Dicyclohexylurea derivatives of amino acids as dye absorbent organogels and anion sensors

Organic & Biomolecular Chemistry
Karabi RoySunanda Chatterjee

Abstract

Dicyclohexyl urea (DCU) derivatives of amino acids Fmoc-Phe-DCU (M1), Fmoc-Phg-DCU (M2) and Fmoc-Gaba-DCU (M3) have been shown to form phase selective, thermoreversible and mechanically robust gels in a large range of organic solvents. This is the first report of low molecular weight gelators (LMWG) from DCU derivatives of amino acids. The self-assembly mechanism of the organogels has been probed using concentration dependent 1H NMR, DMSO titration 1H NMR, fluorescence, FTIR, PXRD and FESEM techniques. Self-assembly leading to gelation process is mainly driven by hydrophobicity and π-π stacking interactions in between Fmoc groups. Interestingly, the gels can absorb several kinds of organic dyes efficiently and can be reused for dye absorption for multiple cycles. Additionally, M1-M3 act as sensors for anions like fluoride, acetate and hydroxide, for which they have specific fluorescence response. Gel formation by M1-M3 is completely arrested in the presence of fluoride. The possible binding mode of fluoride has been delineated using DFT studies. Calculations suggest, involvement of urea NH in a six membered intramolecular hydrogen bond, rendering it unavailable for fluoride binding. Backbone -NH of the amino acids of M1-M3 is r...Continue Reading

References

Jul 1, 1975·Journal of the National Cancer Institute·E Rinde, W Troll
Aug 14, 2001·Journal of Biotechnology·N D LourençoH M Pinheiro
Aug 5, 1997·Chemical Reviews·A. Prasanna de SilvaTerence E. Rice
Feb 20, 2002·Chemical Reviews·Pierre Terech, Richard G. Weiss
Mar 20, 2003·Journal of the American Chemical Society·Shi-Wei Zhang, Timothy M Swager
Dec 11, 2003·Organic & Biomolecular Chemistry·Masahiro SuzukiKenji Hanabusa
Jan 31, 2004·The Journal of Organic Chemistry·Jin Yong LeeKye Chun Nam
Apr 6, 2004·Organic & Biomolecular Chemistry·Masahiro SuzukiKenji Hanabusa
Dec 14, 2004·Chemistry : a European Journal·Nils Mohmeyer, Hans-Werner Schmidt
Aug 12, 2005·Chemical Reviews·Jacopo TomasiRoberto Cammi
Sep 21, 2005·Chemical Society Reviews·Neralagatta M Sangeetha, Uday Maitra
Apr 19, 2007·The Journal of Organic Chemistry·Ian A CoatesDavid K Smith
May 11, 2007·Accounts of Chemical Research·Ayyappanpillai Ajayaghosh, Vakayil K Praveen
May 14, 2008·Chemical Communications : Chem Comm·Tae Hyeon KimTaek Seung Lee
Nov 21, 2009·The Journal of Physical Chemistry. B·P Anilkumar, M Jayakannan
Jul 10, 2010·Chemical Society Reviews·Stefan Kubik
Dec 25, 2010·Journal of the American Chemical Society·Carlo GiansanteAndré Del Guerzo
Jun 22, 2011·Organic Letters·P Rajamalli, Edamana Prasad
Sep 29, 2011·Chemistry : a European Journal·Bimalendu AdhikariArindam Banerjee
Feb 6, 2013·Organic & Biomolecular Chemistry·Pengchong XueHirotaka Ihara
Jan 10, 2014·Chemical Reviews·Sukumaran Santhosh BabuAyyappanpillai Ajayaghosh
Feb 26, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Jongha LeeSoo Young Park
Jun 13, 2014·Journal of Peptide Science : an Official Publication of the European Peptide Society·Laura SzkolarAlberto Saiani
Jul 1, 2014·Chemical Society Reviews·Philip A Gale, Claudia Caltagirone
May 6, 2015·ACS Applied Materials & Interfaces·Ni ChengLi Yu
Jun 11, 2015·Soft Matter·Virender SinghAshwani Kumar Thakur
Jun 18, 2015·Chemical Communications : Chem Comm·Wathsala LiyanageBradley L Nilsson
Aug 2, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Santanu PanjaKumaresh Ghosh
Sep 16, 2017·Chemistry : a European Journal·Carla RizzoFrancesca D'Anna
Dec 23, 2017·Journal of Controlled Release : Official Journal of the Controlled Release Society·Cloé L EspositoV Gaëlle Roullin
Feb 10, 2018·Journal of Colloid and Interface Science·Salvatore MarulloFrancesca D'Anna

❮ Previous
Next ❯

Citations


❮ Previous
Next ❯

Methods Mentioned

BETA
NMR
Scanning Electron Microscopy
rheology
Nuclear Magnetic Resonance
X-ray
column chromatography

Software Mentioned

Gaussian

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.