Fluorogenic Trp(redBODIPY) cyclopeptide targeting keratin 1 for imaging of aggressive carcinomas

Subirós‐Funosas, Ramon; Ho, Vivian Cheuk Lam; Barth, Nicole; Mendive‐Tapia, Lorena; Pappalardo, Morena; Barril, Xavier; Ma, Ruoyu; Zhang, Cheng-Bin; Qian, Bin‐Zhi; Sintes, Miquel; Ghashghaei, Ouldouz; Vendrell, Marc

doi:10.1039/c9sc05558d

Cited by 45 publications

(33 citation statements)

References 49 publications

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“…Thus, they are a good example of a molecule of therapeutic and biological interest that must be conjugated to a fluorophore. Recently, unnatural fluorescent amino acids have been tested as an alternative to the use of fluorophores (Mendive-Tapia et al, 2016;Cheng et al, 2020;Subiros-Funosas et al, 2020), presenting several advantages over fluorophores. Nevertheless, the use of fluorophores is still broadly used to investigate peptide biological activity.…”

Section: Introductionmentioning

confidence: 99%

To What Extent Do Fluorophores Bias the Biological Activity of Peptides? A Practical Approach Using Membrane-Active Peptides as Models

Cavaco

Pérez‐Peinado

Valle

et al. 2020

Front. Bioeng. Biotechnol.

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The characterization of biologically active peptides relies heavily on the study of their efficacy, toxicity, mechanism of action, cellular uptake, or intracellular location, using both in vitro and in vivo studies. These studies frequently depend on the use of fluorescence-based techniques. Since most peptides are not intrinsically fluorescent, they are conjugated to a fluorophore. The conjugation may interfere with peptide properties, thus biasing the results. The selection of the most suitable fluorophore is highly relevant. Here, a comprehensive study with blood-brain barrier (BBB) peptide shuttles (PepH3 and PepNeg) and antimicrobial peptides (AMPs) (vCPP2319 and Ctn[15-34]), tested as anticancer peptides (ACPs), having different fluorophores, namely 5(6)-carboxyfluorescein (CF), rhodamine B (RhB), quasar 570 (Q570), or tide fluor 3 (TF3) attached is presented. The goal is the evaluation of the impact of the selected fluorophores on peptide performance, applying routinely used techniques to assess cytotoxicity/toxicity, secondary structure, BBB translocation, and cellular internalization. Our results show that some fluorophores significantly modulate peptide activity when compared with unlabeled peptides, being more noticeable in hydrophobic and charged fluorophores. This study highlights the need for a careful experimental design for fluorescently labeled molecules, such as peptides.

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Section: Introductionmentioning

confidence: 99%

To What Extent Do Fluorophores Bias the Biological Activity of Peptides? A Practical Approach Using Membrane-Active Peptides as Models

Cavaco

Pérez‐Peinado

Valle

et al. 2020

Front. Bioeng. Biotechnol.

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“…91], the image in part B was reproduced with permission from ref. [56], published by The Royal Society of Chemistry, and all images in part C were reprinted (adapted) with permission from (S. Shao, Z. Li, H. Cheng, S. Wang, N. G. Perkins, P. Sarkar, W. Wei, M. Xue . J Am Chem Soc .…”

Section: Biological Applications Of Fluorescent Cyclic Peptide Probesmentioning

confidence: 99%

“…Recently, our group disclosed the preparation of a red fluorescent analogue of a cyclopeptide with high affinity for keratin‐1 (KRT1) cell receptor, overexpressed in aggressive breast cancer tumors, that enabled the simultaneous imaging of KRT1+ cancerous cells in combination with tumor‐associated macrophage markers in tumor tissue samples (Figure 3B). [ 56 ] Finally, other peptides have been reported to target EGFR, which is central in multiple signaling pathways related to cell proliferation and differentiation. EGFR are often over‐expressed in cancer cells and Tamamura et al .…”

Section: Biological Applications Of Fluorescent Cyclic Peptide Probesmentioning

confidence: 99%

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Fluorescent cyclic peptides for cell imaging

2020

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Fluorescent cyclic peptides are excellent chemical scaffolds to build optical agents for molecular imaging. In addition to their favorable physicochemical properties, they can be modified with multiple organic fluorophores and generate useful probes for biological assays targeting specific proteins, namely receptors or enzymes. In this article, we review recent advances in the synthetic approaches for the preparation of fluorescent cyclic peptides as well as some of their applications in biological imaging, from in vitro live‐cell imaging studies to in vivo characterization of preclinical models.

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“…They are involved in a variety of molecular recognition phenomena of physiological and biological relevance as well as in pathological events, such as cancer or bacterial infections. [26,27] Their skeletons, composed of one or more furanose and/or pyranose cycles, have multiple hydroxyl groups in different orientations, depending on the type of saccharide, that can be linked to suitable molecules or can be opportunely transformed into other functional groups, [28] generating an impressive multiplicity of different compounds and providing an excellent platform to tailor molecular diversity. For these reasons, recently, a number of small-molecule carbohydrate-based fluorophores have been involved in the investigation of biological processes.…”

Section: Carbohydrates and Bodipys: Access To Biocompatible Nir Probesmentioning

confidence: 99%

BODIPY on Board of Sugars: A Short Enlightened Journey up to the Cells

et al. 2020

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BODIPY dyes have unique properties including: good stability in many solvents, high extinction coefficients, stability to light, sharp fluorescence emissions in the visible region with high fluorescence quantum yields. Moreover, through small chemical modifications of the skeleton, their luminescence properties can be finely tuned. As a consequence, during the last decades, this family of chromophores found extensive application in a wide range of fields. Carbohydrates play a relevant role in living organisms: their tasks range from energy storage to structural constituents of cells and tissues, they are involved in a variety of molecular recognition phenomena of physiological and biological relevance. The cyclic structure of natural D‐monosaccharides, also offers the conditions to use carbohydrates as building‐blocks in the construction of more complex, supramolecular structures. With these assumptions, in the last years our research in this field has focused on the study of synthesis, the photophysical features, and the application in the biomedical field of molecules that bear the synergic presence of these two tools. Pointing on the rationalization of this research, this article will provide a synthetic review of our last‐year's results in the field of BODIPY/glycosyl species, that can be classified in two principal sections: a) the rational synthesis and the photophysical studies of BODIPY dyads and antennas containing different kind of sugar units as scaffolds, ranging from mono‐ to disaccharide patterns, and b) the synthetic functionalization and modification of suitable BODIPY structures, for their punctual application in the field of bio‐imaging.

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Fluorogenic Trp(redBODIPY) cyclopeptide targeting keratin 1 for imaging of aggressive carcinomas

Abstract: Trp(redBODIPY) is the first red-emitting Trp-based amino acid for the preparation of fluorogenic peptides with retention of target binding affinity.

Cited by 45 publications

References 49 publications

To What Extent Do Fluorophores Bias the Biological Activity of Peptides? A Practical Approach Using Membrane-Active Peptides as Models

To What Extent Do Fluorophores Bias the Biological Activity of Peptides? A Practical Approach Using Membrane-Active Peptides as Models

Fluorescent cyclic peptides for cell imaging

BODIPY on Board of Sugars: A Short Enlightened Journey up to the Cells

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