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@ARTICLE{Leypold:866048,
author = {Leypold, Tim and Bonus, Michele and Spiegelhalter, Felix
and Schwede, Frank and Schwabe, Tina and Gohlke, Holger and
Kusch, Jana},
title = {{N} 6 -modified c{AMP} derivatives that activate protein
kinase {A} also act as full agonists of murine {HCN}2
channels},
journal = {The journal of biological chemistry},
volume = {294},
issn = {1083-351X},
address = {Bethesda, Md.},
publisher = {Soc.72889},
reportid = {FZJ-2019-05294},
pages = {17978-17987},
year = {2019},
abstract = {cAMP acts as a second messenger in many cellular processes.
Three protein types mainly mediate cAMP-induced effects:
PKA, exchange protein directly activated by cAMP (Epac), and
cyclic nucleotide–modulated channels (cyclic
nucleotide–gated or hyperpolarization-activated and cyclic
nucleotide–modulated (HCN) channels). Discrimination among
these cAMP signaling pathways requires specific targeting of
only one protein. Previously, cAMP modifications at position
N6 of the adenine ring (PKA) and position 2′-OH of the
ribose (Epac) have been used to produce target-selective
compounds. However, cyclic nucleotide–modulated ion
channels were usually outside of the scope of these previous
studies. These channels are widely distributed, so possible
channel cross-activation by PKA- or Epac-selective agonists
warrants serious consideration. Here we demonstrate the
agonistic effects of three PKA-selective cAMP derivatives,
N6-phenyladenosine-3′,5′-cyclic monophosphate
(N6-Phe-cAMP), N6-benzyladenosine-3′,5′-cyclic
monophosphate (N6-Bn-cAMP), and
N6-benzoyl-adenosine-3′,5′-cyclic monophosphate
(N6-Bnz-cAMP), on murine HCN2 pacemaker channels.
Electrophysiological characterization in Xenopus oocytes
revealed that these derivatives differ in apparent
affinities depending on the modification type but that their
efficacy and effects on HCN2 activation kinetics are similar
to those of cAMP. Docking experiments suggested a pivotal
role of Arg-635 at the entrance of the binding pocket in
HCN2, either causing stabilizing cation–π interactions
with the aromatic ring in N6-Phe-cAMP or N6-Bn-cAMP or a
steric clash with the aromatic ring in N6-Bnz-cAMP. A
reduced apparent affinity of N6-Phe-cAMP toward the variants
R635A and R635E strengthened that notion. We conclude that
some PKA activators also effectively activate HCN2 channels.
Hence, when studying PKA-mediated cAMP signaling with cAMP
derivatives in a native environment, activation of HCN
channels should be considered.},
cin = {JSC / NIC / ICS-6},
ddc = {540},
cid = {I:(DE-Juel1)JSC-20090406 / I:(DE-Juel1)NIC-20090406 /
I:(DE-Juel1)ICS-6-20110106},
pnm = {511 - Computational Science and Mathematical Methods
(POF3-511) / Forschergruppe Gohlke $(hkf7_20170501)$ /
Energetic and structural characterization of the activation
processes of the human HCN2 ion channel $(hdd17_20180501)$ /
Disinhibition and inhibition of HCN2 channel function by
ligand binding to the cyclic nucleotide bin
$(hdd17_20170501)$},
pid = {G:(DE-HGF)POF3-511 / $G:(DE-Juel1)hkf7_20170501$ /
$G:(DE-Juel1)hdd17_20180501$ / $G:(DE-Juel1)hdd17_20170501$},
typ = {PUB:(DE-HGF)16},
pubmed = {pmid:31615893},
UT = {WOS:000504206800023},
doi = {10.1074/jbc.RA119.010246},
url = {https://juser.fz-juelich.de/record/866048},
}