Combinatorial discovery of full-color-tunable emissive fluorescent probes using a single core skeleton, 1,2-dihydropyrrolo[3,4-beta]indolizin-3-one

Journal of the American Chemical Society
Eunha KimSeung Bum Park

Abstract

We developed a novel fluorescent core skeleton, 1,2-dihydropyrrolo[3,4-beta]indolizin-3-one, by complexity-generating one-pot reactions through 1,3-dipolar cyclization followed by oxidative aromatization. This fluorescent core skeleton can accommodate various wavelengths of emission maxima by changing the electronic properties of substituents, which was postulated by computational studies. The full-color-tunable emission maxima were achieved with a single core skeleton by changing the substituents using the combinatorial approach. These novel fluorophores have excellent photophysical and photochemical properties: moderate to excellent quantum yields, resistance to the photobleaching, pH-independent fluorescence, large Stokes shifts, druglike lipophilicity for membrane permeability, etc. Further, we successfully demonstrated the bioapplication of fluorophores B1 and B5 in the immunofluorescence for visualizing cellular compartments of HeLa cells.

Citations

Feb 16, 2013·Pflügers Archiv : European journal of physiology·Takuya Terai, Tetsuo Nagano
Aug 25, 2012·ACS Combinatorial Science·Shinichiro FuseTakashi Takahashi
May 24, 2012·Chemical Reviews·Marc VendrellYoung-Tae Chang
Apr 9, 2011·Journal of the American Chemical Society·Sudath HapuarachchigeJeffrey B Arterburn
Jul 24, 2012·Journal of the American Chemical Society·Lin YuanSasa Zhu
Sep 12, 2013·Journal of the American Chemical Society·Dominik S AllgäuerHerbert Mayr
Apr 2, 2011·The Journal of Organic Chemistry·Inmaculada R LahozMaría-Magdalena Cid
Apr 23, 2011·Organic Letters·Huajian ZhuHongbin Zou
May 10, 2011·Organic Letters·Diliang GuoHong Liu
Jan 24, 2012·Chemical Communications : Chem Comm·Eunha KimSeung Bum Park
Mar 16, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Simon BonteMartine Demeunynck
Jul 21, 2015·The Journal of Organic Chemistry·Jian-Jun WangZhi-Bin Huang
Mar 30, 2017·The Journal of Organic Chemistry·Ju Young LeeEun Jeong Yoo
Jul 30, 2016·Chemistry : a European Journal·Ja Young KooSeung Bum Park
Jul 8, 2017·Organic & Biomolecular Chemistry·Guillermo Martinez-ArizaChristopher Hulme
Jul 12, 2016·Organic & Biomolecular Chemistry·Bartłomiej SadowskiDaniel T Gryko
Sep 18, 2009·Chemistry, an Asian Journal·Eunha Kim, Seung Bum Park
May 5, 2011·Angewandte Chemie·Yoshinori KawazoeMotonari Uesugi
Jun 19, 2019·Chemical Communications : Chem Comm·Doina SirbuFranck Suzenet
Apr 17, 2013·Chemistry : a European Journal·Xiaoqing XiongXiaojun Peng
Mar 7, 2019·Nature Communications·Oluwafemi S OjambatiJeremy J Baumberg

❮ Previous
Next ❯

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.