Deciphering the Structure-Property Relations in Substituted Heptamethine Cyanines.

The Journal of Organic Chemistry
Lenka ŠtackováPetr Klán

Abstract

Heptamethine cyanines (Cy7) are fluorophores essential for modern bioimaging techniques and chemistry. Here, we systematically evaluated the photochemical and photophysical properties of a library of Cy7 derivatives containing diverse substituents in different positions of the heptamethine chain. A single substitution allows modulation of their absorption maxima in the range of 693-805 nm and photophysical properties, such as quantum yields of singlet-oxygen formation, decomposition, and fluorescence or affinity to singlet oxygen, within 2-3 orders of magnitude. The same substituent in different positions of the chain often exhibits distinctly contradictory effects, demonstrating that both the type and position of the substituent are pivotal for the design of Cy7-based applications. The combination of experimental results with quantum-chemical calculations provides insights into the structure-property relationship, the elucidation of which will accelerate the development of cyanines with properties tailored for specific applications, such as fluorescent probes and sensors, photouncaging, photodynamic therapy, or singlet-oxygen detection.

References

Jan 1, 1978·Physics in Medicine and Biology·R C Benson, H A Kues
Jan 1, 1976·Photochemistry and Photobiology·G W ByersP M Henrichs
Aug 21, 2003·Molecular Imaging·Atif ZaheerJohn V Frangioni
Feb 12, 2004·Biophysical Chemistry·Alexander S Tatikolov, Sílvia M B Costa
Aug 12, 2005·Chemical Reviews·Jacopo TomasiRoberto Cammi
Jun 7, 2007·Physical Chemistry Chemical Physics : PCCP·Ester Livshits, Roi Baer
Jun 15, 2007·The Journal of Physical Chemistry. a·B AradiTh Frauenheim
Oct 24, 2007·The Journal of Chemical Physics·Stefan Grimme, Frank Neese
Oct 3, 2009·Organic Letters·Pierre-Antoine BouitNazario Martin
Dec 23, 2009·The Journal of Chemical Physics·Ulrike Salzner, Roi Baer
Sep 11, 2010·Chemical Communications : Chem Comm·Animesh SamantaYoung-Tae Chang
Jan 22, 2011·Analytical Chemistry·Knut Rurack, Monika Spieles
Feb 24, 2011·Journal of the American Chemical Society·Takuya MyochinTetsuo Nagano
Mar 3, 2011·The Journal of Chemical Physics·Michele CeriottiMichele Parrinello
Jun 3, 2011·Journal of the American Chemical Society·Naama Karton-LifshinDoron Shabat
Aug 15, 2012·Proceedings of the National Academy of Sciences of the United States of America·Sang-Hee ShimXiaowei Zhuang
Sep 14, 2012·The Journal of Physical Chemistry. a·Michael J G Peach, David J Tozer
Oct 30, 2012·Nature Methods·Joshua C VaughanXiaowei Zhuang
Aug 9, 2013·Nature Reviews. Cancer·Quyen T Nguyen, Roger Y Tsien
May 20, 2014·The Journal of Physical Chemistry. a·Simon PascalOlivier Maury
Sep 12, 2014·Journal of the American Chemical Society·Alexander P GorkaMartin J Schnermann
Jan 15, 2015·Journal of the American Chemical Society·Jason Boyang WuJean C Shih
Feb 25, 2015·Accounts of Chemical Research·Boris Le Guennic, Denis Jacquemin
Apr 24, 2015·Clinical Cancer Research : an Official Journal of the American Association for Cancer Research·Eben L RosenthalKurt R Zinn
Jun 9, 2015·Organic & Biomolecular Chemistry·Alexander P GorkaMartin J Schnermann
Oct 29, 2015·Chemical Science·Roger R NaniMartin J Schnermann
Nov 21, 2015·Journal of Chemical Theory and Computation·Siwar ChibaniDenis Jacquemin
Aug 12, 2014·Journal of Chemical Theory and Computation·Hristina ZhekovaTom Ziegler
Jan 8, 2013·Journal of Chemical Theory and Computation·Michael GausMarcus Elstner

❮ Previous
Next ❯

Citations

Sep 5, 2020·Chemistry : a European Journal·Lenka ŠtackováPetr Klán
Nov 17, 2020·Organic & Biomolecular Chemistry·Lan FengJun Yin
Sep 26, 2020·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Pengjuan SunJing Liu
May 4, 2021·Journal of the American Chemical Society·Emily D CoscoEllen M Sletten
May 24, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Mingshui ZhangGuangjiu Zhao

❮ 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.