Design, Synthesis, and Anticancer and Antibacterial Activities of Quinoline-5-Sulfonamides
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biological Screening
2.2.1. In Vitro Cell Viability
2.2.2. Additional Antiproliferative Tests
Violet-WST-LDH
Wound Healing Assay
Transcriptional Activity
2.2.3. In Vitro Antimicrobial Activity
3. Materials and Methods
3.1. Chemistry
3.2. Synthesis
3.2.1. Synthesis of 8-Hydroxyquinoline-5-Sulfonyl Chloride (2)
3.2.2. Synthesis of 8-Hydroxyquinoline-5-Sulfonamides (3)
3.2.3. Synthesis of 8-Methoxyquinoline (4)
3.2.4. Synthesis of 8-Methoxyquinoline-5-Sulfochloride (5)
3.2.5. Synthesis of 8-Methoxyquinoline-5-Sulfonamides (6)
3.2.6. Synthesis of 1,2,3-Triazole Derivatives of 8-Methoxyquinoline-5-Sulfonamide (7)
Procedure A: Preparation of Derivative 7a
Procedure B: Preparation of Derivatives 7b, c, and 7e–h
Procedure C: Preparation of Derivative 7d
3.3. Biological Evaluation
3.3.1. Cell Culture
3.3.2. Effect of Compounds on Number and Viability of Cells
3.3.3. Wound Healing Assay
3.3.4. Transcriptional Activity of H3, BCL-2, BAX, P21, and P53 Genes
3.3.5. In Vitro Antibacterial Evaluation
3.3.6. Determination of Minimum Bactericidal Concentrations
3.3.7. MTT Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Comp. | IC50 [µM] | |||
---|---|---|---|---|
C-32 | MDA-MB-231 | A549 | HFF-1 | |
3a | 19.8 ±1.1 | 23.3 ± 1.2 | 23.1 ± 0.7 | ˃100 |
3b | 22.1 ±1.5 | 55.8 ± 1.9 | 17.2 ± 1.5 | ˃100 |
3c | 9.8 ± 0.6 | 2.2 ± 0.1 | 13.9 ± 0.6 | ˃100 |
3d | 10.4 ± 0.5 | 45.3 ± 5.4 | 12.9 ± 1.1 | ˃100 |
3e | 8.6 ± 0.9 | 15.2 ± 0.8 | 11.5 ± 0.7 | ˃100 |
3f | 29.6 ± 2.6 | 14.7 ± 1.2 | 19.1 ± 0.8 | 28.1 ± 2.2 |
6a | ˃100 | ˃100 | ˃100 | – |
6b | 40.6 ± 4.9 | ˃100 | ˃100 | – |
6c | 70.1 ± 8.4 | ˃100 | ˃100 | – |
6d | 86.4 ± 3.9 | ˃100 | ˃100 | – |
6e | 32.2 ± 4.8 | ˃100 | ˃100 | – |
6f | 27.7 ± 2.2 | ˃100 | ˃100 | – |
CPT | 10.6 ± 0.5 | 10.3 ± 0.7 | 17.3 ± 1.3 | 26.0 ± 2.0 |
DOX | 0.3 ± 0.02 | 0.6 ± 0.1 | 1.0 ± 0.1 | 1.4 ± 0.1 |
Comp. | IC50 [µM] | ||
---|---|---|---|
C-32 | MDA-MB-231 | A549 | |
7a | ˃100 | ˃100 | ˃100 |
7b | ˃100 | ˃100 | ˃100 |
7c | 89.0 ± 3.5 | ˃100 | ˃100 |
7d | ˃100 | ˃100 | ˃100 |
7e | ˃100 | 72.2 ± 3.6 | ˃100 |
7f | ˃100 | ˃100 | ˃100 |
7g | 42.6 ± 3.4 | ˃100 | ˃100 |
7h | ˃100 | ˃100 | ˃100 |
CPT | 10.6 ± 0.5 | 10.3 ± 0.7 | 17.3 ± 1.3 |
DOX | 0.3 ± 0.02 | 0.6 ± 0.1 | 1.0 ± 0.1 |
Comp. | MIC/MBC [µM] | ||||||
---|---|---|---|---|---|---|---|
SA | MRSA1 | MRSA2 | EF | VRE1 | VRE2 | VRE3 | |
3a | 122/122 | 122/122 | 244/244 | 977/>977 | 977/NT | 977/NT | 977/NT |
3b | 55.2/110 | 55.2/110 | 110/110 | 883/>883 | 883/NT | 883/NT | 883/NT |
3c | 29.0/29.0 | 29.0/29.0 | 29.0/29.0 | 464/>464 | 464/NT | 464/NT | 464/NT |
3d | 45.2/45.2 | 45.2/45.2 | 90.4/90.4 | 362/362 | 362/NT | 362/NT | 362/NT |
3e | 45.2/45.2 | 45.2/90.4 | 90.4/90.4 | 362/362 | 362/NT | 362/NT | 362/NT |
3f | 45.2/45.2 | 45.2/90.4 | 90.4/90.4 | 362/362 | 362/NT | 362/NT | 362/NT |
AMP | 5.72/5.72 | >45.8/>45.8 | >45.8/>45.8 | 2.81/2.81 | 11.5/11.5 | 11.5/11.5 | 11.5/11.5 |
OXA | 1.25/1.25 | 79.8/79.8 | 29.7/29.7 | – | – | – | – |
CPX | 1.51/3.02 | 48.3/96.6 | 193/386 | 1.51/3.02 | 1.51/3.02 | 3.02/3.02 | 193/386 |
Comp. | Conc. | S. aureus Respiration Inhibition [%] |
---|---|---|
3a | 1× MIC (1× MBC) | 92.5 |
3b | 2× MIC (2× MBC) | 94.4 |
3c | 2× MIC (2× MBC) | 95.2 |
3d | 1× MIC (1× MBC) | 73.0 |
3e | 1× MIC (1× MBC) | 73.7 |
3f | 1× MIC (1× MBC) | 81.6 |
APM | 16× MIC (>16× MBC) | 81.9 |
CPX | 32× MIC (16× MBC) | 95.0 |
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Zieba, A.; Pindjakova, D.; Latocha, M.; Plonka-Czerw, J.; Kusmierz, D.; Cizek, A.; Jampilek, J. Design, Synthesis, and Anticancer and Antibacterial Activities of Quinoline-5-Sulfonamides. Molecules 2024, 29, 4044. https://doi.org/10.3390/molecules29174044
Zieba A, Pindjakova D, Latocha M, Plonka-Czerw J, Kusmierz D, Cizek A, Jampilek J. Design, Synthesis, and Anticancer and Antibacterial Activities of Quinoline-5-Sulfonamides. Molecules. 2024; 29(17):4044. https://doi.org/10.3390/molecules29174044
Chicago/Turabian StyleZieba, Andrzej, Dominika Pindjakova, Malgorzata Latocha, Justyna Plonka-Czerw, Dariusz Kusmierz, Alois Cizek, and Josef Jampilek. 2024. "Design, Synthesis, and Anticancer and Antibacterial Activities of Quinoline-5-Sulfonamides" Molecules 29, no. 17: 4044. https://doi.org/10.3390/molecules29174044