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Peptide and glycopeptide dendrimers and analogous dendrimeric structures and their biomedical applications

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Abstract

The size of information that can be stored in nucleic acids, proteins, and carbohydrates was calculated. The number of hexamers for peptides is 64,000,000 (206) and seems to be impressive in comparison with 4,096 (46) hexanucleotides, but the number of isomers of hexasaccharides is 1.44 × 1015. Carbohydrates are therefore the best high-density coding system. This language has been named glycocode resp. sugar code. In comparison with peptide dendrimers, the amount of information carried by glycopeptide dendrimers or glycodendrimers is therefore much higher. This is reflected by the variability of structures and functions (activities). This review is about the broad area of peptide and glycopeptide dendrimers. The dendrimeric state and physicochemical properties and general consequences are described, together with a cluster effect. The impact of cluster effect to biological, chemical, and physical properties is discussed. Synthesis of dendrimers by convergent and divergent approaches, “Lego” chemistry, ligation strategies, and click chemistry is given with many examples. Purification and characterization of dendrimers by chromatographic methods, electromigration methods, and mass spectrometry are briefly mentioned. Different types of dendrimers with cyclic core, i.e. RAFTs, TASPs and analogous cyclic structures, carbopeptides, carboproteins, octopus glycosides, inositol-based dendrimers, cyclodextrins, calix[4]arenes, resorcarenes, cavitands, and porphyrins are given. Dendrimers can be used for creation of libraries, catalysts, and solubilizing agents. Biocompatibility and toxicity of dendrimers is discussed, as well as their applications in nanoscience, nanotechnology, drug delivery, and gene delivery. Carbohydrate interactions of glycopeptide dendrimers (bacteria, viruses, and cancer) are described. Examples of dendrimers as anti-prion agents are given. Dendrimers represent a fast developing area which partly overlaps with nanoparticles and nanotechnologies.

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Abbreviations

ACE:

Affinity capillary electrophoresis

AChE:

Acetylcholinesterase

AFM:

Atomic force microscopy

AMINAP:

6-Aminomethyl-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene

ATRP:

Atom transfer radical polymerization

BINAP:

2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene

BNNTs:

Boron nitride nanotubes

Carbo-BINAP:

2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene-6-carboxylic acid

CCIs:

Carbohydrate–carbohydrate interactions

CD:

Circular dichroism, or Cyclodextrin

CE:

Capillary electrophoresis

CNTs:

Carbon nanotubes

ConA:

Canavalia ensiformis agglutinin; Concanavalin A

CSP:

Chiral stationary phase

CZE:

Capillary zone electrophoresis

DC:

Dendritic cell

DCL:

Dynamic combinatorial library

DCR:

Dendritic chain reaction

DFT:

Density functional theory

Dns:

Dansyl

DTPA:

Diethylenetriaminepentaacetic acid

ELLA:

Enzyme-linked lectin assay

EM:

Electrophoretic mobility

EPO:

Erythropoietin

EPR:

Electron paramagnetic resonance

FimH:

A protein found at the tip of a bacterial pilus which adheres to the urinary bladder

FITC:

5-Fluorescein isothiocyanate

FTICR-MS:

Fourier transform-ion cyclotron resonance-MS

Gd-DTPA:

Gd(III)-diethylenetriaminepentaacetic acid

GM3:

(N-Acetylneuraminyl)-galactosylglucosylceramide

GNA:

Galanthus nivalis agglutinin from the snowdrop bulb

GNPs:

Gold glyconanoparticles

HPA:

Helix pomatia agglutinin

HRPO:

Horseradish peroxidase

IL-1β :

Interleukin-1-β

INF-γ :

Interferon-γ

ITC:

Isothermal titration calorimetry

Lea :

Galβ3(Fucα4)GlcNAcβ3Galβ4Glc

Lex :

Galβ4(Fucα3)GlcNAcβ3Galβ4Glc

MAG:

Multiple antigen glycopeptide

MD:

Molecular dynamics

MRI:

Magnetic resonance imaging

NAC:

N-alkyl cysteine

NKR:

Natural killer cell receptor

PAGE:

Polyacrylamide gel electrophoresis

PAMAM:

Polyamidoamine Starburst dendrimer

PAMAM-SAH:

PAMAM succinamic acid dendrimers

PEC:

Pentaerythritol core

PEG:

Polyethylene glycol

PEGA:

Polyethylene glycol polyacrylamide resin

PEI:

Poly(ethyleneimines)

PePO:

Propargylated pentaerythritol phosphodiester oligomer

PNA:

Arachis hypogaea agglutinin

POEPOP:

Polyoxyethylene–polyoxypropylene resin

PPI:

Poly(propyleneimine)

PSP:

Pseudostationary phase

PTA:

Psophocarpus tetragonolobus agglutinin

PXM:

Piroxicam

QqTOF-MS:

Quadrupole–quadrupole time-of-flight mass spectrometry

RAFT:

Regioselectively addressable functional template

Rho:

Rhodamine

RIP:

Relative inhibitory potency

SAL:

Sugar-assisted ligation

SAMs:

Self-assembled monolayers

SDS:

Sodium dodecylsulphate

SDS-PAGE:

Sodium dodecylsulphate polyacrylamide gel electrophoresis

SEC:

Size exclusion chromatography

Slex :

Neolactoseries antigens sialyl-Lewis x

SPGS:

Solid phase glycopeptide synthesis

SPOCC:

Superpermeable organic combinatorial chemistry resin

SPPS:

Solid phase peptide synthesis

SPR:

Surface plasmon resonance

SRCD:

Synchrotron radiation-based circular dichroism

STM:

Scanning tunneling microscopy

SWNTs:

Single-walled carbon nanotubes

TASP:

Template-assembled synthetic protein

TEM:

Transmission electron microscopy

TentaGel:

PEG-grafted resin

TF antigen:

Galβ(1 → 3)GalNAcα(1 → O)Ser/Thr

TN antigen:

GalNAcα(1 → O)Ser/Thr

TNF-α :

Tumor necrosis factor-α

UPLC:

Ultra performance liquid chromatography

WGA:

Wheat germ (Triticum vulgaris) agglutinin

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Acknowledgments

This work was supported by grant of Czech Science Foundation (GA CR) No. 203/07/1517; by grants from Grant Agency of the Czech Academy of Sciences (grant No. KAN200520703 and grant No. 200100801); and Research Project Z40550506. Our thanks are due to Anna Kovalová, Ph.D. for a critical reading of the manuscript.

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  1. Institute of Organic Chemistry and Biochemistry, v.v.i., Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 166 10, Prague 6, Czech Republic

    Jaroslav Sebestik, Petr Niederhafner & Jan Jezek

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  1. Jaroslav Sebestik
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  2. Petr Niederhafner
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  3. Jan Jezek
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Correspondence to Jaroslav Sebestik or Jan Jezek.

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Dedicated to Miroslav Ledvina, Ph.D. on the occasion of his 60th birthday.

Standard abbreviations have been followed throughout this paper (J Peptide Sci 12:1–12, 2006). When not stated otherwise, amino acids are of L-configuration and carbohydrates are of D-configuration.

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Sebestik, J., Niederhafner, P. & Jezek, J. Peptide and glycopeptide dendrimers and analogous dendrimeric structures and their biomedical applications. Amino Acids 40, 301–370 (2011). https://doi.org/10.1007/s00726-010-0707-z

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