Straightforward synthesis of Solomon-red-BAPTA as NIR fluorescent sensors via metal-free oxidative coupling

Gergő Riszter; László Forgách; Zoltán Mucsi; Laura Molnár; Dóra Bogdán; Fatemeh Heydari; Domokos Máthé; István Mándity; Ágnes Gömöry; Zoltán Kaleta

doi:10.1039/D6RA01589A

Straightforward synthesis of Solomon-red-BAPTA as NIR fluorescent sensors via metal-free oxidative coupling

Gergő Riszter,^abc László Forgách,

^def Zoltán Mucsi,^gh Laura Molnár,^b Dóra Bogdán,^a Fatemeh Heydari,

^de Domokos Máthé,

^dei István Mándity,^acj Ágnes Gömöry^k and Zoltán Kaleta

*^acj

Author affiliations

* Corresponding authors

^a Institute of Organic Chemistry, Semmelweis University, Hőgyes Endre Street 7, H-1092 Budapest, Hungary
E-mail: kaleta.zoltan@semmelweis.hu

^b PROGRESSIO Engineering Bureau Ltd, Muhar u. 54, H-1028 Budapest, Hungary

^c Artificial Transporters Research Group, Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, HUN-REN Hungarian Research Network, Magyar Tudósok Körútja 2, Budapest, Hungary

^d Department of Biophysics, Semmelweis University, Tűzoltó utca 37-47, Budapest, Hungary

^e In Vivo Imaging Advanced Core Facility, Hungarian Center of Excellence for Molecular Medicine (HCEMM), Tűzoltó Utca 37-47, Budapest, Hungary

^f Department of Nuclear Medicine, Medical Imaging Centre, Semmelweis University, Üllői út 78b, Budapest, Hungary

^g BrainVisionCenter, 1094 43-45. Liliom Str., Budapest, Hungary

^h Institute of Chemistry, University of Miskolc 3515 Miskolc-Egyetemváros, A/2 Building, Hungary

ⁱ CROmed Translational Research Centers, 37-47 Tűzoltó Street, Budapest, Hungary

^j Centre for Pharmacology and Drug Research & Development, Semmelweis University, Budapest, Hungary

^k MS Proteomics Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, HUN-REN Hungarian Research Network, Magyar Tudósok Körútja 2, Budapest, Hungary

Abstract

An effective, near-infrared (NIR) fluorescent Ca²⁺ sensor, Solomon-red-BAPTA, featuring a dioxothioxanthene moiety was developed for microscopy. A rapid and operationally simple synthetic route is described. The key step involves a room-temperature DDQ-mediated cross-dehydrogenative coupling (CDC) of the fluorescent precursor and BAPTA followed by a one-pot oxidation. The sensor exhibited excellent photophysical characteristics including a 160-fold fluorescence enhancement with excitation and emission maxima at 712 nm and 736 nm, respectively, suggesting high tissue-penetrating capacity. Based on the experimental data, the structure–property relationship was elucidated and further supported by DFT calculations, particularly with respect to the photoinduced electron transfer (PET)-based fluorescence turn-on mechanism.

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Straightforward synthesis of Solomon-red-BAPTA as NIR fluorescent sensors via metal-free oxidative coupling

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Straightforward synthesis of Solomon-red-BAPTA as NIR fluorescent sensors via metal-free oxidative coupling

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