Synthesis, structural characterisation and antiproliferative activity of a new fluorescent 4-amino-1,8-naphthalimide Tröger's base–Ru(<scp>ii</scp>)–curcumin organometallic conjugate

Shanmugaraju, Sankarasekaran; Poulsen, Bjørn la Cour; Arisa, Tobi; Umadevi, Deivasigamani; Dalton, Hannah L.; Hawes, Chris S.; Estalayo-Adrián, Sandra; Savyasachi, Aramballi J.; Watson, Graeme W.; Williams, D.C.; Gunnlaugsson, Thorfinnur

doi:10.1039/c8cc01584h

Cited by 35 publications

(15 citation statements)

References 25 publications

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“…), the ISC of Tröger's bases has not been reported. Recently an NI‐derived Tröger's base/Ru II –curcumin organometallic conjugate was demonstrated to show cytotoxicity against cervical cancer cells, but the phototoxicity and the ISC of the base itself were not studied …”

Section: Introductionmentioning

confidence: 99%

“…Recently an NI-derived Trçger's base/Ru II -curcumin organometallic conjugate was demonstrated to showc ytotoxicity against cervical cancer cells, but the phototoxicitya nd the ISC of the base itselfw ere not studied. [41] On the basis of these previous studies on Trçger's bases, that is, the quenching of the fluorescencei np olar solvents and the orthogonal geometry,w es upposed that SOCT-ISC may occur in Trçger's bases through symmetry-breaking CT (SBCT), that is, one NI moiety in the Trçger's base acts as the electron donor,a nd the othera st he electron acceptor. [42] Herein, we propose using the rigid, almosto rthogonal geometry of the two subunits in Trçger's base to implement SOCT-ISC.…”

Section: Introductionmentioning

confidence: 99%

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Efficient Intersystem Crossing in the Tröger's Base Derived From 4‐Amino‐1,8‐naphthalimide and Application as a Potent Photodynamic Therapy Reagent

Zhao

Chen

Yıldız

et al. 2020

Chemistry A European J

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Intersystem crossing (ISC) was observed for naphthalimide (NI)‐derived Tröger's base, and the ISC was confirmed to occur by a spin‐orbital charge‐transfer (SOCT) mechanism. Conventional electron donor/acceptor dyads showing SOCT‐ISC have semirigid linkers. In contrast, the linker between the two chromophores in Tröger's base is rigid and torsion is completely inhibited, which is beneficial for efficient SOCT‐ISC. Femtosecond transient absorption (TA) spectra demonstrated charge‐separation and charge‐recombination‐induced ISC processes. Nanosecond TA spectroscopy confirmed the ISC, and the triplet state is long‐lived (46 μs, room temperature). The ISC quantum yield is dependent on solvent polarity (8–41 %). The triplet state was studied by pulsed‐laser‐excited time‐resolved EPR spectroscopy, and both the NI‐localized triplet state and triplet charge‐transfer state were observed, which is in good agreement with the spin‐density analysis. The Tröger's base was confirmed to be a potent photodynamic therapy reagent with HeLa cells (EC50=5.0 nm).

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Efficient Intersystem Crossing in the Tröger's Base Derived From 4‐Amino‐1,8‐naphthalimide and Application as a Potent Photodynamic Therapy Reagent

Zhao

Chen

Yıldız

et al. 2020

Chemistry A European J

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“…A DNA docking study of this complex revealed the same mechanism of action as in platinum chemotherapy. The Ru(II) complex with Tröger’s base, p-cymene, and curcuminato ligands shows fast cellular uptake and displays good luminescence and cytotoxicity against cervical cancer cells [27]. Platinum(II) complexes with curcuminate can act as chemotherapeutic agents which release photoactive curcumin and an active Pt(II) species upon irradiation with visible light [28,29].…”

Section: Introductionmentioning

confidence: 99%

Zn(II) Curcuminate Complexes with 2,2′-bipyridine and Carboxylates

Grabner

Modec

2019

Molecules

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Two novel zinc(II) compounds with curcuminate (abbreviated as cur–), [Zn(CH3COO)(cur)(bpy)](1)·CH3OH·2H2O (bpy = 2,2’-bipyridine) and [Zn(PhCOO)(cur)(bpy)] (2)·CH3OH, have been synthesized and characterized. Their composition has been determined by single-crystal X-ray structure analysis. Complexes 1 and 2 are similar: in both a five-fold coordination environment of zinc(II) consists of a monodentate carboxylate, a chelating bidentate 2,2’-bipyridine, and curcuminate, which is bound via a deprotonated 1,3-dione moiety. In 1, 2,2’-bipyridine nitrogen atoms and curcuminate oxygen atoms form the base of a square pyramid, whereas the acetate oxygen occupies its apex. The O3N2 donor set in 2 defines a polyhedron which more closely resembles a trigonal bipyramid. The packing in the crystal lattices of both compounds is governed by hydrogen-bonds. Complexes 1 and 2 display higher stability than curcumin in buffered media at pH = 7.0, however, the degradation of coordinated cur– is comparable to that of yellow pigment curcumin (curH) when the pH is raised to 7.2. Both complexes 1 and 2 in DMSO exhibit fluorescence with Stokes shifts of 5367 and 4634 cm−1, respectively.

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“…Curcumin, the core ingredient of turmeric, is known to have a broad range of pharmacological properties and is a popular antimicrobial, antidiabetic, anti‐inflammatory, anticancer, and antioxidant agent [26] . Also, the intrinsic green fluorescence of curcumin was used as an optical biomarker [27] . Though curcumin has a wide range of applications, but its poor solubility in water limits its bioavailability and pharmacological potential [28] .…”

Section: Resultsmentioning

confidence: 99%

“…[26] Also, the intrinsic green fluorescence of curcumin was used as an optical biomarker. [27] Though curcumin has a wide range of applications, but its poor solubility in water limits its bioavailability and pharmacological potential. [28] We have shown previously that the hydrophobic interior of the cage 1 can efficiently encapsulate curcumin [18] and we found that, 15 μM cage 1 can encapsulate 16.3 μM of curcumin (Supporting Information).…”

Section: Antibacterial Activity Against Mrsamentioning

confidence: 99%

Supramolecular Interaction of Molecular Cage and β‐Galactosidase: Application in Enzymatic Inhibition, Drug Delivery and Antimicrobial Activity

et al. 2021

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Enzyme inhibitors play a crucial role in diagnosis of a wide spectrum of diseases related to bacterial infections. We report here the effect of a water‐soluble self‐assembled PdII8 molecular cage towards β‐galactosidase enzyme activity. The molecular cage is composed of a tetrapyridyl donor (L) and cis‐[(en)Pd(NO3)2] (en=ethane‐1,2‐diamine) acceptor and it has a hydrophobic internal cavity. We have observed that the acceptor moiety mainly possesses the ability to inactivate the β‐galactosidase enzyme activity. Kinetic investigation revealed the mixed mode of inhibition. This inhibition strategy was extended to control the growth of methicillin‐resistant Staphylococcus aureus. The internalization of the Pd(II) cage inside the bacteria was confirmed when bacterial solutions were incubated with curcumin loaded cage. The intrinsic green fluorescence of curcumin made the bacteria glow when put under an optical microscope. Furthermore, this curcumin loaded molecular cage shows an enhanced antibacterial activity. Thus, PdII8 molecular cage is quite attractive due to its dual role as enzyme inhibitor and drug carrier.

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Synthesis, structural characterisation and antiproliferative activity of a new fluorescent 4-amino-1,8-naphthalimide Tröger's base–Ru(ii)–curcumin organometallic conjugate

Cited by 35 publications

References 25 publications

Efficient Intersystem Crossing in the Tröger's Base Derived From 4‐Amino‐1,8‐naphthalimide and Application as a Potent Photodynamic Therapy Reagent

Efficient Intersystem Crossing in the Tröger's Base Derived From 4‐Amino‐1,8‐naphthalimide and Application as a Potent Photodynamic Therapy Reagent

Zn(II) Curcuminate Complexes with 2,2′-bipyridine and Carboxylates

Supramolecular Interaction of Molecular Cage and β‐Galactosidase: Application in Enzymatic Inhibition, Drug Delivery and Antimicrobial Activity

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