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Synthesis, Characterization, and Antifungal Property of Hydroxypropyltrimethyl Ammonium Chitosan Halogenated Acetates.
Synthesis, Characterization, and Antifungal Property of Hydroxypropyltrimethyl Ammonium Chitosan Halogenated Acetates.
- Source :
-
Marine drugs [Mar Drugs] 2018 Sep 05; Vol. 16 (9). Date of Electronic Publication: 2018 Sep 05. - Publication Year :
- 2018
-
Abstract
- Hydroxypropyltrimethyl ammonium chitosan halogenated acetates were successfully synthesized from six different haloacetic acids and hydroxypropyltrimethyl ammonium chloride chitosan (HACC) with high substitution degree, which are hydroxypropyltrimethyl ammonium chitosan bromacetate (HACBA), hydroxypropyltrimethyl ammonium chitosan chloroacetate (HACCA), hydroxypropyltrimethyl ammonium chitosan dichloroacetate (HACDCA), hydroxypropyltrimethyl ammonium chitosan trichloroacetate (HACTCA), hydroxypropyltrimethyl ammonium chitosan difluoroacetate (HACDFA), and hydroxypropyltrimethyl ammonium chitosan trifluoroacetate (HACTFA). These chitosan derivatives were synthesized by two steps: first, the hydroxypropyltrimethyl ammonium chloride chitosan was synthesized by chitosan and 3-chloro-2-hydroxypropyltrimethyl ammonium chloride. Then, hydroxypropyltrimethyl ammonium chitosan halogenated acetates were synthesized via ion exchange. The structures of chitosan derivatives were characterized by Fourier transform infrared spectroscopy (FTIR), ¹H Nuclear magnetic resonance spectrometer (¹H NMR), <superscript>13</superscript> C Nuclear magnetic resonance spectrometer ( <superscript>13</superscript> C NMR), and elemental analysis. Their antifungal activities against Colletotrichum lagenarium , Fusarium graminearum , Botrytis cinerea , and Phomopsis asparagi were investigated by hypha measurement in vitro. The results revealed that hydroxypropyltrimethyl ammonium chitosan halogenated acetates had better antifungal activities than chitosan and HACC. In particular, the inhibitory activity decreased in the order: HACTFA > HACDFA > HACTCA > HACDCA > HACCA > HACBA > HACC > chitosan, which was consistent with the electron-withdrawing property of different halogenated acetates. This experiment provides a potential idea for the preparation of new antifungal drugs by chitosan.
- Subjects :
- Acetates chemistry
Antifungal Agents chemistry
Carbon-13 Magnetic Resonance Spectroscopy
Chitosan chemistry
Chitosan pharmacology
Fungicides, Industrial adverse effects
Halogenation
Hyphae drug effects
Microbial Sensitivity Tests
Molecular Structure
Plant Diseases microbiology
Proton Magnetic Resonance Spectroscopy
Quaternary Ammonium Compounds chemistry
Spectroscopy, Fourier Transform Infrared
Structure-Activity Relationship
Antifungal Agents pharmacology
Ascomycota drug effects
Chitosan analogs & derivatives
Mitosporic Fungi drug effects
Plant Diseases prevention & control
Quaternary Ammonium Compounds pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1660-3397
- Volume :
- 16
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Marine drugs
- Publication Type :
- Academic Journal
- Accession number :
- 30189609
- Full Text :
- https://doi.org/10.3390/md16090315