BODIPY appended copper(<scp>ii</scp>) complexes of curcumin showing mitochondria targeted remarkable photocytotoxicity in visible light

Bhattacharyya, Arnab; Dixit, Akanksha; Mitra, Koushambi; Banerjee, Samya; Karande, Anjali A.; Chakravarty, Akhil R.

doi:10.1039/c4md00425f

Cited by 54 publications

(43 citation statements)

References 37 publications

(20 reference statements)

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“…To enhance the PDT activity of the ternary iron(III) catecholates, we have designed new ternary complexes of formulation [Fe III (L)(cat)Cl], where L is BODIPY‐based photosensitizers that are capable of generating singlet oxygen on visible light irradiation for PDT or can be used for cellular imaging based on their spectral properties. The BODIPY (boron‐dipyrromethene) derivatives have been extensively used as photosensitizers generating singlet oxygen on light activation . Many BODIPY compounds have been studied as in vitro fluorescent probes to study their subcellular localization.…”

Section: Introductionmentioning

confidence: 99%

“…The BODIPY (borondipyrromethene) derivatives have been extensively used as photosensitizers generating singlet oxygen on light activation. [18][19][20][21][22] Many BODIPY compounds have been studied as in vitro fluorescent probes to study their subcellular localization. Besides, this moiety like Photofrin can selectively accumulate in the mitochondria of the cells in preference to the nucleus and induce cell apoptosis.…”

Section: Introductionmentioning

confidence: 99%

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Mitochondria‐Targeted Anticancer Activity of BODIPY‐Appended Iron(III) Catecholates in Red Light

et al. 2017

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Iron(III) catecholates of dipicolylamine (dpa) bases having appended Benzyl (in bzdpa) or BODIPY (borondipyrromethene) moiety (in L1 and L2), viz. [Fe(Bzdpa)(cat)Cl] (1), [Fe(L1)(cat)Cl] (2) and [Fe(L2)(cat)Cl] (3), were prepared and characterized (H2cat=catechol). The iron(III) complexes with a ligand‐to‐metal charge transfer (LMCT) band within 600–800 nm were studied for their photocytotoxicity in visible (400–700 nm) and red (600–720 nm) light. Complex 2 with a BODIPY fluorophore in L1 gave IC50 values of 2.2±0.5 and 15.0±0.7 μM in visible and red light, respectively, in HeLa cells. Complex 3 with a diiodo‐BODIPY moiety showed excellent PDT activity giving respective IC50 values of 0.8±0.2 and 12.6±1.1 μM. They are less toxic in dark (IC50: ≥85 μM). A similar activity was observed in MCF‐7 cancer cells. The BODIPY complexes showed significant mitochondrial localization. Annexin FITC assay showed apoptotic cell death involving reactive oxygen species (ROS). Photo‐generation of ROS was evidenced from dichlorofluorescein diacetate (DCFDA) assay. Mechanistic studies on DNA photocleavage reactions showed the presence of two types of ROS. Singlet oxygen formation from BODIPY was evidenced from the 1,3‐diphenylisobenzofuran (DPBF) experiments. Hydroxyl radical was generated on red light photo‐activation of the LMCT band within photodynamic therapy (PDT) spectral window.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Mitochondria‐Targeted Anticancer Activity of BODIPY‐Appended Iron(III) Catecholates in Red Light

et al. 2017

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“…Images were acquired using Apotome.2 fluorescence microscope (Carl Zeiss, Germany) using an oil immersion lens at 63X magnification. The images were analyzed using the AxioVision Rel 4.8.2 (Carl Zeiss, Germany) software . To understand the sub‐cellular localization, HeLa cells (4 x 10 4 cells/mm 2 ) were incubated with 5 μM of complex 6 for 4 hours, following which, the cells were treated with 0.5 μmol of mitrotracker Red in serum‐free medium for 30 min at 37 °C.…”

Section: Methodsmentioning

confidence: 99%

Ferrocene conjugated copper(II) complexes of terpyridine and traditional Chinese medicine (TCM) anticancer ligands showing selective toxicity towards cancer cells

Deka¹,

Bhattacharyya

Mukherjee

et al. 2018

Applied Organom Chemis

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Six novel mixed-ligand copper(II) complexes, namely, [Cu(R-tpy)(L)]NO 3 (1-6), where R-tpy is 4′-phenyl-2,2′:6′,2′′-terpyridine (Ph-tpy; 1-3) and 4′-ferrocenyl-2,2′:6′,2′′-terpyridine (Fc-tpy; 4-6), L is the bidentate O,O donor monoanion of plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone; plum in 1, 4), chrysin (5,7-dihydroxyflavone; chry in 2, 5) and curcumin (bis(4-hydroxy-3methoxyphenyl)-1,6-diene-3,5-dione; curc in 3, 6) have been synthesized and characterized and their in vitro cytotoxicity against cancer cells is evaluated.The energy optimized structures and the frontier orbitals of the complexes have been obtained from the DFT calculations. Complexes 4-6 with a conjugated ferrocenyl moiety and TCM anticancer ligands, namely, plum (in 4), chry (in 5) and curc (in 6) showed potent cytotoxicity giving respective IC 50 values of 1.2 μM, 0.62 μM and 0.21 μM in HeLa and 2.0 μM and 1.0 μM and 0.34 μM in MCF-7 cancer cells while being much less toxic to MCF-10A normal cells (IC 50 : 8.3-17.1 μM). In contrast, complexes 1-3 with a conjugated phenyl moiety were appreciably less toxic to HeLa cells with respective IC 50 values of 10.4 μM, 8.1 μM and 5.5 μM when compared with their ferrocenyl analogues 4-6. Mechanistic studies using Hoechst staining and Annexin-V-FITC assays on cancer cells revealed an apoptotic pathway of cell death induced by the complexes. Fluorescence imaging study showed that complex 6 having curcumin as ligand localized primarily in the mitochondria of HeLa cells. Thus, we demonstrate in this study that ferrocene conjugation to copper(II) complexes of TCM anticancer ligands significantly increases the selectivity and cytotoxicity of the resulting complexes towards cancer cells over normal cells.

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“…In this case, the introduction of halogen atoms has been shown to influence a strong localization of the fluorescent probes to lipid droplets within the cells . In another study, the introduction of a diiodinated BODIPY ligand into a copper(II) complex of curcumin has been shown to enhance the mitochondria targeting ability and photocytotoxicity of the Cu II complex in visible light . The halogenated ligand appears to facilitate the intersystem crossing (ISC), which leads to the generation of the triplet state of the photosensitizer.…”

Section: Cellular Uptake Of Halogen Compoundsmentioning

confidence: 99%

Directing Traffic: Halogen‐Bond‐Mediated Membrane Transport

Govindaraj

Ungati

Jakka

et al. 2019

Chemistry A European J

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The plasma membrane regulates the transport of molecules into the cell. Small hydrophobic molecules can diffuse directly across the lipid bilayer. However, larger molecules require specific transporters for their entry into the cell. Regulating the cellular entry of small molecules and proteins is a challenging task. The introduction of halogen, particularly iodine, to small molecules and proteins is emerging to be a promising strategy to improve the cellular uptake. Recent studies reveal that a simple substitution of hydrogen atom with iodine not only increases the cellular uptake, but also regulates the membrane transport. The strong halogen‐bond‐forming ability of iodine atoms plays a crucial role in the transport and the introduction of iodine may provide an efficient strategy for studying membrane activity and cellular functions and improving the delivery of therapeutic agents. This Concept article does not provide a comprehensive picture of membrane transport but highlights halogen‐substitution as a novel strategy for understanding and regulating the cell‐membrane traffic.

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BODIPY appended copper(ii) complexes of curcumin showing mitochondria targeted remarkable photocytotoxicity in visible light

Abstract: BODIPY-appended copper(ii) complexes of curcumin show a remarkable PDT effect in visible light in HeLa cells via apoptosis with mitochondrial localization.

Cited by 54 publications

References 37 publications

Mitochondria‐Targeted Anticancer Activity of BODIPY‐Appended Iron(III) Catecholates in Red Light

Mitochondria‐Targeted Anticancer Activity of BODIPY‐Appended Iron(III) Catecholates in Red Light

Ferrocene conjugated copper(II) complexes of terpyridine and traditional Chinese medicine (TCM) anticancer ligands showing selective toxicity towards cancer cells

Directing Traffic: Halogen‐Bond‐Mediated Membrane Transport

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