Fluorogenic Trp(redBODIPY) cyclopeptide targeting keratin 1 for imaging of aggressive carcinomas
Keratin 1 (KRT1) is overexpressed in squamous carcinomas and associated with aggressive pathologies in breast cancer. Herein we report the design and preparation of the first Trp-based red fluorogenic amino acid, which is synthetically accessible in a few steps and displays excellent photophysical p...
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| Vydáno v: | Chemical science (Cambridge) Ročník 11; číslo 5; s. 1368 - 1374 |
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| Hlavní autoři: | , , , , , , , , , , , , |
| Médium: | Journal Article |
| Jazyk: | angličtina |
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CAMBRIDGE
Royal Soc Chemistry
2020
Royal Society of Chemistry The Royal Society of Chemistry |
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| ISSN: | 2041-6520, 2041-6539 |
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| Abstract | Keratin 1 (KRT1) is overexpressed in squamous carcinomas and associated with aggressive pathologies in breast cancer. Herein we report the design and preparation of the first Trp-based red fluorogenic amino acid, which is synthetically accessible in a few steps and displays excellent photophysical properties, and its application in a minimally-disruptive labelling strategy to prepare a new fluorogenic cyclopeptide for imaging of KRT1+ cells in whole intact tumour tissues.
Trp(redBODIPY) is the first red-emitting Trp-based amino acid for the preparation of fluorogenic peptides with retention of target binding affinity. |
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| AbstractList | Keratin 1 (KRT1) is overexpressed in squamous carcinomas and associated with aggressive pathologies in breast cancer. Herein we report the design and preparation of the first Trp-based red fluorogenic amino acid, which is synthetically accessible in a few steps and displays excellent photophysical properties, and its application in a minimally-disruptive labelling strategy to prepare a new fluorogenic cyclopeptide for imaging of KRT1+ cells in whole intact tumour tissues. Keratin 1 (KRT1) is overexpressed in squamous carcinomas and associated with aggressive pathologies in breast cancer. Herein we report the design and preparation of the first Trp-based red fluorogenic amino acid, which is synthetically accessible in a few steps and displays excellent photophysical properties, and its application in a minimally-disruptive labelling strategy to prepare a new fluorogenic cyclopeptide for imaging of KRT1+ cells in whole intact tumour tissues. Trp(redBODIPY) is the first red-emitting Trp-based amino acid for the preparation of fluorogenic peptides with retention of target binding affinity. Keratin 1 (KRT1) is overexpressed in squamous carcinomas and associated with aggressive pathologies in breast cancer. Herein we report the design and preparation of the first Trp-based red fluorogenic amino acid, which is synthetically accessible in a few steps and displays excellent photophysical properties, and its application in a minimally-disruptive labelling strategy to prepare a new fluorogenic cyclopeptide for imaging of KRT1+ cells in whole intact tumour tissues. Trp(redBODIPY) is the first red-emitting Trp-based amino acid for the preparation of fluorogenic peptides with retention of target binding affinity. Keratin 1 (KRT1) is overexpressed in squamous carcinomas and associated with aggressive pathologies in breast cancer. Herein we report the design and preparation of the first Trp-based red fluorogenic amino acid, which is synthetically accessible in a few steps and displays excellent photophysical properties, and its application in a minimally-disruptive labelling strategy to prepare a new fluorogenic cyclopeptide for imaging of KRT1+ cells in whole intact tumour tissues.Keratin 1 (KRT1) is overexpressed in squamous carcinomas and associated with aggressive pathologies in breast cancer. Herein we report the design and preparation of the first Trp-based red fluorogenic amino acid, which is synthetically accessible in a few steps and displays excellent photophysical properties, and its application in a minimally-disruptive labelling strategy to prepare a new fluorogenic cyclopeptide for imaging of KRT1+ cells in whole intact tumour tissues. |
| Author | Qian, Bin-Zhi Barril, Xavier Barth, Nicole D Ma, Ruoyu Lavilla, Rodolfo Subiros-Funosas, Ramon Zhang, Cheng-Bin Sintes, Miquel Ghashghaei, Ouldouz Ho, Vivian Cheuk Lam Mendive-Tapia, Lorena Pappalardo, Morena Vendrell, Marc |
| AuthorAffiliation | Facultat de Farmàcia University of Barcelona and Institut de Biomedicina de la Universitat de Barcelona (IBUB) University of Edinburgh Centre for Inflammation Research Laboratory of Physical Chemistry Universitat de Barcelona and Institut de Biomedicina de la Universitat de Barcelona (IBUB) Faculty of Pharmacy Laboratory of Medicinal Chemistry MRC Centre for Reproductive Health |
| AuthorAffiliation_xml | – name: MRC Centre for Reproductive Health – name: Laboratory of Medicinal Chemistry – name: University of Edinburgh – name: Centre for Inflammation Research – name: Faculty of Pharmacy – name: Facultat de Farmàcia – name: Laboratory of Physical Chemistry – name: Universitat de Barcelona and Institut de Biomedicina de la Universitat de Barcelona (IBUB) – name: University of Barcelona and Institut de Biomedicina de la Universitat de Barcelona (IBUB) |
| Author_xml | – sequence: 1 givenname: Ramon surname: Subiros-Funosas fullname: Subiros-Funosas, Ramon – sequence: 2 givenname: Vivian Cheuk Lam surname: Ho fullname: Ho, Vivian Cheuk Lam – sequence: 3 givenname: Nicole D surname: Barth fullname: Barth, Nicole D – sequence: 4 givenname: Lorena surname: Mendive-Tapia fullname: Mendive-Tapia, Lorena – sequence: 5 givenname: Morena surname: Pappalardo fullname: Pappalardo, Morena – sequence: 6 givenname: Xavier surname: Barril fullname: Barril, Xavier – sequence: 7 givenname: Ruoyu surname: Ma fullname: Ma, Ruoyu – sequence: 8 givenname: Cheng-Bin surname: Zhang fullname: Zhang, Cheng-Bin – sequence: 9 givenname: Bin-Zhi surname: Qian fullname: Qian, Bin-Zhi – sequence: 10 givenname: Miquel surname: Sintes fullname: Sintes, Miquel – sequence: 11 givenname: Ouldouz surname: Ghashghaei fullname: Ghashghaei, Ouldouz – sequence: 12 givenname: Rodolfo surname: Lavilla fullname: Lavilla, Rodolfo – sequence: 13 givenname: Marc surname: Vendrell fullname: Vendrell, Marc |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/34123261$$D View this record in MEDLINE/PubMed |
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| Keywords | BREAST-CANCER TRYPTOPHAN AMINO-ACID FLUORESCENT-PROBE PEPTIDE RAY CRYSTAL-STRUCTURE |
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| Snippet | Keratin 1 (KRT1) is overexpressed in squamous carcinomas and associated with aggressive pathologies in breast cancer. Herein we report the design and... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Keratin Organic chemistry Physical Sciences Science & Technology |
| Title | Fluorogenic Trp(redBODIPY) cyclopeptide targeting keratin 1 for imaging of aggressive carcinomas |
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