- A caged substrate peptide for matrix metalloproteinases
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Based on the widely applied fluorogenic peptide FS-6 (Mca-Lys-Pro-Leu-Gly-Leu-Dpa-Ala-Arg-NH2; Mca = methoxycoumarin-4-acetyl; Dpa = N-3-(2,4-dinitrophenyl)l-α,β-diaminopropionyl) a caged substrate peptide Ac-Lys-Pro-Leu-Gly-Lys-Lys-Ala-Arg-NH
- Decaneto, Elena,Abbruzzetti, Stefania,Heise, Inge,Lubitz, Wolfgang,Viappiani, Cristiano,Knipp, Markus
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Read Online
- Photoactivatable Fluorophore for Stimulated Emission Depletion (STED) Microscopy and Bioconjugation Technique for Hydrophobic Labels
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The use of photoactivatable dyes in STED microscopy has so far been limited by two-photon activation through the STED beam and by the fact that photoactivatable dyes are poorly solvable in water. Herein, we report ONB-2SiR, a fluorophore that can be both
- Weber, Michael,Khan, Taukeer A.,Patalag, Lukas J.,Bossi, Mariano,Leutenegger, Marcel,Belov, Vladimir N.,Hell, Stefan W.
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supporting information
p. 451 - 458
(2020/11/30)
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- Polysilsesquioxane-based nano drug loading system capable of controllably releasing drugs through light triggering and preparation method thereof
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The invention relates to a light-triggered polysilsesquioxane-based nano drug loading system capable of controllably releasing drugs and a preparation method thereof. An o-nitrobenzyl bridged polysilsesquioxane nano-carrier with photoresponsive charge rev
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Paragraph 0072-0074; 0077; 0082-0084; 0087; 0092-0094; 0097
(2020/08/22)
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- Trigger-responsive chain-shattering polymers
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Disclosed are polymers containing a backbone comprising alternating N-protected hydroxymethylaniline units (“spacer”) and linker units.
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Page/Page column 30
(2017/04/29)
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- UV-responsive degradable polymers derived from 1-(4-aminophenyl) ethane-1,2-diol
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A UV-responsive polymer was prepared via condensation polymerization of 2-nitrobenzyl(4-(1,2-dihydroxyethyl)phenyl)carbamate and azalaic acid dichloride. When the polymer was irradiated with UV light, the nitrobenzyl urethane protecting group was removed and the deprotected aniline underwent spontaneous 1,6-elimination reactions, resulting in degradation of the polymer. Nanoparticles with encapsulated Nile Red were formulated with the degradable polymer and triggered burst release of Nile Red was observed when the nanoparticles were irradiated by UV light.
- Ma, Liang,Baumgartner, Ryan,Zhang, Yanfeng,Song, Ziyuan,Cai, Kaimin,Cheng, Jianjun
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p. 1161 - 1168
(2015/03/31)
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- Chain-shattering polymeric therapeutics with on-demand drug-release capability
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Trigger happy: Trigger-responsive chain-shattering polymeric therapeutics (CSPTs) were prepared by condensation polymerization of a UV- or hydrogen peroxide-responsive domain and a drug as co-monomers. Drug release can be started and stopped by starting and stopping the trigger treatment. Chemotherapeutic-containing CSPTs showed trigger-responsive in vitro and in vivo antitumor efficacy. Copyright
- Zhang, Yanfeng,Yin, Qian,Yin, Lichen,Ma, Liang,Tang, Li,Cheng, Jianjun
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supporting information
p. 6435 - 6439
(2013/07/27)
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- Light-triggered charge reversal of organic-silica hybrid nanoparticles
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A functional nanoparticle with light-triggered charge reversal based on a protected amine-bridged polysilsesquioxane was designed. An emulsion- and amine-free sol-gel synthesis was developed to prepare uniform nanospheres. Photolysis of suspensions of these nanoparticles results in a reversal of the χ potential. This behavior has been used to trigger nanoparticle self-assembly, nanocomposite hydrogel formation, and nanoparticle release, showing the potential of this material in nanoscale manipulation and nanoparticle therapy.
- Hu, Li-Chih,Yonamine, Yusuke,Lee, Shih-Hui,Van Der Veer, Wytze E.,Shea, Kenneth J.
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supporting information; experimental part
p. 11072 - 11075
(2012/08/28)
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- De Novo design and utilization of photolabile caged substrates as probes of hydrogen tunneling with horse liver alcohol dehydrogenase at sub-zero temperatures: A cautionary note
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In order to understand the influence of protein dynamics on enzyme catalysis and hydrogen tunneling, the horse liver alcohol dehydrogenase (HLADH) catalyzed oxidation of benzyl alcohol was studied at sub-zero temperatures. Previous work showed that wild t
- Tsai, Shiou-Chuan,Klinman, Judith P.
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p. 172 - 190
(2007/10/03)
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- Hydrolytic stabilization of protected p-hydroxybenzyl halides designed as latent quinone methide precursors
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The hydrolysis rates of a series of protected p-hydroxybenzyl halides designed to generate a p-quinone methide through 1,6-elimination following photolytic deprotection have been investigated in order to optimize hydrolytic stability. A number of p-hydroxybenzyl halides containing an ether or carbonate-linked photolabile hydroxy protecting group and a fluoride, chloride, or bromide benzylic leaving group have been synthesized. The hydrolysis rates of these derivatives in different water acetonitrile mixtures and temperatures have been determined. The hydrolysis half-life of the benzyl bromide with the p-hydroxy protected as the carbonate-linked α- methylnitroveratryl (18c) is more than 750 times that of the ether-linked analogue (16c). These studies afford a Hammett σp+ of +0.28 for the carbonate-linked derivatives compared to a σ+ of -0.39 for the ether-linked derivatives. The theoretical hydrolysis half-life of the most stable benzyl fluoride in 100% water was sufficiently long so as to preclude extrapolation, while the chloride was approximately 50 h, and even the bromide was estimated to be nearly 5 h.
- Dyer, Robert G.,Turnbull, Kenneth D.
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p. 7988 - 7995
(2007/10/03)
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- Synthesis of caged peptides using caged lysine: Application to the synthesis of caged AIP, a highly specific inhibitor of calmodulin-dependent protein kinase II
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N(α)-Fmoc-N(ε)-(2-nitrobenzyloxycarbonyl)-lysine has been prepared and used in the solid-phase synthesis of caged peptides. The synthesized caged AIP (cagedKcageKALRRQEAVDAL) showed characteristics required for caged peptides including a significantly red
- Tatsu, Yoshiro,Shigeri, Yasushi,Ishida, Atsuhiko,Kameshita, Isamu,Fujisawa, Hitoshi,Yumoto, Noboru
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p. 1093 - 1096
(2007/10/03)
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- Automated RNA-synthesis with photocleavable sugar and nucleobase protecting groups
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A new synthetic method for the N-alkyloxycarbonylation of adenine and guanine nucleosides was developed and used for the preparation of RNA- phosphoramidites carrying photolabile sugar and nucleobase protecting groups. From these building blocks, a heptam
- Stutz, Alfred,Pitsch, Stefan
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p. 930 - 934
(2007/10/03)
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- Photolabile protecting groups for nucleosides: Synthesis and photodeprotection rates
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o-Nitrobenzyloxycarbonyl and a number of related groups have been tested for the photolabile protection of nucleoside 5'-hydroxyls. The rates of photodeprotection were found to vary by approximately 17-fold in a series of 5'-O-protected thymidine derivati
- Hasan, Ahmad,Stengele, Klaus-Peter,Giegrich, Heiner,Cornwell, Paul,Isham, Kenneth R.,Sachleben, Richard A.,Pfleiderer, Wolfgang,Foote, Robert S.
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p. 4247 - 4264
(2007/10/03)
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- Synthesis, photoreactivity and cytotoxic activity of caged compounds of L-leucyl-L-leucine methyl ester, an apoptosis inducer
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L-Leucyl-L-leucine methyl ester (Leu-Leu-OMe), an apoptosis inducer in natural killer cells and macrophages, was caged with trans-o-hydroxycinnamoyl (3a-d), trans-o-mercaptocinnamoyl (4) and o-nitrobenzyl derivatives (5a, b), and the photochemical reactivity of these derivatives in phosphate-buffered saline containing 1% dimethyl sulfoxide and their immunological properties were studied. All of the derivatives exhibited absorption at wavelengths longer than the UVB region. Although 3a-d and 4 were expected to isomerize to a cis isomer, which then cyclizes intramolecularly to give LeuLeu-OMe and a coumarin derivative, cyclization efficiency was not satisfactory except for 3a. However, 3a itself caused necrosis (cell swelling) of U937 cells (a myeloid cell line). In contrast, 5a and b released Leu-Leu-OMe quickly and efficiently and did not affect U937 cells. Although irradiated 5b induced necrosis, irradiated 3a and 5a induced apoptosis in these cells, as evidenced by a decrease in cell size.
- Odaka, Mitsuyo,Furuta, Toshiaki,Kobayashi, Yoshiro,Iwamura, Michiko
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p. 800 - 806
(2007/10/03)
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- S-(Nitrocarbobenzoxy)glutathiones: Potent Competitive Inhibitors of Mammalian Glyoxalase II
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Three potent competitive inhibitors of mammalian liver glyoxalase II, the S-(o-, m-, and p-nitrocarbobenzoxy)glutathiones, have been synthesized and studied.The Ki values of the ortho, meta, and para isomers, as inhibitors of rat liver glyoxala
- Bush, P. E.,Norton, S. J.
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p. 828 - 830
(2007/10/02)
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