NDLI: Stabilizing and Solubilizing Effects of Sulfobutyl Ether β-Cyclodextrin on Prostaglandin E1 Analogue

Content Provider	Springer Nature Link
Author	Uekama, Kaneto Hieda, Yukako Hirayama, Fumitoshi Arima, Hidetoshi Sudoh, Masao Yagi, Akira Terashima, Hiroshi
Copyright Year	2001
Abstract	Purpose. Parent cyclodextrins are known to accelerate the degradations such as dehydration and isomerization of E-type prostaglandins in neutral and alkaline solutions. The objective of this study was to attempt the stabilization and solubilization of E$_{1}$-type prostaglandin analogue in aqueous solution by biocompatible cyclodextrin derivatives. Methods. The interaction of an E$_{1}$-type prostaglandin, methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-(3S)-3-hydroxy-4-(m-methoxymethylphenyl)1-butenyl]-5-oxocyclopentyl]-5-thiaheptanoate (MEester) with cyclodextrins (CyDs) was studied by spectroscopies and the solubility method. The degradation of MEester was monitored by high-performance liquid chromatography. Results. $^{1}$H-nuclear magnetic resonance spectroscopic studies indicated that MEester forms 1:1 inclusion complexes with α-, β-, and γ-CyDs in solutions, where α-CyD interacts with the α-side chain containing methyl ester moiety of the drug, whereas β- and γ-CyDs preferentially include around the five-membered ring and both side chains of the drug. Parent α-CyD and hydrophilic derivatives, such as 2-hydoxypropyl-α- and -β-CyDs, sulfobutyl ether β-CyD (SBE-β-CyD) and maltosyl β-CyD showed higher solubilizing abilities against MEester over parent β- and γ-CyDs. SBE-β-CyD and 2,6-dimethyl-β-CyD (DM-β-CyD) significantly decelerated the degradation of MEester, particularly the base-catalyzed dehydration, in neutral and alkaline solutions, whereas other CyDs accelerated the degradation. The acid-catalyzed degradation of MEester (pH < 3) was decelerated by the addition of CyDs, especially α-CyD. Conclusions. SBE-β-CyD with low hemolytic activity and low toxicity is useful as a pharmaceutical carrier for the preparation of injectable MEester, because of its higher stabilizing and solubilizing effects on MEester. Furthermore, SBE-β-CyD can be useful as a stabilizing agent for drugs, that are subject to base-catalyzed degradations, probably because of the electric repulsion between anionic charges of the sulfobutyl moiety and catalytic anionic species such as hydroxide ion.
Starting Page	1578
Ending Page	1585
Page Count	8
File Format	PDF
ISSN	07248741
Journal	Pharmaceutical Research
Volume Number	18
Issue Number	11
e-ISSN	1573904X
Language	English
Publisher	Kluwer Academic Publishers-Plenum Publishers
Publisher Date	2001-01-01
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Pharmacology/Toxicology Pharmacy Biochemistry Medical Law Biomedical Engineering
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Pharmacology Molecular Medicine Pharmacology (medical) Biotechnology Pharmaceutical Science

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