Synthesis, Crystallography, and Anti-Leukemic Activity of the Amino Adducts of Dehydroleucodine
| Autor: | Darin E. Jones, Monica L. Guzman, Omar Malagón, Saumyadip Nemu, Raúl G. Enríquez, Darcy C. Burns, William F. Reynolds, Cesar M. Compadre, David E Mery, Paola E. Ordóñez, Krishan K. Sharma |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
HMOX1
Morpholines Tyramine Pharmaceutical Science Crystallography X-Ray Sesquiterpene lactone 01 natural sciences Peripheral blood mononuclear cell Article Analytical Chemistry lcsh:QD241-441 Lactones chemistry.chemical_compound Piperidines lcsh:Organic chemistry Cell Line Tumor Morpholine Drug Discovery sesquiterpene lactone Humans HSP70 Heat-Shock Proteins Proline 0101 mathematics Physical and Theoretical Chemistry Cell Proliferation chemistry.chemical_classification Gene Expression Regulation Leukemic 010405 organic chemistry Organic Chemistry NF-kappa B p50 Subunit amino adducts 0104 chemical sciences 010101 applied mathematics Heme oxygenase Leukemia Myeloid Acute chemistry Biochemistry Chemistry (miscellaneous) anti-leukemic activity Leukocytes Mononuclear Molecular Medicine dehydroleucodine Piperidine Sesquiterpenes Heme Oxygenase-1 |
| Zdroj: | Molecules, Vol 25, Iss 4825, p 4825 (2020) Molecules Volume 25 Issue 20 |
| ISSN: | 1420-3049 |
| Popis: | Dehydroleucodine is a bioactive sesquiterpene lactone. Herein, four dehydroleucodine amino derivatives were synthesized using the amines proline, piperidine, morpholine, and tyramine, and spectroscopic methods and single-crystal X-ray diffraction unambiguously established their structures. The cytotoxic activity of these compounds was evaluated against eight acute myeloid leukemia cell lines, and their toxicity to peripheral blood mononuclear cells was also determined. The proline adduct was the most active compound, it showed anti-leukemic activity, upregulated heme oxygenase 1 (HMOX1) and the primary stress-inducible isoform of the heath shock 70 kDa protein 1 (HSPA1A), and downregulated NFkB1 transcription, it was also found to be about 270 times more water soluble than dehydroleucodine. |
| Databáze: | OpenAIRE |
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