32327-47-2Relevant articles and documents
New fluorescent probes for carbonic anhydrases
Banerjee, Jayati,Haldar, Manas K.,Manokaran, Sumathra,Mallik, Sanku,Srivastava
, p. 2723 - 2725 (2007)
We report the synthesis and fluorescence properties of naphthalenesulfonamide derivatives as active site probes for carbonic anhydrases. The Royal Society of Chemistry.
Small polar molecules: A challenge in marine chemical ecology
Ternon, Eva,Wang, Yanfei,Coyne, Kathryn J.
, (2019)
Due to increasing evidence of key chemically mediated interactions in marine ecosystems, a real interest in the characterization of the metabolites involved in such intra and interspecific interactions has emerged over the past decade. Nevertheless, only a small number of studies have succeeded in identifying the chemical structure of compounds of interest. One reason for this low success rate is the small size and extremely polar features of many of these chemical compounds. Indeed, a major challenge in the search for active metabolites is the extraction of small polar compounds from seawater. Yet, a full characterization of those metabolites is necessary to understand the interactions they mediate. In this context, the study presented here aims to provide a methodology for the characterization of highly polar, low molecular weight compounds in a seawater matrix that could provide guidance for marine ecologists in their efforts to identify active metabolites. This methodology was applied to the investigation of the chemical structure of an algicidal compound secreted by the bacteria Shewanella sp. IRI-160 that was previously shown to induce programmed cell death in dinoflagellates. The results suggest that the algicidal effects may be attributed to synergistic effects of small amines (ammonium, 4-aminobutanal) derived from the catabolization of putrescine produced in large quantities (0.05-6.5 fmol/cell) by Shewanella sp. IRI- 160.
Using quenching kinetics and thermodynamics of amino-fluorophores as empirical tools for predicting boronic acid sensors suitable for use in physiological conditions
McGregor, Nicholas,Pardin, Christophe,Skene
, p. 1438 - 1446 (2012/02/04)
A series of water-soluble 1-amino-naphthalenes and 2-amino-fluorenes are prepared. These serve as model fluorophores for measuring the thermodynamics and kinetics of fluorescence quenching with phenylboronic acids and aliphatic amines. Steady-state and ti
Stabilization of anionic and neutral forms of a fluorophoric ligand at the active site of human carbonic anhydrase I
Manokaran, Sumathra,Banerjee, Jayati,Mallik, Sanku,Srivastava
, p. 1965 - 1973 (2011/12/02)
We synthesized a fluorogenic dansylamide derivative (JB2-48), which fills the entire (15? deep) active site pocket of human carbonic anhydrase I, and investigated the contributions of sulfonamide and hydrophobic regions of the ligand structure on the spectral, kinetic, and thermodynamic properties of the enzyme-ligand complex. The steady-state and fluorescence lifetime data revealed that the deprotonation of the sulfonamide moiety of the enzyme bound ligand increases the fluorescence emission intensity as well as the lifetime of the fluorophores. This is manifested via the electrostatic interaction between the active site resident Zn2+ cofactor and the negatively charged sulfonamide group of the ligand, and such interaction contributes to about 2.2kcal/mol (ΔΔG°) and 0.89kcal/mol (ΔΔG?) energy in stabilizing the ground and the putative transition states, respectively. We provide evidence that the anionic and neutral forms of JB2-48 are stabilized by the complementary microscopic/conformational states of the enzyme. The implication of the mechanistic studies presented herein in rationale design of carbonic anhydrase inhibitors is discussed.
