Mitochondria localizing high-spin iron complexes of curcumin for photo-induced drug release

Jana, Avishek; Verma, Brijesh Kumar; Garai, Aditya; Kondaiah, Paturu; Chakravarty, Akhil R.

doi:10.1016/j.ica.2018.09.008

Cited by 6 publications

(3 citation statements)

References 51 publications

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“…Light promoted bond cleavage reactions of photocaged compounds serve as powerful tools to create materials in a highly spatially and temporally controlled manner. As a result, these substances have found wide applications in tissue engineering, biosensing, counterfeit detection, controlled release of functional molecules, and regulation of gene expression. − Moreover, owing to their use of noninvasive optical triggers, and its high spatial and temporal precision, photocaged substances have been utilized to explore biological processes and elucidate their mechanistic nature. − Arylcarbonylmethyl, nitroaryl ( ortho -nitrobenzyl, ortho -nitroanilides), azobenzene, xanthene, coumarin-4-ylmethyl, − and indoline groups , are the commonly used photoreaction triggers to construct photocages for controlled release of metal ions (Ca 2+ , Zn 2+ , Cu 2+ ), drugs, and other bioactive substances. − Particularly, incorporation of nitrobenzene derivatives along with metal ion-binding ligands has become a prevailing tool to investigate the signaling processes in biological systems that are governed by metal ions. − In addition, photocage containing metal ion complexes along with fluorophores whose optical properties are altered by metal ion binding and release have been employed to elucidate cellular processes and signaling …”

Section: Introductionmentioning

confidence: 99%

Sanger’s Reagent Sensitized Photocleavage of Amide Bond for Constructing Photocages and Regulation of Biological Functions

Wei

Sun

et al. 2020

J. Am. Chem. Soc.

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Photolabile groups offer promising tools to study biological processes with high spatial and temporal control. In the investigation, we designed and prepared several new glycine amide derivatives of Sanger's reagent and demonstrated that they serve as a new class of photocages for Zn 2+ and an acetylcholinesterase (AChE) inhibitor. We showed that the mechanism for photocleavage of these substances involves initial light-driven cyclization between the 2,4dinitrophenyl and glycine methylene groups to form acyl benzimidazole N-oxides, which undergo secondary photoinduced decarboxylation in association with rupture of an amide bond. The cleavage reactions proceed with modest to high quantum yields. We demonstrated that these derivatives can be used in targeted intracellular delivery of Zn 2+ , fluorescent imaging by light-triggered Zn 2+ release, and regulation of biological processes including the enzymatic activity of carbonic anhydrase (CA), negative regulation of N-methyl-D-aspartate receptors (NMDARs), and pulse rate of cardiomyocytes. The successful proof-of-concept examples described above open a new avenue for using Sanger's reagentbased glycine amides as photocages for the exploration of complex cellular functions and signaling pathways.

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Section: Introductionmentioning

confidence: 99%

Sanger’s Reagent Sensitized Photocleavage of Amide Bond for Constructing Photocages and Regulation of Biological Functions

Wei

Sun

et al. 2020

J. Am. Chem. Soc.

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“…The analogous charge-neutral Fe III complex 191 ( Figure 29 ) and two other high-spin iron complexes reportedly released curcumin upon irradiation with visible light, and thus exhibited cytotoxicity in multiple cell lines. 1056 In addition, Fe III –polysaccharide hydrogels were found to be visible-light (405 nm) responsive because of the photoreduction of the Fe III ions to Fe II , which rendered the Fe complexes incapable of functioning as cross-linkers for the polymer. 1057 …”

Section: Photorelease From Coordination Compoundsmentioning

confidence: 99%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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Photoactivatable (alternatively, photoremovable, photoreleasable, or photocleavable) protecting groups (PPGs), also known as caged or photocaged compounds, are used to enable non-invasive spatiotemporal photochemical control over the release of species of interest. Recent years have seen the development of PPGs activatable by biologically and chemically benign visible and near-infrared (NIR) light. These long-wavelength-absorbing moieties expand the applicability of this powerful method and its accessibility to non-specialist users. This review comprehensively covers organic and transition metal-containing photoactivatable compounds (complexes) that absorb in the visible- and NIR-range to release various leaving groups and gasotransmitters (carbon monoxide, nitric oxide, and hydrogen sulfide). The text also covers visible- and NIR-light-induced photosensitized release using molecular sensitizers, quantum dots, and upconversion and second-harmonic nanoparticles, as well as release via photodynamic (photooxygenation by singlet oxygen) and photothermal effects. Release from photoactivatable polymers, micelles, vesicles, and photoswitches, along with the related emerging field of photopharmacology, is discussed at the end of the review.

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“…Biotin has been established to have a strong binding affinity for protein receptors like avidin and streptavidin (∼10 14 M) [20] . The present work stems from our continued interest towards designing mixed‐ligand iron(III) based anticancer agents for cancer cell targeting and apoptotic cell death [21–24] . Recent studies have indicated that curcumin can modulate different biological processes involved in cell cycle regulation, mutagenesis, tumorigenesis and apoptosis.…”

Section: Introductionmentioning

confidence: 99%

Biotin‐Appended Iron(III) Complexes of Curcumin for Targeted Photo‐Chemotherapy

et al. 2021

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Iron(III) complexes of curcumin (Hcur) having a tridentate NNN‐donor dipicolylamine‐based ligand L1 and its biotinylated analogue L2, namely, [Fe(L1)(cur)Cl] (1) and [Fe(L2)(cur)Cl] (2), were prepared, characterized and their photo‐induced cytotoxicity studied. The complexes exhibited curcumin‐based absorption band near 430 nm and emission maxima at 520 nm. Complex 2 with a biotin moiety showed enhanced cellular uptake and higher cytotoxicity compared to its non‐biotin analogue 1. The visible light induced cytotoxicity was studied in HeLa, MCF‐7 and HepG2 cell lines. Complex 2 displayed photodynamic effect (400–700 nm, 10 J cm−2) giving an IC50 value of ∼4 μM in HeLa and MCF‐7 cells, while being significantly non‐toxic in the dark (IC50>100 μM). A 5‐fold increase in cytotoxicity was observed in HepG2 cells (IC50∼0.7 μM) for the biotin‐appended complex 2. In vitro generation of reactive oxygen species (ROS) was observed from dichlorofluorescein diacetate (DCFDA) assay. The mode of cell death was apoptotic. Formation of hydroxyl radicals as the ROS was evidenced from the plasmid pUC19 DNA photo‐cleavage studies. The complexes demonstrated the ability to act as targeted PDT (photodynamic therapy) drugs.

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Mitochondria localizing high-spin iron complexes of curcumin for photo-induced drug release

Cited by 6 publications

References 51 publications

Sanger’s Reagent Sensitized Photocleavage of Amide Bond for Constructing Photocages and Regulation of Biological Functions

Sanger’s Reagent Sensitized Photocleavage of Amide Bond for Constructing Photocages and Regulation of Biological Functions

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Biotin‐Appended Iron(III) Complexes of Curcumin for Targeted Photo‐Chemotherapy

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