A BODIPY-Based Fluorescent Sensor for Amino Acids Bearing Thiol

Abstract

Herein, we describe the synthetic route to access a red-emitting BODIPY from its α-diformylated precursor. The photophysical signatures of this dye are sensitive to the presence of thiol-containing amino acids (like cysteine, homocysteine, and glutathione) in the surrounding environment. This sensor provides up to three detection channels to monitor and quantify these biomolecules, even at low concentrations (down to micromolar). Moreover, owing to the pronounced splitting of the spectral band profile induced by these amino acids, the detection can be visualized following just the evolution of the fluorescence color by the naked eye.

BODIPY- and Porphyrin-Based Sensors for Recognition of Amino Acids and Their Derivatives

“…In 2019, Avellanal-Zaballa et al presented a BODIPY probe designed with functionalities responsive to thiol containing amino acids [ 38 ]. The sensor presents two α,β -unsaturated esters on both α positions of the BODIPY core ( 22 , see Figure 1 ) as the reactive points that are able to react with the nucleophilic groups of the sensed targets.…”

Luminiszentzia, baliabide aproposa ioien eta biomolekulen presentzia agerian jartzeko

“…Are gehiago, joera espektral horien ondorioz AAen detekzioa erraz egin daiteke begi hutsez, kontzentrazioa handitzen den heinean disoluzioaren igorpen-kolorea desberdina baita (gorritik laranjara, eta gero horira, 9. irudia). Horregatik, sentsore hau, ratiometrikoa izateaz gain, kolorimetrikoa ere badela esan dezakegu [31]. Detekzioa erraza eta azkarra izateaz gain, hiru kanalak (edo uhin-luzera) erabiliz eta sentikortasun itzelarekin (mikromolar azpitik) AAen kontzentrazioa kuantifikatzea posiblea da.…”

“…Kolore aldaketaz gain, irudian beha daiteke nola 525 nm-ean eta 560 nm-ean gertatzen diren fluoreszentzia handipenak AA detektatzeko eta kuantifikatzeko kanalik egokienak diren. Gainera, BODIPYn oinarritutako sentsore fluoreszente hori sentikorragoa da CYS eta HCYS kasuetarako GSHrako baino, non intentsitate fluoreszentearen aldaketak AA kontzentrazioarekiko ahulagoak diren (10. irudia) [31]. Litekeena da sentikortasun desberdintasun hori A Aren tamainarekin erlazionatuta egotea.…”