TY  - JOUR
AU  - Petrović, Milena M.
AU  - Roschger, Cornelia
AU  - Lang, Kevin
AU  - Zierer, Andreas
AU  - Mladenović, Milan
AU  - Trifunović, Snežana S.
AU  - Mandić, Boris
AU  - Joksović, Milan D.
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5696
AB  - Fourteen novel quinoline-4-carboxylic acid-chalcone hybrids were obtained via Claisen–Schmidt condensation and evaluated as potential human dihydroorotate dehydrogenase (hDHODH) inhibitors. The ketone precursor 2 was synthesized by the Pfitzinger reaction and used for further derivatization at position 3 of the quinoline ring for the first time. Six compounds showed better hDHODH inhibitory activity than the reference drug leflunomide, with IC50 values ranging from 0.12 to 0.58 μM. The bioactive conformations of the compounds within hDHODH were resolved by means of molecular docking, revealing their tendency to occupy the narrow tunnel of hDHODH within the N-terminus and to prevent ubiquinone as the second cofactor from easily approaching the flavin mononucleotide as a cofactor for the redox reaction within the redox site. The results of the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay revealed that 4d and 4h demonstrated the highest cytotoxic activity against the A375 cell line, with IC50 values of 5.0 and 6.8 µM, respectively. The lipophilicity of the synthesized hybrids was obtained experimentally and expressed as logD7.4 values at physiologicalpH while the solubility assay was conducted to define physicochemical characteristics influencing the ADMET properties.
PB  - Wiley
T2  - Archiv der Pharmazie
T1  - Synthesis and biological evaluation of new quinoline-4-carboxylic acid-chalcone hybrids as dihydroorotate dehydrogenase inhibitors
VL  - 356
IS  - 2
SP  - e2200374
DO  - 10.1002/ardp.202200374
ER  - 

@article{
author = "Petrović, Milena M. and Roschger, Cornelia and Lang, Kevin and Zierer, Andreas and Mladenović, Milan and Trifunović, Snežana S. and Mandić, Boris and Joksović, Milan D.",
year = "2023",
abstract = "Fourteen novel quinoline-4-carboxylic acid-chalcone hybrids were obtained via Claisen–Schmidt condensation and evaluated as potential human dihydroorotate dehydrogenase (hDHODH) inhibitors. The ketone precursor 2 was synthesized by the Pfitzinger reaction and used for further derivatization at position 3 of the quinoline ring for the first time. Six compounds showed better hDHODH inhibitory activity than the reference drug leflunomide, with IC50 values ranging from 0.12 to 0.58 μM. The bioactive conformations of the compounds within hDHODH were resolved by means of molecular docking, revealing their tendency to occupy the narrow tunnel of hDHODH within the N-terminus and to prevent ubiquinone as the second cofactor from easily approaching the flavin mononucleotide as a cofactor for the redox reaction within the redox site. The results of the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay revealed that 4d and 4h demonstrated the highest cytotoxic activity against the A375 cell line, with IC50 values of 5.0 and 6.8 µM, respectively. The lipophilicity of the synthesized hybrids was obtained experimentally and expressed as logD7.4 values at physiologicalpH while the solubility assay was conducted to define physicochemical characteristics influencing the ADMET properties.",
publisher = "Wiley",
journal = "Archiv der Pharmazie",
title = "Synthesis and biological evaluation of new quinoline-4-carboxylic acid-chalcone hybrids as dihydroorotate dehydrogenase inhibitors",
volume = "356",
number = "2",
pages = "e2200374",
doi = "10.1002/ardp.202200374"
}

Petrović, M. M., Roschger, C., Lang, K., Zierer, A., Mladenović, M., Trifunović, S. S., Mandić, B.,& Joksović, M. D.. (2023). Synthesis and biological evaluation of new quinoline-4-carboxylic acid-chalcone hybrids as dihydroorotate dehydrogenase inhibitors. in Archiv der Pharmazie
Wiley., 356(2), e2200374.
https://doi.org/10.1002/ardp.202200374

Petrović MM, Roschger C, Lang K, Zierer A, Mladenović M, Trifunović SS, Mandić B, Joksović MD. Synthesis and biological evaluation of new quinoline-4-carboxylic acid-chalcone hybrids as dihydroorotate dehydrogenase inhibitors. in Archiv der Pharmazie. 2023;356(2):e2200374.
doi:10.1002/ardp.202200374 .

Petrović, Milena M., Roschger, Cornelia, Lang, Kevin, Zierer, Andreas, Mladenović, Milan, Trifunović, Snežana S., Mandić, Boris, Joksović, Milan D., "Synthesis and biological evaluation of new quinoline-4-carboxylic acid-chalcone hybrids as dihydroorotate dehydrogenase inhibitors" in Archiv der Pharmazie, 356, no. 2 (2023):e2200374,
https://doi.org/10.1002/ardp.202200374 . .

Petrović, M. M., Roschger, C., Chaudary, S., Zierer, A., Mladenović, M., Marković, V., Trifunović, S. S.,& Joksović, M. D.. (2021). Low cytotoxic quinoline-4-carboxylic acids derived from vanillin precursors as potential human dihydroorotate dehydrogenase inhibitors. in Bioorganic & Medicinal Chemistry Letters
Elsevier., 46.
https://doi.org/10.1016/j.bmcl.2021.128194

Petrović MM, Roschger C, Chaudary S, Zierer A, Mladenović M, Marković V, Trifunović SS, Joksović MD. Low cytotoxic quinoline-4-carboxylic acids derived from vanillin precursors as potential human dihydroorotate dehydrogenase inhibitors. in Bioorganic & Medicinal Chemistry Letters. 2021;46.
doi:10.1016/j.bmcl.2021.128194 .

Petrović, Milena M., Roschger, Cornelia, Chaudary, Sidrah, Zierer, Andreas, Mladenović, Milan, Marković, Violeta, Trifunović, Snežana S., Joksović, Milan D., "Low cytotoxic quinoline-4-carboxylic acids derived from vanillin precursors as potential human dihydroorotate dehydrogenase inhibitors" in Bioorganic & Medicinal Chemistry Letters, 46 (2021),
https://doi.org/10.1016/j.bmcl.2021.128194 . .

TY  - DATA
AU  - Petrović, Milena M.
AU  - Roschger, Cornelia
AU  - Chaudary, Sidrah
AU  - Zierer, Andreas
AU  - Mladenović, Milan
AU  - Marković, Violeta
AU  - Trifunović, Snežana S.
AU  - Joksović, Milan D.
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4551
PB  - Elsevier
T2  - Bioorganic & Medicinal Chemistry Letters
T1  - Supplementary data for the article: Petrović, M. M.; Roschger, C.; Chaudary, S.; Zierer, A.; Mladenović, M.; Marković, V.; Trifunović, S.; Joksović, M. D. Low Cytotoxic Quinoline-4-Carboxylic Acids Derived from Vanillin Precursors as Potential Human Dihydroorotate Dehydrogenase Inhibitors. Bioorganic & Medicinal Chemistry Letters 2021, 46, 128194. https://doi.org/10.1016/j.bmcl.2021.128194.
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4551
ER  - 

@misc{
author = "Petrović, Milena M. and Roschger, Cornelia and Chaudary, Sidrah and Zierer, Andreas and Mladenović, Milan and Marković, Violeta and Trifunović, Snežana S. and Joksović, Milan D.",
year = "2021",
publisher = "Elsevier",
journal = "Bioorganic & Medicinal Chemistry Letters",
title = "Supplementary data for the article: Petrović, M. M.; Roschger, C.; Chaudary, S.; Zierer, A.; Mladenović, M.; Marković, V.; Trifunović, S.; Joksović, M. D. Low Cytotoxic Quinoline-4-Carboxylic Acids Derived from Vanillin Precursors as Potential Human Dihydroorotate Dehydrogenase Inhibitors. Bioorganic & Medicinal Chemistry Letters 2021, 46, 128194. https://doi.org/10.1016/j.bmcl.2021.128194.",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4551"
}

Petrović, M. M., Roschger, C., Chaudary, S., Zierer, A., Mladenović, M., Marković, V., Trifunović, S. S.,& Joksović, M. D.. (2021). Supplementary data for the article: Petrović, M. M.; Roschger, C.; Chaudary, S.; Zierer, A.; Mladenović, M.; Marković, V.; Trifunović, S.; Joksović, M. D. Low Cytotoxic Quinoline-4-Carboxylic Acids Derived from Vanillin Precursors as Potential Human Dihydroorotate Dehydrogenase Inhibitors. Bioorganic & Medicinal Chemistry Letters 2021, 46, 128194. https://doi.org/10.1016/j.bmcl.2021.128194.. in Bioorganic & Medicinal Chemistry Letters
Elsevier..
https://hdl.handle.net/21.15107/rcub_cherry_4551

Petrović MM, Roschger C, Chaudary S, Zierer A, Mladenović M, Marković V, Trifunović SS, Joksović MD. Supplementary data for the article: Petrović, M. M.; Roschger, C.; Chaudary, S.; Zierer, A.; Mladenović, M.; Marković, V.; Trifunović, S.; Joksović, M. D. Low Cytotoxic Quinoline-4-Carboxylic Acids Derived from Vanillin Precursors as Potential Human Dihydroorotate Dehydrogenase Inhibitors. Bioorganic & Medicinal Chemistry Letters 2021, 46, 128194. https://doi.org/10.1016/j.bmcl.2021.128194.. in Bioorganic & Medicinal Chemistry Letters. 2021;.
https://hdl.handle.net/21.15107/rcub_cherry_4551 .

Petrović, Milena M., Roschger, Cornelia, Chaudary, Sidrah, Zierer, Andreas, Mladenović, Milan, Marković, Violeta, Trifunović, Snežana S., Joksović, Milan D., "Supplementary data for the article: Petrović, M. M.; Roschger, C.; Chaudary, S.; Zierer, A.; Mladenović, M.; Marković, V.; Trifunović, S.; Joksović, M. D. Low Cytotoxic Quinoline-4-Carboxylic Acids Derived from Vanillin Precursors as Potential Human Dihydroorotate Dehydrogenase Inhibitors. Bioorganic & Medicinal Chemistry Letters 2021, 46, 128194. https://doi.org/10.1016/j.bmcl.2021.128194." in Bioorganic & Medicinal Chemistry Letters (2021),
https://hdl.handle.net/21.15107/rcub_cherry_4551 .