HİDROKSİL RADİKALİNİN HIZLI TESPİTİ İÇİN LÜMİNESANS KEMOSENSÖR OLARAK iNDİRGENMİŞ GRAFEN OKSİT VE Tb-DO3A KONJÜGATI

Year 2024, Volume: 10 Issue: 2, 21 - 30, 31.12.2024

Fatih Algı , Meltem Alp

https://doi.org/10.22531/muglajsci.1507403

Abstract

Hidroksil radikallerinin (HO•) tespiti için kemosensörlerin geliştirilmesi, HO•’nun son derece kısa bir ömre sahip olması (in vivo yarılanma ömrü ~1 ns) nedeniyle zorlu bir iştir. Bu çalışmada biyolojik olarak önemli iyonlar ve reaktif oksijen türleri (ROS) arasında HO•’nun tespiti için kullanılabilecek çok yönlü bir prob Tb@rGO tasarladık ve sentezledik. Tasarımımız indirgenmiş grafen oksidin (rGO) terbiyum (III)-1,4,7,10-tetraazasiklododekan-1,4,7-triasetik asit (Tb-DO3A) ile kovalent konjugasyonuna dayanmaktadır. Tb@rGO, XRD, SEM, TEM ve zeta potansiyel analizini içeren geleneksel spektroskopik yöntemlerle karakterize edilmiştir. Ayrıca Tb@rGO’nun fotofiziksel özelliklerini de detaylandırdık. Buna göre, sonuçlarımız Tb@rGO’nun benzersiz lüminesans özelliklere sahip olduğunu ve bu özelliğin onu HO• tespitinde son derece etkili kıldığını doğrulamaktadır. Dikkat çekici bir şekilde Tb@rGO fosfat tamponlu salin (0,1 M PBS, pH 7,4) çözeltisinde biyolojik açıdan önemli birçok tür arasında HO•’ya karşı oldukça seçicidir. HO• için tespit sınırının (LOD) 0,92 M olması da dikkat çekicidir. Bu nedenle, bu yeni malzeme, seçici lüminesans sönümlemeli HO• probu olarak umut vaat etmektedir.

Keywords

Terbiyum (III), İndirgenmiş grafen oksit, Reaktif oksijen türleri, Hidroksil radikali, Lüminesans prob

Project Number

BAP 2019-19

REDUCED GRAPHENE OXIDE AND Tb-DO3A CONJUGATE AS LUMINESCENT CHEMOSENSOR FOR AGILE DETECTION OF HYDROXYL RADICAL

Abstract

The development of chemosensors for the detection of hydroxyl radicals (HO•) is a challenging task since HO• has an exceptionally short lifetime (in vivo half-life of 1 ns). In this work, we have designed and synthesized a versatile probe, viz. Tb@rGO, for the detection of HO• amongst the biologically important ions and reactive oxygen species (ROS). Our design is based on covalent conjugation of reduced graphene oxide (rGO) with terbium (III)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid (Tb-DO3A). Tb@rGO is characterized by traditional spectroscopic methods including XRD, SEM, TEM, and zeta potential analysis. Furthermore, we elaborate the photophysical properties of Tb@rGO. Accordingly, our results attest that Tb@rGO has unique luminescence features, rendering it highly effective in the detection of HO•. Remarkably, Tb@rGO is highly selective to HO• among many biologically important species in 0.1 M pH 7.4 phosphate buffered saline solution. It is also noteworthy that the limit of detection (LOD) is 0.92 M for HO•. Therefore, this novel material hold promises as selective turn-off luminescent HO• probe.

Keywords

Terbium (III), Reduced graphene oxide, Reactive oxygen species, Hydroxyl radical, Luminescent probe

Ethical Statement

None to declare

Supporting Institution

Aksaray University, the Scientific and Technological Research Council of Turkey, Turkish Academy of Sciences (TUBA)

Project Number

BAP 2019-19

Thanks

Partial financial supports were provided by Aksaray University (Grant No. BAP 2019-19) and the Scientific and Technological Research Council of Turkey (TUBITAK, Grant No. 118Z293). F. A. is indebted to the Turkish Academy of Sciences (TUBA) for Outstanding Young Investigator Award (TUBA GEBIP). M.A. thanks TUBITAK for a scholarship.

References

• X. Bai, K. K.-H. Ng, J. J. Hu, S. Ye, and D. Yang, “Small-molecule-based fluorescent sensors for selective detection of reactive oxygen species in biological systems,” Annu. Rev. Biochem., vol. 88, pp. 605–633, 2019.
• T. D. Pollard and B. O’Shaughnessy, “Molecular mechanism of cytokinesis,” Annu. Rev. Biochem., vol. 88, pp. 661–689, 2019.
• Y. Geng, Z. Wang, J. Zhou, M. Zhu, J. Liu, and T. D. James, “Recent progress in the development of fluorescent probes for imaging pathological oxidative stress,” Chem. Soc. Rev., vol. 52, no. 11, pp. 3873–3926, 2023, doi: 10.1039/D2CS00172A.
• S. K. Kailasa, G. N. Vajubhai, J. R. Koduru, and T. J. Park, “Recent progress of nanomaterials for colorimetric and fluorescence sensing of reactive oxygen species in biological and environmental samples,” Trends Environ. Anal. Chem., vol. 37, p. e00196, 2023, doi: https://doi.org/10.1016/j.teac.2023.e00196.
• H.-S. Wang, “Development of fluorescent and luminescent probes for reactive oxygen species,” TrAC Trends Anal. Chem., vol. 85, pp. 181–202, 2016.
• N. Kwon, D. Kim, K. M. K. Swamy, and J. Yoon, “Metal-coordinated fluorescent and luminescent probes for reactive oxygen species (ROS) and reactive nitrogen species (RNS),” Coord. Chem. Rev., vol. 427, p. 213581, 2021, doi: https://doi.org/10.1016/j.ccr.2020.213581.
• H. Sies et al., “Defining roles of specific reactive oxygen species (ROS) in cell biology and physiology,” Nat. Rev. Mol. Cell Biol., vol. 23, no. 7, pp. 499–515, 2022, doi: 10.1038/s41580-022-00456-z.
• Y. You and W. Nam, “Designing photoluminescent molecular probes for singlet oxygen, hydroxyl radical, and iron–oxygen species,” Chem. Sci., vol. 5, no. 11, pp. 4123–4135, 2014.
• X. Jiao, Y. Li, J. Niu, X. Xie, X. Wang, and B. Tang, “Small-molecule fluorescent probes for imaging and detection of reactive oxygen, nitrogen, and sulfur species in biological systems,” Anal. Chem., vol. 90, no. 1, pp. 533–555, 2018.
• E. Sassetti, M. H. Clausen, and L. Laraia, “Small-molecule inhibitors of reactive oxygen species production,” J. Med. Chem., vol. 64, no. 9, pp. 5252–5275, 2021.
• S. Ding, M. Li, H. Gong, Q. Zhu, G. Shi, and A. Zhu, “Sensitive and selective measurement of hydroxyl radicals at subcellular level with tungsten nanoelectrodes,” Anal. Chem., vol. 92, no. 3, pp. 2543–2549, 2020.
• X. Qu, Y. Bian, Y. Chen, and X. Wei, “A sensitive BODIPY-based fluorescent probe for detecting endogenous hydroxyl radicals in living cells,” RSC Adv., vol. 10, no. 48, pp. 28705–28710, 2020.
• X. Qu, W. Song, and Z. Shen, “A highly selective NIR fluorescent turn-on probe for hydroxyl radical and its application in living cell images,” Front. Chem., vol. 7, p. 598, 2019.
• Y. Zhao, H. Li, Z. Chai, W. Shi, X. Li, and H. Ma, “An endoplasmic reticulum-targeting fluorescent probe for imaging˙ OH in living cells,” Chem. Commun., vol. 56, no. 47, pp. 6344–6347, 2020.
• L. Chen et al., “An edaravone-guided design of a rhodamine-based turn-on fluorescent probe for detecting hydroxyl radicals in living systems,” Anal. Chem., vol. 93, no. 42, pp. 14343–14350, 2021.
• Y. Wu et al., “Synthesis of dihydroquinolines as scaffolds for fluorescence sensing of hydroxyl radical,” Org. Lett., vol. 23, no. 1, pp. 135–139, 2020.
• A. Degirmenci and F. Algi, “Synthesis, chemiluminescence and energy transfer efficiency of 2, 3-dihydrophthalazine-1, 4-dione and BODIPY dyad,” Dye. Pigment., vol. 140, pp. 92–99, 2017.
• S. Karakaya and F. Algi, “A novel dual channel responsive zinc (II) probe,” Tetrahedron Lett., vol. 55, no. 40, pp. 5555–5559, 2014.
• M. Pamuk and F. Algi, “Incorporation of a 2, 3-dihydro-1H-pyrrolo [3, 4-d] pyridazine-1, 4 (6H)-dione unit into a donor–acceptor triad: synthesis and ion recognition features,” Tetrahedron Lett., vol. 53, no. 52, pp. 7117–7120, 2012.
• A. Degirmenci, D. Iskenderkaptanoglu, and F. Algi, “A novel turn-off fluorescent Pb (II) probe based on 2, 5-di (thien-2-yl) pyrrole with a pendant crown ether,” Tetrahedron Lett., vol. 56, no. 4, pp. 602–607, 2015.
• G. Cui, Z. Ye, J. Chen, G. Wang, and J. Yuan, “Development of a novel terbium (III) chelate-based luminescent probe for highly sensitive time-resolved luminescence detection of hydroxyl radical,” Talanta, vol. 84, no. 3, pp. 971–976, 2011.
• F. Ahmed, M. Muzammal Hussain, W. Ullah Khan, and H. Xiong, “Exploring recent advancements and future prospects on coordination self-assembly of the regulated lanthanide-doped luminescent supramolecular hydrogels,” Coord. Chem. Rev., vol. 499, p. 215486, 2024, doi: https://doi.org/10.1016/j.ccr.2023.215486.
• R. Sivakumar and N. Y. Lee, “Recent advances in luminescent lanthanides and transition metal complex-based probes for imaging reactive oxygen, nitrogen, and sulfur species in living cells,” Coord. Chem. Rev., vol. 501, p. 215563, 2024, doi: https://doi.org/10.1016/j.ccr.2023.215563.
• C. Galaup, C. Picard, F. Couderc, V. Gilard, and F. Collin, “Luminescent lanthanide complexes for reactive oxygen species biosensing and possible application in Alzheimer’s diseases,” FEBS J., vol. 289, no. 9, pp. 2516–2539, May 2022, doi: https://doi.org/10.1111/febs.15859.
• S. E. Page, K. T. Wilke, and V. C. Pierre, “Sensitive and selective time-gated luminescence detection of hydroxyl radical in water,” Chem. Commun., vol. 46, no. 14, pp. 2423–2425, 2010.
• Y. Xiao, Z. Ye, G. Wang, and J. Yuan, “A ratiometric luminescence probe for highly reactive oxygen species based on lanthanide complexes,” Inorg. Chem., vol. 51, no. 5, pp. 2940–2946, 2012.
• K. L. Peterson, M. J. Margherio, P. Doan, K. T. Wilke, and V. C. Pierre, “Basis for sensitive and selective time-delayed luminescence detection of hydroxyl radical by lanthanide complexes,” Inorg. Chem., vol. 52, no. 16, pp. 9390–9398, 2013.
• J. Gao, Q. Li, C. Wang, and H. Tan, “Ratiometric detection of hydroxy radicals based on functionalized europium (III) coordination polymers,” Microchim. Acta, vol. 185, pp. 1–8, 2018.
• D. M. D. Leguerrier, R. Barré, J. K. Molloy, and F. Thomas, “Lanthanide complexes as redox and ROS/RNS probes: A new paradigm that makes use of redox-reactive and redox non-innocent ligands,” Coord. Chem. Rev., vol. 446, p. 214133, 2021.
• S.-Y. Wu, X.-Q. Guo, L.-P. Zhou, and Q.-F. Sun, “Fine-tuned visible and near-infrared luminescence on self-assembled lanthanide-organic tetrahedral cages with triazole-based chelates,” Inorg. Chem., vol. 58, no. 10, pp. 7091–7098, 2019.
• M. C. Heffern, L. M. Matosziuk, and T. J. Meade, “Lanthanide probes for bioresponsive imaging,” Chem. Rev., vol. 114, no. 8, pp. 4496–4539, 2014.
• L. Xu et al., “Continuously tunable nucleotide/lanthanide coordination nanoparticles for DNA adsorption and sensing,” ACS omega, vol. 3, no. 8, pp. 9043–9051, 2018.
• M. Bilmez, A. Degirmenci, M. P. Algi, and F. Algi, “A phosphorescent fluoride probe based on Eu (ııı)-DO3A clicked with a 2, 5-di (thien-2-yl) pyrrole scaffold,” New J. Chem., vol. 42, no. 1, pp. 450–457, 2018.
• M. Alp, M. Pamuk Algi, and F. Algi, “Eu(III)–DO3A and BODIPY dyad as a chemosensor for anthrax biomarker,” Luminescence, 2021, doi: 10.1002/BIO.4129.
• M. Alp, M. P. Algi, and F. Algi, “Tb (III)-DO3A and BODIPY dyad as multimode responsive hypochlorite probe,” Spectrochim. Acta Part A Mol. Biomol. Spectrosc., vol. 264, p. 120310, 2022.
• J.-C. G. Bünzli, “Lanthanide light for biology and medical diagnosis,” J. Lumin., vol. 170, pp. 866–878, 2016.
• Q. Zhang, S. O’Brien, and J. Grimm, “Biomedical applications of lanthanide nanomaterials, for imaging, sensing and therapy,” Nanotheranostics, vol. 6, no. 2, p. 184, 2022.
• F. R. Baptista, S. A. Belhout, S. Giordani, and S. J. Quinn, “Recent developments in carbon nanomaterial sensors,” Chem. Soc. Rev., vol. 44, no. 13, pp. 4433–4453, 2015.
• C. Chien et al., “Tunable photoluminescence from graphene oxide,” Angew. Chemie Int. Ed., vol. 51, no. 27, pp. 6662–6666, 2012.
• S. Pang, Z. Zhou, and Q. Wang, “Terbium-containing graphene oxide and its opto-electrochemical response for hypochlorite in water,” Carbon N. Y., vol. 58, pp. 232–237, 2013.
• Z. Zhou and Q. Wang, “An efficient optical-electrochemical dual probe for highly sensitive recognition of dopamine based on terbium complex functionalized reduced graphene oxide,” Nanoscale, vol. 6, no. 9, pp. 4583–4587, 2014.
• B. Liu et al., “From graphite to graphene oxide and graphene oxide quantum dots,” Small, vol. 13, no. 18, p. 1601001, 2017.
• A. Degirmenci, O. Sonkaya, C. Soylukan, T. Karaduman, and F. Algi, “BODIPY and 2, 3-Dihydrophthalazine-1, 4-Dione Conjugates As Heavy Atom-Free Chemiluminogenic Photosensitizers,” ACS Appl. Bio Mater., 2021.
• L. Shahriary and A. A. Athawale, “Graphene oxide synthesized by using modified hummers approach,” Int. J. Renew. Energy Environ. Eng, vol. 2, no. 01, pp. 58–63, 2014.
• J. Han, X. Bu, D. Zhou, H. Zhang, and B. Yang, “Discriminating Cr (III) and Cr (VI) using aqueous CdTe quantum dots with various surface ligands,” RSC Adv., vol. 4, no. 62, pp. 32946–32952, 2014.
• D. Dinda, A. Gupta, B. K. Shaw, S. Sadhu, and S. K. Saha, “Highly selective detection of trinitrophenol by luminescent functionalized reduced graphene oxide through FRET mechanism,” ACS Appl. Mater. Interfaces, vol. 6, no. 13, pp. 10722–10728, 2014.
• W. Wei, R. Lu, S. Tang, and X. Liu, “Highly cross-linked fluorescent poly (cyclotriphosphazene-co-curcumin) microspheres for the selective detection of picric acid in solution phase,” J. Mater. Chem. A, vol. 3, no. 8, pp. 4604–4611, 2015.
• J. Liu et al., “A superamplification effect in the detection of explosives by a fluorescent hyperbranched poly (silylenephenylene) with aggregation-enhanced emission characteristics,” Polym. Chem., vol. 1, no. 4, pp. 426–429, 2010.
• N. G. de Barros et al., “Graphene Oxide: A Comparison of Reduction Methods,” C, vol. 9, no. 3, p. 73, 2023.
• J. Jiao, M. Pan, X. Liu, B. Li, J. Liu, and Q. Chen, “A non-enzymatic sensor based on trimetallic nanoalloy with poly (diallyldimethylammonium chloride)-capped reduced graphene oxide for dynamic monitoring hydrogen peroxide production by cancerous cells,” Sensors, vol. 20, no. 1, p. 71, 2019.
• H. Saleem, M. Haneef, and H. Y. Abbasi, “Synthesis route of reduced graphene oxide via thermal reduction of chemically exfoliated graphene oxide,” Mater. Chem. Phys., vol. 204, pp. 1–7, 2018.
• D. Konios, M. M. Stylianakis, E. Stratakis, and E. Kymakis, “Dispersion behaviour of graphene oxide and reduced graphene oxide,” J. Colloid Interface Sci., vol. 430, pp. 108–112, 2014.
• U. Holzwarth and N. Gibson, “The Scherrer equation versus the’Debye-Scherrer equation’,” Nat. Nanotechnol., vol. 6, no. 9, p. 534, 2011.
• P. Saini, R. Sharma, and N. Chadha, “Determination of defect density, crystallite size and number of graphene layers in graphene analogues using X-ray diffraction and Raman spectroscopy,” Indian J. Pure Appl. Phys., vol. 55, no. 9, pp. 625–629, 2017.
• P. W. Albers, V. Leich, A. J. Ramirez-Cuesta, Y. Cheng, J. Hönig, and S. F. Parker, “The characterisation of commercial 2D carbons: graphene, graphene oxide and reduced graphene oxide,” Mater. Adv., vol. 3, no. 6, pp. 2810–2826, 2022.
• C. Jiao, R. Zhong, Y. Zhou, and H. Zhang, “Preparation and Characterization of a Novel Terbium Complex Coordinated with 10-Undecenoic Acid for UV-Cured Coatings,” Int. J. Polym. Sci., vol. 2020, 2020.
• E. Montes et al., “Effect of pH on the optical and structural properties of HfO2: Ln3+, synthesized by hydrothermal route,” J. Lumin., vol. 175, pp. 243–248, 2016.
• B. Konkena and S. Vasudevan, “Understanding aqueous dispersibility of graphene oxide and reduced graphene oxide through p K a measurements,” J. Phys. Chem. Lett., vol. 3, no. 7, pp. 867–872, 2012.
• S. Lee, S. Bong, J. Ha, M. Kwak, S.-K. Park, and Y. Piao, “Electrochemical deposition of bismuth on activated graphene-nafion composite for anodic stripping voltammetric determination of trace heavy metals,” Sensors Actuators B Chem., vol. 215, pp. 62–69, 2015.
• T. A. Tabish et al., “In vitro toxic effects of reduced graphene oxide nanosheets on lung cancer cells,” Nanotechnology, vol. 28, no. 50, p. 504001, 2017.
• X. H. Yau, F. W. Low, C. S. Khe, C. W. Lai, S. K. Tiong, and N. Amin, “An investigation of the stirring duration effect on synthesized graphene oxide for dye-sensitized solar cells,” PLoS One, vol. 15, no. 2, p. e0228322, 2020.
• V. H. Pham et al., “Chemical functionalization of graphene sheets by solvothermal reduction of a graphene oxide suspension in N-methyl-2-pyrrolidone,” J. Mater. Chem., vol. 21, no. 10, pp. 3371–3377, 2011.
• F. T. Johra, J.-W. Lee, and W.-G. Jung, “Facile and safe graphene preparation on solution based platform,” J. Ind. Eng. Chem., vol. 20, no. 5, pp. 2883–2887, 2014.