Cordova-Chávez, R.I.; Trujillo-Ferrara, J.G.; Padilla-Martínez, I.I.; González-Espinosa, H.; Abad-García, A.; Farfán-García, E.D.; Ortega-Camarillo, C.; Contreras-Ramos, A.; Soriano-Ursúa, M.A. One-Step Synthesis, Crystallography, and Acute Toxicity of Two Boron–Carbohydrate Adducts That Induce Sedation in Mice. Pharmaceuticals2024, 17, 781.
Cordova-Chávez, R.I.; Trujillo-Ferrara, J.G.; Padilla-Martínez, I.I.; González-Espinosa, H.; Abad-García, A.; Farfán-García, E.D.; Ortega-Camarillo, C.; Contreras-Ramos, A.; Soriano-Ursúa, M.A. One-Step Synthesis, Crystallography, and Acute Toxicity of Two Boron–Carbohydrate Adducts That Induce Sedation in Mice. Pharmaceuticals 2024, 17, 781.
Cordova-Chávez, R.I.; Trujillo-Ferrara, J.G.; Padilla-Martínez, I.I.; González-Espinosa, H.; Abad-García, A.; Farfán-García, E.D.; Ortega-Camarillo, C.; Contreras-Ramos, A.; Soriano-Ursúa, M.A. One-Step Synthesis, Crystallography, and Acute Toxicity of Two Boron–Carbohydrate Adducts That Induce Sedation in Mice. Pharmaceuticals2024, 17, 781.
Cordova-Chávez, R.I.; Trujillo-Ferrara, J.G.; Padilla-Martínez, I.I.; González-Espinosa, H.; Abad-García, A.; Farfán-García, E.D.; Ortega-Camarillo, C.; Contreras-Ramos, A.; Soriano-Ursúa, M.A. One-Step Synthesis, Crystallography, and Acute Toxicity of Two Boron–Carbohydrate Adducts That Induce Sedation in Mice. Pharmaceuticals 2024, 17, 781.
Abstract
Background: Boronic acids form di-ester bonds with cis-hydroxyl groups in carbohydrates. The formation of these adducts could impair the physical and chemical properties of the precursors, even their biological activity. Methods: Two carbohydrate-derivatives from D-fructose and D-arabinose and phenylboronic acid were synthesized in a straightforward one-step procedure and chemically characterized by spectroscopy and X-ray diffraction crystallography. Also, an acute toxicity test was performed to determine their Lethal Dose50 (LD50) by using the Lorke’s method. Results: Analytical chemistry assays confirmed adducts by the generation of the diester bonds with a β-D-pyranose of carbohydrates, including signals corresponding to the formation of new bonds, like the stretching of B-O bonds. The NMR spectra yielded information about the stereoselectivity in the synthesis reaction by the finding of just one signal in the range for the anomeric carbon in the 13C NMR spectra of both adducts. The acute toxicity tests showed that LD50 value for both compounds is 1265 mg/kg, while Effective Dose 50 for sedation is 531 mg/kg. However, differences were in the onset and lapse of sedation. Conclusions: These adducts are bioactive and highly safe agents. Further biological evaluation is desirable to explore medical purposes.
Chemistry and Materials Science, Medicinal Chemistry
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
,
*
