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@ARTICLE{Ziehm:821057,
author = {Ziehm, Tamar and Brener, Oleksandr and van Groen, Thomas
and Kadish, Inga and Frenzel, Daniel and Tusche, Markus and
Kutzsche, Janine and Reiß, Kerstin and Gremer, Lothar and
Nagel-Steger, Luitgard and Willbold, Dieter},
title = {{I}ncrease of {P}ositive {N}et {C}harge and
{C}onformational {R}igidity {E}nhances the {E}fficacy of d
-{E}nantiomeric {P}eptides {D}esigned to {E}liminate
{C}ytotoxic {A}β {S}pecies},
journal = {ACS chemical neuroscience},
volume = {7},
number = {8},
issn = {1948-7193},
address = {Washington, DC},
publisher = {ACS Publ.},
reportid = {FZJ-2016-06301},
pages = {1088 - 1096},
year = {2016},
abstract = {Alzheimer’s disease (AD) is a neurodegenerative disorder
and the most common type of dementia. Until now, there is no
curative therapy available. Previously, we selected the
amyloid-beta (Aβ) targeting peptide D3 consisting of 12
D-enantiomeric amino acid residues by mirror image phage
display as a potential drug candidate for the treatment of
AD. In the current approach, we investigated the
optimization potential of the net charge was investigated
and second, cyclization was introduced which is a well-known
tool for the optimization of peptides for enhanced target
affinity. Following this strategy, three D3 derivatives in
addition to D3COOH were designed: C-terminally amidated
linear D3 (D3CONH2), cyclic D3 (cD3), and cyclic D3 with an
additional arginine residue (cD3r) to maintain the net
charge of linear D3CONH2. These four compounds were compared
to each other according to their binding affinities to
Aβ(1−42), their efficacy to eliminate cytotoxic
oligomers, and consequently their potency to neutralize
Aβ(1−42) oligomer induced neurotoxicity. D3CONH2 and cD3r
versions with equally increased net charge showed superior
properties over D3COOH and cD3, respectively. The cyclic
versions showed superior properties compared to their linear
version with equal net charge, suggesting cD3r to be the
most efficient compound among these four. Indeed, treatment
of the transgenic AD mouse model Tg-SwDI with cD3r
significantly enhanced spatial memory and cognition of these
animals as revealed by water maze performance. Therefore,
charge increase and cyclization imply suitable modification
steps for an optimization approach of the Aβ targeting
compound D3.},
cin = {ICS-6},
ddc = {540},
cid = {I:(DE-Juel1)ICS-6-20110106},
pnm = {553 - Physical Basis of Diseases (POF3-553)},
pid = {G:(DE-HGF)POF3-553},
typ = {PUB:(DE-HGF)16},
UT = {WOS:000381717300009},
pubmed = {pmid:27240424},
doi = {10.1021/acschemneuro.6b00047},
url = {https://juser.fz-juelich.de/record/821057},
}