Synthesis and in Vitro Evaluation of Monodisperse Amino-Functional Polyester Dendrimers with Rapid Degradability and Antibacterial Properties

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Fältnamn	Indikatorer	Metadata
000		04089naa a2200409 4500
001		oai:DiVA.org:kth-221021
003		SwePub
008		180112s2017 \| \|\|\|\|\|\|\|\|\|\|\|000 \|\|eng\|
009		oai:prod.swepub.kib.ki.se:137342661
024	7	a https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-2210212 URI
024	7	a https://doi.org/10.1021/acs.biomac.7b013642 DOI
024	7	a http://kipublications.ki.se/Default.aspx?queryparsed=id:1373426612 URI
040		a (SwePub)kthd (SwePub)ki
041		a engb eng
042		9 SwePub
072	7	a ref2 swepub-contenttype
072	7	a art2 swepub-publicationtype
100	1	a Stenström, Patriku KTH,Fiber- och polymerteknologi4 aut0 (Swepub:kth)u14if6dt
245	1 0	a Synthesis and in Vitro Evaluation of Monodisperse Amino-Functional Polyester Dendrimers with Rapid Degradability and Antibacterial Properties
264		c 2017-11-22
264	1	b American Chemical Society (ACS),c 2017
338		a print2 rdacarrier
500		a QC 20180112
520		a Amine functional polymers, especially cationically charged, are interesting biomacromolecules for several reasons, including easy cell membrane entrance, their ability to escape endosomes through the proton sponge effect, spontaneous complexation and delivery of drugs and siRNA, and simple functionalization in aqueous solutions. Dendrimers, a subclass of precision polymers, are monodisperse and exhibit a large and exact number of peripheral end groups in relation to their size and have shown promise in drug delivery, biomedical imaging and as antiviral agents. In this work, hydroxyl functional dendrimers of generation 1 to 5 based on 2,2-bis(methylol)propionic acid (bis-MPA) were modified to bear 6 to 96 peripheral amino groups through esterification reactions with beta-alanine. All dendrimers were isolated in high yields and with remarkable monodispersity. This was successfully accomplished utilizing the present advantages of fluoride-promoted esterification (FPE) with imidazole-activated monomers. Straightforward postfunctionalization was conducted on a second generation amino functional dendrimer with tetraethylene glycol through NHS-amidation and carbonyl diimidazole (CDI) activation to full conversion with short reaction times. Fast biodegradation of the dendrimers through loss of peripheral beta-alanine groups was observed and generational- and dose-dependent cytotoxicity was evaluated with a set of cell lines. An increase. in neurotoxicity compared to hydroxyl-functional dendrimers was shown in neuronal cells, however, the dendrimers were slightly less neurotoxic than commercially available poly(amidoamine) dendrimers (PAMAMs). Additionally, their effect on bacteria was evaluated and the second generation dendrimer was found unique inhibiting the growth of Escherichia coli at physiological conditions while being nontoxic toward human cells. Finally, these results cement a robust and sustainable synthetic route to amino-functional polyester dendrimers with interesting chemical and biological properties.
650	7	a NATURVETENSKAPx Biologix Biokemi och molekylärbiologi0 (SwePub)106022 hsv//swe
650	7	a NATURAL SCIENCESx Biological Sciencesx Biochemistry and Molecular Biology0 (SwePub)106022 hsv//eng
700	1	a Hjorth, Eriku Karolinska Institutet4 aut
700	1	a Zhang, Yuningu KTH,Ytbehandlingsteknik4 aut0 (Swepub:kth)u1bh78yi
700	1	a Andrén, Oliver C. J.u KTH,Ytbehandlingsteknik4 aut0 (Swepub:kth)u1fshusr
700	1	a Guette-Marquet, Simon4 aut
700	1	a Schultzberg, Marianneu Karolinska Institutet4 aut
700	1	a Malkoch, Michael,d 1974-u KTH,Fiber- och polymerteknologi4 aut0 (Swepub:kth)u18z6ljf
710	2	a KTHb Fiber- och polymerteknologi4 org
773	0	t Biomacromoleculesd : American Chemical Society (ACS)g 18:12, s. 4323-4330q 18:12<4323-4330x 1525-7797x 1526-4602
856	4 8	u https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-221021
856	4 8	u https://doi.org/10.1021/acs.biomac.7b01364
856	4 8	u http://kipublications.ki.se/Default.aspx?queryparsed=id:137342661

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