Academic Journal
View in EDS
Linked Full Text

A Novel Anthraquinone Derivative as a Chemiluminescence Enhancer in Luminol Assays: Insights Into the CRET Mechanism.

Bibliographic Details
Title: A Novel Anthraquinone Derivative as a Chemiluminescence Enhancer in Luminol Assays: Insights Into the CRET Mechanism.
Authors: Kocabas A; Department of Forensic Sciences, Uskudar University, Uskudar, Istanbul, Türkiye., Kucuk A; Department of Chemistry, Istanbul University-Cerrahpasa, Avcilar, Istanbul, Türkiye., Ozkok F; Department of Chemistry, Istanbul University-Cerrahpasa, Avcilar, Istanbul, Türkiye., Onul N; Department of Chemistry, Istanbul University-Cerrahpasa, Avcilar, Istanbul, Türkiye., Catal T; Department of Molecular Biology and Genetics, Uskudar University, Istanbul, Türkiye.
Source: Luminescence : the journal of biological and chemical luminescence [Luminescence] 2026 Apr; Vol. 41 (4), pp. e70481.
Publication Type: Journal Article
Language: English
Journal Info: Publisher: Wiley & Sons Country of Publication: England NLM ID: 100889025 Publication Model: Print Cited Medium: Internet ISSN: 1522-7243 (Electronic) Linking ISSN: 15227235 NLM ISO Abbreviation: Luminescence Subsets: MEDLINE
Imprint Name(s): Original Publication: Chichester, Sussex, UK : Wiley & Sons, c1999-
MeSH Terms: Luminol*/chemistry , Anthraquinones*/chemistry , Anthraquinones*/chemical synthesis , Luminescent Measurements*/methods , Luminescence* , Fluorescence Resonance Energy Transfer*, Molecular Structure ; Spectrometry, Fluorescence
Abstract: Chemiluminescence (CL) reactions are an effective reaction type frequently used in both in vivo and in vitro studies for the determination of many analytes. Some of the molecules used for this purpose are structures that act as enhancers of fluorescence-active molecules, whose activity can be enhanced via chemiluminescence resonance energy transfer (CRET). Such molecules, which are active in terms of fluorescence and operate through the CRET mechanism, are used in combination with molecules such as luminol to produce reaction systems that are more effective. In this study, a model system combining a synthesized anthraquinone derivative with luminol was investigated for its potential use as a CRET-based fluorescent enhancer. Chemical characterization of the molecule was performed using UV, IR, and fluorescence spectroscopy. Additionally, the anthraquinone sample, which was tested in conjunction with luminol as an enhancer on bloodstains, was observed to cause the bloodstains to luminesce for a longer duration and at a higher intensity than when luminol was used alone. As a result, it was observed that unlike conventional luminol enhancers, the synthesized anthraquinone molecule functions as a CRET-based fluorescent acceptor, enabling indirect signal amplification through energy transfer, and could be used as a new type of tracer in biological applications.
(© 2026 John Wiley & Sons Ltd.)
References: A. Karabchevsky, A. Mosayyebi, and A. V. Kavokin, “Tuning the Chemiluminescence of a Luminol Flow Using Plasmonic Nanoparticles,” Light: Science & Applications 5 (2016): e16164, https://doi.org/10.1038/lsa.2016.164.
M. A. Tzani, D. K. Gioftsidou, M. G. Kallitsakis, et al., “Direct and Indirect Chemiluminescence: Reactions, Mechanisms and Challenges,” Molecules 26 (2021): 7664, https://doi.org/10.3390/molecules26247664.
J. Fan, M. Hu, P. Zhan, and X. Peng, “Energy Transfer Cassettes Based on Organic Fluorophores: Construction and Applications in Ratiometric Sensing,” Chemical Society Reviews 42 (2013): 29, https://doi.org/10.1039/C2CS35273G.
Y. Yan, P. Shi, W. Song, and S. Bi, “Chemiluminescence and Bioluminescence Imaging for Biosensing and Therapy: In Vitro and In Vivo Perspectives,” Theranostics 9 (2019): 4047–4065, https://doi.org/10.7150/thno.33228.
X. Liu, Y. Luo, Y. Zhang, Z. Xie, and C. Xu, “Gold Nanoparticle‐Mediated Fluorescence Resonance Energy Transfer for Analytical Applications in the Fields of Life Health and Safety,” Talanta 282 (2025): 127023, https://doi.org/10.1016/j.talanta.2024.127023.
J. Tang, L. Wang, W. Ma, et al., “An Amplified AuNP‐Mediated Chemiluminescence Resonance Energy Transfer Aptasensor Based on Nb.BbvCI‐Powered DNA Walker for Detecting Ochratoxin A in Foods,” Microchemical Journal 208 (2025): 112503, https://doi.org/10.1016/j.microc.2024.112503.
Y. Yan, X. Y. Wang, X. Hai, et al., “Carbon‐Based Dots: Preparation, Properties, and Applications in Electrochemical Biosensing,” TrAC Trends in Analytical Chemistry 123 (2020): 115755, https://doi.org/10.1016/j.trac.2019.115755.
X. Liu, J. Li, T. Wen, et al., “Highly Specific Electrochemical DNA Sensor for Detecting HBV DNA Based on CHA Cascade Cycle and Nanomaterial Signal Amplification Strategy,” Microchemical Journal 187 (2023): 108386, https://doi.org/10.1016/j.microc.2023.108386.
Y. Zhou, S. Xie, M. Li, L. Xin, X. Zhang, and Y. Liu, “CRISPR/Cas12a Controlled Chemiluminescence Resonance Energy Transfer Sensor for Detection of Carcinoembryonic Antigen,” Sensors and Actuators. B, Chemical 401 (2024): 135094, https://doi.org/10.1016/j.snb.2023.135094.
X. Mai, J. Li, P. Ma, D. Song, and Q. Fei, “A High‐Performance Electrochemical Biosensor for the Determination of microRNA‐21 Based on a Dual‐Signal Amplification Strategy of 3D DNA Walker and Metal‐Organic Frameworks,” Talanta 296 (2025): 128449, https://doi.org/10.1016/j.talanta.2025.128449.
A. B. Solea and M. D. Ward, “A Chemiluminescent Lantern: A Coordination Cage Catalysed Oxidation of Luminol Followed by Chemiluminescence Resonance Energy‐Transfer,” Dalton Transactions 52 (2023): 4456–4461, https://doi.org/10.1039/D3DT00689A.
N. Kishikawa, M. El‐Maghrabey, M. Tobo, and N. Kuroda, “A Comparative Study on the Reduction Modes for Quinone to Determine Ubiquinone by HPLC With Luminol Chemiluminescence Detection Based on the Redox Reaction,” Molecules 28 (2022): 96, https://doi.org/10.3390/molecules28010096.
H. Ozdinc, N. Onul, and F. Ozkok, “Novel N,S‐Substituted Naphthoquinone Analogues From Aminonaphthoquinones,” European Chemical Biotechnology Journal 1 (2024): 1, https://doi.org/10.62063/ecb‐13.
X. H. Tian, L. L. Hong, W. H. Jiao, and H. W. Lin, “Polycyclic Polyprenylated Acylphloroglucinols (PPAPs): Structures, Biosynthesis, and Biological Activities,” Natural Product Reports 40 (2023): 718, https://doi.org/10.1039/D2NP00045H.
F. Kaladari, M. El‐Maghrabey, M. Kawazato, N. Kishikawa, and N. Kuroda, “Biotinylated Quinone as a Chemiluminescence Sensor for Biotin‐Avidin Interaction and Biotin Detection Application,” Sensors 23 (2023): 9611, https://doi.org/10.3390/s23239611.
M. Dong, X. Ming, T. Xiang, et al., “Recent Research on the Physicochemical Properties and Biological Activities of Quinones and Their Practical Applications: A Comprehensive Review,” Food & Function 15 (2024): 8973–8997, https://doi.org/10.1039/D4FO02600D.
F. Ozkok, D. S. Mansuroglu, O. Z. Pinar, et al., “Synthesis of a Novel Thio‐Anthraquinone Derivative‐Based Tissue Dye,” Revue Roumaine de Chimie 69 (2024): 5.
L. Frederic, K. Cedric, and R. Frederic, “WO Patent 2015, WO2015177062A1.”.
F. Ozkok and Y. M. Şahin, “TR Patent 2016/19610,” (2016).
J. M. Gavira, A. Hernanz, and I. Bratu, “Dehydration of β‐Cyclodextrin,” Vibrational Spectroscopy 32 (2003): 137–146, https://doi.org/10.1016/S0924‐2031(03)00029‐8.
C. M. Topală and I. Rusea, “Determination of Some Heavy Metals in Medicinal Plants From Argeș County, Romania,” Current Trends in Natural Sciences 7 (2018): 286–292.
X. Ji and T. E. Li, “Selective Excitation of IR‐Inactive Modes via Vibrational Polaritons: Insights From Atomistic Simulations,” Journal of Physical Chemistry Letters 16 (2025): 5034–5042, https://doi.org/10.1021/acs.jpclett.5c00848.
S. F. Abd Karima, J. Jaia, K. H. K. Hamida, M. H. M. Muzamina, N. Kamarrudina, and R. A. A. Aziza, “Full Factorial Design Analysis and Characterization of Polyethylene, Starch and Aloe Vera Gel Thin Film Formulation,” International Journal on Advanced Science, Engineering and Information Technology 11, no. 6 (2021): 2139.
S. M. Hiremath, C. S. Hiremath, S. S. Khemalapure, and N. R. Patil, “Investigation on Effect of Thickness on Structural and Optical Properties of Thermal Evaporated CdTe Thin Films,” AIP Conference Proceedings 1 (1953): 140025, https://doi.org/10.1063/1.5033200.
V. M. Bassey, C. G. Apebende, P. S. Idante, et al., “Vibrational Characterization and Molecular Electronic Investigations of 2‐Acetyl‐5‐Methylfuran Using FT‐IR, FT‐Raman, UV–VIS, NMR, and DFT Methods,” Journal of Fluorescence 32 (2022): 1005–1017, https://doi.org/10.1007/s10895‐022‐02903‐8.
F. Ozkok, Y. M. Sahin, V. E. Atalay, K. Asgarova, N. Onul, and T. Çatal, “Spectrophotometric Determination of Iron (II) Sulfate With a Novel Anthraquinone Derivative: Catal's Reagent,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 240 (2020): 118631, https://doi.org/10.1016/j.saa.2020.118631.
R. Chauhan, R. Kumar, V. Kumar, K. Sharma, and V. Sharma, “On the Discrimination of Soil Samples by Derivative Diffuse Reflectance UV–Vis‐NIR Spectroscopy and Chemometric Methods,” Forensic Science International 319 (2021): 110655, https://doi.org/10.1016/j.forsciint.2020.110655.
V. Sharma, R. Kumar, and P. Kaur, “Forensic Examination of Textile Fibers Using UV‐Vis Spectroscopy Combined With Multivariate Analysis,” Journal of Applied Spectroscopy 86 (2019): 96–100, https://doi.org/10.1007/s10812‐019‐00787‐4.
D. H. Ebner, M. Tortora, D. E. Bedolla, et al., “Comparative Investigation of Chemical and Structural Properties of Charred Fir Wood Samples by Raman and FTIR Spectroscopy as well as X‐Ray‐Micro‐CT Technology,” Holzforschung 77 (2023): 734–742, https://doi.org/10.1515/hf‐2023‐0024.
L. Völkel, M. Beaumont, L. S. Johansson, et al., “Assessing Fire‐Damage in Historical Papers and Alleviating Damage With Soft Cellulose Nanofibers,” Small 18 (2022): 2105420, https://doi.org/10.1002/smll.202105420.
Y. Xiong, L. Zhou, X. Peng, et al., “Highly Sensitive Electrochemical Sensor for the Detection of Quercetin Based on Carbon Dots and Gold Nanoparticles‐Modified Glass Carbon Electrode,” Sensors and Actuators. B, Chemical 320 (2020): 128411, https://doi.org/10.1016/j.snb.2020.128411.
N. Hananya, O. Press, A. Das, et al., “Persistent Chemiluminescent Glow of Phenoxy‐Dioxetane Luminophore Enables Unique CRET‐Based Detection of Proteases,” Chemistry–A European Journal 25 (2019): 14679–14687, https://doi.org/10.1002/chem.201903489.
Y. Xiong, L. Zhou, X. Peng, et al., “A Specific Short Peptide‐Assisted Enhanced Chemiluminescence Resonance Energy Transfer (CRET) for Label‐Free and Ratiometric Detection of Copper Ions in Complex Samples,” Sensors and Actuators. B, Chemical 320 (2020): 128411, https://doi.org/10.1016/j.snb.2020.128411.
J. Li, M. Xu, X. Huang, and J. Ren, “Study of the Efficiency of Chemiluminescence Resonance Energy Transfer System Based on Hemin/G‐Quadruplex DNAzyme Catalysis by Chemiluminescence Imaging,” Talanta 245 (2022): 123447, https://doi.org/10.1016/j.talanta.2022.123447.
G. Song, Z. Yang, J. Cheng, et al., “High‐Efficiency Capture and In‐Situ Photocatalytic Eradication of Drug‐Resistant Bacteria by Cationic Conjugated Polymer‐Modified Metal‐Organic Frameworks,” Angewandte Chemie, International Edition 64 (2025): e202423792, https://doi.org/10.1002/anie.202423792.
S. Xu, J. Li, X. Li, et al., “A Chemiluminescence Resonance Energy Transfer System Composed of Cobalt(II), Luminol, Hydrogen Peroxide and CdTe Quantum Dots for Highly Sensitive Determination of Hydroquinone,” Microchimica Acta 183 (2016): 667–673, https://doi.org/10.1007/s00604‐015‐1707‐1.
S. Bag, J. C. Tseng, and J. Rochford, “A BODIPY‐Luminol Chemiluminescent Resonance Energy‐Transfer (CRET) Cassette for Imaging of Cellular Superoxide,” Organic & Biomolecular Chemistry 13 (2015): 1763–1767, https://doi.org/10.1039/C4OB02413C.
Y. Yu, W. Guan, Z. Yuan, and C. Lu, “Cationic AIEgen Micelle‐Improved Chemiluminescent H2O2 Assay by Integrating Reactant Approach and CRET,” Analytical Methods 14 (2022): 1671–1677, https://doi.org/10.1039/D2AY00372D.
S. Al and O. Sagirli, “Application of Salt‐Assisted Liquid‐Liquid Extraction in Bioanalytical Methods,” Euchembioj Reviews 1 (2025): 70, https://doi.org/10.62063/rev‐13.
B. Kul, “Biosensor Applications in the Monitoring of Elderly Patients,” Euchembioj Reviews 1 (2025): 35, https://doi.org/10.62063/rev‐12.
S. Kanwal, Z. Traore, C. Zhao, and X. Su, “Enhancement Effect of CdTe Quantum Dots–IgG Bioconjugates on Chemiluminescence of Luminol–H2O2 System,” Journal of Luminescence 130, no. 10 (2010): 1901–1906, https://doi.org/10.1016/j.jlumin.2010.05.004.
C. Huang, W. Zhou, R. Wu, W. Guan, and N. Ye, “Recent Advances in Nanomaterial‐Based Chemiluminescence Probes for Biosensing and Imaging of Reactive Oxygen Species,” Nanomaterials 13, no. 11 (2023): 1726, https://doi.org/10.3390/nano13111726.
C. Dutta, A. Bezbaruah, S. S. Bhattacharya, and P. Nath, “Spectrometric Analysis of Chemiluminescence Resonance Energy Transfer on a Smartphone‐Enabled Analytical Device,” Microchimica Acta 192, no. 10 (2025): 633, https://doi.org/10.1007/s00604‐025‐07497‐z.
K. Yang, C. Wang, X. Wei, et al., “Self‐Illuminating Photodynamic Therapy With Enhanced Therapeutic Effect by Optimization of the Chemiluminescence Resonance Energy Transfer Step to the Photosensitizer,” Bioconjugate Chemistry 31, no. 3 (2019): 595–604, https://doi.org/10.1021/acs.bioconjchem.9b00740.
M. Faizan, P. Nutthawadee, C. H. Liu, et al., “Electrochemiluminescent Magnetic Biosensor for Simultaneous MicroRNA and Parathyroid Hormone Detection via Resonance Energy Transfer,” Sensors and Actuators Reports 10 (2025): 5380400.
Y. Tang, Y. Li, P. Chen, S. Zhong, and Y. Yang, “Nucleic Acid Aptamer‐Based Sensors for Bacteria Detection: A Review,” BioEssays 47, no. 3 (2025): e202400111, https://doi.org/10.1002/bies.202400111.
M. Shellaiah, E. Manikandan, K. W. Sun, and V. Venkatachalam, “Luminescent Probes/Conjugates Derived From Quantum Dots, Nanoparticles, and Nanoclusters for Cyanide (CN−) Detection,” Nano Express 5, no. 4 (2024): 042001, https://doi.org/10.1088/2632‐959X/ad9297.
H. Sklenářová, I. Voráčová, P. Chocholouš, and M. Polášek, “Quantum Dots as Chemiluminescence Enhancers Tested by Sequential Injection Technique: Comparison of Flow and Flow‐Batch Conditions,” Journal of Luminescence 184 (2017): 235–241, https://doi.org/10.1016/j.jlumin.2016.12.030.
Contributed Indexing: Keywords: anthraquinone; chemiluminescence; fluorescence; luminol; spectrophotometer
Substance Nomenclature: 5EXP385Q4F (Luminol)
0 (Anthraquinones)
Entry Date(s): Date Created: 20260414 Date Completed: 20260715 Latest Revision: 20260715
Update Code: 20260715
DOI: 10.1002/bio.70481
PMID: 41978255
Database: MEDLINE
Description
ISSN:1522-7243
DOI:10.1002/bio.70481