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A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.
This article focuses on the most recent research efforts by the
Wang group in the field of a-Gal oligosaccharides. a-Gal oligosaccharides are
carbohydrate structures bearing a Gala1-3Galterminus. This class of compounds are believed to act as xenoactive antigens that instigate the hyperacute rejection in xenotransplantation. Enzymatic methods using recombinant a1-3 galactosyltransferase were employed to synthesize several a- Gal oligosaccharides. In addition, a chemical synthetic scheme was devised in order to produce readily acessible amounts of a-Gal. Conformational analysis was done using both NMR techniques and molecular modeling protocols. These studies provide important information in the structure-function relationship of a-Gal and anti-a-Gal antibodies.
The second part of this article deals with the use of a-Gal in immunotherapy. Based on the abundance of anti-a-Gal antibodies lgM and lgG in human blood serum, a-Gal conjugates may act as effective immunotheraputic drugs. Recent studies have discovered characteristic peptide sequences containing Arg-Giy-Asp (RGD) motif that binds to integrins on the surface of cancer cells. A a-Gal conjugate was developed by chemical coupling a a-Gal trisacchpride to a RGD peptide. Preliminary studies using the conjugate on prostate DU-145 cancer cells showed a reduction in the survival rate of the cells.
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