- Photosensitizing properties of hollow microcapsules built by multilayer self-assembly of poly(allylamine hydrochloride) modified with rose Bengal
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A polymeric photosensitizer based on poly(allylamine hydrochloride) (PAH) and rose Bengal (RB) was synthesized. The modified polycation PAH-RB was demonstrated to be suitable for construction of microcapsules via a layer-by-layer (LbL) assembly technique, using sodium poly(styrene sulfonate) (PSS) as counter-polyelectrolyte and CaCO3 microcrystals as templates. After CaCO3 core removal, a stable suspension of hollow microcapsules with shells incorporating RB (HM-RB) was obtained. The spectroscopic and photophysical behavior of both PAH-RB and HM-RB in aqueous environments were studied and described in terms of dye-dye interactions and dye hydrophobicity. Only HM-RB was able to generate singlet molecular oxygen with similar efficiency to free RB in air-saturated solutions upon green light irradiation. In order to explore possible practical applications as a supramolecular photosensitizer, experiments of HM-RB irradiation in the presence of chemically and biologically relevant target molecules were carried out. It was observed that is possible to use visible light to initiate the photooxidation of biological compounds in water, with many interesting advantages compared to low-molecular-weight photosensitizers such as an enhancement of the photosensitizing effect, due to a significant reduction of dye-dye interaction, or improved reuse given the straightforward size-based separation from the reaction mixture without loss of efficiency.
- Serrano, Mariana P.,Rafti, Matías,Thomas, Andrés H.,Borsarelli, Claudio D.
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- Photocatalysis Enables Visible-Light Uncaging of Bioactive Molecules in Live Cells
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The photo-manipulation of bioactive molecules provides unique advantages due to the high temporal and spatial precision of light. The first visible-light uncaging reaction by photocatalytic deboronative hydroxylation in live cells is now demonstrated. Using Fluorescein and Rhodamine derivatives as photocatalysts and ascorbates as reductants, transient hydrogen peroxides were generated from molecular oxygen to uncage phenol, alcohol, and amine functional groups on bioactive molecules in bacteria and mammalian cells, including neurons. This effective visible-light uncaging reaction enabled the light-inducible protein expression, the photo-manipulation of membrane potentials, and the subcellular-specific photo-release of small molecules.
- Wang, Haoyan,Li, Wei-Guang,Zeng, Kaixing,Wu, Yan-Jiao,Zhang, Yixin,Xu, Tian-Le,Chen, Yiyun
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p. 561 - 565
(2019/01/04)
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- Synthetic β-Cyclodextrin Dimers for Squaraine Binding: Effect of Host Architecture on Photophysical Properties, Aggregate Formation and Chemical Reactivity
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Reported herein is the synthesis and application of three novel β-cyclodextrin dimer hosts for the complexation of near infrared (NIR) squaraine dyes in aqueous solution. A series of eight different N-substituted N-methyl anilino squaraine dyes with variable terminal groups are investigated, with an optimal n-hexyl-substituted squaraine guest demonstrating binding constants orders of magnitude higher than the other squaraine–host combinations and comparable to literature-reported systems. Moreover, hydrophobic complexation of the squaraine dyes with the β-cyclodextrin dimer hosts causes drastic changes in the squaraine's photophysical properties, propensity for aggregation and susceptibility to hydrolytic decay.
- Chaudhuri, Sauradip,Verderame, Molly,Mako, Teresa L.,Bandara, Y. M. Nuwan D. Y.,Fernando, Ashvin I.,Levine, Mindy
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p. 1964 - 1974
(2018/05/15)
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- Photoinduced upregulation of calcitonin gene-related peptide in A549 cells through HNO release from a hydrophilic photocontrollable HNO donor
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Nitroxyl (HNO), a one-electron-reduced form of nitric oxide, has various biological activities, including a cardioprotective effect. Here, we first synthesized another, more hydrophilic photocontrollable HNO donor (3), which can release HNO in a spatially and temporally controlled manner, and then examined the properties of our series of compounds as practical HNO donors in a cellular system under photocontrol. We selected compound 2 as the preferred donor, and used it to show that calcitonin gene-related peptide (CGRP) can be upregulated in A549 cells via photocontrolled HNO release. This result demonstrates the suitability of this photocontrollable HNO donor for biological investigations.
- Matsuo, Kazuya,Nakagawa, Hidehiko,Adachi, Yusuke,Kameda, Eri,Aizawa, Kazuyuki,Tsumoto, Hiroki,Suzuki, Takayoshi,Miyata, Naoki
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p. 1055 - 1062
(2012/09/25)
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- Alternative photoinduced release of HNO or NO from an acyl nitroso compound, depending on environmental polarity
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A hydrophilic hetero-Diels-Alder cycloadduct was synthesized as a novel photocontrollable donor of reactive nitrogen species. Production of either nitric oxide (NO) or nitroxyl (HNO) was photoinduced from this compound, depending on the environmental polarity.
- Matsuo, Kazuya,Nakagawa, Hidehiko,Adachi, Yusuke,Kameda, Eri,Tsumoto, Hiroki,Suzuki, Takayoshi,Miyata, Naoki
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supporting information; experimental part
p. 3788 - 3790
(2010/08/07)
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- Synthesis of a hydrophilic and non-ionic anthracene derivative, the N,N′-di-(2,3-dihydroxypropyl)-9,10-anthracenedipropanamide as a chemical trap for singlet molecular oxygen detection in biological systems
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We report herein the synthesis of a new hydrophilic and non-ionic anthracene derivative, the N,N′-di-(2,3-dihydroxypropyl)-9,10-anthracenedipropanamide. The evaluation of this compound as chemical trap of singlet molecular oxygen by using labeling experiments and HPLC-MS analysis showed that it could be efficiently used in biological investigations.
- Martinez, Glaucia R.,Garcia, Flávia,Catalani, Luiz H.,Cadet, Jean,Oliveira, Mauricio C.B.,Ronsein, Graziella E.,Miyamoto, Sayuri,Medeiros, Marisa H.G.,Mascio, Paolo Di
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p. 10762 - 10770
(2007/10/03)
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