Host-guest complexation of neutral red with macrocyclic host molecules: contrasting pK(a) shifts and binding affinities for cucurbit[7]uril and beta-cyclodextrin

The Journal of Physical Chemistry. B
J MohantyHaridas Pal

Abstract

The photophysical properties of the phenazine-based dye neutral red were investigated in aqueous solution in the presence of the macrocyclic host molecule cucurbit[7]uril (CB7) using ground-state absorption as well as steady-state and time-resolved fluorescence measurements. The results are contrasted to those previously obtained for beta-cyclodextrin (beta-CD; Singh et al. J. Phys. Chem. A 2004, 108, 1465). Both the neutral (NR) and cationic (NRH+) forms of the dye formed inclusion complexes with CB7, with the larger binding constant for the latter (K = 6.5 x 10(3) M(-1) versus 6.0 x 10(5) M(-1)). This result differed from that for beta-CD, where only the neutral form of the dye was reported to undergo sizable inclusion complex formation. From the difference in binding constants and the pK(a) value of protonated neutral red in the absence of CB7 (6.8), an increased pK(a) value of the dye when complexed by CB7 was projected (approximately 8.8). This shift differed again from the behavior of the dye with beta-CD, where a decreased pK(a) value (ca. 6.1) was reported. The photophysical properties of both NR and NRH+ forms showed significant changes in the presence of CB7. Fluorescence anisotropy studies indicated that the inclusio...Continue Reading

References

Oct 1, 1984·Analytical Biochemistry·J C LaManna, K A McCracken
Feb 19, 2002·Chemical Reviews·Mikhail V. Rekharsky, Yoshihisa Inoue
Aug 5, 1997·Chemical Reviews·Kenneth A. Connors
Sep 24, 2004·IEEE Transactions on Nanobioscience·Cesar MarquezWerner M Nau
Dec 1, 2004·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Jyotirmayee Mohanty, Werner M Nau
May 12, 2005·Angewandte Chemie·Jyotirmayee Mohanty, Werner M Nau
Jul 30, 2005·Angewandte Chemie·Jason LagonaLyle Isaacs
Jul 21, 2006·The Journal of Physical Chemistry. B·Brian D WagnerLyle Isaacs
Sep 3, 2001·Angewandte Chemie·Christian LettmannWilhelm F Maier

❮ Previous
Next ❯

Citations

Sep 10, 2013·Advances in Colloid and Interface Science·Artur J M Valente, Olle Söderman
Nov 15, 2011·Journal of the American Chemical Society·Hao TangCornelia Bohne
Apr 8, 2011·The Journal of Physical Chemistry. a·Denis A IvanovMichael V Alfimov
Sep 30, 2006·Chemical Communications : Chem Comm·Ruibing WangDonal H Macartney
Aug 9, 2008·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Mhejabeen ShaikhHaridas Pal
Apr 22, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Ruibing WangDonal H Macartney
May 18, 2010·Physical Chemistry Chemical Physics : PCCP·Mhejabeen ShaikhHaridas Pal
Jun 30, 2011·Chemical Communications : Chem Comm·Achikanath C BhasikuttanJyotirmayee Mohanty
Jul 16, 2011·Chemical Communications : Chem Comm·Nilotpal BarooahJyotirmayee Mohanty
Jun 22, 2011·Physical Chemistry Chemical Physics : PCCP·Nilotpal BarooahAchikanath C Bhasikuttan
Nov 14, 2015·Journal of the American Chemical Society·Jong Wha LeeHugh I Kim
Sep 15, 2010·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Jyotirmayee MohantyHaridas Pal
Apr 22, 2015·Chemical Reviews·Casey J BrownKenneth N Raymond
Mar 31, 2015·The Journal of Organic Chemistry·Nikola BasarićCornelia Bohne
Mar 12, 2015·The Journal of Physical Chemistry. B·Jong Wha LeeHugh I Kim
Dec 6, 2011·The Journal of Physical Chemistry. B·Jyotirmayee MohantyAchikanath C Bhasikuttan
Mar 6, 2012·The Journal of Physical Chemistry. B·Nilotpal BarooahAchikanath C Bhasikuttan
Feb 14, 2012·Advanced Drug Delivery Reviews·Indrajit Ghosh, Werner M Nau
Nov 4, 2016·The Journal of Physical Chemistry. B·Shrikant S ThakareNagayan Sekar
Feb 28, 2009·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Noufal KandothHaridas Pal
Dec 10, 2016·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Monika GuptaAlok K Ray
Oct 16, 2014·Chemical Society Reviews·Khaleel I Assaf, Werner M Nau
Jul 22, 2017·Chemical Communications : Chem Comm·Silvia SonziniChristopher F van der Walle
Jul 23, 2016·Chemical Communications : Chem Comm·Bin HuaFeihe Huang
Aug 5, 2017·Physical Chemistry Chemical Physics : PCCP·V S KalyaniJ Mohanty
Aug 23, 2017·Chemical Society Reviews·Matthew J Webber, Robert Langer
Nov 19, 2014·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Ankita JadhavJyotirmayee Mohanty
Nov 7, 2018·Chemical Communications : Chem Comm·Bin ZhangXin Zhou

❮ Previous
Next ❯

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.

Related Papers

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
Mhejabeen ShaikhHaridas Pal
Langmuir : the ACS Journal of Surfaces and Colloids
Luis García-RíoP Rodriguez-Dafonte
Journal of Pharmaceutical Sciences
Thorsteinn Loftsson, Marcus E Brewster
© 2021 Meta ULC. All rights reserved