Platinum(II) Complexes of Curcumin Showing Photocytotoxicity in Visible Light

Mitra, Koushambi; Gautam, Srishti; Kondaiah, Paturu; Chakravarty, Akhil R.

doi:10.1002/ejic.201601078

Cited by 28 publications

(41 citation statements)

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“…Carboplatin and its 7‐azaindole based analogues were shown to form bifunctional Pt‐DNA adducts on UVA light exposure ,. Another similar example constitutes the novel Pt II complexes of curcumin, which demonstrated visible‐light‐enhanced formation of Pt‐DNA crosslinks ,. However, these approaches are limited by 1) collateral tissue damage caused by UVA light and 2) the poor tissue penetration of light at these wavelengths .…”

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A Platinum(II) Complex of Heptamethine Cyanine for Photoenhanced Cytotoxicity and Cellular Imaging in Near‐IR Light

2018

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Controlled generation of cytotoxic agents with near-IR light is ac urrent focus of photoactivated cancer therapy, including that involving cytotoxic platinum species.Ah eptamethine cyanine scaffolded Pt II complex, IR797-Platin exhibits unprecedented PtÀObond scission and enhancement in DNA platination in near-IR light. This complex also displayed significant singlet oxygen quantum yield therebyqualifying as an ear-IR photodynamic therapeutic agent. The complex showed 30-60 fold enhancement of cytotoxicity in near-IR light in various cancer cell lines.T he cellular imaging properties were also leveraged to observe its significant co-localization in cytoplasmic organelles.T his is the first demonstration of anear-IR light-initiated therapyinvolving the cytotoxic effects of both active cisplatin and singlet oxygen.The FDAvalidated platinum-based anticancer drugs cisplatin, oxaliplatin, and carboplatin form the centerpiece of metal-based anticancer drug therapy. [1] Thep utative mechanism of cytotoxicity relies on an initial Pt À X(X= Cl, O) bond scission to form aquated Pt II species.T hese activated Pt II species can then react with nuclear DNAa nd form cytolethal Pt-DNAcrosslinks ultimately leading to apoptotic cell death. [2] However,t he anarchic hydrolytic behavior of these drugs leads to undesired systemic toxicity and limits the administration of higher drug-dosage levels.C ontrolled generation of the bioactive (aquated) form of platinum(II) drugs specifically within the targeted tumor is,t herefore,a ni deal way to prevent the off-target toxicity. [3] To gain control over the kinetics of metal-ligand bond rupture,P t IV complexes were introduced as inert prodrugs,w hich produce DNA damaging platinum(II) species only upon reduction by cellabundant glutathione. [4, 5] These Pt IV complexes showed promising tumor-targeted anticancer activities and oftentimes resulted in delivery of multiple drugs and adjuvants.T hough efficacious,this strategy relies on endogenous entities for drug activation and thus the regulation of cytotoxicityi sl ost once the drug is administered. In another approach, platinum(II) cytotoxins were generated from photosensitive Pt IV diazido molecules with light.

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A Platinum(II) Complex of Heptamethine Cyanine for Photoenhanced Cytotoxicity and Cellular Imaging in Near‐IR Light

2018

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“…[11a] Carboplatin and its 7-azaindole based analogues were shown to form bifunctional Pt-DNA adducts on UVA light exposure. [11b,c] Another similar example constitutes the novel Pt(II) complexes of curcumin which demonstrated visible light enhanced formation of Pt-DNA crosslinks. [11d,e] However, these approaches are limited by i) collateral tissue damage caused by UVA light and ii) the poor tissue penetration of light at these wavelengths.…”

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“…[11b,c] Another similar example constitutes the novel Pt(II) complexes of curcumin which demonstrated visible light enhanced formation of Pt-DNA crosslinks. [11d,e] However, these approaches are limited by i) collateral tissue damage caused by UVA light and ii) the poor tissue penetration of light at these wavelengths. [8e] Thus, an ideal Pt(II) based photo-initiated chemotherapeutic agent should be activated in the “biological window” of 650–850 nm which has improved tissue compatibility and penetrating properties.…”

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“…Based on the precedent of existing platinum(II) photoactivatable complexes, [11a] we posited that a diammine bound Pt(II) system having a photodetachable O^O bidentate donor in direct conjugation with the heptamethine cyanine framework would release an active cisplatin on near-IR light exposure. To realize our hypothesis, we successfully designed a Pt(II) conjugate of heptamethine cyanine, which we call IR797-Platin, 1 (Figure 1a).…”

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“…[16] This finding, coupled with the observations suggesting that the Pt(II)-O bonds are photolabile, [11] prompted us to examine the photo-degradation pathways of 1 . We performed the stability studies in solvents relevant to cell-culture settings i.e.…”

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A Platinum(II) Complex of Heptamethine Cyanine for Photoenhanced Cytotoxicity and Cellular Imaging in Near‐IR Light

2018

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Hyaluronic acid targeted metal organic framework based on iron (III) for delivery of platinum curcumin cytotoxic agent to triple negative breast cancer cell line

Moradi

Aliomrani

Tangestaninejad

et al. 2022

Applied Organom Chemis

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Platinum‐based drugs are an essential class of chemotherapy drugs in breast cancer. However, suffer from side effects and drug resistance; structural changes and applying drug carriers can lead to new drug candidates in this class. The metal‐organic frameworks (MOFs) as porous carriers have recently attracted much attention in drug delivery. In this study, for the first time, hyaluronic acid (HA)‐targeted MOF (NH2‐MIL‐101 (Fe)) nanoparticles (Pt‐CUR@MIL@HA NPs) were evaluated in delivery of platinum‐curcumin (Pt‐CUR) prodrug to the MDA‐MB‐231 triple‐negative breast cancer cell line; in this regard, the cytotoxicity, ROS production, and cellular uptake of designed NPs have been studied. Different analysis methods confirmed chemical structures, the prepared NPs had a uniform morphology, and the hydrodynamic size of the optimized non‐targeted loaded particles increased to about 252 nm with a zeta potential of +26.9 mV, after targeting with HA, the size increased to 310 nm, and the zeta potential changed to −28 mV. Based on TGA and atomic absorption (ICP‐MS) results, the drug loading percent was determined to be about 30%–35%. Drug release from the HA targeted Pt‐CUR@MIL@HA system in the neutral condition was slow and sustained, and after 36 h, a maximum of 60% of the drug was released, but in acidic conditions, the release was increased, and by 18 h, the release was about 80%. The cytotoxicity of MOF NPs containing Pt‐CUR was more significant than that of the free drug, and HA targeted has resulted in more cellular uptake than the non‐targeted NPs. In conclusion, these new MOF‐ based HA‐coated NPs of PT‐CUR can be introduced to pre‐clinical researches after completing in vitro and in vivo studies.

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Platinum(II) Complexes of Curcumin Showing Photocytotoxicity in Visible Light

Cited by 28 publications

References 87 publications

A Platinum(II) Complex of Heptamethine Cyanine for Photoenhanced Cytotoxicity and Cellular Imaging in Near‐IR Light

A Platinum(II) Complex of Heptamethine Cyanine for Photoenhanced Cytotoxicity and Cellular Imaging in Near‐IR Light

A Platinum(II) Complex of Heptamethine Cyanine for Photoenhanced Cytotoxicity and Cellular Imaging in Near‐IR Light

Hyaluronic acid targeted metal organic framework based on iron (III) for delivery of platinum curcumin cytotoxic agent to triple negative breast cancer cell line

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