Modular Synthetic Approach to Silicon-Rhodamine Homologues and Analogues Via Bis-aryllanthanum Reagents

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2021 Mar 15

PMID 33720740

Citations 5

Authors

Alexey N Butkevich

Affiliations

Soon will be listed here.

Abstract

A modular synthetic approach toward diverse analogues of the far-red fluorophore silicon-rhodamine (SiR), based on a regioselective double nucleophilic addition of aryllanthanum reagents to esters, anhydrides, and lactones, is proposed. The reaction has improved functional group tolerance and represents a unified strategy toward cell-permeant, spontaneously blinking, and photoactivatable SiR fluorescent labels. In tandem with Pd-catalyzed hydroxy- or aminocarbonylation, it serves a streamlined synthetic pathway to a series of validated live-cell-compatible fluorescent dyes.

Citing Articles

Optimized Red-Absorbing Dyes for Imaging and Sensing.

Grimm J, Tkachuk A, Patel R, Hennigan S, Gutu A, Dong P J Am Chem Soc. 2023; 145(42):23000-23013.

PMID: 37842926 PMC: 10603817. DOI: 10.1021/jacs.3c05273.

Rejuvenating old fluorophores with new chemistry.

Schnermann M, Lavis L Curr Opin Chem Biol. 2023; 75:102335.

PMID: 37269674 PMC: 10524207. DOI: 10.1016/j.cbpa.2023.102335.

A general highly efficient synthesis of biocompatible rhodamine dyes and probes for live-cell multicolor nanoscopy.

Bucevicius J, Gerasimaite R, Kiszka K, Pradhan S, Kostiuk G, Koenen T Nat Commun. 2023; 14(1):1306.

PMID: 36894547 PMC: 9998615. DOI: 10.1038/s41467-023-36913-2.

A long-wavelength xanthene dye for photoacoustic imaging.

Zhou X, Fang Y, Wimalasiri V, Stains C, Miller E Chem Commun (Camb). 2022; 58(85):11941-11944.

PMID: 36196957 PMC: 9634815. DOI: 10.1039/d2cc03947h.

Radiolabeled Silicon-Rhodamines as Bimodal PET/SPECT-NIR Imaging Agents.

Kanagasundaram T, Laube M, Wodtke J, Kramer C, Stadlbauer S, Pietzsch J Pharmaceuticals (Basel). 2021; 14(11).

PMID: 34832938 PMC: 8623702. DOI: 10.3390/ph14111155.

References

Bucevicius J, Kostiuk G, Gerasimaite R, Gilat T, Lukinavicius G . Enhancing the biocompatibility of rhodamine fluorescent probes by a neighbouring group effect. Chem Sci. 2021; 11(28):7313-7323. PMC: 7983176. DOI: 10.1039/d0sc02154g. View

Koide Y, Urano Y, Hanaoka K, Piao W, Kusakabe M, Saito N . Development of NIR fluorescent dyes based on Si-rhodamine for in vivo imaging. J Am Chem Soc. 2012; 134(11):5029-31. DOI: 10.1021/ja210375e. View

Kozma E, Estrada Girona G, Paci G, Lemke E, Kele P . Bioorthogonal double-fluorogenic siliconrhodamine probes for intracellular super-resolution microscopy. Chem Commun (Camb). 2017; 53(50):6696-6699. DOI: 10.1039/c7cc02212c. View

Grzybowski M, Taki M, Senda K, Sato Y, Ariyoshi T, Okada Y . A Highly Photostable Near-Infrared Labeling Agent Based on a Phospha-rhodamine for Long-Term and Deep Imaging. Angew Chem Int Ed Engl. 2018; 57(32):10137-10141. DOI: 10.1002/anie.201804731. View

Uno S, Kamiya M, Yoshihara T, Sugawara K, Okabe K, Tarhan M . A spontaneously blinking fluorophore based on intramolecular spirocyclization for live-cell super-resolution imaging. Nat Chem. 2014; 6(8):681-9. DOI: 10.1038/nchem.2002. View

Koide Y, Urano Y, Hanaoka K, Terai T, Nagano T . Evolution of group 14 rhodamines as platforms for near-infrared fluorescence probes utilizing photoinduced electron transfer. ACS Chem Biol. 2011; 6(6):600-8. DOI: 10.1021/cb1002416. View

Grimm J, Muthusamy A, Liang Y, Brown T, Lemon W, Patel R . A general method to fine-tune fluorophores for live-cell and in vivo imaging. Nat Methods. 2017; 14(10):987-994. PMC: 5621985. DOI: 10.1038/nmeth.4403. View

Werther P, Yserentant K, Braun F, Grussmayer K, Navikas V, Yu M . Bio-orthogonal Red and Far-Red Fluorogenic Probes for Wash-Free Live-Cell and Super-resolution Microscopy. ACS Cent Sci. 2021; 7(9):1561-1571. PMC: 8461766. DOI: 10.1021/acscentsci.1c00703. View

Luo X, Qian L, Xiao Y, Tang Y, Zhao Y, Wang X . A diversity-oriented rhodamine library for wide-spectrum bactericidal agents with low inducible resistance against resistant pathogens. Nat Commun. 2019; 10(1):258. PMC: 6335415. DOI: 10.1038/s41467-018-08241-3. View

10.

Weber M, Leutenegger M, Stoldt S, Jakobs S, Mihaila T, Butkevich A . MINSTED fluorescence localization and nanoscopy. Nat Photonics. 2021; 15(5):361-366. PMC: 7610723. DOI: 10.1038/s41566-021-00774-2. View

11.

Butkevich A, Belov V, Kolmakov K, Sokolov V, Shojaei H, Sidenstein S . Hydroxylated Fluorescent Dyes for Live-Cell Labeling: Synthesis, Spectra and Super-Resolution STED. Chemistry. 2017; 23(50):12114-12119. PMC: 5599963. DOI: 10.1002/chem.201701216. View

12.

Bucevicius J, Keller-Findeisen J, Gilat T, Hell S, Lukinavicius G . Rhodamine-Hoechst positional isomers for highly efficient staining of heterochromatin. Chem Sci. 2019; 10(7):1962-1970. PMC: 6385482. DOI: 10.1039/c8sc05082a. View

13.

Fukazawa A, Suda S, Taki M, Yamaguchi E, Grzybowski M, Sato Y . Phospha-fluorescein: a red-emissive fluorescein analogue with high photobleaching resistance. Chem Commun (Camb). 2015; 52(6):1120-3. DOI: 10.1039/c5cc09345g. View

14.

Balzarotti F, Eilers Y, Gwosch K, Gynna A, Westphal V, Stefani F . Nanometer resolution imaging and tracking of fluorescent molecules with minimal photon fluxes. Science. 2016; 355(6325):606-612. DOI: 10.1126/science.aak9913. View

15.

Jradi F, Lavis L . Chemistry of Photosensitive Fluorophores for Single-Molecule Localization Microscopy. ACS Chem Biol. 2019; 14(6):1077-1090. DOI: 10.1021/acschembio.9b00197. View

16.

Butkevich A, Mitronova G, Sidenstein S, Klocke J, Kamin D, Meineke D . Fluorescent Rhodamines and Fluorogenic Carbopyronines for Super-Resolution STED Microscopy in Living Cells. Angew Chem Int Ed Engl. 2016; 55(10):3290-4. PMC: 4770443. DOI: 10.1002/anie.201511018. View

17.

Fernandez-Suarez M, Ting A . Fluorescent probes for super-resolution imaging in living cells. Nat Rev Mol Cell Biol. 2008; 9(12):929-43. DOI: 10.1038/nrm2531. View

18.

Korsager S, Taaning R, Skrydstrup T . Effective palladium-catalyzed hydroxycarbonylation of aryl halides with substoichiometric carbon monoxide. J Am Chem Soc. 2013; 135(8):2891-4. DOI: 10.1021/ja3114032. View

19.

Krasovskiy A, Kopp F, Knochel P . Soluble lanthanide salts (LnCl3.2LiCl) for the improved addition of organomagnesium reagents to carbonyl compounds. Angew Chem Int Ed Engl. 2006; 45(3):497-500. DOI: 10.1002/anie.200502485. View

20.

Sauer M, Nasufovic V, Arndt H, Vilotijevic I . Robust synthesis of NIR-emissive P-rhodamine fluorophores. Org Biomol Chem. 2020; 18(8):1567-1571. DOI: 10.1039/d0ob00189a. View