Comparative in vitro Studies of the Topoisomerase I Inhibition and Anticancer Activities of Metallated N‐Confused Porphyrins and Metallated Porphyrins

Halder, Nyancy; Dzhemileva, Lilya U.; Ramazanov, Ilfir R.; D’yakonov, Vladimir A.; Джемилев, У. М.; Rath, Harapriya

doi:10.1002/cmdc.201900633

Cited by 9 publications

(4 citation statements)

References 59 publications

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“…The photophysical properties of the metallo-PMPs, like those of regular porphyrins, are the basis for their potential applications as fluorescent sensors in phototheranostic, phototherapeutic, ,− and technical fields, , in artificial light-harvesting systems, ,,− or in optical switches or logic gates, though it is not always clear to which degree the metallo-PMP carries functional advantages over the corresponding regular metalloporphyrins. The larger coordination sphere of the texaphyrins, for example, has proven to be of tremendous utility: They can readily form stable complexes with lanthanides, and the clinical studies of lutetium(III) and gadolinium(III) complexes of a water-soluble texaphyrin have shown their potential applications as photosensitizers and radiation enhancers for arteriosclerotic disease and cancer, respectively .…”

Section: Relevance Of Metallo-pmpsmentioning

confidence: 99%

Metal Complexes of Porphyrinoids Containing Nonpyrrolic Heterocycles

Thuita

Brückner

2022

Chem. Rev.

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The replacement of one or more pyrrolic building block(s) of a porphyrin by a nonpyrrolic heterocycle leads to the formation of so-called pyrrole-modified porphyrins (PMPs), porphyrinoids of broad structural variability. The wide range of coordination environments (type, number, charge, and architecture of the donor atoms) that the pyrrole-modified frameworks provide to the central metal ions, the frequent presence of donor atoms at their periphery, and their often observed nonplanarity or conformational flexibility distinguish the complexes of the PMPs clearly from those of the traditional square-planar, dianionic, N 4 -coordinating (hydro)porphyrins. Their different coordination properties suggest their utilization in areas beyond which regular metalloporphyrins are suitable. Following a general introduction to the synthetic methodologies available to generate pyrrole-modified porphyrins, their general structure, history, coordination chemistry, and optical properties, this Review highlights the chemical, electronic (optical), and structural differences of specific classes of metalloporphyrinoids containing nonpyrrolic heterocycles. The focus is on macrocycles with similar "tetrapyrrolic" architectures as porphyrins, thusly excluding the majority of expanded porphyrins. We highlight the relevance and application of these metal complexes in biological and technical fields as chemosensors, catalysts, photochemotherapeutics, or imaging agents. This Review provides an introduction to the field of metallo-PMPs as well as a comprehensive snapshot of the current state of the art of their synthesis, structures, and properties. It also aims to provide encouragement for the further study of these intriguing and structurally versatile metalloporphyrinoids.

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Section: Relevance Of Metallo-pmpsmentioning

confidence: 99%

Metal Complexes of Porphyrinoids Containing Nonpyrrolic Heterocycles

Thuita

Brückner

2022

Chem. Rev.

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“…34) to stabilize the topoisomerase–DNA covalent complex due to minor groove binding. 80 High cytotoxic activity in vitro against K562, U937, HL-60, Jurkat, A549 and HeLa cancer cell lines along the apoptotic pathway was observed. Additionally, 168 / 169 exhibited a predominant dose-dependent effect on the S and G2 phases of the cell cycle.…”

Section: Four Membered Aromatic N-confused Porphyrinoids With Nir Absorptionmentioning

confidence: 93%

Tailor-made aromatic porphyrinoids with NIR absorption

2022

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“…As the results, 8- and 2-fold increases in cytotoxicity against superficial and deeper tumor tissues, respectively, were revealed compared to the unsubstituted NCP . Cytotoxicities of NCP metal complexes were also examined to show that the NCP copper(II) complex exhibited higher cytotoxic activity than free-base NCP and regular porphyrin copper(II) complexes against various cancer cell lines along the apoptotic pathway, which would be attributed to the initiation of DNA breaks . In addition, the higher inhibitory activity of the NCP copper(II) complex to human topoisomerase I was indicated.…”

Section: Applicationsmentioning

confidence: 99%

Creation from Confusion and Fusion in the Porphyrin World─The Last Three Decades of N-Confused Porphyrinoid Chemistry

Toganoh

Furuta

2022

Chem. Rev.

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Confusion is a novel concept of isomerism in porphyrin chemistry, delivering a steady stream of new chemistry since the discovery of N-confused porphyrin, a porphyrin mutant, in 1994. These days, the number of confused porphyrinoids is increasing, and confusion and associated fusion are found in various fields such as supramolecular chemistry, materials chemistry, biological chemistry, and catalysts. In this review, the birth and growth of confused porphyrinoids in the last three decades are described.

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Comparative in vitro Studies of the Topoisomerase I Inhibition and Anticancer Activities of Metallated N‐Confused Porphyrins and Metallated Porphyrins

Cited by 9 publications

References 59 publications

Metal Complexes of Porphyrinoids Containing Nonpyrrolic Heterocycles

Metal Complexes of Porphyrinoids Containing Nonpyrrolic Heterocycles

Tailor-made aromatic porphyrinoids with NIR absorption

Creation from Confusion and Fusion in the Porphyrin World─The Last Three Decades of N-Confused Porphyrinoid Chemistry

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