):

2000725914

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

The affinity of irbesartan (IRB) to form inclusion   complexes with ββ\beta -cyclodextrin (ββ\beta -CD), hydroxypropyl-ββ\beta   -cyclodextrin (HP-ββ\beta -CD), and γγ\gamma -cyclodextrin (γγ\gamma -CD)   was investigated in aqueous buffered solutions at pH 1.7, 4.1, and 7.0.   Analysis of the UV absorption-pH profiles revealed that IRB has two   pKaKaK_{a} values: pKa1=Ka1=K_{a1\, }= 3.60 (imidazolinone ring moiety) and   pKa2=Ka2=K_{a2\, }= 4.70 (tetrazole moiety). In the presence of 5.0 mmol   L−1β−1β^{-1}  \beta -CD, the tetrazole moiety became more acidic, indicating   its inclusion within the ββ\beta -CD cavity. Phase-solubility diagrams   (PSDs) were obtained for IRB in aqueous buffered solutions of ββ\beta -CD,   HP-ββ\beta -CD, and γγ\gamma -CD at pH 4.1 (zwitterionic IRB), pH 1.7   (protonated IRB), and pH 7.0 (deprotonated IRB). Rigorous nonlinear   regression analysis of IRB/CD PSDs at pH 4.1, where IRB is poorly soluble,   yielded estimates of complex formation constants (K11)K11)K_{11}) that followed the   decreasing order of  HP-ββ\beta -CD > γγ\gamma -CD >   ββ\beta -CD.  The highest solubility enhancement of IRB was achieved by   complexation with HP-ββ\beta -CD at pH 4.1. The formation of the IRB/ββ\beta   -CD inclusion complex in solution and in the solid state has been proven   through NMR, DSC, FT-IR, and XRD studies. Analysis of 11^{1}H and   1313^{13}C-NMR spectra indicated the inclusion of the tetrazole-biphenyl   moiety within the ββ\beta -CD cavity.

Makale detayları

Effect of pH on the complexation of irbesartan with β -, hydroxypropyl-β -, and γ -cyclodextrin: solubility enhancement and physicochemical characterization

Yazarlar: Fakhri YOUSEF

Yayıncı: TUBITAK

Ana Başlıklar: Uygulamalı fizik

Dergi: Turkish Journal of Chemistry 2018 Vol.42 Issue 6, pp.1544-1558

Belge Tipi: Makale

Yayın Tarihi: 11/2018

Belge Dili: İngilizce

Document ID (Org No.): 2000725914

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Fakhri YOUSEF

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2018 Vol.42 Issue 6, pp.1544-1558

Belge Tipi:

Makale

Yayın Tarihi:

11/2018

Belge Dili:

İngilizce

Document ID (Org No.):

2000725914

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527