Abstract
In this work, a novel fluorescent probe CBO was synthesized for detecting Fe2+ using the natural monoterpenketone camphor as the starting material. The probe CBO displayed turn-on fluorescence to Fe2+ accompanied by the solution change from colorless to green. As expected, there was an excellent linear relationship between the fluorescence intensity of probe CBO and the concentration of Fe2+ (0–20 μM), and the detection limit was as low as 1.56×10−8 M. In particular, CBO could selectively sense Fe2+ more than other analytes (Fe3+ included) through the N-oxide strategy, and quickly responded to Fe2+ (60 s) over a wide pH (4–14) range. Additionally, based on the rapid fluorescence response of CBO to Fe2+, a simple test strip-based detector was designed for boosting practical applicability. The probe CBO had been successfully applied to the fluorescence imaging of Fe2+ in onion cells and living zebrafish. The probe CBO was a powerful tool of detecting Fe2+ level in organisms, which was of significance to understand the role of Fe2+ in Fe2+-related physical processes and diseases.
Graphical abstract
Similar content being viewed by others
References
Aron AT, Reeves AG, Chang CJ. Activity-based sensing fluorescent probes for iron in biological systems. Curr Opin Chem Biol. 2018;43:113–8.
Wilson MT, Reeder BJ. Oxygen-binding haem proteins. Exp Physiol. 2008;93(1):128–32.
Rouault TA, Tong WH. Iron-sulphur cluster biogenesis and mitochondrial iron homeostasis. Nat Rev Mol Cell Biol. 2005;6(4):345–51.
Miller WL, Bose HS. Early steps in steroidogenesis: Intracellular cholesterol trafficking. J Lipid Res. 2011;52(12):2111–35.
Sornjai W, Van Long FN, Pion N, Pasquer A, Saurin JC, Marcel V. Iron and hepcidin mediate human colorectal cancer cell growth. Chem Biol Interact. 2020;319:109021.
Tong WH, Rouault T. Distinct iron–sulfur cluster assembly complexes exist in the cytosol and mitochondria of human cells. EMBO J. 2014;19(21):5692–700.
Reczek CR, Chandel NS. ROS-dependent signal transduction. Curr Opin Cell Biol. 2015;33:8–13.
Wang J, Pantopoulos K. Regulation of cellular iron metabolism. Biochem J. 2011;434(3):365–81.
Prabhu J, Santhoshkumar S, Velmurugan K. A naphthalene derived Schiff base as a selective fluorescent probe for Fe2+. Inorganica Chim Acta. 2016;439:1–7.
Long L, Wang N, Han Y, Huang M, Yuan X, Cao S. A coumarin-based fluorescent probe for monitoring labile ferrous iron in living systems. Analyst. 2018;143(11):2555–62.
Hou GG, Wang CH, Sun JF, Yang MZ, Lin D, Li HJ. Rhodamine-based “turn-on” fluorescent probe with high selectivity for Fe2+ imaging in living cells. Biochem Biophys Res Commun. 2013;439(4):459–63.
Xu Y, Zhang Z, Lv P, Duan Y, Li G, Ye B. Ratiometric fluorescence sensing of Fe 2+/3+ by carbon dots doped lanthanide coordination polymers. J Lumin. 2019;205:519–24.
Liu T, Liu W, Zhang M, Yu W, Gao F, Li C. Ferrous-Supply-Regeneration Nanoengineering for Cancer-Cell-Specific Ferroptosis in Combination with Imaging-Guided Photodynamic Therapy. ACS Nano. 2018;12(12):12181–92.
Ascher NL, Lake JR, Emond J. Liver transplantation for hepatitis C virus related cirrhosis. Best Pract. Res Clin Gastroenterol. 2000;4(2):307–25.
Haehling SV, Jankowska EA, Veldhuisen DV, Ponikowski P, Anker SD. Iron deficiency and cardiovascular disease. Nat Rev. Cardiol. 2015;12:659–69.
Xie Y, Hou W, Song X, Yu Y, Huang J, Sun X. Ferroptosis: process and function. Cell Death Differ. 2016;23(3):369–79.
Dixon S, Lemberg K, Lamprecht M, Skouta R, Zaitsev E, Gleason C. Ferroptosis: an iron-dependent form of nonapoptotic cell death. Cell. 2012;149(5):1060–72.
Gao M, Yi J, Zhu J, Minikes AM, Monian P, Thompson CB. Role of Mitochondria in Ferroptosis. Mol Cell. 2019;73(2):354–363.e3.
Richardson DR, Lane RJR, Becker RM, Huang LH, Whitnall M, Rahmanto YS. Mitochondrial iron trafficking and the integration of iron metabolism between the mitochondrion and cytosol. Proc. Natl Acad Sci US A. 2010;107(24):10775–107782.
Qu Z, Li P, Zhang X, Han K. A turn-on fluorescent chemodosimeter based on detelluration for detecting ferrous iron (Fe2+) in living cells. J Mater Chem. B. 2016;4(5):887–92.
Liang ZQ, Wang CX, Yang JX, Gao HW, Tian YP, Tao XT. A highly selective colorimetric chemosensor for detecting the respective amounts of iron(II) and iron(III) ions in water. New J Chem. 2007;31(6):906–10.
Malik LA, Bashir A, Qureashi A, Pandith AH. Detection and removal of heavy metal ions: a review. Environ Chem Lett. 2019;17(4):1495–7521.
Weeks DA, Bruland KW. Improved method for shipboard determination of iron in seawater by flow injection analysis. Anal Chim Acta. 2002;453(1):21–32.
Sikdar S, Kundu M. A Review on Detection and Abatement of Heavy Metals. Chem Bio Eng Rev. 2017;5(1):18–29.
Lee S, Uliana A, Taylor M, et al. Iron Detection and Remediation with a Functionalized Porous Polymer Applied to Environmental Water Samples. Chem Sci. 2019;10(27):6651–60.
Munzert SM, Schwarz G, Kurth DG. Kinetic Studies of the Coordination of Mono-and Ditopic Ligands with First Row Transition Metal Ions. Inorg Chem. 2016;55(5):2565–73.
Laschuk NO, Ebralidze II, Quaranta S, et al. Rational design of a material for rapid colorimetric Fe2+ detection. Mater Des. 2016;107(oct.5):18–25.
Huang Y, Zhang Y, Huo F, Wen Y, Yin C. Design strategy and bioimaging of small organic molecule multicolor fluorescent probes. Sci China Chem. 2020;63(12):1742–55.
Terai T, Nagano T. Small-molecule fluorophores and fluorescent probes for bioimaging. Pflugers Arch Eur J Physiol. 2013;465(3):347–59.
Tang YY, Wang CJ, Chen S, Dai HY. A terbium(III) organic framework as a fluorescent probe for selectively sensing of organic small molecules and metal ions especially nitrobenzene and Fe3+. J Coord Chem. 2017;70(24):3996–4007.
Shi H, Chen H, X Li, Xing J et al. A simple colorimetric and ratiometric fluoride ion probe with large color change. RSC Adv. 2021; 11(1):1-6
Cheng Y, Shabir G, Li X, Fang L, Xu L. Development of a deep-red fluorescent glucose-conjugated bioprobe for in vivo tumor targeting. Chem Commun. 2020;56(7):1070–3.
Ma S, Fang DC, Ning B. The rational design of a highly sensitive and selective fluorogenic probe for detecting nitric oxide. Chem Commun. 2014;50(49):6475–8.
Tian X, Murfin LC, Wu L, Lewis SE, James TD. Fluorescent small organic probes for biosensing. Chem Sci. 2021;12(10):3406–26.
Khatun S, Biswas S, Binoy A, et al. Highly chemoselective turn-on fluorescent probe for ferrous (Fe2+) ion detection in cosmetics and live cells. J. Photochem. Photobiol. B Biol. 2020;209:111943.
Park SH, Kwon N, Lee JH, Yoon J, Shin I. Synthetic ratiometric fluorescent probes for detection of ions. Chem Soc Rev. 2020;49(1):143–79.
Oppolzer W. Camphor derivatives as chiral auxiliaries in asymmetric synthesis. Tetrahedron. 1987;43(9):1969–2004.
Wang Y, Busch-Petersen J, Feng W, Kiesow TJ, Graybill TL, Jian J. Camphor sulfonamide derivatives as novel, potent and selective CXCR3 antagonists. Bioorg Med Chem Lett. 2009;19(1):114–8.
Stavrakov G, Valcheva V, Philipova I, Doytchinova I. Novel camphane-based anti-tuberculosis agents with nanomolar activity. Eur J Med Chem. 2013;70:372–9.
Hirayama T, Okuda K, Nagasawa H. A highly selective turn-on fluorescent probe for iron(II) to visualize labile iron in living cells. Chem Sci. 2013;4(3):1250–6.
Gao G, Wang X, Wang Z, Jin X, Ou L, Zhou J. A simple and effective dansyl acid based “turn-on” fluorescent probe for detecting labile ferrous iron in physiological saline and live cells. Talanta. 2020;215:120908.
Yang L, Chen Q, Gan S, Guo Q, Zhang J, Zhang H. An activatable AIEgen probe for in-situ monitoring and long-term tracking of ferrous ions in living cells. Dyes Pigments. 2021;190:109271.
Bhuvanesh N, Velmurugan K, Suresh S, Prakash P, John N, Murugan S. Naphthalene based fluorescent chemosensor for Fe2+-ion detection in microbes and real water samples. J Lumin. 2017;188:217–22.
Ping L. Haibin, Xiao, Bo, Chemistry TJCJo. A Near-infrared Fluorescent Probe for Selective Simultaneous Detection of Fe2+ and Cl− in Living Cells. Chin J Chem. 2012;30(9):1992–8.
Funding
This work received financial support from the National Natural Science Foundation of China (No. 32071707).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Ethics approval
All animal experiments were approved by the Animal Ethical Committee of the Medical School of Southeast University and conducted in strict accordance with the National Care and use of Laboratory Animals by the National Animal Research Authority (China).
Conflict of interest
The authors declare no competing interests.
Additional information
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary information
ESM 1
(PDF 411 kb)
Rights and permissions
About this article
Cite this article
Liang, Y., Zhang, Y., Li, M. et al. A highly effective “turn-on” camphor-based fluorescent probe for rapid and sensitive detection and its biological imaging of Fe2+. Anal Bioanal Chem 413, 6267–6277 (2021). https://doi.org/10.1007/s00216-021-03581-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00216-021-03581-4