Heterocyclic Crown Ethers with Potential Biological and Pharmacological Properties: From Synthesis to Applications
Source abstract
Abstract
Cyclic organic compounds with several ether linkages in their structure are of much concern in our daily life applications. Crown ethers (CEs) are generally heterocyclic and extremely versatile compounds exhibiting higher binding affinity. In recent years, due to their unique structure, crown ethers are widely used in drug delivery, solvent extraction, cosmetics manufacturing, material studies, catalysis, separation, and organic synthesis. Beyond their conventional place in chemistry, this review article summarizes the synthesis, biological, and potential pharmacological activities of CEs. We have emphasized the prospects of CEs as anticancer, anti-inflammatory, antibacterial, and antifungal agents and have explored their amyloid genesis inhibitory activity, electrochemical, and potential metric sensing properties. The central feature of these compounds is their ability to form selective and stable complexes with various organic and inorganic cations. Therefore, CEs can be used in gas chromatography as the stationary phase and are also valuable for cation chromatographic to determine and separate alkali and alkaline-earth cations.
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Molecular Sensors and Ion Detection · Supramolecular Chemistry and Complexes · Chemical Synthesis and Analysis
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Department of Chemistry, Quaid I Azam University, Islamabad 45320, Pakistan
Institute of Chemistry, University of Sargodha, Sargodha 40100, Pakistan
Department of Chemistry, International Islamic University, Islamabad 45320, Pakistan
Department of Pharmacy, Quaid I Azam University, Islamabad 45320, Pakistan
Department of Chemistry, Allama Iqbal Open University, Islamabad 45320, Pakistan
Department of Zoology, Government College University, Faisalabad 38000, Pakistan
Department of Chemistry, Sub Campus, University of Sargodha, Bhakkar 30000, Pakistan
Department of Histology, Embryology and Cytophysiology, Medical University of Lublin, Radziwiłłowska 11, 20-080 Lublin, Poland
Department of Chemistry, Siedlce University of Natural Sciences and Humanities, 3-go Maja 54, 08-110 Siedlce, Poland
References (90)
Show source-provided references
1. Ethers, A., Basok, S.S., Schepetkin, I.A., Khlebnikov, A.I., Lutsyuk, A.F., Kirichenko, T.I., Kirpotina, L.N., Pavlovsky, V.I., Leonov, K.A., and Vishenkova, D.A. (2021). Synthesis, Biological Evaluation, and Molecular Modeling of Aza-Crown Ethers. Molecules, 26.10.3390/molecules26082225 ↗
2. Davis, F., and Higson, S. (2011). Crown Ethers, Cryptands and Other Compounds, John Wiley and Sons.
3. Synthesis, Characterization and Antibacterial Activity of New Complexes of Some Lanthanide Ions with Benzo 18-Crown-6 and 221-Cryptand10.9790/5736-0643239 ↗
4. De Capacitive Sensing of Amino Acids Using Caliraxene-Coated Silicon Transducers10.1002/elan.200603729 ↗
5. Crown Ethers: Their Complexes and Analytical Applications
6. First- and second-sphere coordination chemistry of alkali metal crown ether complexes10.1016/S0010-8545(01)00317-4 ↗
7. Novel Electron-Transfer Reactions Mediated by Alkali Metals Complexed by Macrocyclic Ligand10.1021/ar9702076 ↗
8. Crown Ether Based Optical Molecular Sensors and Photocontrolled Crown Ether-Based Optical Molecular Sensors and Photocontrolled Ionophores10.6060/mhc2010.4.189 ↗
9. Crown ethers: Sensors for ions and molecular scaffolds for materials and biological models10.1021/cr020080k ↗
10. Cyclic polyethers and their complexes with metal salts10.1021/ja01002a035 ↗
11. Lee, W., Bang, E., Yun, J., Paik, M., and Lee, W. (2019). Enantiodiscrimination Using a Chiral Crown Ether as a Chiral Solvating Agent Using NMR Spectroscopy. J. SAGE.10.1177/1934578X19849191 ↗
12. Application of nanoparticle modified with crown ether in colorimetric determinations10.1016/j.arabjc.2015.07.012 ↗
13. Record Low Ionization Potentials of Alkali Metal Complexes with Crown Ethers and Cryptands10.1002/cphc.201900422 ↗
14. Davis, F., and Higson, S. (2011). Macrocycles (Construction, Chemistry and Nanotechnology Applications)II Front Matter, John Wiley and Sons.10.1002/9780470980200 ↗
15. Permeation selectivity of alkali metal ions through crown ether based ion channels10.1016/j.molliq.2020.112577 ↗
16. Crown Thioether Chemistry10.1021/ar00148a002 ↗
17. Incorporating size selectivity into synergistic solvent extraction: A review of crown ether-containing systems10.1021/ie000356j ↗
18. The role of crown ethers in drug delivery10.1080/10610278.2019.1568432 ↗
19. Conductometric studies on cation-crown ether complexes: A review10.1080/10408347.2011.589284 ↗
20. Stability and Reactivity of Crown-Ether Complexes
21. A dual-responsive supramolecular polymer gel formed by crown ether based molecular recognition10.1002/anie.201006999 ↗
22. Highly mechanosensitive ion channels from graphene-embedded crown ethers10.1038/s41563-018-0220-4 ↗
23. Oral toxicity of the cyclic polyethers-12-crown-4, 15-crown-5, and 18-crown-6-in mice10.1016/0041-008X(78)90188-6 ↗
24. Development and application of crown ether-based HPLC chiral stationary phases10.5012/bkcs.2005.26.8.1153 ↗
25. Crown ether assembly of gold nanoparticles: Melamine sensor10.1016/j.bios.2010.08.081 ↗
26. Surveying macrocyclic chemistry: From flexible crown ethers to rigid cyclophanes10.1039/C7CS00185A ↗
27. Crown Ether-Functionalized Polybenzoxazine for Metal Ion Adsorption10.1021/acs.macromol.9b02519 ↗
28. A new crown ether as vesicular carrier for 5-fluoruracil: Synthesis, characterization and drug delivery evaluation10.1016/j.colsurfb.2007.03.010 ↗
29. Chiral crown ether pillared lamellar lanthanide phosphonates10.1021/ja027892i ↗
30. Crown Ether Complexes of Alkali-Metal Chlorides from SO210.1002/chem.201701174 ↗
31. Cationic Crown Ether Complexes of Germanium(II)10.1002/ange.200901351 ↗
32. The crown ether size and stereochemistry affect the self-assembly, hydrogelation, and cellular interactions of crown ether/peptide conjugates10.1039/D0TB01913E ↗
33. Synthesis and electroluminescence of novel copolymers containing crown ether spacers10.1039/b209469j ↗
34. Organic chemosensors with crown-ether groups (review)10.1007/s10593-008-0132-3 ↗
35. Organogels and their use in drug delivery—A review10.1016/j.jconrel.2007.09.014 ↗
36. Antitumor potential of crown ethers: Structure-activity relationships, cell cycle disturbances, and cell death studies of a series of ionophores10.1021/jm061162u ↗
37. Supramolecular chemistry anniversary10.1039/C7CS90037F ↗
38. Complexation Study of Alkali Metal Ions by Crown Ether Derivatives in Nonaqueous Solvents by Potentiometric Methods10.4152/pea.200204167 ↗
39. Trace Metal role on Crown ethers Stability by DET Abstract
40. Synthesis and Application of Crown Ethers
41. Double-armed crown ethers for calcium optical sensors10.1016/j.talanta.2009.01.046 ↗
42. The condensation of methyl ketones with furan10.1021/jo01126a001 ↗
43. Free, Grafted on Polymers and Intercaled Ethers-Crowns in Clays and Applications
44. Host-Guest Complexation. 1. Concept and Illustration10.1021/ja00450a026 ↗
45. Fluorescent supramolecular polymers formed by crown ether based host guest interaction10.3389/fchem.2020.00560 ↗
46. Gokel, G.W. (1993). Supramolecular Chemistry. Supramol. Chem., 3.
47. Ammonium ion binding property of naphtho-crown ethers containing thiazole as sub-cyclic unit10.5012/bkcs.2004.25.10.1465 ↗
48. Synthesis and characterization of a novel (E,E)-dioxime and its mono- and heterotrinuclear complexes containing a 21-membered trioxadithiadiaza macrocycle10.1039/b004623j ↗
49. Enantiomeric recognition of amine compounds by chiral macrocyclic receptors10.1021/cr960144p ↗
50. The effect of substitution and stereochemistry on ion binding in the polyether ionophore monensin10.1021/ja00231a076 ↗
51. Crown Ethers as Solvent Extraction Reagents: Where do We Stand?10.1080/01496398808075628 ↗
52. Solvent extraction separation of strontium as 18-crown-6 complex with picrate ion10.1021/ac00135a027 ↗
53. Synthesis of 4-Substituted 2-(4-Methylpiperazino) pyrimidines and Quinazoline Analogs as Serotonin 5-HT 2A Receptor Ligands10.1002/jhet.236 ↗
54. Novel bis-crown ethers and their sodium complexes as antimicrobial agent: Synthesis and spectroscopic characterizations10.1007/s00044-014-0937-9 ↗
55. Synthesis and biological evaluation of aza-crown ether-squaramide conjugates as anion/cation symporters10.4155/fmc-2018-0595 ↗
56. Synthesis, DNA-binding, cleavage, and cytotoxic activity of new 1,7-dioxa-4,10-diazacyclododecane artificial receptors containing bisguanidinoethyl or diaminoethyl double side arms10.1002/chem.200700549 ↗
57. Squaramide-based tripodal receptors for selective recognition of sulfate anion10.1039/c3cc00196b ↗
58. Tripodal squaramide conjugates as highly effective transmembrane anion transporters10.1016/j.bmcl.2017.03.024 ↗
59. Synthesis and biological activity of (γ-arylpyridino)-dibenzoaza-14-crown-4 ethers10.1016/j.mencom.2015.05.023 ↗
60. 2-Thienyl-4-furyl-6-aryl pyridine derivatives: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study10.1016/j.bmc.2009.10.049 ↗
61. Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study of hydroxylated 2,4-diphenyl-6-aryl pyridines10.1016/j.bmc.2010.03.051 ↗
62. Investigation of photophysical behaviours and antimicrobial activity of novel benzo-15-crown-5 substituted coumarin and chromone derivatives10.1016/j.molstruc.2019.127569 ↗
63. Synthesis and biological evaluation of crown ether acyl derivatives10.1016/j.bmcl.2016.09.066 ↗
64. Further Approaches in the Design of Antitumor Agents with Response to Cell Resistance: Looking toward Aza Crown Ether-dtc Complexes10.1021/acs.inorgchem.0c02068 ↗
65. Toxicological responses of the earthworm Eisenia fetida to 18-crown-6 under laboratory conditions10.1007/s00128-014-1345-z ↗
66. Crown Ethers as Transthyretin Amyloidogenesis Inhibitors10.1021/acs.jmedchem.8b01700 ↗
67. Electrochemical Determination of Neurotransmitters at Crown Ether Modified Carbon Nanotube Composite: Application for Sub-nano-sensing of Serotonin in Human Serum10.1002/elan.201800065 ↗
68. A novel crown ether-acylhydrazone turn-on fluorescent chemosensor for Al3+ ion10.1016/j.saa.2018.11.040 ↗
69. A potassium-selective electrochemical sensor based on crown-ether functionalized self assembled monolayer10.1016/j.jelechem.2017.12.051 ↗
70. Rapid colorimetric detection of potassium ions based on crown ether modified Au NPs sensor10.1016/j.snb.2018.10.139 ↗
71. Crown Ether/Carbon Nanotubes Based Biperiden Disposable Potentiometric Sensor10.1002/elan.201600635 ↗
72. Asymmetric Phase Transfer Reactions Catalyzed by Chiral Crown Ethers Derived from Monosaccharides10.2174/157017810793811669 ↗
73. Crown ether modified peptide interactions with model membranes10.1080/10610278.2019.1574349 ↗
74. Crown ethers reverse P-glycoprotein-mediated multidrug resistance in cancer cells10.1038/s41598-018-32770-y ↗
75. Lipidated Polyaza Crown Ethers as Membrane Anchors for DNA-Controlled Content Mixing between Liposomes10.1038/s41598-019-49862-y ↗
76. The determination of the carbonic anhydrases activators in vitro effect of mixed donor crown ethers10.1002/jbt.22032 ↗
77. Benzo-15-crown-5 functionalized polydiacetylene-based colorimetric self-assembled vesicular receptors for lead ion recognition10.1039/c0jm03062g ↗
78. Enhancement of transfection activity in HEK293 cells by lipoplexes containing cholesteryl nitrogen-pivoted aza-crown ethers10.1007/s00044-012-0252-2 ↗
79. Synthesis and biological evaluation of crown ether fused quinazoline analogues as potent EGFR inhibitors10.1016/j.bmcl.2012.06.067 ↗
80. Buckyball-Based Spherical Display of Crown Ethers for de Novo Custom Design of Ion Transport Selectivity10.1021/jacs.0c09655 ↗
81. Computational and NMR Studies on the Complexation of Lithium Ion to 8-Crown-410.1002/cphc.201900496 ↗
82. A far-red aza-crown ether fluorescent probe for selective G-quadruplex DNA targeting10.1016/j.dyepig.2020.108222 ↗
83. The solvent effect on selectivity of four well-known cryptands and crown ethers toward Na+ and K+ cations; A computational study10.1016/j.molliq.2020.113149 ↗
84. Crown ether modified peptides: Length and crown ring size impact on membrane interactions10.1016/j.bbamem.2020.183261 ↗
85. An, S., Xu, Q., Ni, Z., Hu, J., Peng, C., Zhai, L., Guo, Y., and Liu, H. (2021). Construction of Covalent Organic Frameworks with Crown Ether Struts. Angew. Chem.-Int. Ed., 9959–9963.10.1002/anie.202101163 ↗
86. Crystalline C-C and C=C Bond-Linked Chiral Covalent Organic Frameworks10.1021/jacs.0c11050 ↗
87. Synthesis, complexation and biological effects studies of new thiacrown ethers derived quinoline: Part I10.1080/17415993.2019.1579816 ↗
88. Synthesis and bioactivity of novel (γ-piperidono)dibenzo-33-aza-14-crown-3 ethers10.1007/s10593-019-02512-7 ↗
89. Comparison of classic and microwave-assisted synthesis of benzo-thio crown ethers, and investigation of their ion pair extractions10.1016/j.molstruc.2017.07.081 ↗
90. Synthesis of Novel 4-((Substituted bis-indolyl)methyl)-benzo-15-crown-5 for the Colorimetric Detection of Hg2+ Ions in an Aqueous Medium10.1002/jhet.3422 ↗