Biomedical Applications of Peptide-, Glyco- and Glycopeptide Dendrimers, and Analogous Dendrimeric Structures

244 Pages·2012·4.32 MB·English

by  Jaroslav Sebestik

Biomedical Applications of Peptide-, Glyco-
and Glycopeptide Dendrimers,
and Analogous Dendrimeric Structures
•
ˇ
Jaroslav Sebest´ık Milan Reinisˇ Jan Jezˇek
(cid:2) (cid:2)
Biomedical Applications
of Peptide-, Glyco-
and Glycopeptide
Dendrimers, and Analogous
Dendrimeric Structures
123
JaroslavSˇebest´ık JanJezˇek
DepartmentofMolecularSpectroscopy LaboratoryofGlycoconjugates
InstituteofOrganicChemistry InstituteofOrganicChemistry
andBiochemistry,ASCR,vvi andBiochemistry,ASCR,vvi
Prague Prague
CzechRepublic CzechRepublic
MilanReinisˇ
InstituteofMolecularGeneticsASCR,vvi
Prague
CzechRepublic
ISBN978-3-7091-1205-2 ISBN978-3-7091-1206-9(eBook)
DOI10.1007/978-3-7091-1206-9
SpringerWienHeidelbergNewYorkDordrechtLondon
LibraryofCongressControlNumber:2012954529
©Springer-VerlagWien2012
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Preface
The purpose of this book is to show the progress in the field of synthesis and
biomedicalapplicationsofpeptide-,glyco-,glycopeptidedendrimersandanalogous
dendrimeric structures. This booklet is intended to graduate students, advanced
undergraduates,and scientists workingin the area of organicchemistry,biochem-
istry,nanoscience,biology,medicinalchemistry,andbiomedicalapplications.
Dendrimers and dendritic macromolecules were pioneered in the 1980s. They
represent a dynamically expanding field spreading from physics, chemistry, and
biologytoabroadareaofbiomedicalapplications.Dendrimerspenetratetotillnow
isolatedareasofscienceandcreateaninterconnected,logical,mutuallyinfluencing
scientificnetwork,thedendrimerscience(dendrimerology).
Thereaderwillbeintroducedtoaverydiversegroupofmethodologiesspanning
fromchemistry,physics,bioengineering,materialsscience,biomedicalapplications,
andbeyond.
Many problems, when seen from the “dendrimeric point of view,” could be
overcome if people would use the broad scale of dendrimeric properties and
applications. The “cluster effect” (“multivalency”) plays a key role and serves as
aconnectinggluebetweendifferentstructures.
During the last years the number of papers about dendrimers and their appli-
cationsreachedabout1,600annually,i.e.,twicesomuchincomparisonwith2001.
Thatmeansthattheinformationwaveisatthetop.Duetospacelimitation,thisbook
couldnotcoverallpapersandreviewsandweapologizetoresearchersinvolvedin
thefieldwhoseworkshavenotbeencoveredherein.Morereferencescanbefound
inourearlierreviews(2005;2008a,b,c;2011).
Prague,CzechRepublic JanJezˇek
September2012 MilanReinisˇ
JaroslavSˇebest´ık
v
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Acknowledgements
ThisworkwassupportedbygrantoftheCzechScienceFoundation(GACR)Nos.
203/07/1517and P208/11/0105;by grants from the Ministry of Education, Youth
and Sports (MSMT) No. LH11033; and Research Projects Z40550506 and RVO
61388963.OurthanksareduetoDr.LenkaSˇebest´ıkova´,Dr.PetrNiederhafner,and
Dr.AnnaFisˇerova´foracriticalreadingofthemanuscript.
vii
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Contents
1 Introduction................................................................. 1
References.................................................................... 4
PartI ChemistryandStructureofDendrimers
2 DefinitionofTermsandNomenclature................................... 9
2.1 DendriplexesandDendrisomes...................................... 11
2.2 Dendrigraft ........................................................... 12
2.3 Glycotope............................................................. 12
2.4 Glycocluster.......................................................... 13
2.5 Glycocluster–Cluster................................................. 13
2.6 ClusterEffectandMultivalency..................................... 13
2.7 MacromolecularEffect............................................... 14
2.8 SugarBall............................................................. 15
2.9 “Smart”Glycodendrimers ........................................... 15
References.................................................................... 15
3 SugarCode(Glycocode)................................................... 23
References.................................................................... 25
4 ClassesofPeptide-,Glyco-,andGlycopeptideDendrimers............ 29
References.................................................................... 34
5 TheDendriticStateandDendriticEffects............................... 45
References.................................................................... 51
6 SynthesisofDendrimers:ConvergentandDivergentApproaches.... 55
6.1 Divergent ............................................................. 57
6.2 Convergent............................................................ 58
6.3 LegoChemistry ...................................................... 58
6.4 Ligations.............................................................. 60
6.5 ClickChemistry...................................................... 64
References.................................................................... 70
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