Journal of Thermal Analysis and Calorimetry
Volume/Issue:
Volume 95: Issue 2
Effect of pH on the formation of inclusion complexes between β-lactam antibiotics and 2-hydroxypropyl-β-cyclodextrin in aqueous solution
Authors:
H. Aki Fukuoka University Faculty of Pharmaceutical Sciences 8-19-1 Nanakuma, Jonan-ku Fukuoka 814-0180 Japan

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H. Ikeda Fukuoka University Faculty of Pharmaceutical Sciences 8-19-1 Nanakuma, Jonan-ku Fukuoka 814-0180 Japan

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M. Yukawa Fukuoka University Faculty of Pharmaceutical Sciences 8-19-1 Nanakuma, Jonan-ku Fukuoka 814-0180 Japan

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Y. Iwase Fukuoka University Faculty of Pharmaceutical Sciences 8-19-1 Nanakuma, Jonan-ku Fukuoka 814-0180 Japan

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N. Mibu Fukuoka University Faculty of Pharmaceutical Sciences 8-19-1 Nanakuma, Jonan-ku Fukuoka 814-0180 Japan

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Pages:
421–426
Online Publication Date:
12 Mar 2009
Publication Date:
01 Feb 2009
Article Category:
Research Article
DOI:
https://doi.org/10.1007/s10973-008-9251-4
Keywords:
amoxicillin; ampicillin; benzylpenicillin; 2-hydroxypropyl-β-cyclodextrin; inclusion complex; microcalorimetry; molecular dynamic simulation
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Abstract  

The complexation of β-lactam antibiotics, amoxicillin (AMPC), ampicillin (ABPC) and benzylpenicillin (PCG), with 2-hydroxypropyl-β-cyclodextrin (HPCD) was studied at various pH values using microcalorimetry, 1H NMR spectroscopy, and molecular dynamic simulation. In the strong acid solution, two different types of inclusion complex with a 1:1 stoichiometry, Complex I with a phenyl ring of β-lactam antibiotics penetrated into the cavity of HPCD and Complex II with a penam included in the cavity, were formed by hydrophobic interaction, and Complex II was more stable than Complex I. In aqueous solution at pH≥4.5, only Complex I was formed, where the penam of PCG was more deeply penetrated into the cavity to keep it stable than those of AMPC and ABPC. The charged carboxyl-group on the penam was less affinity to form Complex II.

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Cover Journal of Thermal Analysis and Calorimetry
Journal of Thermal Analysis and Calorimetry
Print ISSN:
1388-6150
Online ISSN:
1572-8943

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Journal of Thermal Analysis and Calorimetry
Language English
Size A4
Year of
Foundation		 1969
Volumes
per Year		 1
Issues
per Year		 24
Founder Akadémiai Kiadó
Founder's
Address		 H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address		 H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11.
Responsible
Publisher		 Chief Executive Officer, Akadémiai Kiadó
ISSN 1388-6150 (Print)
ISSN 1588-2926 (Online)

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