Photocontrol of Contracting Muscle Fibers

Hoppmann, Christian; Schmieder, Peter; Domaing, Petra; Vogelreiter, Gabriela; Eichhorst, Jenny; Wiesner, Burkhard; Morano, Ingo; Rück‐Braun, K.; Beyermann, Michael

doi:10.1002/anie.201101398

Cited by 55 publications

(44 citation statements)

References 53 publications

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“…[48] Starting from this well-investigated b-fingers tructure,arather flexible photoswitchable cyclized azopeptide wasd eveloped. [53][54][55] This cyclic azopeptide in the Z states uccessfullym odulates thei nteraction with synthrophin, [54] andt he inhibition of muscle contractioni n muscle cellsand in musclefiberscould also be demonstrated. [55] In addition,the mHTI w-amino acid wasu sedt op repare ar elated larger cyclized b hairpin( Scheme 4) with ap reorganzieds equence forbindinginthe Z form.The flexibilityo fmHTI, accordingt ometa substitution andt he rotary axis b,i ss hown in Scheme4.W ith the HTI b-hairpin peptide, unfolding within the hairpin upon light-triggered Z!E isomerization was studied in methanol.…”

Section: B-hairpin Peptidesmentioning

confidence: 84%

Light‐Switchable Peptides with a Hemithioindigo Unit: Peptide Design, Photochromism, and Optical Spectroscopy

et al. 2016

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This Minireview focuses on the hemithioindigo photoswitch and its use for the reversible control of three-dimensional peptide structure and related biological functions. Both the general design aspects and biophysical properties of various hemithioindigo-based chromopeptides are summarized. Hemithioindigo undergoes reversible Z→E photoisomerization after absorption of visible light. The unique ultrafast switching mechanism of hemithioindigo combines picosecond isomerization kinetics with strong double-bond torsion after light absorption, making it the ideal tool for instantaneous modulation of biological structure. Various inhibitors and model peptides based on hemithioindigo are described that can directly regulate biological signaling or allow the fastest events in peptide folding to be studied. Finally, a diverse range of chromopeptides with photoswitchable β-hairpin structures based on azobenzenes, stilbenes, and hemithioindigo are compared to emphasize the unique properties of hemithioindigo.

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Section: B-hairpin Peptidesmentioning

confidence: 84%

Light‐Switchable Peptides with a Hemithioindigo Unit: Peptide Design, Photochromism, and Optical Spectroscopy

et al. 2016

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“…27,29,30,72 Two major possibilities should be distinguished: (i) having an azobenzene as an amino acid residue and (ii) having an azoswitch in the peptide backbone. While the former has been used to gain optical control over binding affinity of transcription factor and cell adhesion molecules, 71,73 the latter was successfully applied to the optical control of muscle contraction 31 and secondary structure formation. 74 We envision our design herein, together with AzoChig 28 and LirAzo, 8 to be highly applicable to all kinds of peptides ( e.g.…”

Section: Discussionmentioning

confidence: 99%

“…1a). The NPR-A was endowed with light-sensitivity by incorporation of the photoswitchable amino acid [3-(3-aminomethyl)phenylazo]phenylacetic acid (AMPP) 27,28 into ANP, which along with related derivatives, 8,29–31 has proven to be a valuable building block for photocontrol of peptide conformation and activity (Fig. 1b).…”

Section: Introductionmentioning

confidence: 99%

Optical control of a receptor-linked guanylyl cyclase using a photoswitchable peptidic hormone

et al. 2017

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The optical control over biological function with small photoswitchable molecules has gathered significant attention in the last decade. Herein, we describe the design and synthesis of a small library of photoswitchable peptidomimetics based upon human atrial natriuretic peptide (ANP), in which the photochromic amino acid [3-(3-aminomethyl)phenylazo]phenylacetic acid (AMPP) is incorporated into the peptide backbone. The endogeneous hormone ANP signals via the natriuretic peptide receptor A (NPR-A) through raising intracellular cGMP concentrations, and is involved in blood pressure regulation and sodium homeostasis, as well as lipid metabolism and pancreatic function. The cis-and trans-isomers of one of our peptidomimetics, termed TOP271, exhibit a four-fold difference in NPR-A mediated cGMP synthesis in vitro. Despite this seemingly small difference, TOP271 enables large, optically-induced conformational changes ex vivo and transforms the NPR-A into an endogenous photoswitch. Thus, application of TOP271 allows the reversible generation of cGMP using light and remote control can be afforded over vasoactivity in explanted murine aortic rings, as well as pancreatic beta cell function in islets of Langerhans. This study demonstrates the broad applicability of TOP271 to enzyme-dependent signalling processes, extends the toolbox of photoswitchable molecules to all classes of transmembrane receptors and utilizes photopharmacology to deduce receptor activation on a molecular level.

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“…Several studies have been conducted on smaller peptide sequences and simpler elements of protein secondary structure, such as α-helices and β-hairpins, using photoswitchable cross-linked groups [9,12,[54][55][56][57][58][59][60][61][62][63][64][65]. The structural distortion can often be predicted to some degree by comparing the distance between the attachment points in the peptide and the distance between the linkage sites on the chromophore [61,66].…”

Section: Selected Examples 375mentioning

confidence: 99%

“…Photochromic cyclic peptides have been exploited in the past using azobenzenes to control muscle fiber contraction [63]. Recently, Ulrich and Komarov prepared a cyclic peptidomimetic containing a dithienylethene group based on the antimicrobial peptide gramicidin S (Figure 9.8) [67].…”

Section: Cyclic Antimicrobial Peptidementioning

confidence: 99%