Abstract
Iron ion is an essential metal ion that plays a crucial role in various metabolic processes in living organisms. It is involved in cellular metabolism, acts as a catalyst for enzymatic reactions, and functions as an oxygen carrier in hemoglobin. Insufficient levels of iron in the body can lead to adverse health conditions such as diabetes, anemia, liver and kidney damage, and heart diseases. Considering these factors, the development of an effective fluorescent probe for the detection of excessive Fe3+ levels is necessary to protect both environment and human health. Numerous fluorescent probes have been reported thus far for Fe3+ detection. However, the most of these probes rely on a single emission intensity alteration mechanism, such as photoinduced electron transfer (PET). In this study, we have developed fluorescent probes using chitosan functionalized with rhodamine B and coumarin derivatives, for efficient detection of Fe3+ and Zn2+ ions. The hybrid chitosan/rhodamine B (CS/RB) and hybrid chitosan/coumarin (CS/MCMC) fluorescent probes exhibit strong fluorescence intensity under ultraviolet light. When iron ions are introduced to CS/RB and CS/MCMC solution, they coordinate with weak-field ligands (such as N and O) in the structure of CS/RB through a high-spin method. This coordination leads to the self-assembly of Fe3+ on the CS/RB surface, generating single electrons and resulting in high paramagnetism, which in turn quenches the fluorescence. The quenching effect of Fe3+ on the CS/RB and CS/MCMC fluorescent probes enables efficient detection of Fe3+ ions. Importantly, this fluorescence quenching effect is specific to Fe3+ and is not affected by other metal ions. In summary, the developed fluorescent probes based on chitosan derivatives offer a promising approach for the sensitive and specific detection of iron ions in aqueous solutions.
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Data availability
The datasets generated and/or analyzed during the current study are not publicly available at this time as the data form part of an ongoing study. However, the datasets are available from the corresponding author (Mehdi Salami-Kalajahi, m.salami@sut.ac.ir) on reasonable request.
References
Balewski Ł, Szulta S, Jalińska A, Kornicka A (2018) A Review on Pharmacological Properties of Coumarins. Mini-Rev Med Chem 18:113–141. https://doi.org/10.2174/1389557516666160801094919
Bansod B, Kumar T, Thakur R, Rana S, Singh I (2017) A review on various electrochemical techniques for heavy metal ions detection with different sensing platforms. Biosen Bioelect 94:443–455. https://doi.org/10.1016/j.bios.2017.03.031
Fan Y, Wu Y, Hou J, Wang P, Peng X, Ge G (2023) Coumarin-based near-infrared fluorogenic probes: Recent advances, challenges and future perspectives. Coordin Chem Rev 480:215020. https://doi.org/10.1016/j.ccr.2023.215020
Gheitarani B, Golshan M, Hosseini MS, Salami-Kalajahi M (2022) Reflectance and photophysical properties of rhodamine 6G/2-(4-methyl-2-oxo-2H-chromen-7-yloxy) acetic acid as cold hybrid colorant. Sci Rep 12:6145. https://doi.org/10.1038/s41598-022-10001-9
Gheitarani B, Golshan M, Safavi-Mirmahalleh S-A, Salami-Kalajahi M, Hosseini MS, Alizadeh AA (2023) Fluorescent polymeric sensors based on N-(rhodamine-6G) lactam-N′-allyl-ethylenediamine and 7-(allyloxy)-2H-chromen-2-one for Fe3+ ion detection. Colloids Surf A-Physicochem Eng Asp 656:130473. https://doi.org/10.1016/j.colsurfa.2022.130473
Ghezelsefloo S, Rad JK, Hajiali M, Mahdavian AR (2021) Rhodamine-based fluorescent polyacrylic nanoparticles: A highly selective and sensitive chemosensor for Fe (II) and Fe (III) cations in water. J Environ Chem Eng 9:105082. https://doi.org/10.1016/j.jece.2021.105082
Girdthep S, Hanmeng O, Triamnak N, Chailek N, Wanichacheva N (2021) Theoretical solvent selection for nanostructured surface fabrication of reusable and colourimetric visual-eye sensor strips with rhodamine derivative-encapsulated polymeric membranes for highly sensitive and selective detection of Hg2+. Polym Test 97:107151. https://doi.org/10.1016/j.polymertesting.2021.107151
Golshan M, Amani F, Salami-Kalajahi M (2021) Photophysical and reflectance properties of perylene-3,4,9,10-tetracarboxylic diimide (PTCDI)/rhodamine 6G hybrid for application in cold paints. Prog Org Coat 157:106308. https://doi.org/10.1016/j.porgcoat.2021.106308
Golshan M, Gheitarani B, Salami-Kalajahi M, Hosseini MS (2022) Synthesis and characterization of fluorescence poly(amidoamine) dendrimer-based pigments. Sci Rep 12:15180. https://doi.org/10.1038/s41598-022-19712-5
Guo X, Song S, Wang X, Jiang X, Lv W, Yu X, Han Y, Wang L (2019) Dual-functional Fluorescent Sensors Based on CaMoO4: Eu3+ for Detection of Iron (III) and Dichromate Ions in Aqueous. Opt Mater 96:109342. https://doi.org/10.1016/j.optmat.2019.109342
Javanbakht F, Najafi H, Jalili K, Salami-Kalajahi M (2023) A review on photochemical sensors for lithium ion detection: relationship between structure and performance. J Mater Chem A 11:26371–26392. https://doi.org/10.1039/D3TA06113B
Johnson AD, Curtis RM, Wallace KJ (2019) Low molecular weight fluorescent probes (LMFPs) to detect the group 12 metal triad. Chemosensors 7:22. https://doi.org/10.3390/chemosensors7020022
Kontoghiorghes GJ, Kontoghiorghe CN (2020) Iron and chelation in biochemistry and medicine: new approaches to controlling iron metabolism and treating related diseases. Cells. https://doi.org/10.3390/cells9061456
Liu Z, Li N, Liu P, Qin Z, Jiao T (2022) Highly sensitive detection of iron ions in aqueous solutions using fluorescent chitosan nanoparticles functionalized by rhodamine B. ACS Omega 7:5570–5577. https://doi.org/10.1021/acsomega.1c07071
Lou C, Yin Y, Tian XD, Deng H, Wang Y, Jiang X (2020) Hydrophilic Finishing of PET Fabrics by Applying Chitosan and the Periodate Oxidized β-cyclodextrin for Wash Resistance Improvement. Fibers Polym 21:73–81. https://doi.org/10.1007/s12221-020-9269-1
Ma C, Ma Z, He Z, Wang X, Zhao L, Chen X (2023) A hydrophilic polymer based on alkoxyl chain modified fluorene: the novel fluorescence colorimetric sensor for Fe3+, Fe2+, and Cu2+ in aqueous media. J Macromol Sci A 60:397–408. https://doi.org/10.1080/10601325.2023.2210165
Pipattanawarothai A, Trakulsujaritchok T (2020) Hybrid polymeric chemosensor bearing rhodamine derivative prepared by sol-gel technique for selective detection of Fe3+ ion. Dyes Pigm 173:107946. https://doi.org/10.1016/j.dyepig.2019.107946
Qin JC, Yang ZY, Wang GQ, Li CR (2015) FRET-based rhodamine–coumarin conjugate as a Fe3+ selective ratiometric fluorescent sensor in aqueous media. Tetrahed Lett 56:5024–5029. https://doi.org/10.1016/j.tetlet.2015.07.023
Ravingerová T, Kindernay L, Barteková M, Ferko M, Adameová A, Zohdi V, Lazou A (2020) The molecular mechanisms of iron metabolism and its role in cardiac dysfunction and cardioprotection. Int J Mol Sci 21:7889. https://doi.org/10.3390/ijms21217889
Rawat A, Reddy AVB (2022) Recent advances on anticancer activity of coumarin derivatives. Eur J Med Chem Rep 5:100038. https://doi.org/10.1016/j.ejmcr.2022.100038
Safavi-Mirmahalleh S-A, Golshan M, Gheitarani B, Hosseini MS, Salami-Kalajahi M (2023) A review on applications of coumarin and its derivatives in preparation of photo-responsive polymers. Eur Polym J 198:112430. https://doi.org/10.1016/j.eurpolymj.2023.112430
Sahoo SK, Crisponi G (2019) Recent advances on iron (III) selective fluorescent probes with possible applications in bioimaging. Molecules 24:3267. https://doi.org/10.3390/molecules24183267
Sarih NM, Ciupa A, Moss S, Myers P, Slater AG, Abdullah Z, Maher S (2020) Furo [3, 2-c] coumarin-derived Fe3+ selective fluorescence sensor: synthesis, fluorescence study and application to water analysis. Sci Rep 10:1–11. https://doi.org/10.1038/s41598-020-63262-7
Sedighi M, Mahmoudi Z, Ghasempour A, Shakibaie M, Ghasemi F, Akbari M, Shahbazi MA (2023) Nanostructured multifunctional stimuli-responsive glycopolypeptide-based copolymers for biomedical applications. J Control Rel 354:128–145. https://doi.org/10.1016/j.jconrel.2022.12.058
Shakeri KZ, Farzaneh S, Reza Z (2020) Determination of iron(II) and iron(III) via static quenching of the fluorescence of tryptophanprotected copper nanoclusters. Microchim Acta 187:1–9
Shellaiah JM, Thirumalaivasan N, Aazaad B, Awasthi K, Sun KW, Wu SP, Lin MC, Ohta N (2020) Novel rhodamine probe for colorimetric and fluorescent detection of Fe3+ ions in aqueous media with cellular imaging. Spectrochim Acta A-Mol Biomol Spectros 242:118757. https://doi.org/10.1016/j.saa.2020.118757
Tsivileva OM, Koftin OV, Evseeva NV (2022) Coumarins as fungal metabolites with potential medicinal properties. Antibiotics 11:1156. https://doi.org/10.3390/antibiotics11091156
Wang J, Yang XQ, Li N, Wang LL, Xu XY, Zhang C (2023) A cyclodextrin-based turn-off fluorescent probe for naked-eye detection of copper ions in aqueous solution. Spectrochim Acta A-Mol Biomol Spect 287:122069. https://doi.org/10.1016/j.saa.2022.122069
Xu HL, Wei Y, Hao S (2022) 4-Methylumbelliferone fused oxazole thioether derivatives: synthesis, characterization and antifungal activities. Nat Prod Res 36:707–713. https://doi.org/10.1080/14786419.2020.1798665
Yelchuri V, RBN P, Karuna MS, Poornachandra Y, Kumar CG, (2016) Synthesis of novel fatty substituted 4-methyl-2HChromen-2-one via cross metathesis: potential antioxidants and chemotherapeutic agents. Chem Organ Synth 65:1023–1031. https://doi.org/10.5650/jos.ess15221
Zayane M, Romdhane A, Daami-Remadi M, Jannet HB (2015) Access to new antimicrobial 4-methylumbelliferone derivatives. J Chem Sci 127:1619–1626. https://doi.org/10.1007/s12039-015-0927-6
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SMA: Methodology, Formal Analysis, Investigation, Writing—Original Draft, Visualization. MG: Validation, Formal Analysis, Investigation, Writing—Original Draft, Visualization. MSH: Validation, Resources, Visualization, Supervision. MSK: Conceptualization, Validation, Resources, Writing—Review & Editing, Visualization, Supervision, Funding Acquisition.
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Alavifar, SM., Golshan, M., Salami Hosseini, M. et al. Rhodamine B- and coumarin-modified chitosan as fluorescent probe for detection of Fe3+ using quenching effect. Cellulose 31, 3015–3027 (2024). https://doi.org/10.1007/s10570-024-05806-y
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DOI: https://doi.org/10.1007/s10570-024-05806-y