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Файл:Ординатура / Хирургия / Библиотека им академика М.И. Перельмана / Книга_5720_Библиотеки_им_академика_М_И_Перельмана
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x Contents
7 Purification and Characterization of Dendrimers ...................... 83
7.1 Chromatographic Methods........................................... 84
7.2 Electromigration Methods ........................................... 85
7.3 Mass Spectrometry ................................................... 87
7.4 Miscellaneous Selected Examples................................... 88
References.................................................................... 89
8 Dendrimeric Libraries ..................................................... 93
References.................................................................... 96
9 Dendrimers in Catalysis ................................................... 99
References.................................................................... 101
Part II Dendrimers and Their Biological and Therapeutic
Applications
10 Dendrimers and Solubility................................................. 105
References.................................................................... 108
11 Biocompatibility and Toxicity of Dendrimers ........................... 111
References.................................................................... 112
12 Dendrimers in Nanoscience and Nanotechnology ....................... 115
References.................................................................... 125
13 Dendrimers in Drug Delivery ............................................. 131
References.................................................................... 137
14 Dendrimers in Gene Delivery ............................................. 141
References.................................................................... 146
15 Dendrimers and Bacteria .................................................. 149
15.1 Escherichia coli ...................................................... 149
15.2 Vibrio cholerae ....................................................... 152
15.3 Pseudomonas aeruginosa ............................................ 153
15.4 Haemophilus influenzae.............................................. 154
15.5 Mycobacterium tuberculosis......................................... 155
References.................................................................... 156
16 Dendrimers and Viruses ................................................... 161
16.1 Influenza .............................................................. 161
16.2 HIV ................................................................... 162
16.3 Other Viruses ......................................................... 164
References.................................................................... 166
17 Dendrimers and Parasites ................................................. 171
References.................................................................... 172
Contents xi
18 Cancer ....................................................................... 175
18.1 Adjuvant Effects on Dendritic Cells................................. 176
18.2 Direct Effects on Tumor Cells ....................................... 177
References.................................................................... 181
19 Diagnostics, Lectin Detection and Cell–Cell Interactions.............. 183
References.................................................................... 188
20 Dendrimers as Biosensors and Imaging Tools ........................... 191
References.................................................................... 194
21 Dendrimers Regulating Intracellular Signaling Pathways ............. 197
References.................................................................... 198
22 Vaccines and Immunomodulation ........................................ 199
22.1 Antitumor Vaccines .................................................. 201
22.2 Antiviral Vaccines .................................................... 203
References.................................................................... 204
23 Dendrimers in Neurodegenerative Diseases ............................. 209
23.1 Dendrimers as Anti-prion Agents ................................... 209
23.2 Dendrimers and Alzheimer’s Disease ............................... 213
23.3 Dendrimers and Parkinson’s disease ................................ 216
23.4 Miscellaneous Applications of Dendrimers
in Neurodegenerative Disorders ..................................... 217
References.................................................................... 218
24 Conclusions and Perspectives ............................................. 223
Index ............................................................................... 225
•
Acronyms
Nomenclature and abbreviations: Standard nomenclature and abbreviations
of amino acids and peptides have been used (Jones, JH (2006) J. Pept. Sci.
12:1–12). Nomenclature and abbreviations of carbohydrates are in accord with
IUPAC (McNaught, AD (1996) Pure Applied Chem. 68: 1919–2008). Unless
stated otherwise, amino acids are of L-configuration and carbohydrates are of
D-configuration. Other abbreviations and notations used are given below.
AB5 AB5 hexameric assembly of cholera toxin consisting of a
single copy of the enzymatic subunit A and five copies of the
receptor subunit B
Abs Antibodies
ACE Affinity capillary electrophoresis
AChE Acetylcholinesterase
AD Alzheimer’s disease
AFM Atomic force microscopy
AIDS Acquired immunodeficiency syndrome
AIE Aggregation-induced emission
APC Antigen presenting cell
ASGPR Asialoglycoprotein receptors on the surface of hepatocytes
ATRP atom transfer radical polymerization
BARAC Biarylazacyclooctynone
BBB Blood-brain barrier
bipy 2,2’-bipyridyl
BNNTs Boron nitride nanotubes
BSA Bovine serum albumin
BSE Bovine spongiform encephalopathy
BSI Back-scattering interferometry
CA Blood clearance agent
CB Cucurbituril-based
CCIs Carbohydrate-carbohydrateinteractions
CD Circular dichroism or cyclodextrin
xiii
xiv Acronyms
CE Capillary electrophoresis
CE-ESI-TOF-MS Capillary electrophoresis electrospray ionization time-of-flight
mass spectrometry
CHD Chitosan dendrimers
CJD Creutzfeld–Jakob’s disease
CNS Central nervous system
CNTs Carbon nanotubes
Con A Canavalia ensiformis agglutinin; Concanavalin A
COSS R
8
Si
8
O
12
cube-octameric silsesquioxanes
CSFV Classical swine fever virus
CZE Capillary zone electrophoresis
DC Dendritic cell
DCLs Dynamic combinatorial libraries
DC-SIGN Dendritic cell-specific intracellular adhesion molecule-3-
grabbing non-integrin
DLS Dynamic light scattering
DNA Deoxyribonucleic acid
DNP Dinitrophenyl group
Dns Dansyl
DOTA 1,4,7,10-tetraazacyclododecane tetraacetic acid
DOX Doxorubicin
DTPA Diethylenetriaminepentaacetic acid
DTT Dithiothreitol
ECM Extracellular matrix proteins
ELISA Enzyme-linked immunosorbent assay
ELLA Enzyme-linked lectin assay
EM Electrophoretic mobility
EPO Erythropoietin
EPR Electron paramagnetic resonance
ESI-MS Electrospray ionization mass spectrometry
FA Folic acid
FGF-1 Fibroblast growth factor-1
FGFR Fibroblast growth factor receptor
FimH Fimbrial lectin
FITC 5-fluorescein isothiocyanate
FMDV Foot-and-mouth disease virus
FTICR-MS Fourier transform ion cyclotron resonance mass spectrometry
FTIR Fourier transform-infra red spectroscopy
glyco-SAMs Glyco-self-assembled monolayers
GABA -aminobutyric acid
GAS Group A Streptococcus
GN4C Glycodendrimer consisting of four GlcNAc residues on
calix[4]arene core
GNA Galanthus nivalis agglutinin – snowdrop lectin
Gn Generation number
Acronyms xv
GNPs Gold nanoparticles
GOX Glucose oxidase
GPC Gel permeation chromatography
GSS Gerstmann-Straussler-Scheinker’s syndrome
HA Hemagglutinin
HbA
1c
Glycated hemoglobin
HBPO Hydrophobic poly(3-ethyl-3-(hydroxymethyl)oxetane)core
HIA Hemagglutination inhibition assay
HIV Human immunodeficiency virus
hMSCs Human mesenchymal stem cells
HPAMAM PAMAM-hyperbranched poly(amido amine) dendrimers
HPLC High performance liquid chromatography
HPMA Hyperbranched polyamidoamines
HPTLC High performance thin layer chromatography
HPV Human papilloma virus
HRPO Horseradish peroxidase
HSV Herpes simplex virus
HuPrP Human prion protein
HUVEC Human umbilical vein endothelial cells
IL Interleukin
IFN- Interferon-
ITAM Immunoreceptor tyrosine based activation motif
ITC Isothermal titration calorimetry
KLH Keyhole limpet hemocyanin
Lac Lactose
LCST Lower critical solution temperature
LecA Pseudomonas aeruginosa lectin LecA (PA-IL)
LecB Pseudomonas aeruginosa lectin speific for L-fucose
LILBID MS Laser induced liquid beam ion desorption mass spectrometry
LnNPs NaGdF
4
:Er
3+
,Yb
3+
upconvertingnanoparticles
LRET Luminescence resonance energy transfer
MAG Multiple antigenic glycopeptide
MALDI-TOF MS Matrix-assisted laser desorption-ionization time of flight mass
spectrometry
MALLS Multi angle laser light scattering
MAP Multiple antigenic peptide
MD Molecular dynamics simulations
MDO Mannosylated dendrimer ovalbumin
MMP-2 Matrix metalloproteinase-2
M Monocyte-macrophagelineage
MP Methylprednisolone
MRI Magnetic resonance imaging
MSC Marrow-derived mesenchymal stromal cells
MSCs Bone marrow-derived mesenchymal stem cells
MS/MS Tandem MS
xvi Acronyms
MT1-MMP Membrane type 1-matrix metalloproteinase
nAChR Nicotinic acetylcholine receptor
NAC N-alkyl cysteine
NA Neuraminidase
NCAM Neural cell adhesion molecule
NMR Nuclear magnetic resonance
NPs Nanoparticles
NT Neurotensin
nvCJD New variant of Creutzfeld-Jakob’s disease
OBOC library One-bead-one-compound library
ODNs CpG Synthetic oligodeoxynucleotides(ODNs) with the CpG-motifs
OSA Oncogenic suppression activity protein
OVA Ovalbumin
P2Y
14
G protein-coupled receptor activated by uridine-5’-
diphosphoglucose
paCDs Polycationic amphiphilic cyclodextrins
PAGE Polyacrylamide gel electrophoresis
PA-IL Pseudomonas aeruginosa lectin I
PA-IIL Pseudomonas aeruginosa lectin II
PAMAM Polyamidoamine dendrimer
PAMAM-SAH PAMAM-succinamic acid dendrimers
PANINT’s Polyaniline nanotubes
PDEAEMA Poly(2-(N,N-diethylamino)ethyl methacrylate)
pDNA Plasmid DNA
PD Parkinson’s disease
PDT Photodynamic therapy
PEC Pentaerythritol core
PEG Polyethylene glycol
PePOs Pentaerythritol phosphodiester oligomers
PGLD Bioactive polyglycerol dendrimers
PLA Poly(L-lactide)
PLGA Poly-D,L-lactide-co-glycolide
PNA Peanut agglutinin, a galactose-binding lectin from Arachis
hypogaea
PPI Poly(propylene imine) dendrimer
proMMP-2 Promatrix metalloprotease-2
PrP
C
Cellular prion protein
PrP
Sc
Scrapie isoform of prion protein
PSMA Prostate-specific membrane antigen
PSP Pseudostationary phase
PTA Psophocarpus tetragonolobus agglutinin
QqTOF MS Quadrupole-quadrupole time-of-flight mass spectrometry
RAFT Regioselectively addressable functional template
Rhod Rhodamine
RIP Relative inhibitory potency
Acronyms xvii
RP-HPLC Reverse-phase HPLC
RVG Rabies virus glycoprotein
SALs Sugar-assisted ligations
SAMs Self-assembled monolayers
SAv Streptavidin
SAXS Small-angle X-ray scattering
scFv Single chain fusionof light and heavy chains in variableregion
of mAb
SDS-PAGE Sodium dodecylsulfate polyacrylamide gel electrophoresis
SDS Sodium dodecylsulfate
SEC Size exclusion chromatography
siRNA Small interfering RNA
SLNs Solid lipid nanoparticles
SOCs Sequential oligopeptide carriers
SPR Surface plasmon resonance
SRCD Synchrotron radiation-based circular dichroism
STM Scanning tunneling microscopy
SWNTs Single-walled carbon nanotubes
Syk Spleen tyrosine kinase
TACA Tumor-associated carbohydrate antigen
TAT The transactivator of transcription of human immunodefi-
ciency virus
TEM Transmission electron microscopy
Th1 Distinct type of T-helper cell
TK Thymidine kinase
TLR2 Toll-like receptor 2
TNF-˛ Tumor necrosis factor ˛
TPEs Mannose substituted tetraphenylethenes
TRIS Tris(hydroxymethyl)aminomethane
UDPGA Uridine-5’-diphosphoglucuronic acid
UPLC Ultra performance liquid chromatography
WGA Plant lectin, wheat germ agglutinin
•
Chapter 1
Introduction
Dendrimer-like structures exist in the universe and on our planet Earth hundreds of
million years. They are present in living and nonliving things, e.g., nerves, nervures,
veins, gekon’s pads, treetops, roots of a tree, the supernova remnant Crab Nebula,
forked lightning, river basins, and snow crystals [8]. Their size is from light-years
to kilometers, to microscale and nanoscales. On the basis of thermodynamic data,
it was shown that branched structures are more stable than the linear ones. For
example, 2,2-dimethylpropane is much more stable than linear n-pentane [10].
Branching is a general tendency in nature. Therefore, when something can get
branched, it will get branched. The branched structures, including dendrimers, have
properties that could result in faster and more efficient transfer, dissipation, and
distribution of matter and/or energy.
The word dendrimer is derived from the Greek word dendron (ıK%o) meaning
“tree” or “branch,” and meros ("%o&) meaning part [1, 7]. The definitions of
dendrimer differ depending on the specialization of authors. Some of the definitions
are as follows:
Dendrimers are versatile, derivatizable, well-defined highly branched three-
dimensional macromolecules (chemical polymers) with characteristic compartmen-
talized structures, the sizes and physicochemical properties of which resemble those
of biomolecules, e.g., proteins, nucleic acids, and polysaccharides, and a tendency
to adopt a globular shape once a certain size is reached. Dendrimers have highly
controlled structures, a large number of controllable “peripheral” functionalities,
and a single molecular weight and can be characterized as chemical entities (with
some limitations). They contain different cores, branches, and surface groups and
have different number of generations[1,5, 12,13]. For more definitions and reviews
see [11, 21]. The composition, valency, generation, structure, etc. determine their
physicochemical properties and biological activities.
Dendrimers are monodisperse polymers that adopt a globular three-dimensional
shape as the generation number (Gn) increases. These branched macromolecules
have a well-defined core, interior region layers connected by branches, and an
exterior crimpy surface. This affords a high surface area-to-volume ratio. The
J.
ˇ
Sebest
´
ık et al., Biomedical Applications of Peptide-, Glyco- and Glycopeptide
Dendrimers, and Analogous Dendrimeric Structures,
DOI 10.1007/978-3-7091-1206-9
1
1, © Springer-Verlag Wien 2012
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