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Redaktion: Lucjan Strekowski
Heterocyclic Polymethine Dyes
Synthesis, Properties and Applications
erschienen Juli 2008 241 Seiten, 429 schw.-w. und 6 farb. Abb., 7 schw.-w. und 6 farb. Fotos, 422 schw.-w. Zeichn., Gebunden
Springer-Verlag GmbH & Co. KG | ISBN: 3540790632
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| VORWORT | öffnen |
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PrefaceThis treatise pertains to dyes composed of a central polymethine moiety and two cyclic terminal subunits. The polymethine linker can be unsubstituted or substituted, and at least one terminal subunit is a heterocyclic system. The classes of compounds reviewed range from classical cyanines, first synthesized in the 1850s, to hemicyanines, to styryl dyes, to merocyanines, to coumarin polymethines, and to squarylium dyes that were synthesized for the first time in the 1960s. These structural...
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| KLAPPENTEXT | öffnen |
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TOPICS IN HETEROCYCLIC CHEMISTRY Heterocyclic Polymethine Dyes Volume Editor L. Strekowski ISBN 978-3-540-79063-1 [weiter lesen] |
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| AUTOR | öffnen |
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Series EditorProf. R. R. Gupta† 10A, Vasundhara Colony Lane No. 1, Tonk Road Jaipur-302 018, India rrg_vg@yahoo.co.in Volume EditorProf. Lucjan Strekowski Professor of Chemistry Department of Chemistry Georgia State University P.O. Box 4098 Atlanta, GA 30302-4098 USA lucjan@gsu.eduEditorial BoardProf. D. Enders RWTH Aachen Institut für Organische Chemie D-52074, Aachen, Germany enders@rwth-aachen.deProf. Steven V. Ley FRS BP 1702 Professor and Head of Organic Chemistry University of Cambridge... [weiter lesen] |
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| INHALTSVERZEICHNIS | öffnen |
Contents Synthesis of Cyanine Dyes M. Mojzych • M. Henary 1 Cyanine Dye-Nucleic Acid Interactions B. A. Armitage 11 Near-Infrared Cyanine Dye-Protein Interactions J. Kim • A. Watson • M. Henary • G. Patonay 31 Cyanine Dye-Based Compounds for Tumor Imaging With and Without Photodynamic ... R. K. Pandey • N. James • Y. Chen • M. P. Dobhal 41 Merocyanines: Synthesis and Application V. Z. Shirinian • A. A. Shimkin 75 Coumarin Polymethines, Their Boron Complexes and Analogs V.F. Traven 107 Squarylium Dyes and Related Compounds S. Yagi • H. Nakazumi 133 Polymethine Dyes as Fluorescent Probes and Visible-Light Photoinitiators for ... J. Pączkowski • J. Kabatc • B. Jędrzejewska 183 Stability and Reactivity of Polymethine Dyes in Solution M. Henary • M. Mojzych 221 Subject Index 239
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Subject Index BBarbituric acid anilinomethylene derivatives 84 Benzothiazole 13 Benzothiazolium 12 Benzothiazolium heptamethine cyanine dye 224 Benzothiazolium trimethine dyes 205 Benzoxazolium 12 Bisquarate-based squarylium 159 Bis-squarylium dyes 153 Boron, coumarin polymethines 108 n-Butyltriphenylborate 203 CCarbocyanine dyes 94 Cathepsin-D-sensitive cyanine dyes 59 CE-LIF, proteins 35 Charge-resonance probes 186 Charge-transfer (CT) probes 186 Cholesteryl laurates 60 Chromen-4-one 80 Circular dichroism (CD) 36 Coinitiator concentration 209 Coumarin merocyanines, polymeric matrices 127 - spiropyranes 117 Coumarin polymethines 107 - 2-pyrone analogs 114 - quinolone analogs 116 Covalent labeling 33 Cyanine borates 184 - photoredox pairs, visible-light photoinitiators 203 Cyanine dyes 11 - N-alkoxypyridinium salt 209 - alkyltriphenylborate salt 202 - Arg-Gly-Asp sequence (RGD) conjugates 54 - cathepsin-D-sensitive 59 - endostatin conjugates 58 - folic acid conjugates 61 - hydrophilic, carbohydrate moieties 51 - nucleophile addition 232, 235 - photodynamic therapy (PDT) 62 - reduction 232 - small peptide conjugates 49 - symmetrical 14 - synthesis 1 - tumor-targeted 48 - unsymmetrical 17 - water-soluble 46 Cyanine-DNA conjugates 24 Cyclodextrins 221, 226 D 1, 3-Dibutyl-2-thiobarbituric acid 88 Dibutylthiobarbituric acid 86 Dimethyl-1-pyrroline N-oxide (DMPO) 224 Dimethylindole 13 DNA nanotag concept 21 DNA-dye assembly 21 Dye aggregates, HJ-types 38, 94, 124, 174, 222, 227 Dyeing photoinitiators 183 Dyes 11 - dimeric 13, 22, 96, 174 - DNA-conjugated 24 - near-infrared 7, 31, 43, 48, 57, 148, 158 - peptideprotein-conjugated 26 - photobleaching 216, 223 - pH-sensitive 221 - PNA-conjugated 25 - unsymmetrical 18 Dyes/coinitiator photoinitiating systems 201 EEncapsulation 221 Endostatin 58 2-Ethyl-2-(hydroxymethyl)-1, 3- propanediol triacrylate (TMPTA) 205 FFluorescence 7, 11, 31, 53, 67, 129 Fluorescence probes 183 Fluorescent fiberoptic immunosensor (FFOI) 36 Fluorodeoxyglucose 41 3-Formyl-4-hydroxycoumarin 107 Förster resonance energy transfer (FRET) 20 GGlioma tumors, in vivo fluorescence imaging/PDT efficacy 67 Glutacondialdehyde dianil monohydrochloride 88 HHemicyanines 19, 186, 207 - modified, photoinitiating photoredox systems 207 - photoinitiators, free radical polymerization 206 Heptamethine cyanines 6, 31 Heptamethine indolium cyanines 7, 43, 48, 57, 236 - SRN 1 reaction 6, 53 3-(l'-Hexyloxyethyl)-3-devinyl- pyropheophorbide-a (HPPH) 41, 65 HSA-dye conjugate, fluorescent lymph tracer 35 Hummel-Dreyer method 36 Hybridization probes, fluorogenic dye 26 Hydrogen energy, merocyanines 987-Hydroxy-4-methyl-8-propionylcoumarin 108 IICG analogs, modified 45 Immunoassays 35 Indocyanine green 41 Indolium pentamethine cyanines 226 Integrated waveguide fluorescence optodes (IWFOs) 94 Intercalation 11 Ion sensors, merocyanines 93 KKetocyanines 83, 86, 94, 231 LLabeling, covalent 33 - noncovalent 36 MMagnetic resonance 41 Malachite green 17 Medicine, merocyanines 99 Merocarbocyanines 77, 79 Merocyanines 78, 234 - long-bridge 86 - medicines 99 Meropolycarbocyanines 77 N-Methoxypyridinium borate salts 208 Methyl methacrylate, probing of thermally initiated polymerization 188 - pyridinium probes, blue shifts 195 1-Methyl-2-pyrrolidinone (MP) 205 Methylene blue 201 4-Methylidenetelluropyran 234 2-(Methylmercapto) benzothiazole 78 Monomethine cyanines 2 Multifunctional dyes 41 NNear-infrared (NIR) dyes 31, 41, 221 Noncovalent interaction 36 Non-linear optics, merocyanines 97 Nucleic acids 11 OOrganic dye-sensitized solar cells (DSSCs) 163 Oxazole yellow 25 PPentamethine cyanines 4, 14, 16, 46, 50, 54 Peptide-conjugated dyes 26 Photobleaching reaction 216, 223 Photochromism 119 Photodynamic antimicrobial chemotherapy 100 Photodynamic therapy (PDT) 41, 76, 99 Photoinduced electron-transfer reaction (PET) 183, 212 Photoinitiation, thermodynamics 212 Photoinitiators, visible light polymerization 200 Photomerocyanines 77 Photooxidizable dye sensitization 201 Photophysics 17 Photoreducible dye sensitization 201 Photosensitizers, tumor-avid 41 Pinacyanol 14 Poly(3-hexylthiophene-2, 5-diyl) (P 3 HT), TiO 2 /P 3 HT solar cell 98 Poly(methyl methacrylate), trapping of probe molecules 193 Polymethine dyes 75, 183 - coumarins 107 - dark reactions 232 - fluorescent probes 185 - monitoring of polymerization process 185 - hydroxide/alkoxide ions 234 - inhibition of aggregation/steric protection 226 - nucleophile addition 232 - photodegradation 222 - rigidization 225 - sensitizers, two-component photoinitiating systems 202 Porphyrin-based photosensitizer-cyanine dye conjugates 63 Probe fluorescence 199 Probe sensitivity parameter 195 Protein labeling 32 Protein-conjugated dyes 26 Pseudoisocyanine 14 Pyroninocyanine dyes 221, 230 QQuantum dots (QDs) 35 Quinolinium 12 RRadical polymerization 183 Rhodacyanine derivatives, Plasmodium falciparum 101 Rhodanine 78 Rigidization 221 Rose bengal 207 Rotaxane 221 SSandwich assay 35 Solar cells, merocyanines 98 - squarylium dye 163 Solvatochromism, merocyanines 91 Spiropyranes 77, 117 Squaraine dye 226 Squaric acid (3, 4-dihydroxy-3-cyclobutene 1, 2-dione)135 Squarylium dyes (squaraines) 133, 229 - analogues bisquarate 156 - biological/environmental analyses 168 - diazacrown-derivatized 172 - π-extended 147 - optical properties 135 - photoconductivity 160 - photosensitizers, photovoltaic devices 162 - supramolecular systems 174 - synthesis 135 - unsymmetrical 139 Squarylium-based conjugated polymers, conductive materials 165 Styryl dyes 20 Styrylpyridinium probe 196, 199 TTellurazole 85 Telluropyrylium dye 234 Tetramethyl-4-piperidone (TEMP) 224 Tetraphenylborate 203 Thiazole orange 13, 17 Thiobarbituric acid 87 Thiochromen-4-one 80 Tricarbocyanine-cholesteryl laurates 60 Trimethine cyanines 3, 204 3, 5, 5-Trimethylcyclohex-2-enone 86 Tumor imaging 41 Tumor-avid photosensitizers 41 Tumor-targeted cyanine dyes 48 Twisted intramolecular charge-transfer 192, 225 Tyrian (Royal purple) 78 VVinyltriphenylborate 203
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