Graphical Abstract

Discover the SciOpen Platform and Achieve Your Research Goals with Ease.
Search articles, authors, keywords, DOl and etc.
Selenium (Se) has been defined as the “Janus element”, with one face showing antioxidant activity and the other pro-oxidant activity. The biological effect of Se depends on both dose and speciation. Se nanoparticles are attracting major interest, although their large-scale preparation for biomedical applications is not trivial. We hypothesize that acid anhydride-coated carbon dots (AA-CD) are an attractive platform for preparing nanoparticles containing chemically defined Se. The reaction of AA-CD with 3-selenocyanatopropan-1-amine yields carbon dots bearing selenocyanate and carboxylate groups (CD-SeCN) that allow for tuning the hydrosolubility. CD-SeCN has a Se content of 0.36 µmol per mg of nanoparticles, and they show the typical photoluminescence of carbon dots. The selenocyanate groups (SeCN) exhibited glutathione peroxidase-like activity and cytotoxicity. Data show that antioxidant behavior differs between normal and tumor cells, and the evaluation on HEK293 and A549 cells reveals that the toxicity of CD-SeCN depends on dose, time, and intracellular glutathione (GSH) content. The toxicity of CD-SeCN decreases with the time of incubation and the cell death mechanism switches from necrosis to apoptosis, indicating that CD-SeCN is neutralized. Additionally, high levels of intracellular GSH exert a protective effect. These results support a pharmacological potential in cancers with low levels of intracellular GSH. The use of AA-CD as nanoplatforms is a general strategy that paves the way for the engineering of advanced nanosystems.
Rotruck, J. T.; Pope, A. L.; Ganther, H. E.; Swanson, A. B.; Hafeman, D. G.; Hoekstra, W. G. Selenium: Biochemical role as a component of glutathione peroxidase. Science 1973, 179, 588–590.
Reich, H. J.; Hondal, R. J. Why nature chose selenium. ACS Chem. Biol. 2016, 11, 821–841.
Sies, H.; Jones, D. P. Reactive oxygen species (ROS) as pleiotropic physiological signalling agents. Nat. Rev. Mol. Cell Biol. 2020, 21, 363–383.
Hayes, J. D.; Dinkova-Kostova, A. T.; Tew, K. D. Oxidative stress in cancer. Cancer Cell 2020, 38, 167–197.
Nogueira, C. W.; Barbosa, N. V.; Rocha, J. B. T. Toxicology and pharmacology of synthetic organoselenium compounds: An update. Arch. Toxicol. 2021, 95, 1179–1226.
Wang, J.; Wang, P.; Dong, C. J.; Zhao, Y.; Zhou, J. X.; Yuan, C. L.; Zou, L. L. Mechanisms of ebselen as a therapeutic and its pharmacology applications. Future Med. Chem. 2020, 12, 2141–2160.
Fernandes, A. P.; Gandin, V. Selenium compounds as therapeutic agents in cancer. Biochim. Biophys. Acta (BBA)-Gen. Subj. 2015, 1850, 1642–1660.
Bisht, N.; Phalswal, P.; Khanna, P. K. Selenium nanoparticles: A review on synthesis and biomedical applications. Mater. Adv. 2022, 3, 1415–1431.
Ali, W.; Álvarez-Pérez, M.; Marć, M. A.; Salardón-Jiménez, N.; Handzlik, J.; Domínguez-Álvarez, E. The anticancer and chemopreventive activity of selenocyanate-containing compounds. Curr. Pharmacol. Rep. 2018, 4, 468–481.
Khurana, A.; Tekula, S.; Saifi, M. A.; Venkatesh, P.; Godugu, C. Therapeutic applications of selenium nanoparticles. Biomed. Pharcother. 2019, 111, 802–812.
Nayak, V.; Singh, K. R. B.; Singh, A. K.; Singh, R. P. Potentialities of selenium nanoparticles in biomedical science. New J. Chem. 2021, 45, 2849–2878.
Manjunatha, C.; Rao, P. P.; Bhardwaj, P.; Raju, H.; Ranganath, D. New insight into the synthesis, morphological architectures and biomedical applications of elemental selenium nanostructures. Biomed. Mater. 2021, 16, 022010.
Zambonino, M. C.; Quizhpe, E. M.; Jaramillo, F. E.; Rahman, A.; Santiago Vispo, N.; Jeffryes, C.; Dahoumane, S. A. Green synthesis of selenium and tellurium nanoparticles: Current trends, biological properties and biomedical applications. Int. J. Mol. Sci. 2021, 22, 989.
Yi, C. X.; Yu, Z. H.; Sun, X.; Zheng, X.; Yang, S. Y.; Liu, H. C.; Song, Y.; Huang, X. FA/Mel@ZnO nanoparticles as drug self-delivery systems for RPE protection against oxidative stress. Adv. Nano Res. 2022, 13, 87–96.
Truskewycz, A.; Yin, H.; Halberg, N.; Lai, D. T. H.; Ball, A. S.; Truong, V. K.; Rybicka, A. M.; Cole, I. Carbon dot therapeutic platforms: Administration, distribution, metabolism, excretion, toxicity, and therapeutic potential. Small 2022, 18, 2106342.
Bayda, S.; Amadio, E.; Cailotto, S.; Frión-Herrera, Y.; Perosa, A.; Rizzolio, F. Carbon dots for cancer nanomedicine: A bright future. Nanoscale Adv. 2021, 3, 5183–5221.
Miao, S. H.; Liang, K.; Zhu, J. J.; Yang, B.; Zhao, D. Y.; Kong, B. Hetero-atom-doped carbon dots: Doping strategies, properties and applications. Nano Today 2020, 33, 100879.
Zhou, D. L.; Huang, H.; Yu, J. R.; Hu, Z. M. Lysosome-targetable selenium-doped carbon nanodots for in situ scavenging free radicals in living cells and mice. Microchim. Acta 2021, 188, 223.
Li, F.; Li, T. Y.; Sun, C. X.; Xia, J. H.; Jiao, Y.; Xu, H. P. Selenium-doped carbon quantum dots for free-radical scavenging. Angew. Chem., Int. Ed. 2017, 56, 9910–9914.
Zhang, L.; Sun, C. X.; Tan, Y. Z.; Xu, H. P. Selenium-sulfur-doped carbon dots with thioredoxin reductase activity. CCS Chem. 2021, 4, 2239–2248.
Ortega-Muñoz, M.; Vargas-Navarro, P.; Hernandez-Mateo, F.; Salinas-Castillo, A.; Capitan-Vallvey, L. F.; Plesselova, S.; Salto-Gonzalez, R.; Giron-Gonzalez, M. D.; Lopez-Jaramillo, F. J.; Santoyo-Gonzalez, F. Acid anhydride coated carbon nanodots: Activated platforms for engineering clicked (bio)nanoconstructs. Nanoscale 2019, 11, 7850–7856.
Iwaoka, M.; Tomoda, S. A model study on the effect of an amino group on the antioxidant activity of glutathione peroxidase. J. Am. Chem. Soc. 1994, 116, 2557–2561.
Würth, C.; Grabolle, M.; Pauli, J.; Spieles, M.; Resch-Genger, U. Relative and absolute determination of fluorescence quantum yields of transparent samples. Nat. Protoc. 2013, 8, 1535–1550.
Ortega-Muñoz, M.; Vargas-Navarro, P.; Plesselova, S.; Giron-Gonzalez, M. D.; Iglesias, G. R.; Salto-Gonzalez, R.; Hernandez-Mateo, F.; Delgado, A. V.; Lopez-Jaramillo, F. J.; Santoyo-Gonzalez, F. Amphiphilic-like carbon dots as antitumoral drug vehicles and phototherapeutical agents. Mater. Chem. Front. 2021, 5, 8151–8160.
El-Bayoumy, K. Effects of organoselenium compounds on induction of mouse forestomach tumors by benzo(a)pyrene. Cancer Res. 1985, 45, 3631–3635.
Pinto, J. T.; Sinha, R.; Papp, K.; Facompre, N. D.; Desai, D.; El-Bayoumy, K. Differential effects of naturally occurring and synthetic organoselenium compounds on biomarkers in androgen responsive and androgen independent human prostate carcinoma cells. Int. J. Cancer 2007, 120, 1410–1417.
Nie, Y. S.; Zhong, M.; Li, S. L.; Li, X. L.; Zhang, Y. M.; Zhang, Y. H.; He, X. R. Synthesis and potential anticancer activity of some novel selenocyanates and diselenides. Chem. Biodivers. 2020, 17, e1900603.
He, X. R.; Zhong, M.; Li, S. L.; Li, X. L.; Li, Y. Y.; Li, Z. T.; Gao, Y. G.; Ding, F.; Wen, D.; Lei, Y. C. et al. Synthesis and biological evaluation of organoselenium (NSAIDs-SeCN and SeCF3) derivatives as potential anticancer agents. Eur. J. Med. Chem. 2020, 208, 112864.
Graf, N.; Yegen, E.; Gross, T.; Lippitz, A.; Weigel, W.; Krakert, S.; Terfort, A.; Unger, W. E. S. XPS and NEXAFS studies of aliphatic and aromatic amine species on functionalized surfaces. Surf. Sci. 2009, 603, 2849–2860.
Hola, K.; Zhang, Y.; Wang, Y.; Giannelis, E. P.; Zboril, R.; Rogach, A. L. Carbon dots—Emerging light emitters for bioimaging, cancer therapy and optoelectronics. Nano Today 2014, 9, 590–603.
Ganther, H. E. Selenotyrosine and related phenylalanine derivatives. Bioorgan. Med. Chem. 2001, 9, 1459–1466.
Clark, E. R.; Al-Turaihi, M. A. S. The reaction of o-nitro- and p-nitro-phenyl selenocyanates with arylthiols. J. Organomet. Chem. 1977, 134, 181–187.
Bhabak, K. P.; Mugesh, G. Functional mimics of glutathione peroxidase: Bioinspired synthetic antioxidants. Acc. Chem. Res. 2010, 43, 1408–1419.
Mukherjee, A. J.; Zade, S. S.; Singh, H. B.; Sunoj, R. B. Organoselenium chemistry: Role of intramolecular interactions. Chem. Rev. 2010, 110, 4357–4416.
Reddy, B. S.; Sugie, S.; Maruyama, H.; El-Bayoumy, K.; Marra, P. Chemoprevention of colon carcinogenesis by dietary organoselenium, benzylselenocyanate, in F344 rats. Cancer Res. 1987, 47, 5901–5904.
Zhang, D. C.; Shen, N.; Zhang, J. R.; Zhu, J. M.; Guo, Y.; Xu, L. A novel nanozyme based on selenopeptide-modified gold nanoparticles with a tunable glutathione peroxidase activity. RSC Adv. 2020, 10, 8685–8691.
Ferro, C.; Florindo, H. F.; Santos, H. A. Selenium nanoparticles for biomedical applications: From development and characterization to therapeutics. Adv. Healthc. Mater. 2021, 10, 2100598.
Bhowmick, D.; Mugesh, G. Insights into the catalytic mechanism of synthetic glutathione peroxidase mimetics. Org. Biomol. Chem. 2015, 13, 10262–10272.
Mayer, C. NMR studies of nanoparticles. Annu. Rep. NMR Spectrosc. 2005, 55, 205–258.
Kennedy, L.; Sandhu, J. K.; Harper, M.-E.; Cuperlovic-Culf, M. Role of glutathione in cancer: From mechanisms to therapies. Biomolecules 2020, 10, 1429.
Giustarini, D.; Galvagni, F.; Tesei, A.; Farolfi, A.; Zanoni, M.; Pignatta, S.; Milzani, A.; Marone, I. M.; Dalle-Donne, I.; Nassini, R. et al. Glutathione, glutathione disulfide, and S-glutathionylated proteins in cell cultures. Free Radic. Biol. Med. 2015, 89, 972–981.
Ranawat, P.; Bansal, M. P. Decreased glutathione levels potentiate the apoptotic efficacy of selenium: Possible involvement of p38 and JNK MAPKs—In vitro studies. Mol. Cell Biochem. 2008, 309, 21–32.
Granchi, D.; Cenni, E.; Ciapetti, G.; Savarino, L.; Stea, S.; Gamberini, S.; Gori, A.; Pizzoferrato, A. Cell death induced by metal ions: Necrosis or apoptosis? J. Mater. Sci. -Mater. Med. 1998, 9, 31–37.
Catelas, I.; Petit, A.; Vali, H.; Fragiskatos, C.; Meilleur, R.; Zukor, D. J.; Antoniou, J.; Huk, O. L. Quantitative analysis of macrophage apoptosis vs. necrosis induced by cobalt and chromium ions in vitro. Biomaterials 2005, 26, 2441–2453.
Mokhtari-Farsani, A.; Hasany, M.; Lynch, I.; Mehrali, M. Biodegradation of carbon-based nanomaterials: The importance of “biomolecular corona” consideration. Adv. Funct. Mater. 2022, 32, 2105649.
Gamcsik, M. P.; Kasibhatla, M. S.; Teeter, S. D.; Colvin, O. M. Glutathione levels in human tumors. Biomarkers 2012, 17, 671–691.
3961
Views
137
Downloads
0
Crossref
1
Web of Science
1
Scopus
1
CSCD
Altmetrics
Copyright: © 2022 by the author(s). This article is an open access article distributed under Creative Commons Attribution License (CC BY 4.0), visit https://creativecommons.org/licenses/by/4.0/.