Imidazole ring is an important five-membered aromatic heterocycle widely present in natural products and synthetic molecules. The unique structural feature of imidazole ring with desirable electron-rich characteristic is beneficial for imidazole derivatives to readily bind with a variety of enzymes and receptors in biological systems through diverse weak interactions, thereby exhibiting broad bioactivities. The related research and developments of imidazole-based medicinal chemistry have become a rapidly developing and increasingly active topic. Particularly, numerous imidazole-based compounds as clinical drugs have been extensively used in the clinic to treat various types of diseases with high therapeutic potency, which have shown the enormous development value. This work systematically gives a comprehensive review in current developments of imidazole-based compounds in the whole range of medicinal chemistry as anticancer, antifungal, antibacterial, antitubercular, anti-inflammatory, antineuropathic, antihypertensive, antihistaminic, antiparasitic, antiobesity, antiviral, and other medicinal agents, together with their potential applications in diagnostics and pathology. It is hoped that this review will be helpful for new thoughts in the quest for rational designs of more active and less toxic imidazole-based medicinal drugs, as well as more effective diagnostic agents and pathologic probes.

Comprehensive Review in Current Developments of Imidazole‐Based Medicinal Chemistry

In this tutorial review we discuss imidazolium receptors for anion recognition and recent contributions between 2006-2009 are reviewed according to target analytes, such as ATP and DNA, as well as structural classification, including cage type imidazoliums, imidazolium calixarenes, ferrocenyl imidazoliums, chiral systems, fluorescent or colorimetric imidazoliums, imidazolium cyclophane, nano assembled structures, bile acid-imidazolium, and tripodal-imidazolium systems.

/pdf/revisit-to-imidazolium-receptors-for-the-recognition-of-569k8b5bmv.pdf

Revisit to imidazolium receptors for the recognition of anions: highlighted research during 2006–2009

Imidazolium salts, distinct from their parent imidazoles, are made up of a discrete cation and anion pair, and have found widespread utility as ionic liquids. A lesser known function of such imidazolium salts includes the application of these salts in biological systems, and several areas of bio-applications, including antitumour, antimicrobial, antioxidant and bioengineering applications, will be presented and discussed in this review. The wide-ranging applications and versatility of these imidazolium salts stem from the ease of their structural variation, in which properties such as amphiphilicity, lipophilicity and solubility can be tuned.

Imidazolium salts and their polymeric materials for biological applications

A suitable method for the synthesis of ruthenium(II) arene benzhydrazone complexes (1–6) of the general formula [(η6-arene)Ru(L)Cl] (arene-benzene or p-cymene; L-monobasic bidentate substituted 9-anthraldehyde benzhydrazone derivatives) has been described. The composition of the complexes has been established by elemental analysis, IR, UV-Vis, emission, NMR and ESI-MS spectral methods. The solid state molecular structure of a representative complex was determined by a single-crystal X-ray diffraction study and indicates the presence of pseudo-octahedral (piano stool) geometry. All the complexes have been thoroughly screened for their cytotoxicity against human cervical cancer cells (HeLa), human breast cancer cell line (MDA-MB-231) and human liver carcinoma cells (Hep G2) under in vitro conditions. Interestingly, the cytotoxic activity of complex 6 is much more potent than cisplatin with low IC50 values against all the cancer cell lines tested. Furthermore, the results of AO–EB, Hoechst 33258 and flow cytometry analyses reveal that these complexes induce cell death only through apoptosis. The comet assay has been employed to determine the extent of DNA fragmentation in cancer cells. A hemolysis assay with human erythrocytes demonstrated good blood biocompatibility of all the ruthenium(II) arene benzhydrazone complexes. These results highlight the strong possibility to develop highly active ruthenium complexes as anticancer agents.

Ruthenium(II) arene complexes containing benzhydrazone ligands: synthesis, structure and antiproliferative activity

A water-soluble imidazolium-based fluorescent chemosensor senses RNA selectively through fluorescence enhancement over other biologically relevant biomolecules in aqueous solution at physiological pH 7.4. Fluorescence image detection of RNA in living cells such as onion cells, HeLa cells, and animal model cells was successfully demonstrated which displays a chelation-enhanced fluorescence effect. These affinities can be attributed to the strong electrostatic (C–H)+···A– ionic H-bonding and the aromatic moiety driven π-stacking of imidazolium-based cyclophane with the size-complementary major groove of RNA.

Selective fluorescent detection of RNA in living cells by using imidazolium-based cyclophane.

Unique X-ray sheet structure of 1,8-bis(imidazolium) anthracene and its application as a fluorescent probe for DNA and DNase

Peptide nucleic acids (PNA) are one of the most widely used synthetic DNA mimics where the four bases are attached to a N-(2-aminoethyl)glycine (aeg) backbone instead of the negative-charged phosphate backbone in DNA. We have developed a chimeric PNA (chiPNA), in which a chiral GNA-like γ3T monomer is incorporated into aegPNA backbone. The base pair opening kinetics of the aegPNA:DNA and chiPNA:DNA hybrid duplexes were studied by NMR hydrogen exchange experiments. This study revealed that the aegPNA:DNA hybrid is much more stable duplex and is less dynamic compared to DNA duplex, meaning that base pairs are opened and reclosed much more slowly. The site-specific incorporation of γ3T monomer in the aegPNA:DNA hybrid can destabilize a specific base pair and its neighbors, maintaining the thermal stabilities and dynamic properties of other base pairs. Our hydrogen exchange study firstly revealed the unique kinetic features of base pairs in the aegPNA:DNA and chiPNA:DNA hybrids, which will provide an insight into the development of methodology for specific DNA recognition using PNA fragments.

/pdf/base-pair-opening-kinetics-study-of-the-aegpna-dna-hydrid-205ogvuo87.pdf

Base pair opening kinetics study of the aegPNA:DNA hydrid duplex containing a site-specific GNA-like chiral PNA monomer

Peptide nucleic acid (PNA) is an oligonucleotide mimic, in which the sugar-phosphate backbone is replaced by a pseudo-peptide skeleton, composed of N-(2-aminoethyl)-glycine (aeg) units carrying nucleobases via methylene carbonyl linkages (Figure 1 a). Owing to its neutral amide backbone, aegPNA has outstanding chemical and enzymatic stability as well as high binding affinities to DNA and RNA, which gives it great potential for development as an antisense agent or diagnostic tools in a chip-based assay.

GNA/aegPNA chimera loaded with RNA binding preference.

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Unique X-ray sheet structure of 1,8-bis(imidazolium) anthracene and its application as a fluorescent probe for DNA and DNase

Base pair opening kinetics study of the aegPNA:DNA hydrid duplex containing a site-specific GNA-like chiral PNA monomer

GNA/aegPNA chimera loaded with RNA binding preference.