Water-soluble perylenediimides: design concepts and biological applications

Chemical Society Reviews
Mengmeng SunMeizhen Yin

Abstract

Water-soluble perylenediimides (PDIs) with high fluorescence intensity, photostability and biocompatibility have been successfully prepared and applied in the biological field. In this tutorial review, we briefly focus on the synthetic strategies for the preparation of water-soluble PDIs by incorporating ionic or non-ionic substituents with multiple polar groups into the bay-region, imide- or ortho-positions of PDIs. These ionic/non-ionic substituents can suppress π-π aggregation and shield the inner perylene chromophores, thus contributing to the water solubility which is essential for biological applications. The optical properties, absorption and emission maxima above 500 nm, minimize the autofluorescence background of cells and provide access to imaging in living cells. The biological applications of water-soluble PDIs are discussed from simple (basic) to complex (advanced) processes, including biosensing in vitro studies, imaging and gene/drug delivering in living cells, tissues and the whole body. The promising future of designed multi-functional water-soluble PDIs will be highlighted in this review.

References

Sep 24, 2004·Chemistry : a European Journal·Christopher KohlKlaus Müllen
Jun 4, 2005·The Journal of Organic Chemistry·George R NewkomeCharles N Moorefield
Apr 24, 2008·Biomacromolecules·Meizhen YinTanja Weil
Jun 3, 2008·Journal of the American Chemical Society·Meizhen YinKlaus Müllen
Jul 4, 2009·Chemistry : a European Journal·Satomi NakazonoAtsuhiro Osuka
Mar 4, 2010·Chemical Communications : Chem Comm·Timm HeekRainer Haag
Feb 22, 2011·Chemical Communications : Chem Comm·Baoxiang GaoXinwu Ba
Apr 13, 2011·Chemistry : a European Journal·Cordula D SchmidtAndreas Hirsch
Jun 16, 2011·Journal of the American Chemical Society·Si Kyung YangSteven C Zimmerman
Jan 10, 2012·Advanced Materials·Chen Li, Henrike Wonneberger
Jan 14, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Glauco BattagliarinKlaus Müllen
May 11, 2012·Angewandte Chemie·Daniel GörlFrank Würthner
Dec 19, 2012·Bioorganic & Medicinal Chemistry Letters·Ke-Rang WangXiao-Liu Li
Jan 9, 2013·Bioconjugate Chemistry·Timm HeekRainer Haag
Mar 6, 2013·Advanced Functional Materials·Si Kyung Yang, Steven C Zimmerman
Jul 4, 2013·Chemistry : a European Journal·Timm HeekRainer Haag
Dec 3, 2013·Chemical Communications : Chem Comm·Shusen YouMeizhen Yin
Jan 11, 2014·Chemical Communications : Chem Comm·Marco MontaltiDamiano Genovese
Feb 6, 2014·Macromolecular Rapid Communications·Ke-Rang WangXiao-Liu Li
Aug 28, 2014·ACS Applied Materials & Interfaces·Shusen YouMeizhen Yin
Jan 14, 2013·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Pradip K SukulSudip Malik
Apr 21, 2014·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Kelan LiuJie Shen
May 28, 2014·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Zejun XuJie Shen
Aug 7, 2014·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Dongxu ShenChunju An

❮ Previous
Next ❯

Citations

Aug 4, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Geraldine EchueCharl F J Faul
Apr 28, 2017·Chemical Communications : Chem Comm·Yingjie MaKlaus Müllen
Jun 2, 2017·Chemical Communications : Chem Comm·Kaushik PalApurba Lal Koner
Apr 7, 2018·Chembiochem : a European Journal of Chemical Biology·Ruchika MishraJeyaraman Sankar
Jul 4, 2018·Advanced Healthcare Materials·Ji QiBen Zhong Tang
Jul 5, 2018·Physical Chemistry Chemical Physics : PCCP·Yongwei HuangDongzhu Jin
Sep 5, 2018·Luminescence : the Journal of Biological and Chemical Luminescence·Fan KongTeng Qiu
Sep 4, 2018·Chembiochem : a European Journal of Chemical Biology·Shukun LiXuehai Yan
Sep 21, 2016·Chemistry, an Asian Journal·Zhen WuMeizhen Yin
Aug 10, 2019·Physical Chemistry Chemical Physics : PCCP·Elisa AlloaSophia C Hayes
Jul 22, 2017·Chemistry : a European Journal·Patricia Calvo-GredillaFernando Fernández-Lázaro
Sep 19, 2019·Chemistry : a European Journal·Lutz GadeHubert Wadepohl
Feb 25, 2020·Chemical Communications : Chem Comm·Guo-Bin HuangXiang-Kui Ren
Jun 5, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Zhonghua LiuYongwei Huang
Oct 2, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Wenkun HanWenjing Tian
May 26, 2018·Chemistry : a European Journal·Natalia BustoBegoña García
Jan 27, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Pagidi SudhakarPakkirisamy Thilagar
Oct 28, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Matt D LaramieMaged Henary
Mar 25, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lou RocardPiétrick Hudhomme
May 5, 2020·Chemistry : a European Journal·Pradeep P N Syamala, Frank Würthner
Jul 24, 2020·Analytical Methods : Advancing Methods and Applications·Prabhpreet SinghKapil Kumar
Sep 14, 2017·BMC Complementary and Alternative Medicine·Yongqiang TianMingquan Guo
Jul 8, 2018·Nature Communications·Stefanie HerbstFrank Würthner

❮ 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.