- Synthesis and evaluation of “Ama-Flash”, a photocaged amatoxin prodrug for light-activated RNA Pol II inhibition and cell death
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Amanitin is used extensively as a research tool to inhibit RNA Pol II thereby implicating its role in mRNA transcription. Recently, amanitin has gained traction as a toxic payload for targeted therapy. Here we report the first-ever photocaged amanitin analog, that is non-toxic and can be pre-loaded into cells. Light provides a means to inhibit RNA Pol II and provoke cell death on-demand.
- Matinkhoo, Kaveh,Pryyma, Alla,Wong, Antonio A. W. L.,Perrin, David M.
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p. 9558 - 9561
(2021/09/28)
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- Multiresponsive hydrogels and organogels based on photocaged cysteine
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Here we present the readily accessible amino acid 4,5-dimethoxy-2-nitrobenzyl-l-cysteine (DNC), as an ultra-low molecular weight gelator (MW = 316 g mol?1). Sonication of DNC in water or organic solvents as well as pH adjustment in water trigge
- Rickhoff, Jonas,Cornelissen, Nicolas V.,Beuse, Thomas,Rentmeister, Andrea,Jan Ravoo, Bart
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supporting information
p. 5913 - 5916
(2021/06/18)
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- Photolabile beta-dicarbonyl compounds
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The present disclosure provides a redox initiator system for initiating polymerization comprising an oxidizing agent, a photolabile reducing agent, and a transition metal complex that participates in a redox cycle. On exposure to actinic radiation, such as UV, the photolabile compound photolyzes, releasing the reducing agent and initiating the redox-initiated polymerization.
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Paragraph 0100
(2020/02/18)
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- One- And Two-Photon-Activated Cysteine Persulfide Donors for Biological Targeting
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Persulfides have been considered as potential signaling compounds similar to the H2S in "S-persulfidation", a sulfur-mediated redox cycle. The research of this sulfur-mediated species is hindered because of the lack of efficient persulfide donors. In this current study, we have developed one- and two-photon-activated persulfide donors based on an o-nitrobenzyl (ONB) phototrigger, which releases the biologically active persulfide (N-acetyl l-cysteine persulfide, NAC-SSH) in a spatiotemporal manner. Next, we have demonstrated the detection of persulfide release both qualitatively and quantitatively using the well-known "turn on" fluorescence probe, that is, monobromobimane, and the trapping agent, that is, 2,4-dinitrofluorobenzene, respectively. Furthermore, we examined the cytotoxicity of synthesized persulfide donors on HeLa cells and the cytoprotective ability in the highly oxidizing cellular environment.
- Chaudhuri, Amrita,Venkatesh, Yarra,Das, Joyjyoti,Gangopadhyay, Moumita,Maiti, Tapas K.,Singh, N. D. Pradeep
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p. 11441 - 11449
(2019/10/02)
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- Cascade photocaging of diazeniumdiolate: A novel strategy for one and two photon triggered uncaging with real time reporting
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We report a new strategy, viz. cascade photocaging, for protecting diethylamine diazeniumdiolate (O2-position), a light sensitive molecule. Upon photolysis, the cascade photocage at first releases the light activatable linker (latent fluorophore) O2-caged diazeniumdiolate, which undergoes spontaneous 1,8-elimination, triggering the release of the diazeniumdiolate anion and the fluorophore.
- Behara, Krishna Kalyani,Rajesh,Venkatesh, Yarra,Pinninti, Bhaskar Rao,Mandal, Mahitosh,Singh, N. D. Pradeep
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p. 9470 - 9473
(2017/09/01)
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- REDOX POLYMERIZABLE COMPOSITION WITH PHOTOLABILE REDUCING AGENTS
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Polymerizable compositions comprising a redox initiator system is disclosed. The redox initiators comprises a photolabile reducing agent, that photolyzes and initiates the redox cycle. Dental compositions comprising dental resins and the photolabile redox initiator system are also described.
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Page/Page column 58
(2017/09/02)
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- Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations
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One pot syntheses of furan, thiophene, and pyrrole were accomplished by oxidative deacetylation using Mn(iii)/Co(ii) catalysts and the Paal-Knorr reaction from 1,5-dicarbonyl compounds, which are prepared from the conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds. The oxidative deacetylation and reductive cyclization of β-ketoesters derived from ethyl acetoacetate and o-nitrobenzyl bromides efficiently produced diversely substituted indoles. This journal is
- Ju, Yeming,Miao, Di,Yu, Ruiyang,Koo, Sangho
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p. 2588 - 2599
(2015/04/21)
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- Photolysis of ortho-nitrobenzylic derivatives: The importance of the leaving group
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Quantum yields for the photoinduced release of seven different commonly used leaving groups (LGs) from the o-nitroveratryl protecting group were measured. It was found that these quantum yields depend strongly on the nature of the LGs. We show that the quantum efficiency with which the LGs are released correlates with the stabilization that these LGs provide to o-nitrobenzyl-type radicals because radical stabilizing groups weaken the C-H bond that is cleaved in the photoinduced hydrogen atom transfer step, and hence lower the barrier for this process. At the same time these substituents lower the endothermicity of the thermal hydrogen atom transfer and thus increase the barrier for the reverse process, thereby enhancing the part of the initially formed aci-nitro intermediates which undergo cyclization (which ultimately leads to LG release). Radical stabilization energies computed by DFT methods are thus a useful predictor of the relative efficiency with which LGs are photoreleased from o-nitrobenzyl protecting groups.
- Solomek, Tomas,Mercier, Sebastien,Bally, Thomas,Bochet, Christian G.
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p. 548 - 555
(2012/06/30)
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- Synthesis and in vitro antibacterial activity of gemifloxacin derivatives containing a substituted benzyloxime moiety
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A series of novel gemifloxacin (GMFX) derivatives containing a substituted benzyloxime moiety with remarkable improvement in lipophilicity were synthesized. The target compounds evaluated for their in vitro antibacterial activity against representative strains. Our results reveal that most of the target compounds have considerable potency against all of the tested Gram-positive strains including MRSA and MRSE (MIC: 90: 1 μg/mL) is 8-fold more active than GMFX, and 2-fold more active than GMFX and moxifloxacin against MRSE clinical isolates (MIC90: 4 μg/mL). Crown Copyright
- Feng, Lianshun,Lv, Kai,Liu, Mingliang,Wang, Shuo,Zhao, Jing,You, Xuefu,Li, Sujie,Cao, Jue,Guo, Huiyuan
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p. 125 - 136
(2012/11/07)
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- Synthesis and biological activity of pyridopyridazin-6-one p38α MAP kinase inhibitors. Part 2
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This manuscript concludes the Structure Activity Relationship (SAR) on the pyridazinone scaffold and identifies a compound with subnanomolar p38α activity and 24 h coverage in the rat arthritis efficacy model.
- Tynebor, Robert M.,Chen, Meng-Hsin,Natarajan, Swaminathan R.,O'Neill, Edward A.,Thompson, James E.,Fitzgerald, Catherine E.,O'Keefe, Stephen J.,Doherty, James B.
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p. 5971 - 5975
(2012/11/07)
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- Synthesis of Photolabile "Precursors" of Amino Acid Neurotransmitters
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The synthesis of photolabile precursors of the neurotransmitters for the aspartic acid, glutamic acid, glycine, and γ-aminobutyric acid receptors are reported.These compounds are designed for the rapid, photochemically initiated release of the neurotransmitter.The importance of rapidly photolyzed, inert (toward a neuronal receptor) precursors of neurotransmitters is in chemical kinetic investigations of the reactions involving the neuronal receptors.In the past, such studies have been hampered because of the insufficient time resolution of the available techniques.A photolyzable precursor of carbamoylcholine, an amino-group-containing analogue of acetylcholine, has been used previously to make measurements of currents flowing through the acetylcholine receptor channel within 100 μs.
- Wilcox, Mary,Viola, Randall W.,Johnson, Katherine W.,Billington, Andrew P.,Carpenter, Barry K.,et al.
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p. 1585 - 1589
(2007/10/02)
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