Lamotrigine–dextran conjugates-synthesis, characterization, and biological evaluation

Synthesis of lamotrigine–dextran conjugates is done by oxidation of dextran using sodium periodate (NaIO 4 ), where the aldehyde groups formed were coupled with the amino (–NH 2 ) group of lamotrigine and reduced to secondary imine groups. Characterization of synthesized conjugates was done by using...

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Published inMedicinal chemistry research Vol. 20; no. 5; pp. 595 - 600
Main Authors Pugazhendhy, S., Shrivastava, Prabhat K., Sinha, Saurabh K., Shrivastava, Sushant K.
Format Journal Article
LanguageEnglish
Published New York Springer-Verlag 01.06.2011
Subjects
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Original Research
Pharmacology/Toxicology
Dextran
Anticonvulsant activity
In vitro hydrolysis
Prodrug
Hepatotoxicity
Lamotrigine
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Summary:Synthesis of lamotrigine–dextran conjugates is done by oxidation of dextran using sodium periodate (NaIO 4 ), where the aldehyde groups formed were coupled with the amino (–NH 2 ) group of lamotrigine and reduced to secondary imine groups. Characterization of synthesized conjugates was done by using ultraviolet, infrared, nuclear magnetic resonance spectroscopy. Viscometer was used to determine molecular weight, and degree of substitution was estimated by complete hydrolysis of conjugates in borate buffer, which was found to be 8%. Buffer solutions with different pH, i.e., 1.2, 7.4, and 9.0 were used to perform the in vitro hydrolysis study and the amount of conjugates released was estimated by high performance liquid chromatography. The study showed that the rate of hydrolysis increases with increase in pH. The anticonvulsant and hepatotoxicity screening of the synthesized conjugates in different rat models showed that lamotrigine–dextran conjugates proved to be potentially safer than parent lamotrigine formulations.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-010-9355-9