Site-selective installation of BASHY fluorescent dyes to Annexin V for targeted detection of apoptotic cells

Cal, Pedro M. S. D.; Sieglitz, Florian; Santos, Fábio M. F.; Carvalho, Cátia Parente; Guerreiro, Ana; Bertoldo, Jean B.; Pischel, Uwe; Góis, Pedro M. P.; Bernardes, Gonçalo J. L.

doi:10.1039/c6cc08671c

Cited by 24 publications

(19 citation statements)

References 29 publications

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“…AnxV was not modified because it usually requires larger excess of reagents, higher temperatures or longer reaction times for the cysteine modification to proceed. 45 As expected, in the presence of DTT, only minor modification of proteins (0-15%) with MI-biotin was observed (Figure 5f, S44). Overall, these data confirm the high selectivity, orthogonality and highlight the suitability of CPO-reagents to label specific proteins in complex mixtures.…”

Section: Cpo-probes React Exclusively With 12-aminothiols On Proteinssupporting

confidence: 76%

Selective N-Terminal Cysteine Protein Modification with Cyclopropenones

Istrate¹,

Navo²,

Sousa³

et al. 2020

Preprint

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<div><div><div><p>Protein conjugates are valuable tools to create therapeutics, such as antibody-drug conjugates, or to study biological processes. Despite a number of protein conjugation strategies having been developed over recent years, the ability to modify one specific amino acid on a protein in the presence of other side chains with similar reactivity remains a challenge. We used the reaction between a monosubstituted cyclopropenone (CPO) probe and the 1,2-aminothiol of an N-terminal cysteine to give a stable 1,4-thiazepa-5-none linkage under mild, biocompatible conditions. The method relies on the ability of cyclopropenones to ring-open after sequential sulfhydryl and α-amine conjugation to be truly specific for N-terminal cysteine. We show that our CPO probes selectively label N-terminal cysteine containing peptides and proteins even in the presence of internal, solvent-exposed cysteines, which can be subsequently modified by using conventional cysteine modification reagents. The ability to distinguish and specifically target N-terminal cysteine residues on a protein will facilitate the construction of elaborate multi-labelled bioconjugates.</p></div></div></div>

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Section: Cpo-probes React Exclusively With 12-aminothiols On Proteinssupporting

confidence: 76%

Selective N-Terminal Cysteine Protein Modification with Cyclopropenones

Istrate¹,

Navo²,

Sousa³

et al. 2020

Preprint

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“…In this context we recently reported the assembly of fluorescent boronic‐acid derived salicylidenehydrazone complexes (BASHY) [27, 28] . This multicomponent reaction proved to be synthetically very efficient, which enabled the straightforward construction of a highly flexible platform of functional dyes that were used for the staining of intracellular organelles [27, 29] and the labelling of proteins [30] …”

Section: Methodsmentioning

confidence: 99%

Cyanine‐Like Boronic Acid‐Derived Salicylidenehydrazone Complexes (Cy‐BASHY) for Bioimaging Applications

Santos

Domínguez

Fernandes

et al. 2020

Chemistry A European J

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Boronic acid‐derived salicylidenehydrazone complex (BASHY) dyes with a polymethine backbone were designed to yield efficient red‐emitting and two‐photon absorbing fluorophores that can be used as markers for astrocytes. The dyes are chemically stable in aqueous solution and do not undergo photodecomposition. Their photophysical properties can be electronically fine‐tuned and thereby adapted to potentially different imaging situations and requirements.

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“…Noteworthy, the scope of the ETC is not limited to the herein discussed examples, but could be expanded through the electronic fine‐tuning of the charge‐transfer properties of the BASHY skeleton or the variation of the second chromophore. This structural flexibility of the photophysical engineering combined with the recently by us demonstrated site‐selective bioconjugability of the BASHY platform make this approach interesting for biotechnological applications. Further, the ETC compounds can be formulated in polymeric nanoparticles and used in bioimaging, as shown herein for dye 3 .…”

Section: Discussionmentioning

confidence: 98%

“…This one builds on straightforward multicomponent condensation reactions, implying salicylidenehydrazones and boronic acids. These dyes were shown to have application potential in bioimaging ,,…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Energy Transfer Cassettes by Assembly of Boronic Acid Derived Salicylidenehydrazone Complexes

et al. 2018

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Energy transfer cassettes that build on the platform of boronic acid derived salicylidenehydrazone (BASHY) complexes were prepared. The functional flexibility of the BASHY chromophore was underpinned by its tunable role as energy donor or acceptor, integrated in compact and non-conjugated bichromophoric dyads. The energy transfer is highly efficient (F ET > 0.95) and is assumed to proceed mainly via a through-bond mechanism. Both constituent chromophores benefit mutually from their integration in the cassettes: a) The pseudo Stokes shift is increased to 110-200 nm; b) the antenna (donor) chromophore improves the light absorption of the acceptor chromophore; and c) the emission window of the BASHY chromophore is expanded in the BASHY-Bodipy dye without using strategies that compromise the observation of high quantum yields. The application of the cassettes for the formulation of fluorescent polymeric nanoparticles, that can be internalized in cells and observed by fluorescence imaging, was demonstrated using the BASHY-Bodipy dye as an example.[a] F.

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Site-selective installation of BASHY fluorescent dyes to Annexin V for targeted detection of apoptotic cells

Cited by 24 publications

References 29 publications

Selective N-Terminal Cysteine Protein Modification with Cyclopropenones

Selective N-Terminal Cysteine Protein Modification with Cyclopropenones

Cyanine‐Like Boronic Acid‐Derived Salicylidenehydrazone Complexes (Cy‐BASHY) for Bioimaging Applications

Highly Efficient Energy Transfer Cassettes by Assembly of Boronic Acid Derived Salicylidenehydrazone Complexes

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