2017
DOI: 10.1021/acs.bioconjchem.7b00211
|View full text |Cite
|
Sign up to set email alerts
|

Synthesis of BODIPY-Peptide Conjugates for Fluorescence Labeling of EGFR Overexpressing Cells

Abstract: Regioselective functionalization of 2,3,5,6,8-pentachloro-BODIPY 1 produced unsymmetric BODIPY 5, bearing an isothiocyanate group suitable for conjugation, in only four steps. The X-ray structure of 5 reveals a nearly planar BODIPY core with aryl dihedral angles in the range 47.4° – 62.9°. Conjugation of 5 to two EGFR-targeting pegylated peptides, 3PEG-LARLLT (6) and 3PEG-GYHWYGYTPQNVI (7), under mild conditions (30 min at room temperature), afforded BODIPY conjugates 8 and 9 in 50–80% isolated yields. These c… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
2
1

Citation Types

1
53
0

Year Published

2018
2018
2024
2024

Publication Types

Select...
7

Relationship

1
6

Authors

Journals

citations
Cited by 52 publications
(54 citation statements)
references
References 92 publications
1
53
0
Order By: Relevance
“…Many functional peptide libraries have actually been described in the literature, with different sequences and functions, offering a versatile platform of delivery agents to localize PS conjugates in different kinds of cells and tissues. 48 Covalently linked PS-peptide biohybrids can be synthesized, taking advantage of mild synthetic organic methodologies such as amide [49][50][51][52][53]77,78,81,[85][86][87]89,[91][92][93]95,97,104,105 or sulphonamide 54 bond formation, palladium-catalysed cross-coupling reactions, 55,56 click-chemistry reactions [57][58][59]81,94 and isothiocyanate chemistry, 60,82 among other strategies. Supramolecular approaches have also been used toward self-assembled peptide nanofibers, 61 nanodots, 62 vesicles, 63 light harvesting complexes, 64 arrays 65 or polymeric micelles with a peptide-decorated surface, 66 among others.…”
Section: Conjugation Of Ps To Short Peptide Sequencesmentioning
confidence: 99%
See 1 more Smart Citation
“…Many functional peptide libraries have actually been described in the literature, with different sequences and functions, offering a versatile platform of delivery agents to localize PS conjugates in different kinds of cells and tissues. 48 Covalently linked PS-peptide biohybrids can be synthesized, taking advantage of mild synthetic organic methodologies such as amide [49][50][51][52][53]77,78,81,[85][86][87]89,[91][92][93]95,97,104,105 or sulphonamide 54 bond formation, palladium-catalysed cross-coupling reactions, 55,56 click-chemistry reactions [57][58][59]81,94 and isothiocyanate chemistry, 60,82 among other strategies. Supramolecular approaches have also been used toward self-assembled peptide nanofibers, 61 nanodots, 62 vesicles, 63 light harvesting complexes, 64 arrays 65 or polymeric micelles with a peptide-decorated surface, 66 among others.…”
Section: Conjugation Of Ps To Short Peptide Sequencesmentioning
confidence: 99%
“…After that, the synthesis of a BODIPY bearing an isothiocyanate group allowed its conjugation with the same peptides. 60 After studies with human Hep2 cells that overexpress the EGFR, the BODIPY conjugates showed a low toxicity, and their targeting ability was much higher compared to that of the non-conjugated BODIPY. Based on these results, the authors proposed the conjugates as potential near-IR fluorescence imaging agents.…”
Section: Conjugation Of Ps To Short Peptide Sequencesmentioning
confidence: 99%
“…Studies have shown that peptide ligands EGFR‐L1 and EGFR‐L2 specifically target EGFR‐overexpressing tumor cells both in vitro and in vivo (9,10). In our previous studies, we reported the conjugation of EGFR‐L1 or EGFR‐L2 to a porphyrin (30), phthalocyanine (23) and a BODIPY, (28,29) using either short (up to 5‐atom) or long (up to 20‐atom) linkers. The use of linkers such as PEG groups is desired in the case or porphyrin and phthalocyanine macrocycles to increase their aqueous solubility and potentially also for increasing their specificity for cell surface sites (51).…”
Section: Resultsmentioning
confidence: 99%
“…Our previous findings suggest that the EGFR‐L1 sequence modified with a glycine or lysine spacer, as in sequences GLARLLT ( 2 ) and KLARLLT ( 4 ), does not alter the binding affinity for EGFR when compared with the parent peptide LARLLT (31). A glycine was also introduced in the amino acid sequence of EGFR‐L2, GYHWYGYTPQNVI ( 3 ), as previously reported (28). Each peptide sequence was synthesized using Fmoc solid‐phase peptide synthesis (SPPS) chemistry on a Fmoc‐Pal‐PEG‐PS using N,N,N’,N’ ‐tetramethyl‐ O ‐tetramethyluronium tetrafluoroborate (TBTU), 1‐hydroxybenzotriazole hydrate (HOBt) and diisopropylethylamine (DIPEA) as the coupling reagents, as previously reported (23,30,52).…”
Section: Resultsmentioning
confidence: 99%
“…[2a,3] Owing to their unique optical and chemical properties, BODIPYs have been used as biological sensors and for cell imaging. However, although some recent methodologies allow the direct labelling of biomolecules with the BODIPY unit, [4] generally, it is necessary to use approaches that are based on conventional coupling reactions from two functionalized substrates, [5] thus requiring tedious modifications of the target biomolecule, including the corresponding linker.…”
Section: Introductionmentioning
confidence: 99%