Synthesis of 9-Hydroxystearic Acid Derivatives and Their Antiproliferative Activity on HT 29 Cancer Cells
9-Hydroxystearic acid (9-HSA) is an endogenous cellular lipid that possesses antiproliferative and selective effects against cancer cells. A series of derivatives were synthesized in order to investigate the effect of the substituent in position 9 and on the methyl ester functionality on the biologi...
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| Format: | Article |
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MDPI AG
2019-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/20/3714 |
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| author | Natalia Calonghi Carla Boga Dario Telese Silvia Bordoni Giorgio Sartor Chiara Torsello Gabriele Micheletti |
| author_facet | Natalia Calonghi Carla Boga Dario Telese Silvia Bordoni Giorgio Sartor Chiara Torsello Gabriele Micheletti |
| author_sort | Natalia Calonghi |
| collection | DOAJ |
| description | 9-Hydroxystearic acid (9-HSA) is an endogenous cellular lipid that possesses antiproliferative and selective effects against cancer cells. A series of derivatives were synthesized in order to investigate the effect of the substituent in position 9 and on the methyl ester functionality on the biological activity. The two separate enantiomers of methyl 9-hydroxystearate and of methyl 9-aminostearate showed antiproliferative activity against the HT29 cell line. This indicates the importance of position 9 groups being able to make hydrogen bonding with the molecular target. Further, this effect must be preserved when the carboxy group of 9-HSA is esterified. The biological tests showed that the amines, contrarily to methyl esters, resulted in cytotoxicity. A deep investigation on the effect of methyl (<i>R</i>)-9-hydroxystearate on HT29 cells showed an antiproliferative effect acting through the CDKN1A and MYCBP gene expression. |
| first_indexed | 2024-12-10T22:05:24Z |
| format | Article |
| id | doaj.art-caa4f25fc8a04648bc721f6d9f9ef24c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T22:05:24Z |
| publishDate | 2019-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-caa4f25fc8a04648bc721f6d9f9ef24c2022-12-22T01:31:46ZengMDPI AGMolecules1420-30492019-10-012420371410.3390/molecules24203714molecules24203714Synthesis of 9-Hydroxystearic Acid Derivatives and Their Antiproliferative Activity on HT 29 Cancer CellsNatalia Calonghi0Carla Boga1Dario Telese2Silvia Bordoni3Giorgio Sartor4Chiara Torsello5Gabriele Micheletti6Department of Pharmacy and Biotechnology, University of Bologna, 40127 Bologna, ItalyDepartment of Industrial Chemistry ‘Toso Montanari’, Alma Mater Studiorum Università di Bologna Viale Del Risorgimento 4, 402136 Bologna, ItalyDepartment of Industrial Chemistry ‘Toso Montanari’, Alma Mater Studiorum Università di Bologna Viale Del Risorgimento 4, 402136 Bologna, ItalyDepartment of Industrial Chemistry ‘Toso Montanari’, Alma Mater Studiorum Università di Bologna Viale Del Risorgimento 4, 402136 Bologna, ItalyDepartment of Pharmacy and Biotechnology, University of Bologna, 40127 Bologna, ItalyDepartment of Pharmacy and Biotechnology, University of Bologna, 40127 Bologna, ItalyDepartment of Industrial Chemistry ‘Toso Montanari’, Alma Mater Studiorum Università di Bologna Viale Del Risorgimento 4, 402136 Bologna, Italy9-Hydroxystearic acid (9-HSA) is an endogenous cellular lipid that possesses antiproliferative and selective effects against cancer cells. A series of derivatives were synthesized in order to investigate the effect of the substituent in position 9 and on the methyl ester functionality on the biological activity. The two separate enantiomers of methyl 9-hydroxystearate and of methyl 9-aminostearate showed antiproliferative activity against the HT29 cell line. This indicates the importance of position 9 groups being able to make hydrogen bonding with the molecular target. Further, this effect must be preserved when the carboxy group of 9-HSA is esterified. The biological tests showed that the amines, contrarily to methyl esters, resulted in cytotoxicity. A deep investigation on the effect of methyl (<i>R</i>)-9-hydroxystearate on HT29 cells showed an antiproliferative effect acting through the CDKN1A and MYCBP gene expression.https://www.mdpi.com/1420-3049/24/20/37149-hydroxystearic acidmethyl 9-hydroxystearatemethyl 9-aminostearatecancer |
| spellingShingle | Natalia Calonghi Carla Boga Dario Telese Silvia Bordoni Giorgio Sartor Chiara Torsello Gabriele Micheletti Synthesis of 9-Hydroxystearic Acid Derivatives and Their Antiproliferative Activity on HT 29 Cancer Cells Molecules 9-hydroxystearic acid methyl 9-hydroxystearate methyl 9-aminostearate cancer |
| title | Synthesis of 9-Hydroxystearic Acid Derivatives and Their Antiproliferative Activity on HT 29 Cancer Cells |
| title_full | Synthesis of 9-Hydroxystearic Acid Derivatives and Their Antiproliferative Activity on HT 29 Cancer Cells |
| title_fullStr | Synthesis of 9-Hydroxystearic Acid Derivatives and Their Antiproliferative Activity on HT 29 Cancer Cells |
| title_full_unstemmed | Synthesis of 9-Hydroxystearic Acid Derivatives and Their Antiproliferative Activity on HT 29 Cancer Cells |
| title_short | Synthesis of 9-Hydroxystearic Acid Derivatives and Their Antiproliferative Activity on HT 29 Cancer Cells |
| title_sort | synthesis of 9 hydroxystearic acid derivatives and their antiproliferative activity on ht 29 cancer cells |
| topic | 9-hydroxystearic acid methyl 9-hydroxystearate methyl 9-aminostearate cancer |
| url | https://www.mdpi.com/1420-3049/24/20/3714 |
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