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Phenothiazine-Biaryl-Containing Fluorescent RGD Peptides

Ghabraie, Elmira ; Kemker, Isabell ; Tonali, Nicolo ; Ismail, Mohamed LU orcid ; Dodero, Veronica I. and Sewald, Norbert (2020) In Chemistry - A European Journal 26(52). p.12036-12042
Abstract

Cyclic RGD peptides are well-known ligands of integrins. The integrins αVβ3 and α5β1 are involved in angiogenesis, and integrin αVβ3 is abundantly present on cancer cells, thus representing a therapeutic target. Hence, synthetic and biophysical studies continuously are being directed towards the understanding of ligand-integrin interaction. In this context, the development of versatile synthetic strategies to obtain fluorescent building blocks that can add molecular diversity and modular spectral characteristics while not compromising binding affinity or selectivity is a relevant task. An on-resin intramolecular Suzuki–Miyaura cross-coupling (SMC) between l- or... (More)

Cyclic RGD peptides are well-known ligands of integrins. The integrins αVβ3 and α5β1 are involved in angiogenesis, and integrin αVβ3 is abundantly present on cancer cells, thus representing a therapeutic target. Hence, synthetic and biophysical studies continuously are being directed towards the understanding of ligand-integrin interaction. In this context, the development of versatile synthetic strategies to obtain fluorescent building blocks that can add molecular diversity and modular spectral characteristics while not compromising binding affinity or selectivity is a relevant task. An on-resin intramolecular Suzuki–Miyaura cross-coupling (SMC) between l- or d-7-bromotryptophan (7BrTrp) and a phenothiazine (Ptz) boronic acid affords fluorescent cyclic RGD pseudopeptides, c(RGD(W/w)Ptz). Ring closure by SMC establishes a phenothiazine–indole moiety with axial chirality. An array of eight novel compounds has been synthesized, among them one fluorescent compound with good affinity to integrin αVβ3. The fluorescence properties of the analogues can be efficiently tuned depending on the substituents in Ptz moiety even for fluorescence emission in the visible (red) spectral range.

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author
; ; ; ; and
publishing date
type
Contribution to journal
publication status
published
keywords
cross-coupling reactions, cyclopeptides, fluorescent peptide, integrin, phenothiazine
in
Chemistry - A European Journal
volume
26
issue
52
pages
7 pages
publisher
Wiley-Blackwell
external identifiers
  • pmid:32297686
  • scopus:85089499891
ISSN
0947-6539
DOI
10.1002/chem.202001312
language
English
LU publication?
no
id
c293f4de-cff0-4e20-9a9b-f9792d40930d
date added to LUP
2023-08-28 11:47:46
date last changed
2024-03-08 08:33:35
@article{c293f4de-cff0-4e20-9a9b-f9792d40930d,
  abstract     = {{<p>Cyclic RGD peptides are well-known ligands of integrins. The integrins α<sub>V</sub>β<sub>3</sub> and α<sub>5</sub>β<sub>1</sub> are involved in angiogenesis, and integrin α<sub>V</sub>β<sub>3</sub> is abundantly present on cancer cells, thus representing a therapeutic target. Hence, synthetic and biophysical studies continuously are being directed towards the understanding of ligand-integrin interaction. In this context, the development of versatile synthetic strategies to obtain fluorescent building blocks that can add molecular diversity and modular spectral characteristics while not compromising binding affinity or selectivity is a relevant task. An on-resin intramolecular Suzuki–Miyaura cross-coupling (SMC) between l- or d-7-bromotryptophan (7BrTrp) and a phenothiazine (Ptz) boronic acid affords fluorescent cyclic RGD pseudopeptides, c(RGD(W/w)Ptz). Ring closure by SMC establishes a phenothiazine–indole moiety with axial chirality. An array of eight novel compounds has been synthesized, among them one fluorescent compound with good affinity to integrin α<sub>V</sub>β<sub>3</sub>. The fluorescence properties of the analogues can be efficiently tuned depending on the substituents in Ptz moiety even for fluorescence emission in the visible (red) spectral range.</p>}},
  author       = {{Ghabraie, Elmira and Kemker, Isabell and Tonali, Nicolo and Ismail, Mohamed and Dodero, Veronica I. and Sewald, Norbert}},
  issn         = {{0947-6539}},
  keywords     = {{cross-coupling reactions; cyclopeptides; fluorescent peptide; integrin; phenothiazine}},
  language     = {{eng}},
  month        = {{09}},
  number       = {{52}},
  pages        = {{12036--12042}},
  publisher    = {{Wiley-Blackwell}},
  series       = {{Chemistry - A European Journal}},
  title        = {{Phenothiazine-Biaryl-Containing Fluorescent RGD Peptides}},
  url          = {{http://dx.doi.org/10.1002/chem.202001312}},
  doi          = {{10.1002/chem.202001312}},
  volume       = {{26}},
  year         = {{2020}},
}