Photophysical properties and application in live cell imaging of B,B-fluoro-perfluoroalkyl BODIPYs

MedChemComm
Atsuhiko TaniguchiMotomu Kanai

Abstract

The photophysical properties of newly identified B,B-fluoro-perfluoroalkyl BODIPYs (2 and 3), which possess a fluoro group and a trifluoromethyl or pentafluoroethyl group at the boron center, were investigated. B,B-Fluoro-perfluoroalkyl BODIPYs 2 and 3 exhibited better photophysical/chemical properties than B,B-difluoro-BODIPY 1, as follows: (1) higher photostability both in methanol solvent and in a live cell environment, (2) higher stability against acid degradation, and (3) improved fluorescence signal-to-noise ratios in a cell system. These favorable properties of B,B-fluoro-perfluoroalkyl BODIPYs are likely due to the highly electron-withdrawing nature of the perfluoroalkyl groups on the boron atom, which reduces the reactivity to 1O2 and strengthens the complexation of the dipyrromethene ligands to the boron atom. Thus, B,B-fluoro perfluoroalkyl BODIPYs may be useful functional molecules for various applications.

References

Aug 3, 2006·Journal of the American Chemical Society·Christine GozeRaymond Ziessel
Oct 11, 2007·Chemical Reviews·Aurore Loudet, Kevin Burgess
Dec 20, 2007·Angewandte Chemie·Gilles UlrichAnthony Harriman
Dec 21, 2011·Organic Letters·Xin-Dong JiangWeili Zhao
May 4, 2013·Bioorganic & Medicinal Chemistry Letters·Peter VerwilstWim M De Borggraeve
Oct 12, 2013·Organic & Biomolecular Chemistry·Bertrand BrizetFranck Denat
Feb 13, 2014·Chemistry, an Asian Journal·Tomoaki NishidaYoichiro Kuninobu
May 7, 2014·Bioconjugate Chemistry·Alexandra M CourtisRalph Mazitschek
Mar 25, 2015·Chemical Society Reviews·Toshiyuki KowadaKazuya Kikuchi
Sep 24, 2016·Nature Chemistry·Atsuhiko TaniguchiMotomu Kanai

❮ Previous
Next ❯

Citations

May 3, 2019·Chemical Communications : Chem Comm·Takanobu SuzukiTaisuke Tomita
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tianbao YangRenhua Qiu
Sep 16, 2020·The Journal of Organic Chemistry·Tianbao YangRenhua Qiu

❮ Previous
Next ❯

Methods Mentioned

BETA
fluorescence imaging
X-ray
column

Software Mentioned

Jaguar
Maestro

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.