Chirality in Anticancer Agents

Valentová, Jindra; Lintnerová, Lucia

doi:10.5772/intechopen.98977

Cited by 4 publications

(3 citation statements)

References 96 publications

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“…This is true not only for purely organic drugs but also for metal-based drugs developed for anticancer applications [ 66 ]. The chiral metal-based anticancer drugs have been comprehensively reviewed in the literature [ 66 , 67 ] and the influence of chirality on the antineoplastic effect of synthetic organic compounds was surveyed by Valentova et al [ 68 ]. The antitumour activity of natural and synthetic chiral flavonoids is the subject of a literature review by Pinto et al [ 69 ].…”

Section: Chirality In Drug Designmentioning

confidence: 99%

Analogues of Anticancer Natural Products: Chiral Aspects

Valentová

Lintnerová

Miklášova

et al. 2023

IJMS

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Life is chiral, as its constituents consist, to a large degree, of optically active molecules, be they macromolecules (proteins, nucleic acids) or small biomolecules. Hence, these molecules interact disparately with different enantiomers of chiral compounds, creating a preference for a particular enantiomer. This chiral discrimination is of special importance in medicinal chemistry, since many pharmacologically active compounds are used as racemates—equimolar mixtures of two enantiomers. Each of these enantiomers may express different behaviour in terms of pharmacodynamics, pharmacokinetics, and toxicity. The application of only one enantiomer may improve the bioactivity of a drug, as well as reduce the incidence and intensity of adverse effects. This is of special significance regarding the structure of natural products since the great majority of these compounds contain one or several chiral centres. In the present survey, we discuss the impact of chirality on anticancer chemotherapy and highlight the recent developments in this area. Particular attention has been given to synthetic derivatives of drugs of natural origin, as naturally occurring compounds constitute a major pool of new pharmacological leads. Studies have been selected which report the differential activity of the enantiomers or the activities of a single enantiomer and the racemate.

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Section: Chirality In Drug Designmentioning

confidence: 99%

Analogues of Anticancer Natural Products: Chiral Aspects

Valentová

Lintnerová

Miklášova

et al. 2023

IJMS

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show abstract

“…Anticancer drugs often derive from nature and typically have more rings and more stereogenic centers in their structures, with respect to the synthetic ones. The antibiotics produced from microbes, such as doxorubicin, bleomycin, actinomycin, and mitomycin C, have been demonstrated to possess good anticancer properties [117]. Moreover, plant-derived compounds are used widely as antitumor agents, namely, the Vinca alkaloids, the camptothecins (42), the epipodophyllotoxins (43), and the taxanes [118].…”

Section: Anticancer Drugsmentioning

confidence: 99%

A Look at the Importance of Chirality in Drug Activity: Some Significative Examples

et al. 2022

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Chirality plays an important role in the development of many pharmaceuticals, being a general property of ‘handedness’; nevertheless, a large number of pharmaceuticals are still marketed and administered as racemates. Chirality is all around and even within us; indeed, receptors and enzymes are chiral entities and interact in a specific manner with chiral drugs. Consequently, controlling enantiomeric purity and isolating the enantiomers from chiral drugs remains a crucial subject for analytical, clinical, and regulatory purposes, thus, improving the drug safety profile. The classical examples of spontaneous enantiomerization and severe toxicity related to chirality are represented by ibuprofen and thalidomide, respectively, but numerous other cases have been reported in the literature. This review intends to offer a brief overview on the most common chiral drugs used in therapy for the treatment of various diseases.

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“…However, it is very likely that interactions between these complexes and targeted biomolecules such as proteins or DNA are involved [23,24,[26][27][28][29][30][31][32]. These interactions could be influenced by the stereochemistry of the complexes, as many studies have already highlighted the intrinsic role of metal compound chirality in biological activity [34][35][36][37]. In comparison with fac-[Re I (CO) 3 ] + species, studies for anticancer properties of rhenium dicarbonyl complexes (cis-[Re II (CO) 2 ] +/2+ ) are extremely rare.…”

Section: Introductionmentioning

confidence: 99%

In Vitro Biological Activity of α-Diimine Rhenium Dicarbonyl Complexes and Their Reactivity with Different Functional Groups

et al. 2023

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Cancer remains one of the leading causes of death worldwide. The interest in organometallic complexes as anticancer drug candidates continues to be pivotal for many researchers. Initially underestimated for their therapeutic potentials, rhenium complexes are now slowly gaining momentum. While tricarbonyl complexes of rhenium are widely investigated, dicarbonyl derivatives of the cis-[Re(CO)2]+ core remain largely unexplored. In this study, we tested in vitro a variety of rhenium dicarbonyl complexes for their activity towards three cancer cell lines (A549, MCF-7 and HCT116) and one healthy cell line (HEK293). The most lipophilic compounds showed, like the tricarbonyl species, good activity against specific cancer lines (IC50 = 1.5–2.5 µM); however, the same were also toxic towards healthy cells. In order to understand these differences, we performed a reactivity study of cis-[Re(CO)2(NN)]+ species (where NN = diimine) with biologically relevant functional groups (-COOH, -NH2, -SH and aromatic nitrogen-based ligands) and compared the chemistry to what is known for the fac-[Re(CO)3]+ core. Overall, we found that the rhenium dicarbonyl complexes only show good reactivity with aromatic nitrogen-based ligands. The reaction of cis-[Re(CO)2(NN)]+ species with common bio-functional groups leads, rather, to the formation of bis-diimine dicarbonyl complexes (cis-[Re(CO)2(NN)2]+) as the major by-product.

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Chirality in Anticancer Agents

Cited by 4 publications

References 96 publications

Analogues of Anticancer Natural Products: Chiral Aspects

Analogues of Anticancer Natural Products: Chiral Aspects

A Look at the Importance of Chirality in Drug Activity: Some Significative Examples

In Vitro Biological Activity of α-Diimine Rhenium Dicarbonyl Complexes and Their Reactivity with Different Functional Groups

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