Preliminary Studies of Antimicrobial Activity of New Synthesized Hybrids of 2-Thiohydantoin and 2-Quinolone Derivatives Activated with Blue Light
<p>(<b>A</b>) Time-resolved singlet oxygen (<sup>1</sup>O<sub>2</sub>, <sup>1</sup>Δ<sub>g</sub>) phosphorescence at 1270 nm detected in DMSO: ethanol solutions (1:1, <span class="html-italic">v</span>/<span class="html-italic">v</span>) of perinaphtenone (PN) and selected samples (<b>4a</b> and <b>5a</b>) upon excitation with 420 nm laser pulses at 35% and 100% of laser energy, respectively. (<b>B</b>) Dependence of the initial intensity of <sup>1</sup>O<sub>2</sub> (<sup>1</sup>Δ<sub>g</sub>) phosphorescence generated by PN and selected samples on relative excitation energy.</p> "> Figure 2
<p>Singlet oxygen (<sup>1</sup>O<sub>2</sub>, <sup>1</sup>Δ<sub>g</sub>) phosphorescence decay detected at 1270 nm after laser excitation of selected samples: <b>4b</b> (<b>A</b>) and <b>4d</b> (<b>B</b>) in DMSO: ethanol solution (1:1, <span class="html-italic">v</span>/<span class="html-italic">v</span>) with 420 nm. Studied samples solutions were equilibrated with air (black) or saturated with argon (grey).</p> "> Figure 3
<p>Atom-numbering scheme of the tested compounds.</p> "> Scheme 1
<p>Synthesis of 1-acetyl-2-thiohydantoin and its condensation with 2-chloroquinoline-3-carbaldehyde derivatives.</p> "> Scheme 2
<p>Synthesis of 2-thiohydantoin-3-acetic acid its condensation with 2-chloro-3-quinolinecarboxaldehyde derivatives.</p> ">
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Direct Detection of Singlet Oxygen (1Δg, 1O2*) Phosphorescence at 1270 nm
2.3. Antibacterial Activity
2.3.1. Antibacterial Activity under Dark Conditions
2.3.2. Antibacterial Activity under Blue Light Irradiation
2.3.3. Structure and Microbiological Activity Relationship
3. Materials and Methods
3.1. Chemistry
3.1.1. General Procedure for the Condensation of 1-acetyl-2-thiohydantoin and 2-thiohydantoin-3-acetic Acid with 2-chloro-3-quinolinecarboxaldehyde Derivatives
3.1.2. Spectrometry and Spectroscopy
3.2. Direct Detection of Singlet Oxygen (1Δg, 1O2*) Phosphorescence at 1270 nm
3.3. Antibacterial Activity Assay In Vitro
3.3.1. Bacterial Strains
3.3.2. Antibacterial Assay Preparation
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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Sample | Relative Efficiency of 1O2 (1Δg) Generation (%) |
---|---|
PN (standard) | 100 |
4c | 12.43 (±0.02) |
4a | 10.90 (±1.07) |
4b | 10.23 (±0.93) |
4f | 9.81 (±0.24) |
4d | 8.54 (±0.23) |
5c | 7.98 (±0.56) |
4e | 7.71 (±0.98) |
5a | 5.91 (±0.66) |
5f | 5.77 (±1.14) |
5d | 5.66 (±0.15) |
5b | 4.93 (±0.22) |
5e | 3.93 (±2.10) |
Microorganism | 4a | 4b | 4c | 4d | 4e | |||||
---|---|---|---|---|---|---|---|---|---|---|
MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | |
E. coli | nd | nd | nd | nd | nd | nd | nd | nd | 500 | nd |
P. aeruginosa | nd | nd | nd | nd | nd | nd | nd | nd | 1000 | nd |
K. pneumoniae | nd | nd | nd | nd | nd | nd | 250 | nd | 31.25 | 1000 |
E. faecalis | nd | nd | 7.82 | 250 | nd | nd | 7.82 | 250 | 7.82 | 500 |
S. aureus | nd | nd | 7.82 | 125 | nd | nd | 125 | nd | 31.25 | 1000 |
B. subtilis | nd | nd | nd | nd | nd | nd | 7.82 | 250 | 62.5 | nd |
Microorganism | 4f | 5b | 5c | 5e | 5f | |||||
---|---|---|---|---|---|---|---|---|---|---|
MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | |
E. coli | 62.5 | 1000 | nd | nd | nd | nd | nd | nd | 500 | nd |
P. aeruginosa | 31.25 | 500 | nd | nd | nd | nd | nd | nd | 250 | nd |
K. pneumoniae | 62.5 | 1000 | nd | nd | nd | nd | nd | nd | 250 | nd |
E. faecalis | 62.5 | 1000 | 250 | nd | 62.5 | 1000 | nd | nd | 250 | nd |
S. aureus | 31.25 | 500 | 250 | nd | 62.5 | 1000 | nd | nd | 250 | nd |
B. subtilis | 31.25 | 500 | 250 | nd | 125 | nd | nd | nd | 62.5 | 1000 |
Microorganism | 4b | 4d | 4e | 4f | 5b | 5c | 5f |
---|---|---|---|---|---|---|---|
E. coli | - | - | - | 16 | - | - | - |
P. aeruginosa | - | - | - | 16 | - | - | - |
K. pneumoniae | - | - | 32 | 16 | - | - | - |
E. faecalis | 32 | 32 | 64 | 16 | - | 16 | - |
S. aureus | 16 | - | 32 | 16 | - | 16 | - |
B. subtilis | - | 32 | - | 16 | - | - | 16 |
Microorganism | Ciprofloxacin | ||
---|---|---|---|
MIC (μg/mL) | MBC (μg/mL) | MBC/MIC Ratio | |
E. coli ATCC 25922 | 0.24 | 0.48 | 2 |
P. aeruginosa ATCC 27853 | 0.26 | 0.31 | 1.19 |
K. pneumoniae ATCC 700603 | 7.81 | 7.81 | 1 |
E. faecalis ATCC 29212 | 1 | 1 | 1 |
S. aureus ATCC 29213 | 7.81 | 7.81 | 1 |
B. subtilis ATCC 6633 | 0.98 | 0.98 | 1 |
Microorganism | 4a | 4b | 4c | 4d | 4e | |||||
---|---|---|---|---|---|---|---|---|---|---|
MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | |
E. coli | nd | nd | 125 | 1000 | nd | nd | 7.82 | 250 | 500 | nd |
P. aeruginosa | nd | nd | 7.82 | 250 | 3.91 | 125 | 3.91 | 125 | 3.91 | 3.91 |
K. pneumoniae | nd | nd | 62.5 | 1000 | nd | nd | 62.5 | 1000 | 15.63 | 500 |
E. faecalis | nd | nd | 7.82 | 250 | nd | nd | 7.82 | 250 | 15.63 | 500 |
S. aureus | nd | nd | 7.82 | 125 | nd | nd | 3.91 | 125 | 31.25 | 1000 |
B. subtilis | nd | nd | 7.82 | 125 | nd | nd | 3.91 | 125 | 3.91 | 250 |
Microorganism | 4f | 5b | 5c | 5e | 5f | |||||
---|---|---|---|---|---|---|---|---|---|---|
MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | MIC (μg/mL) | MBC (μg/mL) | |
E. coli | 62.5 | 1000 | nd | nd | nd | nd | nd | nd | 500 | nd |
P. aeruginosa | 7.82 | 125 | nd | nd | 3.91 | 3.91 | nd | nd | 7.82 | 250 |
K. pneumoniae | 62.5 | 1000 | nd | nd | 62.5 | 1000 | nd | nd | 250 | nd |
E. faecalis | 62.5 | 1000 | 31.25 | 1000 | 62.5 | 1000 | nd | nd | 62.5 | nd |
S. aureus | 3.91 | 250 | 125 | 1000 | 62.5 | 1000 | nd | nd | 15.63 | 500 |
B. subtilis | 3.91 | 250 | 125 | 1000 | 3.91 | 250 | nd | nd | 3.91 | 250 |
Microorganism | 4b | 4d | 4e | 4f | 5b | 5c | 5f |
---|---|---|---|---|---|---|---|
E. coli | 8 | 32 | - | 16 | - | - | - |
P. aeruginosa | 32 | 32 | 1 | 16 | - | 1 | - |
K. pneumoniae | 16 | 16 | 32 | 16 | - | 16 | - |
E. faecalis | 32 | 32 | 32 | 16 | 32 | 16 | - |
S. aureus | 16 | 32 | 32 | 64 | 8 | 16 | 32 |
B. subtilis | 16 | 32 | 64 | 64 | 8 | 64 | 64 |
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Kania, A.; Tejchman, W.; Pawlak, A.M.; Mokrzyński, K.; Różanowski, B.; Musielak, B.M.; Greczek-Stachura, M. Preliminary Studies of Antimicrobial Activity of New Synthesized Hybrids of 2-Thiohydantoin and 2-Quinolone Derivatives Activated with Blue Light. Molecules 2022, 27, 1069. https://doi.org/10.3390/molecules27031069
Kania A, Tejchman W, Pawlak AM, Mokrzyński K, Różanowski B, Musielak BM, Greczek-Stachura M. Preliminary Studies of Antimicrobial Activity of New Synthesized Hybrids of 2-Thiohydantoin and 2-Quinolone Derivatives Activated with Blue Light. Molecules. 2022; 27(3):1069. https://doi.org/10.3390/molecules27031069
Chicago/Turabian StyleKania, Agnieszka, Waldemar Tejchman, Anna M. Pawlak, Krystian Mokrzyński, Bartosz Różanowski, Bogdan M. Musielak, and Magdalena Greczek-Stachura. 2022. "Preliminary Studies of Antimicrobial Activity of New Synthesized Hybrids of 2-Thiohydantoin and 2-Quinolone Derivatives Activated with Blue Light" Molecules 27, no. 3: 1069. https://doi.org/10.3390/molecules27031069