371

Index a aminoacyl-transfer RNA (tRNA) 88, A1B11 SIRT2-selective inhibitors 233, 90, 102 235 ARSs 90, 91 A2B57 SIRT2-selective inhibitors 233, aminoacyl-pdCpA dinucleotide with 235 91, 93 acridine 8 post-aminoacylation modification adenine (A) 25 93 adenosine 88 preparing noncanonical 91 (ATP) 8, 35, aminoacyl-tRNA synthetases (ARSs) 117 90–91, 96, 354 affinity-guided DMAP (AGD) 4-[(2-aminoethyl)carbomoyl]benzyl catalyst-mediated selective thioester (ABT) 95 chemical protein labeling 309 2-amino-4-pentenoic acid 98 affinity-guided DMAP AMPA receptors (4-dimethylaminopyridine) chemical labeling and fluorescent chemistry 309 visualization 303 affinity ligand-tethered DMAP catalyst FRAP analysis 304 309 anti-arrhythmic 43

[1-13C]alanine-NH2 282 antibody-drug conjugates (ADCs) 253 α-amino acid-based HP 13C chemical anti-cancer 43 probes 293 anticodon sequence 88 α-hydroxyl acids 95, 101 anti-malarial agents 43 amacrine/horizontal interneurons 78 antisense oligonucleotides (ASO) amino acids 258–260 incorporation of noncanonical aquaporin 183 101–103 4-armed star-shaped copolymers 209 misacylation of non-proteinogenic ASO conjugated with tocopherol 94–96 (Toc-ASO) 261–262 misincorporation 87 Aspidosperma alkaloids 45, 48, 49, 51, ribosomal 103, 104 64 aminoacylation assembly lines class I ARSs 90 artificial 68 ribozyme 94, 95 biogenetically inspired synthesis tRNA 90–91, 93, 95 58–68 aminoacyl dinucleotide 92 biomimetic 43, 52

Molecular Technology: Life Innovation, Volume 2, First Edition. Edited by Hisashi Yamamoto and Takashi Kato. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA. Published 2018 by Wiley-VCH Verlag GmbH & Co. KGaA. 372 Index

assembly lines (contd.) budding 183 biosynthetic 45, 48, 58 bulk degradation 204 development of 45 bump and hole technology 313 Macmillan’s collective total synthesis 45–52 c nature of 62 [1-13C]α-amino acid 292, 293 synthesis of indole alkaloids 52–57 [1-13C]ascorbate 283–284 atomic force microscope (AFM) 29 13 C-benzylformic acid, for H2O2 detection 284 b [1-13C]bicarbonate,forpHsensing benzodiazepines 306 283 benzoxadiazole 124 [1-13C]dehydroascorbate 284 β-amino acids 87, 95, 335 [13C,D3]-p-anisidine 284–285 β-Cyclodextrin (β-CD) 190 cell-based yeast display method 347 bicycle-phage display approach 352 cell-cycle regulation 75 biodegradable poly(ether urethane) cell-free emulsion based encapsulation 213 method 347 biodegradable thermoplastics 207 cell-free ribosome display method 347 biogenetically inspired synthesis cell membranes 58–68 components of 118 biomimetic cyclization 49 negatively-charged 119 bioorthogonal reaction-based cell-penetrating peptides (CPP) 10 136 cell-surface AMPA receptors, diffusion 1,4-bis(4-phenylethynyl)benzene (BPEB) dynamics 302 units 186, 187 cellular uptake block catiomers efficiency 8, 10, 15 for gene delivery system 1–18 pDNA packaging 2–6 process 17 rod-shape/toroid-shape 17–18 rod-length limitation for 14 systemic gene therapy 14–16 CEST 126 13 blood cells 8 C-ethylenediaminetetraacetic acid blood circulation (EDTA) 285–286 13 of biological compounds 8 C-ethyleneglycol tetraacetic acid 286 capability 14 C–H activation reaction 224–228 capacity 2, 9, 14 chondroitin sulfate (HS) 8 13 in longevity 8 C hyperpolarized molecular probes molecular weight on 115 aminopeptidase N detection time 115 282–283 blood flow 73 [1-13C]ascorbate 283–284 blood vessel 13C-benzylformic acid 284 endothelial cells 114 [1-13C]bicarbonate 283 formation 73 [1-13C]dehydroascorbate 284 BNA/LNA chemistry 260 [13C,D]EDTA 285–286 13 Borromean rings 28 [ C,D3]-p-anisidine 284–285 bow-tie-shape dendrimers 115, 116 [1-13C]pyruvate 277–278 brain-derived neurotrophic factor chemical environment analysis 283 (BDNF) 80 enzymatic activity analysis 277 Index 373

γ-glutamyl transpeptidase 278–281 dissolution dynamic nuclear glycolysis and tricarboxylic acid cycle polarization process 274 analysis 278 1,2-distearoyl-sn-glycero- scaffold structure 292 3-phosphocholine (DSPC) 191 circular dichroism (CD) spectra 188 disuccinimidyl glutarate crosslinker click chemistry approach 352 HDAC3-selective inhibitor disulfide bond 10 identification 221–224 DMAP-antibody conjugates 312 HDAC8-selective inhibitor DMAP-tethered lectins 310 identification 224 DMF 6 SIRT2-selective inhibitors 232–234 DNA-based molecular technologies coordination chemistry-based fluorescence blinking control chemogenetic approach 171–177 312–320 genetic alphabet expansion copper-catalyzed cycloaddition 136 168–171 Coulomb repulsion 118, 120, 122 DNA computing 36 cyanomethyl ester (CME) 94 DNA condensation 1, 5, 18 cyclic peptides 329 DNA duplex 35 cyclization, of peptides 349 DNA forceps 33 cyclosporin 336, 337 DNA intercalators 8 cysteine conjugation 133–136 DNA nanorobot 33 cytidine 88 DNA nanotechnology 25, 26, 36 cytosine (C) 26 DNA origami box-shaped 3D 31 d design 31 d-α-amino acids 95 molecular machines made 33 d-amino acid 87, 101, 335 molecular peg board 32–33 degradation behavior of hydrogels 203 pinching devices 33–35 degree of polymerization (DP) 1, 4 2D nanostructures 31 degree of protonation 11 DNA packaging 1 deoxyribonucleic acids (DNA) 25, 339 DNA pliers 33, 35 characteristic of 26 DNA/RNA heteroduplex design principles 35 oligonucleotide (HDO) DNA-PAINT 36 concept 262–264 immobile DNA junctions 26–28 conjugated with tocopherol molecular architecture 25–36 (Toc-HDO) 264–268 molecule structure of 25–26 DNA sequence 105 nanostructures 25 DNA strands 26, 28 tiles and their assemblies 28–29 chemical synthesis of 339 topologically 28 DNA zipping mechanism 34 unzipping mechanism 35 double-stranded DNA 3 2′-deoxyribose ring 25 doxorubicin 120, 121 De-SPIO 118 DREADD technology 313 D-glucosamine 119 drug delivery system (DDS) 113 Diels–Alder cycloaddition 45 drug discovery platforms 104–105 diethylenetriamine (DET) 11 druggable proteins 330–332 374 Index

Ds–Px pair 169 fluorescent imaging plate reader d-tyrosine 91 (FLIPRTM) 304

dynamic light scattering (DLS) 2 fluorescent labeling, of GABAA receptor 306 e fluorescent nanogel thermometer (FNT) eight-armed PEG 209 124 elastic pressure 204 fluorescent polymeric thermometer emitting fluorescent dye 36 (FPT) 124, 125 endosomal escape 15 fluorescent ZnII chemosensors 314 endosome escape 11–12 2-fluorodeoxy-d-glucose (2FDG) 117 endothelial cells formylmethionine (fMet) 89 growth 72 four-base codon method 98, 100 survival of 73 fucose-glycoconjugates 138 VEGFRs 73 functional peptides enhanced permeable retention (EPR) cell-based yeast display 347 effect 114, 117, 118, 123, 124, cell-free emulsion based 129 encapsulation methods 347 enzymatic activity, 13C molecular probes cell-free ribosome display 347 277 DNA sequencing techniques 346 enzymatic glycosylation 136–137 intracellular peptide selection 340–341 epidermal growth factor receptor mRNA-display method 345–347 (EGFR) 9 natural peptide synthesis 339–340 epigenetics 219–221 phage display method 341–345 ethylene diamine (EDA) 11 ribosomal synthesis 337–339 extracellular matrix (ECM) 74, 78, 118, 119 g

GABAA receptors 306, 307 f galactose-modified proteins 137 flavin adenine dinucleotide (FAD) 239 gamma-aminobutyric acid (GABA) flexizymes 355–356 306 Flory–Rehner model 204 γ-amino acids 95 fluorescence 139, 147, 152 γ-glutamyl-[1-13C]glycine fluorescence-activated cell sorting (γ-Glu-[1-13C]Gly) 278–279, (FACS) device 33 281 fluorescence blinking γ-glutamyl transpeptidase (GGT) blinking kinetics 172 analysis 278–281 isomerization blinking 176 GB-GC-SPIO 118 redox blinking 175 GC-SPIO 117, 119 single molecule detection 171 gene delivery triplet blinking 174 impact for 6 fluorescence correlation spectroscopy nuclease attack 6 (FCS) 172 polyplex micelles 6–14 fluorescence recovery after gene silencing photobleaching (FRAP) method after ASO or Toc-HDO injection 302 265 fluorescent biosensors 305 Toc-ASO 262 Index 375 gene therapy 14–16 h genetic alphabet expansion HDAC3-selective inhibitors 221–224 high-affinity DNA aptamer HDAC6-insensitive inhibitors generation 169 224–228 nucleotide modifications 168 HDAC8-selective inhibitors 224 unnatural base-pair 168 HDO Conjugated with Tocopherol genetic code (Toc-HDO) decoding 88–90 adverse effect 266–268 expansion 352 on ApoB mRNA levels 265 flexizymes 355–356 construction 264 in vitro chemical ligation approach design 264 353 mechanism 268 limitation 354 potency 264–266 messenger RNA (mRNA) Heck cyclization 49 88, 90 Henderson–Hasselbalch equation non-standard base method 101 283 RaPID system 356–361 heparan sulfate (HS) 8 reprogramming 97–98 hexaethylene glycol chains 127 glomerular cells 115, 116 hexammine cobalt 17 glycan molecule technology 132 bioorthogonal reaction-based and 219, glycosylation 136 220 cysteine conjugation 133–136 chemical modification 220 enzymatic glycosylation histone deacetylase (HDAC) inhibitors 136–137 221 in vivo organ selective Au-catalyzed HDAC3-selective inhibitors reactivity 153 221–224 on live cells 148–150 HDAC6-insensitive inhibitors lysine conjugation 133 224–228 as metal carriers 151 HDAC6-selective inhibitors 228, glycans 132 229 natural 155 HDAC8-selective inhibitors 224, protein-conjugation 133 225 glycol chitosan (GC) 117 SIRT1-selective inhibitors 228–232 glycolide 207 SIRT2-selective inhibitors 232–234 glycolysis 117 histone lysine demethylase (KDM) labeling, with inhibitors DMAP-tethered lectin 311 KDM4C inhibitors 235–237 glycosaminoglycans (GAGs) 8–10 KDM5A inhibitor identification gold nanoparticles 32 237–238 gold nanorods 32 KDM7B inhibitor identification G-quadruplex formation 35 238–239 green fluorescent protein-fusion LSD1 inhibitor identification technology 298 239–250 guanine (G) 25 Holliday Junction 28, 33 guanosine 88 H-thymidine labeling technique 77 376 Index

hydrazine-based LSD1-selective of oligosaccharide-modified proteins inhibitors 250 139–150 hydrogels in vivo translation steps 338 degradation behavior 203–205 ion channel type glutamate receptor nondegradable 204 (iGluR) 314 hydrophilic block 3, 7 ion transportation 183 hyperpolarization 273–275 isoleucyl-tRNA synthetase (IleRS) 91 hyperpolarized (HP) molecular imaging isomerization blinking 176 probe isothermal titration calorimetry (ITC) of chemical environment 283–286 198 design strategy 287–294 isothiocyanate method 133 of enzymatic activity 277–283 isozyme-selective histone deacetylase HP 15N molecular probes 286–287 (HDAC) inhibitors 221–234 requirements 275–227 j i Jeffery–Heck cyclization 48, 49 immobile DNA junctions 26–28 indole alkaloids k Aspidosperma families of 52 KDM4C inhibitors 235 biogenetically inspired synthesis 58, KDM5A inhibitors 237–238 68 KDM7B inhibitors 238–239 biosynthetic precursors 44 Kopsia alkaloids 45, 48–50 monoterpene 43 synthesis of terpenoid 43 l systematic synthesis of 52–57 l-α-amino acids 95 injured brain regeneration ligand-directed alkyloxyacyl imidazole biology 71–73 (LDAI) chemistry 302 of cell cycle 75–76 ligand-directed chemistry, for molecular technology to promote neurotransmitter receptor angiogenesis 74–75 proteins neurogenesis 77–78 affinity-based chemical approaches neuron regeneration 78–80 301 potential of 71 AMPA receptors 302 integrated oxidation/reduction/ chemical labeling coupled with BFQR cyclization (iORC) 52, 54–57 system 305 integrin 183 enzyme-/peptide-tagged approaches intracellular peptide selection 301 340–341 fluorescent biosensors 302 intravenous (IV) injection 2 fluorescent protein utilization 300

intravital real-time CLSM (IVRTCLSM) GABAA receptors 306 9 SEP-tagged AMPA receptors 302 in vitro bioconjugation methods 298 synthetic fluorophore 304 in vivo metal-catalyzed reactions ligand-directed dibromophenyl 150–153 benzoate (LDBB) chemistry in vivo kinetics 302 of monosaccharide-modified proteins ligand-directed tosylate (LDT) 137–139 chemistry 301 Index 377 ligand-gated ion transportation 187 synthetic approach 185 linear polymer 119 transmembrane structure analysis Lipinski’s rules 330, 332 192 live-cell surface protein analysis, AGD membrane permeability 336–337 reaction for 308–312 messenger RNA (mRNA) 13, 87, 338 lower critical solution temperature aminoacyl-transfer RNA (tRNA) 88 (LCST) 7, 125, 127 display method lysine-specific demethylase 1 (LSD1) advantage 346 234 origins of 345, 346 catalytic mechanism 239 genetic code 88–90 hydrazine-based 250, 251 micelle-Dox nanoparticles 118 inactivation mechanism 250 microRNA (miRNA) 35 NCL1 and NCL2 242 Mizoroki–Heck reaction 49 PCPA-Lys-4 H3-21 245 molecular analysis 273 PCPA-lysine analogue hybrid molecular crowding environment 298 compounds 242 monosaccharide-modified proteins phenylcyclopropylamine 242 dissection-based kinetc and protein-targeted drug delivery 245 biodistribution studies 137 small-molecule-based drug delivery noninvasive imaging 138 system 250–253 monoterpene indole alkaloid 43 target-guided synthesis 239–250 mPEG-PTMC 208 Müller glial cells 78 m multipass transmembrane (MTM) Macmillan’s collective total synthesis structure formation 185 45–52 macrocyclic multiblock amphiphile n 190 N-acetyl galactosamine (GalNAc) 261 macrocyclization 334 NAc-neuraminic acid 139 macropinocytosis 10 N-acyl-α-amino acids 95 magnetic resonance imaging (MRI) N-alkyl-α-amino acids 101 118, 273 N-alkyl-amino acids 95 mannose-bearing proteins 138 nanoarrays 32 matrix metalloproteinase (MMP) 10 nanobiodevice development 193 membrane functionalization nanofibers 79 with biological molecules 184 nanoparticles 10, 80, 114 genetic engineering 198 nanoscale 29 ligand-gated ion transportation 187 nanotechnology 80 light-triggered membrane budding natural peptide synthesis 333, 190 339–340 multipass transmembrane structure natural proteins 298 formation 185 NCC149 identification 224 nanobiodevice development 193 NCD38 250 semi-biological approach 191 NCDM-32 237 single molecule force spectroscopy NCH-31 226 192 [15N]choline 286 supramolecular ion channel NCO-90 232, 234 15 formation 187 [ N,D9]TMPA 291–292 378 Index

15 [ N,D9]trimethylglutamine 286 On-cell Coordination Chemistry 15 [ N,D9]trimethylphenylammonium (OcCC) 15 ([ N,D 9]TMPA) 288–291 in cultured neuron system 320 neurobiology 77 ion channel type glutamate receptor neuroblasts 74 314 neurodegeneration 80 ionotropic glutamate receptors 319 neurogenesis 77–78 metabotropic glutamate receptors neuronal progenitor cells 74 316, 319 neuropathology 77 Pd(bpy)-mediated allosteric neurotrophin-3 80 activation 320 N-glycoalbumins 145–148 primary cultured neuronal system 15N hyperpolarized molecular probes 317 286 schematic illustration 318 N-isopropyl acrylamide block methyl optochemical genetics 314 methacrylate organocascade catalysis 45–52 (NIPAAm-b-MMA) 125 organocatalyst-based protein labeling N-methyl-α-amino acids 101 method 309 N-methyl-amino acid 101 organocatalytic synthesis 47 N-methylation 335–336 osmotic pressure 204 [15N]-o-aminophenol-N,N,O-triacetic oxidative 117 acid (APTRA) 287 non-proteinogenic amino acids (nPAAs) p 87, 96, 97, 101, 329 palladium-catalyzed decarboxylative non-sense codon method 97, 98 coupling 52 non-standard base method 100 paramagnetic chemical exchange normal (healthy) cells saturation transfer (PARACEST) morphology and temperature 124 125 oxidative phosphorylation 117 paranemic crossover (PX) 29 produce ATP 117 PCPA-drug conjugates (PDCs) 252, tissue applications 124 253 vs. tumor cells 114, 125 PCPA-tamoxifen conjugates 252, 253 N-oxalylglycine (NOG) 236 Pd(bpy)-mediated allosteric activation, [15N]pyridine 286 of glutamate receptors 320

nuclear magnetic resonance (NMR) PEG10k-b-polyphosphoramidate (PPA) 273 6 cyclosporin 336–337 PEG-b-poly{N′-[N-(2-aminoethyl)- nuclear spin detection 274 2-aminoethyl]aspartamide} sensitivity 273 {PEG-b-P[Asp(DET)]} 7 nuclear pore complex (NPC) 13 PEGylation 8, 9 nucleic acid delivery system 8 PEI 11, 12, 14, 15 nucleobases 25 pentameric ligand-gated ion channel nucleotides 88 185 peptide amide backbone modifications o 335 oligodeoxynucleotide (ODN) 123 peptide-amphiphile 79 oligonucleotide (ODN) 123 peptide nucleic acids (PNA) 35 Index 379 peptidyl-tRNA 103, 104 poly-N-n-propylacrylamide (PNNPAM) phage display method 341–345 124 pharmacokinetics poly-(2-n-propyl-2-oxazoline) (PnPrOx) of bow-tie-shape dendrimers 115 7 of particles 114 polypeptides 87 phenylboronic acids (PBA) 8 polyplex micelles phenylcyclopropylamine (PCPA) 242 bioavailability of 8 phosphodiester linkage 25 disintegration of 8 phosphorothioate bond (PS) linkage for efficient cellular entry 9–10 259 for efficient transcription 13–14 photochemical internalization (PCI) mechanism of 2 12 for nuclear translocation 13 photoirradiation 15 pDNA stable encapsulation of 6–9 phthalocyanine-loaded dendrimers of PEG10k-b-polyphosphoramidate (DPc) 12 (PPA) 6 plasma membrane 183 for safe endosome escape 11–12 plasmid DNA (pDNA) systemic gene delivery system 6–14 bioavailability of 1 polyurethane 211 packaging positive allosteric modulator 316 by block catiomers 2–6 positron emission tomography (PET) globule-shape 5 117 into polyplex micelles 1 prestin rod-shape/globule-shape 3–6 application to biological device 194 spooling of 17 isothermal titration calorimetry 198 p-methoxy benzyl (PMB) 49 mRNA expression 192 point accumulation for imaging in mutants 199 nanoscale topography (PAINT) prolyl-tRNA synthetase (ProRS) 91 36 purification 197 poly(β-benzyl-l-aspartate) (PBLA) 11 reconstitution into lipid bilayer 196 polyester synthesis 97 structural analysis 194 poly(ethylene glycol) (PEG) 2, 10, 118, transmembrane structure 192 206 Western blotting 197 polyethylene glycol (PEG)-ylated protein 297 polyester 115 adsorption 9 polyethylene oxide chains 116 immobilization 298 poly(2-ethyl-2-oxazoline) 7 protein-based semisynthetic biosensors polyion exchange reaction 6 304 polylactide (PLA) proteinogenic amino acids (PAAs) 87, copolymer 205 95, 97 stereocomplex (SC) 205 protein-targeted drug delivery 245 polymer binding 16 proton-sponge effect 11 poly-methyl methacrylate (PMMA) pseudo-natural peptide synthesis 125 amino acid replacement 354–355 poly(N-isopropylacrylamide)-b- genetic code expansion 352–354 P(Asp(DET)) (PNIPAM-b- genetic code reprogramming P(Asp(DET)) 7 355–361 380 Index

pseudo-natural peptide synthesis semisynthetic antibody-DMAP (contd.) conjugates 310 intein cyclization 348–351 semisynthetic biosensor construction post-translational modification 305 351–352 semisynthetic fluorescent biosensors SICLOPPS 348–351 307 SPPS limitations of 348 serum proteins 8 PTMC-PEG-PTMC triblock shear stress 9 copolymers 208 short interfering RNA (siRNA) PURE translation system 354 257–258 puromycin 345 single molecule force spectroscopy (SMFS) 192 r single-stranded DNA 28 radical nanoparticles (RNP) 120 siRNA conjugated with tocopherol Random non-standard Peptides (Toc-siRNA) 261 Integrated Discovery (RaPID) small angle X-ray scattering (SAXS) 31 105, 356–361 small-molecule-based drug delivery reactive oxygen species (ROS) 12 system 250–253 redox blinking 175 SNAP-tag based indicator proteins redox status 283 305 retinal progenitors 78 solid phase synthesis of peptides (SPPS) reverse two-hybrid method, in E. coli 348 340 spermidine 17 rhodopsin 185 spirocyclization reaction 174 ribosomal RNA (rRNA) 338 stereocomplex (SC) of polylactide 205 ribosomal synthesis, of peptides 337 stroke 73, 74, 80 ribosomal translation structure-based drug design amino acids 103–104 aminoacyl-tRNA synthetases 90–91 KDM4C inhibitor identification 235 assigning non-proteinogenic amino KDM5A inhibitor identification 237 acids 95–101 KDM7B inhibitor identification 238 drug discovery platforms 104–105 SIRT2-selective inhibitors 232–234 genetic code decoding 88–90 Strychnos alkaloids 45, 48 improvement of substrate tolerance substrate-based drug design, for 103–104 HDAC6-selective inhibitor noncanonical aminoacyl-tRNAs identification 228 91–95 subventricular zone (SVZ) 74 substrate scope 101–103 3-sulfopropyl (SPA) 124 RIKEN click reaction 142 super-paramagnetic iron oxide (SPIO) RNP-TEMDO-UBD 120, 122 117 RNP-TEMDO-UBD-DA 122 super-resolution fluorescent microscopy rod/cone photoreceptor cells 78 36 supramolecular ion channel formation s 187 scaffold structure surface degradation 203 13C hyperpolarized molecular probes systematic evolution of ligands by 292 exponential enrichment (SELEX) 15N HP probes 288 165, 167, 170 Index 381 t tumor cells target-guided synthesis (TGS) aberrant morphology and size LSD1 inhibitor identification 114–117 239–250 aberrant pH microenvironment for SIRT1-selective inhibitor 117–124 identification 228–232 glucose for energy production 124 TEMDO-UBD 120, 122 growth 113 TEMDO-UBD-DA 122 microenvironment temperature of TEMPO 122, 123 124–129 tetraethylenepentamine 11 VEGF 73 therapeutic antibodies 332 tumor growth 72 therapeutic oligonucleotides ASO 258–259, 261–262 u chemical modifications 259–260 [U-13C,U-D]glucose 278 delivery ligand-molecule 261 undruggable proteins 332–333 DNA/RNA heteroduplex unnatural amino acids 335 oligonucleotide 262–268 urea benzene derivatives (UBD) 127 internucleotide linkage modifications uridine 88 259–260 UV light-triggered membrane budding ligand-conjugation for drug delivery 190 systems 261 schematic illustration 263 v siRNA 257–258, 261 vascular endothelial cells 8 sugar moiety modification 260 vascular endothelial growth factor vitamin E 261 (VEGF) 72, 73 thermoresponsive block 7 vascular permeability factor (VPF) 72 thymine (T) 25 VEGF-sponge 75 tissue degeneration 117 visible light-triggered membrane tissue regeneration budding 190 cell scaffolding for 74 vitamin E 261 VEGF-conjugated biomaterials 74 w total internal reflection fluorescence Warburg effect 117, 118, 124, 129 (TIRF) microscope 36 Watson–Crick base pairs 89 trans-cis photo-isomerization whole-cell patch-clamp recording 199 176 Wieland–Gumlich aldehyde 48 transfer RNA (tRNA) 338 triblock copolymers 7 z triethylenetetramine (TET) 11 Z-DNA 28 triplet blinking 174 zeta-potential 2, 9, 10 tumor angiogenic factor (TAF) 72 zipping mechanism 35