A BODIPY-Tagged Phosphono Peptide as Activity-Based Probe for Human Leukocyte Elastase
Human leukocyte elastase plays a crucial role in a variety of inflammatory disorders and represents an important subject of biomedical studies. The chemotype of peptidic phosphonates was employed for the design of a new activity-based probe for human leukocyte elastase. Its structure combines the ph...
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| Published in | ACS medicinal chemistry letters Vol. 9; no. 4; pp. 345 - 350 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
12.04.2018
Amer Chemical Soc |
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| Abstract | Human leukocyte elastase plays a crucial role in a variety of inflammatory disorders and represents an important subject of biomedical studies. The chemotype of peptidic phosphonates was employed for the design of a new activity-based probe for human leukocyte elastase. Its structure combines the phosphonate warhead with an adequate peptide portion and a BODIPY fluorophore with a clickable ethinylphenyl moiety at meso position. The probe 6 was assembled by copper-catalyzed alkyne–azide 1,3-dipolar cycloaddition. It was characterized as an active site-directed elastase inhibitor exhibiting a second-order rate constant of inactivation of 88400 M–1s–1. The suitability of 6 as a fluorescent probe for human leukocyte elastase was demonstrated by in-gel fluorescence analysis. Labeling experiments and inhibition data toward a panel of related proteases underlined the selectivity of the probe for the targeted leukocyte elastase. |
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| AbstractList | Human leukocyte elastase
plays a crucial role in a variety of inflammatory
disorders and represents an important subject of biomedical studies.
The chemotype of peptidic phosphonates was employed for the design
of a new activity-based probe for human leukocyte elastase. Its structure
combines the phosphonate warhead with an adequate peptide portion
and a BODIPY fluorophore with a clickable ethinylphenyl moiety at
meso
position. The probe
6
was assembled by
copper-catalyzed alkyne–azide 1,3-dipolar cycloaddition. It
was characterized as an active site-directed elastase inhibitor exhibiting
a second-order rate constant of inactivation of 88400 M
–1
s
–1
. The suitability of
6
as a fluorescent
probe for human leukocyte elastase was demonstrated by in-gel fluorescence
analysis. Labeling experiments and inhibition data toward a panel
of related proteases underlined the selectivity of the probe for the
targeted leukocyte elastase. Human leukocyte elastase plays a crucial role in a variety of inflammatory disorders and represents an important subject of biomedical studies. The chemotype of peptidic phosphonates was employed for the design of a new activity-based probe for human leukocyte elastase. Its structure combines the phosphonate warhead with an adequate peptide portion and a BODIPY fluorophore with a clickable ethinylphenyl moiety at meso position. The probe 6 was assembled by copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition. It was characterized as an active site-directed elastase inhibitor exhibiting a second-order rate constant of inactivation of 88400 M-1s-1. The suitability of 6 as a fluorescent probe for human leukocyte elastase was demonstrated by in-gel fluorescence analysis. Labeling experiments and inhibition data toward a panel of related proteases underlined the selectivity of the probe for the targeted leukocyte elastase.Human leukocyte elastase plays a crucial role in a variety of inflammatory disorders and represents an important subject of biomedical studies. The chemotype of peptidic phosphonates was employed for the design of a new activity-based probe for human leukocyte elastase. Its structure combines the phosphonate warhead with an adequate peptide portion and a BODIPY fluorophore with a clickable ethinylphenyl moiety at meso position. The probe 6 was assembled by copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition. It was characterized as an active site-directed elastase inhibitor exhibiting a second-order rate constant of inactivation of 88400 M-1s-1. The suitability of 6 as a fluorescent probe for human leukocyte elastase was demonstrated by in-gel fluorescence analysis. Labeling experiments and inhibition data toward a panel of related proteases underlined the selectivity of the probe for the targeted leukocyte elastase. Human leukocyte elastase plays a crucial role in a variety of inflammatory disorders and represents an important subject of biomedical studies. The chemotype of peptidic phosphonates was employed for the design of a new activity-based probe for human leukocyte elastase. Its structure combines the phosphonate warhead with an adequate peptide portion and a BODIPY fluorophore with a clickable ethinylphenyl moiety at meso position. The probe 6 was assembled by copper-catalyzed alkyne azide 1,3-dipolar cycloaddition. It was characterized as an active site-directed elastase inhibitor exhibiting a second-order rate constant of inactivation of 88400 M(-1)s(-1) The suitability of 6 as a fluorescent probe for human leukocyte elastase was demonstrated by in-gel fluorescence analysis. Labeling experiments and inhibition data toward a panel of related proteases underlined the selectivity of the probe for the targeted leukocyte Human leukocyte elastase plays a crucial role in a variety of inflammatory disorders and represents an important subject of biomedical studies. The chemotype of peptidic phosphonates was employed for the design of a new activity-based probe for human leukocyte elastase. Its structure combines the phosphonate warhead with an adequate peptide portion and a BODIPY fluorophore with a clickable ethinylphenyl moiety at position. The probe was assembled by copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition. It was characterized as an active site-directed elastase inhibitor exhibiting a second-order rate constant of inactivation of 88400 M s . The suitability of as a fluorescent probe for human leukocyte elastase was demonstrated by in-gel fluorescence analysis. Labeling experiments and inhibition data toward a panel of related proteases underlined the selectivity of the probe for the targeted leukocyte elastase. Human leukocyte elastase plays a crucial role in a variety of inflammatory disorders and represents an important subject of biomedical studies. The chemotype of peptidic phosphonates was employed for the design of a new activity-based probe for human leukocyte elastase. Its structure combines the phosphonate warhead with an adequate peptide portion and a BODIPY fluorophore with a clickable ethinylphenyl moiety at meso position. The probe 6 was assembled by copper-catalyzed alkyne–azide 1,3-dipolar cycloaddition. It was characterized as an active site-directed elastase inhibitor exhibiting a second-order rate constant of inactivation of 88400 M–1s–1. The suitability of 6 as a fluorescent probe for human leukocyte elastase was demonstrated by in-gel fluorescence analysis. Labeling experiments and inhibition data toward a panel of related proteases underlined the selectivity of the probe for the targeted leukocyte elastase. |
| Author | Schulz-Fincke, Anna-Christina Braune, Annett Gütschow, Michael Blaut, Michael |
| AuthorAffiliation | German Institute of Human Nutrition Potsdam-Rehbruecke Department of Gastrointestinal Microbiology University of Bonn Pharmaceutical Institute, Pharmaceutical Chemistry I |
| AuthorAffiliation_xml | – name: University of Bonn – name: Pharmaceutical Institute, Pharmaceutical Chemistry I – name: Department of Gastrointestinal Microbiology – name: German Institute of Human Nutrition Potsdam-Rehbruecke |
| Author_xml | – sequence: 1 givenname: Anna-Christina surname: Schulz-Fincke fullname: Schulz-Fincke, Anna-Christina organization: University of Bonn – sequence: 2 givenname: Michael surname: Blaut fullname: Blaut, Michael organization: German Institute of Human Nutrition Potsdam-Rehbruecke – sequence: 3 givenname: Annett surname: Braune fullname: Braune, Annett email: braune@dife.de organization: German Institute of Human Nutrition Potsdam-Rehbruecke – sequence: 4 givenname: Michael orcidid: 0000-0002-9376-7897 surname: Gütschow fullname: Gütschow, Michael email: guetschow@uni-bonn.de organization: University of Bonn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29670698$$D View this record in MEDLINE/PubMed |
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| Keywords | human leukocyte elastase phosphonates copper-catalyzed azide−alkyne cycloaddition BOPIPY derivatives serine proteases copper-catalyzed azide-alkyne cycloaddition DESIGN HUMAN NEUTROPHIL ELASTASE FLUORESCENT REPORTERS ENZYME SUBSTRATE HUMAN-DISEASES PROTEINASE-3 CATHEPSIN-G INHIBITORS |
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| Snippet | Human leukocyte elastase plays a crucial role in a variety of inflammatory disorders and represents an important subject of biomedical studies. The chemotype... Human leukocyte elastase plays a crucial role in a variety of inflammatory disorders and represents an important subject of biomedical studies. The chemotype... |
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| Title | A BODIPY-Tagged Phosphono Peptide as Activity-Based Probe for Human Leukocyte Elastase |
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