Abstract
Anthraquinones constitute an important class of compounds with wide applications. The solubility of derivatives at 298.15 K was discussed in ethanol–water solution and at atmospheric pressure, the solubility of 1-amino-4-hydroxy-9,10-anthraquinone (AHAQ) in binary solvents (ethanol–water combinations) was determined. Colour strength and fastening properties depend upon the kind and position of a hydrophobic group connected to the phenoxy ring of Anthraquinone moiety. There is a continuing interest in the creation of novel anthraquinone derivatives with biological activities since they have demonstrated potential for treating multiple sclerosis. For this purpose, by utilizing voltammetric and absorption studies, interactions of various derivatives with calf thymus DNA (ct-DNA) and the cationic surfactant cetyltrimethylammoniumbromide (CTAB) were examined. Here prominent Hydrophobic interaction and electron transfer resulting in binding to CTAB micelles were observed. The polarity index of the media was assessed and associated with the electrochemical parameters. The medicinal behaviour of Anthraquinone derivatives was a result of electron transfer reactions with DNA. UV–Visible and fluorescence properties were due to the transitions between n* and π* orbitals. Large absorption band with low dichroic ratio was characteristic of various derivatives of Anthraquinone. Presence of –NH group proves various derivatives remarkable calorimetric and anionic sensors.
Graphical Abstract
Similar content being viewed by others
Availability of Data and Material
All the written material is new not a copy.
Code Availability
Not Applicable.
References
Tian W et al (2020) Novel anthraquinone compounds as anticancer agents and their potential mechanism. Future Med Chem 12(7):627–644
Pham AN et al (2013) Fenton-like copper redox chemistry revisited: Hydrogen peroxide and superoxide mediation of copper-catalyzed oxidant production. J Catal 301:54–64
Malik EM, Müller CE (2016) Anthraquinones as pharmacological tools and drugs. Med Res Rev 36(4):705–748
Gessler N, Egorova A, Belozerskaya T (2013) Fungal anthraquinones. Appl Biochem Microbiol 49(2):85–99
Pankewitz F et al (2007) Anthraquinones as defensive compounds in eggs of Galerucini leaf beetles: Biosynthesis by the beetles? Arch Insect Biochem Physiol: Publ Collab Entomol Soc Am 66(2):98–108
Malik EM et al (2016) Ullmann reactions of 1-amino-4-bromoanthraquinones bearing various 2-substituents furnishing novel dyes. Dyes Pigm 131:33–40
Caro Y et al (2012) Natural hydroxyanthraquinoid pigments as potent food grade colorants: an overview. Nat Prod Bioprospecting 2(5):174–193
Kulik PH (2008) Van Nostrand's scientific encyclopedia. Wiley-Interscience
Shaw DW (2009) Allergic contact dermatitis from carmine. Dermatitis 20(5):292–295
Dufossé L (2014) Anthraquinones, the Dr Jekyll and Mr Hyde of the food pigment family. Food Res Int 65:132–136
Malik EM, Baqi Y, Müller CE (2015) Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues)–precursors for dyes and drugs. Beilstein J Org Chem 11(1):2326–2333
Forti J et al (2007) Electrochemical synthesis of hydrogen peroxide on oxygen-fed graphite/PTFE electrodes modified by 2-ethylanthraquinone. J Electroanal Chem 601(1–2):63–67
Uchimiya M, Stone AT (2009) Reversible redox chemistry of quinones: Impact on biogeochemical cycles. Chemosphere 77(4):451–458
Kazarian S (2000) Polymer processing with supercritical fluids. Polymer science series CC/C of vysokomolekuliarnye soedineniia 42(1):78–101
Montero GA et al (2000) Supercritical fluid technology in textile processing: an overview. Ind Eng Chem Res 39(12):4806–4812
Miyazaki K, Tabata I, Hori T (2012) Relationship between colour fastness and colour strength of polypropylene fabrics dyed in supercritical carbon dioxide: effect of chemical structure in 1, 4-bis (alkylamino) anthraquinone dyestuffs on dyeing performance. Color Technol 128(1):60–67
Guzel B, Akgerman A (2000) Mordant dyeing of wool by supercritical processing. J Supercrit Fluids 18(3):247–252
Shinoda T, Tamura K (2003) Solubilities of CI Disperse Red 1 and CI Disperse Red 13 in supercritical carbon dioxide. Fluid Phase Equilib 213(1–2):115–123
Torrisi A, Mellot-Draznieks C, Bell RG (2010) Impact of ligands on CO 2 adsorption in metal-organic frameworks: First principles study of the interaction of CO 2 with functionalized benzenes. II. Effect of polar and acidic substituents. J Chem Phys 132(4):044705
Tamura K, Alwi RS (2015) Solubility of anthraquinone derivatives in supercritical carbon dioxide. Dyes Pigm 113:351–356
Imran S et al (2018) Effect of electrolytes on the solubility and solution thermodynamics of 1-amino-4-hydroxy-9, 10-anthraquinone, an analogue of anthracycline anticancer drugs, in aqueous ethanol media using theoretical and UV–Vis spectroscopic study. J Mol Liq 252:151–157
Kadam S, Kanase V (2021) Laxative activity of Ethanolic extract of Capparis moonii W. fruit. Res J Pharm Technol 14(7):3528–3532
Gorkom BV, Vries ED (1999) Anthranoid laxatives and their potential carcinogenic effects. Aliment Pharmacol Ther 13(4):443–452
Huang Q et al (2007) Anti-cancer properties of anthraquinones from rhubarb. Med Res Rev 27(5):609–630
Murdock K et al (1979) Antitumor agents. 1. 1, 4-Bis [(aminoalkyl) amino]-9, 10-anthracenediones. J Med Chem 22(9):1024–1030
Shrestha JP et al (2014) Synthesis and anticancer structure activity relationship investigation of cationic anthraquinone analogs. Eur J Med Chem 77:96–102
Shrestha JP et al (2015) A mode of action study of cationic anthraquinone analogs: A new class of highly potent anticancer agents. MedChemComm 6(11):2012–2022
Khan K et al (2011) Development of anti-acne gel formulation of anthraquinones rich fraction from Rubia cordifolia (Rubiaceae). Int J Appl Res Nat Prod 4(4):28–36
Wuthi-udomlert M, Kupittayanant P, Gritsanapan W (2010) In vitro evaluation of antifungal activity of anthraquinone derivatives of Senna alata. J Health Res 24(3):117–122
Fosso MY et al (2012) Library synthesis and antibacterial investigation of cationic anthraquinone analogs. ACS Comb Sci 14(3):231–235
Gan K-H et al (2008) Antiplatelet effect and selective binding to cyclooxygenase by molecular docking analysis of 3-alkylaminopropoxy-9, 10-anthraquinone derivatives. Biol Pharm Bull 31(8):1547–1551
Seo EJ et al (2012) Chrysophanol-8-O-glucoside, an anthraquinone derivative in rhubarb, has antiplatelet and anticoagulant activities. J Pharmacol Sci 118(2):245–254
Baqi Y et al (2009) High-affinity, non-nucleotide-derived competitive antagonists of platelet P2Y12 receptors. J Med Chem 52(12):3784–3793
Jackson T, Verrier J, Kochanek P (2013) Anthraquinone-2-sulfonic acid (AQ2S) is a novel neurotherapeutic agent. Cell Death Dis 4(1):e451–e451
Kingwell E et al (2010) Cardiotoxicity and other adverse events associated with mitoxantrone treatment for MS. Neurology 74(22):1822–1826
Hussain H et al (2015) A fruitful decade from 2005 to 2014 for anthraquinone patents. Expert Opin Ther Pat 25(9):1053–1064
Pommier Y et al (2010) DNA topoisomerases and their poisoning by anticancer and antibacterial drugs. Chem Biol 17(5):421–433
Leteurtre F et al (1994) Saintopin, a dual inhibitor of DNA topoisomerases I and II, as a probe for drug-enzyme interactions. J Biol Chem 269(46):28702–28707
Taniguchi K et al (1996) Drug-induced down-regulation of topoisomerase I in human epidermoid cancer cells resistant to saintopin and camptothecins. Can Res 56(10):2348–2354
Wu C-C et al (2013) On the structural basis and design guidelines for type II topoisomerase-targeting anticancer drugs. Nucleic Acids Res 41(22):10630–10640
Lown JW (1993) Anthracycline and anthraquinone anticancer agents: current status and recent developments. Pharmacol Ther 60(2):185–214
Gewirtz D (1999) A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem Pharmacol 57(7):727–741
Tacar O, Sriamornsak P, Dass CR (2013) Doxorubicin: an update on anticancer molecular action, toxicity and novel drug delivery systems. J Pharm Pharmacol 65(2):157–170
Black SN et al (1992) Structure of 1-amino-4-hydroxy-2-phenoxy-9, 10-anthracenedione. Acta Crystallogr C 48(2):321–323
Miyazaki K, Hirogaki T, Tabata I, Hori T (2022) The relationship between the substitution position of hydrophobic groups on near‐magenta anthraquinone dyestuffs and the dyeing performance for polypropylene fabric dyed in supercritical carbon dioxide. Color Technol 138(5):538–550
Cao D et al (2022) Adsorption behavior of anthraquinones in deep eutectic solvent on polyester fiber and its application. Sustain Chem Pharm 27:100680
Martorell M et al (2021) An update of anthraquinone derivatives emodin, diacerein, and catenarin in diabetes. Evid-Based Complement Alterna Med: eCAM 2021:1–13
Goodman LS (1996) Goodman and Gilman's the pharmacological basis of therapeutics. Vol. 1549. McGraw-Hill New York
Lim K-H et al (1997) Cellular uptake and antitumor activity of the new anthracycline analog DA-125 in human cancer cell lines. Cancer Chemother Pharmacol 40(1):23–30
Preobrazhenskaya MN et al (2006) Second generation drugs-derivatives of natural antitumor anthracycline antibiotics daunorubicin, doxorubicin and carminomycin. J Med Sci-Taipei 26(4):119
Hu F-Q et al (2009) Synthesis and antitumor activity of doxorubicin conjugated stearic acid-g-chitosan oligosaccharide polymeric micelles. Biomaterials 30(36):6955–6963
Das A et al (2016) Studies on the interaction of 2-amino-3-hydroxy-anthraquinone with surfactant micelles reveal its nucleation in human MDA-MB-231 breast adinocarcinoma cells. RSC Adv 6(34):28200–28212
Mondal P et al (2015) 1-Amino-4-hydroxy-9, 10-anthraquinone–An analogue of anthracycline anticancer drugs, interacts with DNA and induces apoptosis in human MDA-MB-231 breast adinocarcinoma cells: Evaluation of structure–activity relationship using computational, spectroscopic and biochemical studies. Biochem Biophys Rep 4:312–323
Roy S et al (2015) Spectroscopic, computational and electrochemical studies on the formation of the copper complex of 1-amino-4-hydroxy-9, 10-anthraquinone and effect of it on superoxide formation by NADH dehydrogenase. Dalton Trans 44(12):5428–5440
Roy S, Guin PS (2014) Solvation of 1-amino-4-Hydroxy-9, 10-anthraquinone governs its electrochemical behavior in non-aqueous and aqueous media: A cyclic voltammetry study. J Electrochem Soc 162(3):H124
Roy S, Guin PS (2015) Investigation on the interaction of 1-amino-4-hydroxy-9, 10-anthraquinone with calf thymus DNA and CTAB micelles. J Mol Liq 211:846–853
Guin PS, Das S, Mandal P (2009) Studies on the formation of a complex of Cu (II) with sodium 1, 4-dihydroxy-9, 10-anthraquinone-2-sulphonate–An analogue of the core unit of anthracycline anticancer drugs and its interaction with calf thymus DNA. J Inorg Biochem 103(12):1702–1710
Guin PS, Mandal PC, Das S (2012) The Binding of a Hydroxy-9, 10-anthraquinone CuII Complex to Calf Thymus DNA: Electrochemistry and UV/Vis Spectroscopy. ChemPlusChem 77(5):361–369
Rossi S et al (2010) Anthraquinones danthron and quinizarin exert antiproliferative and antimetastatic activity on murine B16–F10 melanoma cells. Anticancer Res 30(2):445–449
Das P et al (2014) Synthesis, crystal structure, DNA interaction and in vitro anticancer activity of a Cu (II) complex of purpurin: dual poison for human DNA topoisomerase I and II. RSC Adv 4(103):59344–59357
Das P et al (2015) Influence of ionic strength on the interaction of THA and its Cu (II) complex with DNA helps to explain studies on various breast cancer cells. RSC Adv 5(89):73099–73111
Das P et al (2011) Cyclic voltammetric studies of 1, 2, 4-trihydroxy-9, 10-anthraquinone, its interaction with calf thymus DNA and anti-leukemic activity on MOLT-4 cell lines: a comparison with anthracycline anticancer drugs. J Phys Org Chem 24(9):774–785
Nakayama T, Okumura N, Uno B (2020) Complementary Effect of Intra-and Intermolecular Hydrogen Bonds on Electron Transfer in β-Hydroxy-Anthraquinone Derivatives. J Phys Chem B 124(5):848–860
Mukherjee Chatterjee S et al (2018) Activity of CoII–Quinalizarin: A novel analogue of anthracycline-based anticancer agents targets human DNA topoisomerase, whereas quinalizarin itself acts via formation of semiquinone on acute lymphoblastic leukemia MOLT-4 and HCT 116 cells. ACS Omega 3(8):10255–10266
Barasch D et al (1999) Novel anthraquinone derivatives with redox-active functional groups capable of producing free radicals by metabolism: are free radicals essential for cytotoxicity? Eur J Med Chem 34(7–8):597–615
Mandal B, Mondal HK, Das S (2019) In situ reactivity of electrochemically generated semiquinone on Emodin and its CuII/MnII complexes with pyrimidine based nucleic acid bases and calf thymus DNA: Insight into free radical induced cytotoxicity of anthracyclines. Biochem Biophys Res Commun 515(3):505–509
Bartoszek-Pączkowska A (2002) Metabolic activation of adriamycin by NADPH-cytochrome P450 reductase; overview of its biological and biochemical effects. Acta Biochim Pol 49:323–331
Kumbhar A, Padhye S, Ross D (1996) Cytotoxic properties of iron-hydroxynaphthoquinone complexes in rat hepatocytes. Biometals 9(3):235–240
Banerjee S et al (2021) A Co (III) Complex of 1-Amino-4-hydroxy-9, 10-anthraquinone Exhibits Apoptotic Action against MCF-7 Human Breast Cancer Cells. ACS Omega 7(1):1428–1436
Stasevych M et al (2021) Amino-and diamino-9, 10-anthracenedione derivatives: Biofocus and applied advantages-a mini-review. Biointerface Res Appl Chem 11(6):14103–14114
Wacławek S et al (2021) Selective spectrophotometric determination of peroxydisulfate based on a by-product formation. Sens Actuators B Chem 344:130214
Waring MJ (1981) DNA modification and cancer. Annu Rev Biochem 50(1):159–192
Enache M, Anghelache I, Volanschi E (2010) Coupled spectral and electrochemical evaluation of the anticancer drug mitoxantrone–sodium dodecyl sulfate interaction. Int J Pharm 390(2):100–106
Ramotowska S et al (2019) Hydrogen bonding and protonation effects in amino acids’ anthraquinone derivatives-Spectroscopic and electrochemical studies. Spectrochim Acta Part A Mol Biomol Spectrosc 222:117226
Sharma BK et al (2017) Synthesis, Spectral, Electrochemical and Theoretical Investigation of indolo [2, 3-b] quinoxaline dyes derived from Anthraquinone for n–type materials. J Chem Sci 129:483–494
Chang JB et al (2012) Dichroic and spectral properties of anthraquinone-based azo dyes for PVA polarizing film. Dyes Pigm 92(1):737–744
Zhang J et al (2016) Dihydroxyanthraquinone derivatives: natural dyes as blue-light-sensitive versatile photoinitiators of photopolymerization. Polym Chem 7(47):7316–7324
Xiao P et al (2013) Cationic and thiol–ene photopolymerization upon red lights using anthraquinone derivatives as photoinitiators. Macromolecules 46(17):6744–6750
Zhang J et al (2018) Disubstituted aminoanthraquinone-based multicolor photoinitiators: photoinitiation mechanism and ability of cationic polymerization under blue, green, yellow, and red LEDs. Macromolecules 51(20):8165–8173
Kaur K, Kumar S (2010) 1-Aminoanthracene-9, 10-dione based chromogenic molecular sensors: effect of nature and number of nitrogen atoms on metal ion sensing behavior. Tetrahedron 66(34):6990–7000
Ranyuk E et al (2011) Rational design of aminoanthraquinones for colorimetric detection of heavy metal ions in aqueous solution. Dalton Trans 40(40):10491–10502
Kaur N, Kumar S (2012) Aminoanthraquinone-based chemosensors: colorimetric molecular logic mimicking molecular trafficking and a set–reset memorized device. Dalton Trans 41(17):5217–5224
Jali BR (2021) A mini-review: quinones and their derivatives for selective and specific detection of specific cations. Biointerface Res Appl Chem 11:11679–11699
Kaur N (2022) Anthraquinone appended chemosensors for fluorescence monitoring of anions and/or metal ions. Inorganica Chimica Acta 120917
Cho EJ et al (2006) Naked eye fluoride ion chemosensors with anthraquinone derivatives. Bull-Korean Chem Soc 27(12):1967
Author information
Authors and Affiliations
Contributions
Concept and design of this article is collective contribution of all authors. They all read and approve the final manuscript of this research article. Bushra Tariq along with Sadia Asim plays a vital role in collecting data regarding the spectroscopic and voltammetric properties of Anthraquinone and its derivatives and their applications as sensors. Fluorescent applications of Anthraquinone derivatives in imaging purpose was collected by Abida Kausar and Asim Mansha. The first draf of manuscript was written by Bushra Tariq which was later refined by Sadia Asim, Abida Kausar and Asim Mansha.
Corresponding author
Ethics declarations
Ethics Approval
Not applicable.
Consent to Participate
Yes, i got permission.
Consent for Publication
Yes, u can publish it.
Conflict of Interest
The review article entitled “Spectroscopic and Voltammetric Analysis of Anthraquinone Derivatives as Fluorescence Sensors”. All the authors involved in the write up of this article do not have any conflict of Interest. The complete details of authors are given as under.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Tariq, B., Mansha, A., Asim, S. et al. Effect of Substituents on Solubility, Medicinal, Absorption, Emission and Cationic/Anionic Detection Properties of Anthraquinone Derivatives. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03410-0
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10895-023-03410-0