A Photo‐Caged Platinum(II) Complex That Increases Cytotoxicity upon Light Activation

Ciesienski, Katie L.; Hyman, Lynne M.; Yang, Daniel T.; Haas, Kathryn L.; Dickens, Marina G.; Holbrook, Robert J.; Franz, Katherine J.

doi:10.1002/ejic.201000098

Cited by 53 publications

(35 citation statements)

References 27 publications

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“…This blue-light-activated caging group may enable orthogonal calcium release together with other light-activated metal ion chelators or signaling elements. Similar to calcium, optical release of Pt 2+ , [60] Zn 2+ , [61] and other ions [57,62] has recently been reported. Advancements in caging group technology in conjunction with two-photon excitation have enabled red-shifted ion release, which is important for adapting the approach for future applications in living systems.…”

Section: Optical Control Of Small Moleculesmentioning

confidence: 96%

Optochemical Control of Biological Processes in Cells and Animals

et al. 2018

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Biological processes are naturally regulated with high spatial and temporal control, as is perhaps most evident in metazoan embryogenesis. Chemical tools have been extensively utilized in cell and developmental biology to investigate cellular processes, and conditional control methods have expanded applications of these technologies toward resolving complex biological questions. Light represents an excellent external trigger since it can be controlled with very high spatial and temporal precision. To this end, several optically regulated tools have been developed and applied to living systems. In this review we discuss recent developments of optochemical tools, including small molecules, peptides, proteins, and nucleic acids that can be irreversibly or reversibly controlled through light irradiation, with a focus on applications in cells and animals.

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Section: Optical Control Of Small Moleculesmentioning

confidence: 96%

Optochemical Control of Biological Processes in Cells and Animals

et al. 2018

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“…35,53,55–58 Nanocarriers including gold (Au) NPs, 59 micelles, 60 liposomes, 61 and peptide-based nanocarriers 35 have been reported to demonstrate photocaging/uncaging behavior. Various cargos such as thiols, 35 platinum(II) complexes, 57 diphospho-myo-inositol pentakisphosphates (InsP 7 ), 62 cyclooxygenase-2 enzyme inhibitors, 63 copper complexes, 58 and anticancer drugs/prodrugs (e.g., camptothecin, coumarin, 5-fluorouracil, doxorubicin (DOX)) 43,59,60,64 have been shown to be protected and carried by the photocaging nanocarriers. The light irradiation has ranged from NIR, 63,65,66 to UV 58 to visible light, 55,67 and using mechanisms such as two photon excitation, 63,68,69 upconversion by UCNPs, 64 or simple one photon excitation 70 can be employed to induce uncaging of the photolabile protecting groups.…”

Section: Miscellaneous Phototriggered Drug Release Mechanismsmentioning

confidence: 99%

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

et al. 2017

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Nanotechnology has begun to play a remarkable role in various fields of science and technology. In biomedical applications, nanoparticles have opened new horizons, especially for biosensing, targeted delivery of therapeutics, and so forth. Among drug delivery systems (DDSs), smart nanocarriers that respond to specific stimuli in their environment represent a growing field. Nanoplatforms that can be activated by an external application of light can be used for a wide variety of photoactivated therapies, especially light-triggered DDSs, relying on photoisomerization, photo-cross-linking/un-cross-linking, photoreduction, and so forth. In addition, light activation has potential in photodynamic therapy, photothermal therapy, radiotherapy, protected delivery of bioactive moieties, anticancer drug delivery systems, and theranostics (i.e., real-time monitoring and tracking combined with a therapeutic action to different diseases sites and organs). Combinations of these approaches can lead to enhanced and synergistic therapies, employing light as a trigger or for activation. Nonlinear light absorption mechanisms such as two-photon absorption and photon upconversion have been employed in the design of light-responsive DDSs. The integration of a light stimulus into dual/multiresponsive nanocarriers can provide spatiotemporal controlled delivery and release of therapeutic agents, targeted and controlled nanosystems, combined delivery of two or more agents, their on-demand release under specific conditions, and so forth. Overall, light-activated nanomedicines and DDSs are expected to provide more effective therapies against serious diseases such as cancers, inflammation, infections, and cardiovascular disease with reduced side effects and will open new doors toward the treatment of patients worldwide.

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“…5–7 Light-activated release of ligands can also open up coordination sites for interaction with biological targets. 8,9 In general, light-activated metal complexes are important tools for basic research applications. 10 They also have potential as highly specific agents for photodynamic therapy that would mitigate damage to surrounding tissue by using light with a targeted photosensitizer to control the site of drug activation.…”

Section: Introductionmentioning

confidence: 99%

Selective Photodissociation of Acetonitrile Ligands in Ruthenium Polypyridyl Complexes Studied by Density Functional Theory

Mazumder

Endicott

et al. 2015

Inorg. Chem.

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Metal complexes that release ligands upon photoexcitation are important tools for biological research and show great potential as highly specific therapeutics. Upon excitation with visible light, [Ru(TQA)(MeCN)2]2+ [TQA = tris(2-quinolinylmethyl)amine] exchanges one of the two acetonitriles (MeCNs), whereas [Ru(DPAbpy)MeCN]2+ [DPAbpy = N-(2,2′-bipyridin-6-yl)-N,N-bis(pyridin-2-ylmethyl)amine] does not release MeCN. Furthermore, [Ru-(TQA)(MeCN)2]2+ is highly selective for release of the MeCN that is perpendicular to the plane of the two axial quinolines. Density functional theory calculations provide a clear explanation for the photodissociation behavior of these two complexes. Excitation by visible light and intersystem crossing leads to a six-coordinate 3MLCT state. Dissociation of acetonitrile can occur after internal conversion to a dissociative 3MC state, which has an occupied dσ* orbital that interacts in an antibonding fashion with acetonitrile. For [Ru(TQA)(MeCN)2]2+, the dissociative 3MC state is lower than the 3MLCT state. In contrast, the 3MC state of [Ru(DPAbpy)MeCN]2+ that releases acetonitrile has an energy higher than that of the 3MLCT state, indicating dissociation is unfavorable. These results are consistent with the experimental observations that efficient photodissociation of acetonitrile occurs for [Ru(TQA)(MeCN)2]2+ but not for [Ru(DPAbpy)MeCN]2+. For the release of the MeCN ligand in [Ru(TQA)(MeCN)2]2+ that is perpendicular to the axial quinoline rings, the 3MLCT state has an occupied quinoline π* orbital that can interact with a dσ* Ru–NCCH3 antibonding orbital as the Ru–NCCH3 bond is stretched and the quinolines bend toward the departing acetonitrile. This reduces the barrier for the formation of the dissociative 3MC state, leading to the selective photodissociation of this acetonitrile. By contrast, when the acetonitrile is in the plane of the quinolines or bpy, no interaction occurs between the ligand π* orbital and the dσ* Ru–NCCH3 orbital, resulting in high barriers for conversion to the corresponding 3MC structures and no release of acetonitrile.

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A Photo‐Caged Platinum(II) Complex That Increases Cytotoxicity upon Light Activation

Cited by 53 publications

References 27 publications

Optochemical Control of Biological Processes in Cells and Animals

Optochemical Control of Biological Processes in Cells and Animals

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

Selective Photodissociation of Acetonitrile Ligands in Ruthenium Polypyridyl Complexes Studied by Density Functional Theory

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