Photo-sensitive Antibacterial Activity of o-Phenylenediamine Carbon Dots

Koranat Dechsri; Cheewita  Suwanchawalit; Auayporn Apirakaramwong; Prasopchai  Patrojanasophon; Theerasak  Rojanarata; Praneet  Opanasopit; Supusson  Pengnam; Thapakorn  Charoenying

doi:10.59796/jcst.V14N2.2024.36

Authors

Koranat Dechsri Pharmaceutical Development of Green Innovations Group (PDGIG), Faculty of Pharmacy, Silpakorn University, Nakhon Pathom 73000, Thailand
Cheewita Suwanchawalit Department of Chemistry, Faculty of Science, Silpakorn University, Nakhon Pathom 73000, Thailand
Auayporn Apirakaramwong Department of Biomedicine and Health Informatics, Faculty of Pharmacy, Silpakorn University, Nakhon Pathom 73000, Thailand
Prasopchai Patrojanasophon Pharmaceutical Development of Green Innovations Group (PDGIG), Faculty of Pharmacy, Silpakorn University, Nakhon Pathom 73000, Thailand
Theerasak Rojanarata Pharmaceutical Development of Green Innovations Group (PDGIG), Faculty of Pharmacy, Silpakorn University, Nakhon Pathom 73000, Thailand
Praneet Opanasopit Pharmaceutical Development of Green Innovations Group (PDGIG), Faculty of Pharmacy, Silpakorn University, Nakhon Pathom 73000, Thailand
Supusson Pengnam Pharmaceutical Development of Green Innovations Group (PDGIG), Faculty of Pharmacy, Silpakorn University, Nakhon Pathom 73000, Thailand
Thapakorn Charoenying Pharmaceutical Development of Green Innovations Group (PDGIG), Faculty of Pharmacy, Silpakorn University, Nakhon Pathom 73000, Thailand

DOI:

https://doi.org/10.59796/jcst.V14N2.2024.36

Keywords:

antibacterial activity, carbon dots, o-phenylenediamine, photodynamic therapy, photosensitizers, reactive oxygen species, Staphylococcus aureus

Abstract

Carbon dots (CDs) are among the famous nanoparticles that have been widely developed due to high biocompatibility, low toxicity, ease of preparation, excellent photoluminescent properties, and outstanding application in biomedicine. Among the various biomedical activities of CDs, they can be applied as antibacterial agents because of their photodynamic properties. Photodynamic therapy (PDT) has been considered an alternative antibacterial agent because of its non-invasive nature and minimal side effects, especially in terms of improving antibacterial activity against multidrug resistant bacteria when compared with traditional antibiotics. In this research, we developed CDs from o-phenylenediamine (OP). The o-phenylenediamine CDs (OPCDs) were synthesized via a hydrothermal method at 180°C for 3 h. After that, they revealed a spherical shape with a size range of 16.38 ± 2.64 nm. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of OPCDs against Staphylococcus aureus (S. aureus) for both light exposure and without light exposure groups were significantly greater than the OP solution because the OPCDs could generate reactive oxygen species (ROS) via a photodynamic mechanism leading to the bacteria cell death. Therefore, the created OPCDs may have the capability to be utilized for treating skin infections caused mainly by S. aureus. In conclusion, OPCDs could be proposed as nanomaterials that enhance antibacterial activity and provide photodynamic properties.

References

Bhattacharyya, A., Jameei, A., Garai, A., Saha, R., Karande, A. A., & Chakravarty, A. R. (2018). Mitochondria-localizing BODIPY-copper(ii) conjugates for cellular imaging and photo-activated cytotoxicity forming singlet oxygen. Dalton Transactions, 47(14), 5019-5030. https://doi.org/10.1039/C8DT00255J

Budimir, M., Marković, Z., Vajdak, J., Jovanović, S., Kubat, P., Humpoliček, P., ... & Marković, B. T. (2021). Enhanced visible light-triggered antibacterial activity of carbon quantum dots/polyurethane nanocomposites by gamma rays induced pre-treatment. Radiation Physics and Chemistry, 185, Article 109499. https://doi.org/10.1016/j.radphyschem.2021.109499

Diez-Pascual, A. M. (2018). Antibacterial Activity of Nanomaterials. Nanomaterials (Basel), 8(6), 359-364. https://doi.org/10.3390/nano8060359

Duan, Q., Ma, Y., Che, M., Zhang, B., Zhang, Y., Li, Y., ... & Sang, S. (2019). Fluorescent carbon dots as carriers for intracellular doxorubicin delivery and track. Journal of Drug Delivery Science and Technology, 49, 527-533. https://doi.org/10.1016/j.jddst.2018.12.015

Ehtesabi, H., & Massah, F. (2021). Improvement of hydrophilicity and cell attachment of polycaprolactone scaffolds using green synthesized carbon dots. Materials Today Sustainability, 13, Article 100075. https://doi.org/10.1016/j.mtsust.2021.100075

Feng, J., Chen, S., Yu, Y.-L., & Wang, J.-H. (2020). Red-emission hydrophobic porphyrin structure carbon dots linked with transferrin for cell imaging. Talanta, 217, Article 121014. https://doi.org/10.1016/j.talanta.2020.121014

Hetta, H. F., Ramadan, Y. N., Al-Harbi, A. I., A. Ahmed, E., Battah, B., Abd Ellah, N. H., ... & Donadu, M. G. (2023). Nanotechnology as a Promising Approach to Combat Multidrug Resistant Bacteria: A Comprehensive Review and Future Perspectives. Biomedicines, 11(2), 413-435. https://doi.org/10.3390/biomedicines11020413

Hu, X., Huang, Y. Y., Wang, Y., Wang, X., & Hamblin, M. R. (2018). Antimicrobial Photodynamic Therapy to Control Clinically Relevant Biofilm Infections. Frontiers in Microbiology, 9, Article 1299. https://doi.org/10.3389/fmicb.2018.01299

Kong, T., Hao, L., Wei, Y., Cai, X., & Zhu, B. (2018). Doxorubicin conjugated carbon dots as a drug delivery system for human breast cancer therapy. Cell Proliferation, 51(5), Article e12488. https://doi.org/10.1111/cpr.12488

Li, Z., Liu, C., Abroshan, H., Kauffman, D. R., & Li, G. (2017). Au38S2(SAdm)20 Photocatalyst for One-Step Selective Aerobic Oxidations. ACS Catalysis, 7(5), 3368-3374. https://doi.org/10.1021/acscatal.7b00239

Liu, C., Zhang, P., Zhai, X., Tian, F., Li, W., Yang, J., ... & Liu, W. (2012). Nano-carrier for gene delivery and bioimaging based on carbon dots with PEI-passivation enhanced fluorescence. Biomaterials, 33(13), 3604-3613. https://doi.org/10.1016/j.biomaterials.2012.01.052

Liu, Y., Roy, S., Sarkar, S., Xu, J., Zhao, Y., & Zhang, J. (2021). A review of carbon dots and their composite materials for electrochemical energy technologies. Carbon Energy, 3(5), 795-826. https://doi.org/10.1002/cey2.134

Mansuriya, B. D., & Altintas, Z. (2021). Carbon Dots: Classification, Properties, Synthesis, Characterization, and Applications in Health Care-An Updated Review (2018-2021). Nanomaterials (Basel), 11(10), 2525-2579. https://doi.org/10.3390/nano11102525

Maťátková, O., Michailidu, J., Miškovská, A., Kolouchová, I., Masák, J., & Čejková, A. (2022). Antimicrobial properties and applications of metal nanoparticles biosynthesized by green methods. Biotechnology Advances, 58, Article 107905. https://doi.org/10.1016/j.biotechadv.2022.107905

Mosquera, J., Garcia, I., & Liz-Marzan, L. M. (2018). Cellular Uptake of Nanoparticles versus Small Molecules: A Matter of Size. Accounts of Chemical Research, 51(9), 2305-2313. https://doi.org/10.1021/acs.accounts.8b00292

Mura, S., Ludmerczki, R., Stagi, L., Garroni, S., Carbonaro, C. M., Ricci, P. C., ... & Innocenzi, P. (2020). Integrating sol-gel and carbon dots chemistry for the fabrication of fluorescent hybrid organic-inorganic films. Scientific Reports, 10(1), 4770-4781. https://doi.org/10.1038/s41598-020-61517-x

Pandit, C., Roy, A., Ghotekar, S., Khusro, A., Islam, M. N., Emran, T. B., ... & Bradley, D. A. (2022). Biological agents for synthesis of nanoparticles and their applications. Journal of King Saud University - Science, 34(3), Article 101869. https://doi.org/10.1016/j.jksus.2022.101869

Qie, X., Zan, M., Gui, P., Chen, H., Wang, J., Lin, K., ... & Song, Y. (2022). Design, Synthesis, and Application of Carbon Dots With Synergistic Antibacterial Activity. Front Bioeng Biotechnol, 10, Article 894100. https://doi.org/10.3389/fbioe.2022.894100

Sweet, M., & Singleton, I. (2011). Silver nanoparticles: a microbial perspective. Advances in Applied Microbiology, 77, 115-133. https://doi.org/10.1016/B978-0-12-387044-5.00005-4

Wang, S., Chen, L., Wang, J., Du, J., Li, Q., Gao, Y., ... & Yang, Y. (2020). Enhanced-fluorescent imaging and targeted therapy of liver cancer using highly luminescent carbon dots-conjugated foliate. Materials Science and Engineering: C, 116, Article 111233. https://doi.org/10.1016/j.msec.2020.111233

Xin, Q., Shah, H., Nawaz, A., Xie, W., Akram, M. Z., Batool, A., ... & Gong, J. R. (2019). Antibacterial Carbon-Based Nanomaterials. Advanced Materials, 31(45), Article e1804838. https://doi.org/10.1002/adma.201804838

Yu, R., Liang, S., Ru, Y., Li, L., Wang, Z., Chen, J., & Chen, L. (2022). A Facile Preparation of Multicolor Carbon Dots. Nanoscale Research Letters, 17(1), Article 32. https://doi.org/10.1186/s11671-022-03661-z