From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials in the Synthesis of Novel Hesperetin Derivatives
2.2. Apparatus
2.2.1. Characterization of HABH
2.2.2. Characterization of Copper(II) Complex with HABH in Solid State
2.2.3. Stoichiometry Determination of the Copper(II) Complex with HABH in Solution
Potentiometry
Spectroscopy and Computational Details
2.3. DNA Studies
2.3.1. Electronic Absorption Titration
2.3.2. Competitive Binding Fluorescence Measurement
2.3.3. Circular Dichroism Spectroscopy Analysis
2.4. Antibacterial Activity
2.5. Antibiofilm Activity
3. Results and Discussion
3.1. Characterization of the Complex CuHABH
3.1.1. IR Spectral Studies
3.1.2. EPR Spectral Studies in Solid State and Solution
3.2. Interaction of the Compounds with CT DNA
3.3. Antibacterial Activity of the HABH and CuHABH Complexes
3.4. Antibiofilm Activity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Species | gx | gy | gz | PD(gz) a | Ax(Cu) b | Ax(Cu) b | Ax(Cu) b | PD(Az) a |
---|---|---|---|---|---|---|---|---|
Powder | c | c | 2.232 | −1.0 | c | c | −193.4 | 3.9 |
DMF | 2.040 | 2.060 | 2.240 | −1.4 | −11.0 | −14.0 | −192.5 | 4.4 |
DMSO | 2.038 | 2.061 | 2.241 | −1.4 | −12.0 | −13.0 | −194.0 | 3.6 |
Aqueous solution d | 2.039 | 2.061 | 2.245 | −1.6 | −11.5 | −13.0 | −188.8 | 6.4 |
DFT calculated e | 2.061 | 2.062 | 2.209 | – | −7.7 | −18.5 | −200.9 | – |
Compound | Kb [M−1] | λmax [nm] | (Afree − Abound)/Afree [%]max (+)Hyperchromism/ (−)Hypochromism |
---|---|---|---|
HESP | 1.20 (±0.15) × 104 | 323 | +5.57 |
HABH | 4.00 (±0.22) × 105 | 330 | −41.78 |
CuHABH | 5.00 (±0.18) × 105 | 371 | −56.52 |
Compound | KSV [M−1] | C50 [μM] | Kapp [M−1] * | Kq [M−1] | n | Ka [M−1] ** |
---|---|---|---|---|---|---|
Hesperetin | 3.73 (±0.06) × 103 | nd *** | nd *** | 1.43 (±0.20) × 1012 | 0.55 ± 0.04 | 1.58 (±0.20) × 103 |
HABH | 3.88 (±0.13) × 104 | 40.4 | 1.86 × 106 | 1.49 (±0.15) × 1013 | 1.01 (±0.03) | 2.78 (±0.15) × 104 |
CuHABH | 1.31 (±0.06) × 105 | 38.4 | 1.95 × 106 | 5.04 (±0.14) × 1013 | 1.63 (±0.03) | 6.74 (±0.14) × 104 |
Compound 0.1 μM | Zone of inhibition [mm] | ||||||
---|---|---|---|---|---|---|---|
Salmonella Choleraesuis ATCC 7001 | Salmonella Typhimurium ATCC 14028 | Escherichia coli ATCC 10536 | Staphylococcus aureus ATCC 25923 | Staphylococcus aureus ATCC 27734 | Listeria monocytogenes ATCC 19111 | Listeria monocytogenes ATCC 19115 | |
CuHABH | 0.0 ± 0.0 aA | 0.0 ± 0.0 aA | 0.0 ± 0.0 aA | 10.5 ± 0.50 aA | 10.5 ± 0.50 aA | 0.0 ± 0.0 aA | 12.5 ± 0.50 aA |
HABH | 0.0 ± 0.0 aA | 0.0 ± 0.0 aA | 0.0 ± 0.0 aA | 11.5 ± 0.50 aA | 12.0 ± 0.0 bA | 0.0 ± 0.0 aA | 13.5 ± 0.50 bA |
HESP | 0.0 ± 0.0 aA | 0.0 ± 0.0 aA | 0.0 ± 0.0 aA | 9.0 ± 0.0 bA | 9.0 ± 0.50 cA | 0.0 ± 0.0 aA | 14.5 ± 0.50 cA |
DMSO | 0.0 ± 0.0 aA | 0.0 ± 0.0 aA | 0.0 ± 0.0 aA | 0.0 ± 0.0 cA | 0.0 ± 0.0 dA | 0.0 ± 0.0 aA | 0.0 ± 0.0 dA |
Vancomycin | 10.5 ± 0.00B | Nd | 14.5 ± 0.50B | 16.00 ± 0.00 B | 17.5 ± 0.00 B | 20.0 ± 0.80 B | 30.5 ± 0.50 B |
Ampicillin | Nd | 12.60 ± 0.90 B | Nd | Nd | Nd | 21.0 ± 0.80 B | 16.5 ± 0.50 C |
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Sykuła, A.; Łodyga-Chruścińska, E.; Garribba, E.; Kręgiel, D.; Dzeikala, A.; Klewicka, E.; Piekarska-Radzik, L. From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects. Molecules 2022, 27, 845. https://doi.org/10.3390/molecules27030845
Sykuła A, Łodyga-Chruścińska E, Garribba E, Kręgiel D, Dzeikala A, Klewicka E, Piekarska-Radzik L. From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects. Molecules. 2022; 27(3):845. https://doi.org/10.3390/molecules27030845
Chicago/Turabian StyleSykuła, Anna, Elżbieta Łodyga-Chruścińska, Eugenio Garribba, Dorota Kręgiel, Aliaksandr Dzeikala, Elżbieta Klewicka, and Lidia Piekarska-Radzik. 2022. "From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects" Molecules 27, no. 3: 845. https://doi.org/10.3390/molecules27030845