LMCT transition-based red-light photochemotherapy using a tumour-selective ferrocenyl iron(<scp>iii</scp>) coumarin conjugate

Sarkar, Tukki; Bhattacharyya, Arnab; Banerjee, Samya; Hussain, Akhtar

doi:10.1039/d0cc03240a

Cited by 31 publications

(33 citation statements)

References 29 publications

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“…For the free esculetin molecule (H 2 esc), the corresponding absorption occurs at ∼347 nm. It follows that a bathochromic shift of this ligand-centered band is observed upon coordination to cobalt(III). , The d 6 low-spin (t 2g 6 ) complexes also displayed a ligand-field d–d band in the range 650–800 nm originating from the 1 A 1g → 1 T 2g and 1 A 1g → 1 T 1g transitions (Figure S28). For complexes 3 and 6 , while the longer-wavelength regions for the d–d transitions could be seen in the spectra, the shorter-wavelength regions were masked by the appearance of the high-intensity ligand-based transitions of the coordinated dppz bases.…”

Section: Resultsmentioning

confidence: 88%

“…The UV–visible spectra of complexes 1 – 6 measured in DMF/PBS [1:9 (v/v), pH = 7.2] displayed a common absorption band at ∼275 nm attributable to a π → π* transition (Figures a and S27). , A common band at ∼345 nm due to the n → π* transition involving the quinoxaline moiety was observed for the dipyridoquinoxaline (dpq) complexes 2 and 5 . , For the dipyridophenazine (dppz) complexes 3 and 6 , two additional absorption bands at 361 and 377 nm were observed that can be attributed to the n → π* transitions of the phenazine moiety. , Furthermore, complexes 4 – 6 showed an esculetin-based π → π* visible absorption band at ∼402 nm . For the free esculetin molecule (H 2 esc), the corresponding absorption occurs at ∼347 nm.…”

Section: Resultsmentioning

confidence: 97%

“…Although the photosensitizing properties of coumarins are reported, studies that focus on the photodynamic action of coumarins in a metal-bound form are scarce . Very recently, we have reported a ferrocene-conjugated iron(III) complex of esculetin that shows significant light-induced cytotoxicity against cancer cells . However, cobalt(III) coumarin complexes as photocytotoxic agents have not been explored.…”

Section: Introductionmentioning

confidence: 99%

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Mixed-Ligand Cobalt(III) Complexes of a Naturally Occurring Coumarin and Phenanthroline Bases as Mitochondria-Targeted Dual-Purpose Photochemotherapeutics

Sarkar¹,

Kumar

Sahoo

et al. 2021

Inorg. Chem.

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The bioessential nature of cobalt and the rich photochemistry of its coordination complexes can be exploited to develop potential next-generation photochemotherapeutics. A series of six novel mixed-ligand cobalt(III) complexes of the formulation [Co(B)2(L)]ClO4 (1–6), where B is an N,N-donor phenanthroline base, namely, 1,10-phenanthroline (phen in 1 and 4), dipyrido[3,2-d:2′,3′-f]quinoxaline (dpq in 2 and 5), and dipyrido[3,2-a:2′,3′-c]phenazine (dppz in 3 and 6), and L is an O,O-donor dianionic ligand derived from catechol (1,2-dihydroxybenzene, cat2–, in 1–3) or esculetin (6,7-dihydoxycoumarin, esc2–, in 4–6), have been prepared and characterized, and their light-triggered cytotoxicity has been studied in cancer cells. The single-crystal X-ray diffraction structures of complexes 1 (as PF6 – salt, 1a) and 2 show distorted octahedral geometries around the cobalt(III) center formed by the set of N4O2 donor atoms. The low-spin and 1:1 electrolytic complexes 1–6 display a d–d transition around 700 nm. Complexes 4–6 with a coordinated esc2– ligand additionally display a π → π* intraligand transition centered at 403 nm. Complexes 4–6 possessing a naturally occurring and photoactive esc2– ligand show high visible-light-triggered cytotoxicity against HeLa and MCF-7 cancer cells, yielding remarkably low micromolar IC50 values while being much less toxic under dark conditions. Control complexes 1–3 possessing the photoinactive cat2– ligand show significantly less cytotoxicity either in the presence of light or in the dark. The complex-induced cell death is apoptotic in nature caused by the formation of reactive oxygen species via a type 1 photoredox pathway. Fluorescence microscopy of HeLa cells treated with complex 6 reveals mitochondrial localization of the complex. A significant decrease in the dark toxicity of free esculetin and dppz base is observed upon coordination to cobalt(III). Complexes bind to calf-thymus DNA with significant affinity, but 6 binds with the greatest affinity. Complex 6 efficiently photocleaves supercoiled DNA to its nicked circular form when irradiated with visible light via a photoredox type 1 pathway involving hydroxyl radicals (HO•). Thus, complex 6 showing remarkable visible-light-triggered cytotoxicity but negligible toxicity in the dark is a good candidate for cancer photochemotherapy applications.

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Section: Resultsmentioning

confidence: 88%

Section: Resultsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

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Mixed-Ligand Cobalt(III) Complexes of a Naturally Occurring Coumarin and Phenanthroline Bases as Mitochondria-Targeted Dual-Purpose Photochemotherapeutics

Sarkar¹,

Kumar

Sahoo

et al. 2021

Inorg. Chem.

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“…This is the case of the in vivo photolysis of the microtubule inhibitor 4-pyridinomethylcoumarin ( Figure 8 , compound XLVIII ) [ 72 ]. 7-Hydroxymethyl substituted aminocoumarins are used as iron complexes ( Figure 8 , general structures XLIX and L ), and can be used to photochemotherapeutically target the mitochondria in the treatment of cancer [ 60 , 73 ].…”

Section: Discussionmentioning

confidence: 99%

Cancer‐Mitochondria Dual‐Targeting Glycol/Ferrocenium‐Based Polydopamine Nanoparticles for Synergistic Photothermal and Photodynamic Therapy

Wang

Pei

et al. 2021

ChemMedChem

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A cancer-mitochondria dual-targeting nanoparticle based on lactose and ferrocenium derivatives conjugated polydopamine (PDA@Lac/Fc/Hyp) was constructed, which exhibited cancertargeting and mitochondria-targeting ability deriving from lactose and ferrocenium derivatives due to the specific carbohydrate-protein interaction and cationic species properties, respectively. Moreover, PDA@Lac/Fc/Hyp showed great biocompatibility and phototherapeutic efficiency. This work displays a good example of constructing cancer-mitochondria dual-targeting nanoparticle for synergistic phototherapy.

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LMCT transition-based red-light photochemotherapy using a tumour-selective ferrocenyl iron(iii) coumarin conjugate

Abstract: A mitochondria-targeted ferrocenyl iron(iii) coumarin complex shows red-light toxicity against cancer cells but remains harmless in the dark and to normal cells.

Cited by 31 publications

References 29 publications

Mixed-Ligand Cobalt(III) Complexes of a Naturally Occurring Coumarin and Phenanthroline Bases as Mitochondria-Targeted Dual-Purpose Photochemotherapeutics

Mixed-Ligand Cobalt(III) Complexes of a Naturally Occurring Coumarin and Phenanthroline Bases as Mitochondria-Targeted Dual-Purpose Photochemotherapeutics

Trending Topics on Coumarin and Its Derivatives in 2020

Cancer‐Mitochondria Dual‐Targeting Glycol/Ferrocenium‐Based Polydopamine Nanoparticles for Synergistic Photothermal and Photodynamic Therapy

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