Cyclopropyl Substituents Transform the Viscosity-Sensitive BODIPY Molecular Rotor into a Temperature Sensor

Cyclopropyl Substituents Transform the Viscosity-Sensitive BODIPY Molecular Rotor into a Temperature Sensor Full article

Journal

ACS Sensors
ISSN: 2379-3694

Output data

Year: 2021, Volume: 6, Number: 6, Pages: 2158-2167 Pages count : 10 DOI: 10.1021/acssensors.0c02275

Authors

Vyšniauskas Aurimas ^1,2 , Cornell Bethan ³ , Sherin Peter S ² , Maleckaitė Karolina ¹ , Kubánková Markéta ² , Izquierdo Maria Angeles ² , Vu Thanh Truc ² , Volkova Yulia A ^2,4 , Budynina Ekaterina M ^5,2 , Molteni Carla ³ , Kuimova Marina K ²

Affiliations

1	Center of Physical Sciences and Technology, Saulėtekio av. 3, Vilnius 10257, Lithuania
2	Department of Chemistry, Molecular Sciences Research Hub, White City Campus, Imperial College London, Exhibition Road, London W12 0BZ, U.K.
3	Physics Department, King’s College London, Strand, London WC2R 2LS, U.K.
4	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russia
5	Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russia

A quantitative fluorescent probe that responds to changes in temperature is highly desirable for studies of biological environments, particularly in cellulo. Here, we report new cell-permeable fluorescence probes based on the BODIPY moiety that respond to environmental temperature. The new probes were developed on the basis of a well-established BODIPY-based viscosity probe by functionalization with cyclopropyl substituents at α and β positions of the BODIPY core. In contrast to the parent BODIPY fluorophore, α-cyclopropyl-substituted fluorophore displays temperature-dependent time-resolved fluorescence decays showing greatly diminished viscosity dependence, making it an attractive sensor to be used with fluorescence lifetime imaging microscopy (FLIM). We performed theoretical calculations that help rationalize the effect of the cyclopropyl substituents on the photophysical behavior of the new BODIPYs. In summary, we designed an attractive new quantitative FLIM-based temperature probe that can be used for temperature sensing in live cells.

Vyšniauskas A. , Cornell B. , Sherin P.S. , Maleckaitė K. , Kubánková M. , Izquierdo M.A. , Vu T.T. , Volkova Y.A. , Budynina E.M. , Molteni C. , Kuimova M.K.
Cyclopropyl Substituents Transform the Viscosity-Sensitive BODIPY Molecular Rotor into a Temperature Sensor
ACS Sensors. 2021. V.6. N6. P.2158-2167. DOI: 10.1021/acssensors.0c02275 WOS Scopus OpenAlex

≡ Web of science:	WOS:000668374500013
≡ Scopus:	2-s2.0-85108410572
≡ OpenAlex:	W3164625840