Synthesis, Crystal Structure, and Biological Activity of a Multidentate Calix[4]arene Ligand Doubly Functionalized by 2-Hydroxybenzeledene-Thiosemicarbazone
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of the Ligand and Metal Derivatives
2.2. Characterization
2.3. Solid-State Structure of L
2.4. Determination of Antimicrobial and Antifungal Activities
2.5. Cytotoxicity Assay
2.6. Morphology of Cell Nuclei
2.7. Biocompatibility Evaluation
3. Materials and Methods
3.1. Reagents
3.2. Instrumentation
3.3. Synthesis
3.3.1. Preparation of Ligand
3.3.2. Preparation of Metal Derivatives
Cobalt Derivative:
Nickel Derivative:
Copper Derivative:
Zinc Derivative:
3.4. Crystal Structure Determination and Refinement of L
3.5. Antimicrobial Studies
3.5.1. Preparation of Microorganism’s Suspensions
3.5.2. Broth Microdilution Method
3.6. Cell Culture and MTT Assay
3.7. DAPI Staining
3.8. Erythrocytes Hemolysis Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compound L are available from the authors. |
D •••A a | d (D•••A) (Å) |
---|---|
Intramolecular H-Bonds on Calix[4]arene Lower Rim | |
O(1B)•••O(1A) | 2.871 |
O(1D)•••O(1C) | 2.922 |
Intramolecular H-Bonds on Thiosemicarbazone Substituents | |
O(2A)•••N(3A) | 2.710 |
O(2C)•••N(3C) | 2.742 |
Interactions between Water Molecule and Thiosemicarbazone Substituents b | |
N(1A)•••O(1W) | 2.978 |
N(1C)•••O(1W) | 3.185 |
O(2A)•••O(1W) | 2.850 (phenol hydroxy) |
O(2C)•••O(1W) | 3.051 (phenol hydroxy) |
Interactions between Water Molecule and Calix[4]arene Lower Rim Oxygen Atoms b | |
O(1D)•••O(1W) | 2.872 (hydroxy) |
O(1B)•••O(1W) | 2.986 (hydroxy) |
O(1C)•••O(1W) | 3.094 (alkoxy) |
O(1A)•••O(1W) | 3.258 (alkoxy) |
Microorganism | S. aureus | B. subtilis | E. coli | P. aeruginosa | C. albicans | C. glabrata |
---|---|---|---|---|---|---|
Ligand L | - | 31.25 | 31.25/31.25 | 31.25/- | 31.25/125 | - |
Complex Co | - | 31.25/1000 | 31.25/31.25 | 31.25/250 | 62.5/- | - |
Complex Ni | - | 31.25 | 31.25/31.25 | 31.25/2000 | - | - |
Complex Cu | 31.25 | 31.25 | 31.25/31.25 | 31.25/500 | - | - |
Complex Zn | - | 31.25 | 31.25/31.25 | 31.25/31.25 | - | - |
Gentamicin * | 0.12/0.25 | 2/2 | 0.5/0.5 | 2/2 | - | - |
Nystatin * | - | - | - | - | 1.25 | 0.625 |
Compound | Saos-2 | MG-63 |
---|---|---|
Ligand L | <25 | >200 |
Complex Co | 80 | 195 |
Complex Ni | 62 | 173 |
Complex Cu | 43 | 140 |
Complex Zn | >200 | >200 |
MTX | 7.9 | 14.5 |
DOX | 2.1 | 10.1 |
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Bahojb Noruzi, E.; Shaabani, B.; Geremia, S.; Hickey, N.; Nitti, P.; Kafil, H.S. Synthesis, Crystal Structure, and Biological Activity of a Multidentate Calix[4]arene Ligand Doubly Functionalized by 2-Hydroxybenzeledene-Thiosemicarbazone. Molecules 2020, 25, 370. https://doi.org/10.3390/molecules25020370
Bahojb Noruzi E, Shaabani B, Geremia S, Hickey N, Nitti P, Kafil HS. Synthesis, Crystal Structure, and Biological Activity of a Multidentate Calix[4]arene Ligand Doubly Functionalized by 2-Hydroxybenzeledene-Thiosemicarbazone. Molecules. 2020; 25(2):370. https://doi.org/10.3390/molecules25020370
Chicago/Turabian StyleBahojb Noruzi, Ehsan, Behrouz Shaabani, Silvano Geremia, Neal Hickey, Patrizia Nitti, and Hossein Samadi Kafil. 2020. "Synthesis, Crystal Structure, and Biological Activity of a Multidentate Calix[4]arene Ligand Doubly Functionalized by 2-Hydroxybenzeledene-Thiosemicarbazone" Molecules 25, no. 2: 370. https://doi.org/10.3390/molecules25020370