Bioactive Properties of a Novel Antibacterial Dye Obtained from Laccase-Mediated Oxidation of 8-Anilino-1-naphthalenesulfonic Acid
Abstract
:1. Introduction
2. Results and Discussion
2.1. Laccase-Mediated Transformation of 8-Anilinonaphthalenesulfonic Acid
2.2. Properties of the Dye
3. Materials and Methods
3.1. Chemicals
3.2. Preparations of Purified Laccase
3.3. Substrate Characterisation
3.4. Laccase-Mediated Transformation of Substrate ANS—Optimisation Process
3.5. Large-Scale Synthesis of the Dye
3.6. Characterisation of the Dye
3.7. Properties of Dye
3.7.1. Toxicity
Environmental Toxicity
Cytotoxicity
3.7.2. Antimicrobial Properties
3.7.3. Antioxidant Properties
3.7.4. Dyeing Properties
3.7.5. Allergenicity—Patch Test
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Chemical Structure | Oxygen Demand (nM/min/mL) | Eo vs. NHE (V) | Optimal pH | KM (mM) | λ max1 (nm) | λ max2 (nm) |
---|---|---|---|---|---|---|
| 1583 | 0.768 | 4 | 0.435 | 340–350 | 420–440 |
Tested Compounds | EC50 (mg/mL) |
---|---|
ANS | 0.019 |
Dye | 0.067 |
Tested Compounds | Colon Epithelial Cells | Fibroblasts | ||
---|---|---|---|---|
LDH | MTT | LDH | MTT | |
ANS | 0.382 | 0.322 | 0.247 | 0.295 |
Dye | 0.436 | 0.473 | 0.321 | 0.363 |
Tested Compounds | S. aureus (0.51 × 102 cfu/mL) | S. epidermidis (0.05 × 102 cfu/mL) | Inhibition Zone Caused by Dye (S. aureus) | ||
---|---|---|---|---|---|
MIC | MBC | MIC | MBC | ||
ANS | 0.2 | 0.4 | 0.025 | 0.4 | |
Dye | 0.4 | 1.0 | 0.025 | 0.1 |
Tested Compounds | Method | ||
---|---|---|---|
ABTS | DPPH | Luminol | |
ANS | 0.027 | 153 | 6 |
Dye | 0.115 | 660 | 42 |
Tested Parameters of Colour Fastness (ISO Standard) | Scale * | |
---|---|---|
Artificial light (1) (PN-EN ISO 105-B02:2014-11) | (a) | 6–7 |
Distilled water (2) (PN-EN ISO 105-E01:2013-06) | (a) | 4 |
(b) | 4–5 | |
(c) | 4 | |
Washing 40 °C (2) (PN-EN ISO 105-C06:2010) | (a) | 2 |
(b) | 4–5 | |
(c) | 4–5 | |
Alkaline sweat (2) (PN-EN ISO 105-E04:2013-06) | (a) | 4–5 |
(b) | 3–4 | |
(c) | 3 | |
Acidic sweat (2) (PN-EN ISO 105-E01:2013-06) | (a) | 4–5 |
(b) | 4–5 | |
(c) | 4 | |
Dry rubbing (2) (PN-EN ISO 105-X12:2005) | (b) | 3 |
Wet rubbing (2) (PN-EN ISO 105-X12:2005) | (b) | 3–4 |
Probant No. | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 | 32 | 33 | 34 | 35 | 36 | 37 | 38 | 39 | 40 | 41 | 42 | 43 | 44 | 45 | 46 | 47 | 48 | 49 | 50 | |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Sex (1) | M | F | F | F | F | F | F | F | F | M | M | F | F | F | F | F | M | F | F | F | M | M | M | F | M | M | F | M | F | M | F | M | M | M | M | F | F | F | F | F | F | F | F | F | F | M | F | F | F | F | |
Age | 33 | 28 | 50 | 54 | 42 | 39 | 26 | 70 | 49 | 51 | 70 | 33 | 19 | 53 | 22 | 22 | 30 | 23 | 50 | 70 | 40 | 69 | 23 | 70 | 36 | 65 | 70 | 40 | 37 | 40 | 20 | 67 | 38 | 69 | 66 | 33 | 65 | 35 | 40 | 31 | 40 | 41 | 24 | 24 | 35 | 27 | 54 | 31 | 31 | 29 | |
Skin type (2) | S | S | S | SA | S | S | S | S | S | SA | S | S | S | S | S | S | SA | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | S | SA | SA | S | |
Skin response (3) | 48 h | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | |
72 h | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
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Polak, J.; Grąz, M.; Wlizło, K.; Szałapata, K.; Kapral-Piotrowska, J.; Paduch, R.; Jarosz-Wilkołazka, A. Bioactive Properties of a Novel Antibacterial Dye Obtained from Laccase-Mediated Oxidation of 8-Anilino-1-naphthalenesulfonic Acid. Molecules 2022, 27, 487. https://doi.org/10.3390/molecules27020487
Polak J, Grąz M, Wlizło K, Szałapata K, Kapral-Piotrowska J, Paduch R, Jarosz-Wilkołazka A. Bioactive Properties of a Novel Antibacterial Dye Obtained from Laccase-Mediated Oxidation of 8-Anilino-1-naphthalenesulfonic Acid. Molecules. 2022; 27(2):487. https://doi.org/10.3390/molecules27020487
Chicago/Turabian StylePolak, Jolanta, Marcin Grąz, Kamila Wlizło, Katarzyna Szałapata, Justyna Kapral-Piotrowska, Roman Paduch, and Anna Jarosz-Wilkołazka. 2022. "Bioactive Properties of a Novel Antibacterial Dye Obtained from Laccase-Mediated Oxidation of 8-Anilino-1-naphthalenesulfonic Acid" Molecules 27, no. 2: 487. https://doi.org/10.3390/molecules27020487