51874-27-2Relevant academic research and scientific papers
Thiol- And Disulfide-Containing Vancomycin Derivatives against Bacterial Resistance and Biofilm Formation
Gademann, Karl,Shchelik, Inga S.
supporting information, p. 1898 - 1904 (2021/11/16)
Antibiotic-resistant and biofilm-associated infections constitute a rapidly growing issue. Use of the last-resort antibiotic vancomycin is under threat due to the increasing appearance of vancomycin-resistant bacteria as well as the formation of biofilms. Herein, we report a series of novel vancomycin derivatives carrying thiol- and disulfide-containing moieties. The new compounds exhibited enhanced antibacterial activity against a broad range of bacterial strains, including vancomycin-resistant microbes and Gram-negative bacteria. Moreover, all obtained derivatives demonstrated improved antibiofilm formation activity against VanB-resistant Enterococcus compared to vancomycin. This work establishes a promising strategy for combating drug-resistant bacterial infections or disrupting biofilm formation and advances the knowledge on the structural optimization of antibiotics with sulfur-containing modifications.
A bicyclic pentapeptide-based highly potent and selective pan-SIRT1/2/3 inhibitor harboring Nε-thioacetyl-lysine
Li, Renwu,Sun, Xun,Yan, Lingling,Zheng, Weiping
, (2020/02/22)
Past few years have seen an active pursuit of the inhibitors for the deacylation catalyzed by the seven human sirtuins (i.e. SIRT1-7) as valuable chemical biological/pharmacological probes of this enzymatic deacylation and lead compounds for developing novel therapeutics for human diseases. In the current study, we prepared eight monocyclic and one bicyclic analogs of a linear pentapeptide-based potent (sub-μM IC50’s) pan-SIRT1/2/3 inhibitor Zheng laboratory discovered recently that harbors the catalytic mechanism-based SIRT1/2/3 inhibitory warhead Nε-thioacetyl-lysine at its central position. We found that the bicyclic analog exhibited largely comparable SIRT1/2/3 inhibitory potencies to those of the parent linear pentapeptide, however, the former is proteolytically much more stable than the latter. Moreover, the bicyclic analog displayed very weak inhibition against SIRT5/6/7, was cell permeable, and exhibited an anti-proliferative effect on the human SK-MEL-2 melanoma cells. This bicyclic analog could be a lead for the future development of more potent and still selective pan-SIRT1/2/3 inhibitors whose use in studies on human sirtuin biology, pharmacology, and medicinal chemistry could complement with the use of the potent inhibitors selective for a single human sirtuin.
An acyl-SAM analog as an affinity ligand for identifying quorum sensing signal synthases
Kai, Kenji,Fujii, Hiroki,Ikenaka, Rui,Akagawa, Mitsugu,Hayashi, Hideo
supporting information, p. 8586 - 8589 (2014/07/22)
N-Acylhomoserine lactones (AHLs) are quorum sensing signals produced by Gram-negative bacteria. We here report the affinity purification of AHL synthases using beads conjugated with an enzyme inhibitor, which was designed based on the catalytic intermediate acyl-SAM. the Partner Organisations 2014.
Synthesis of Phidianidine B, a highly cytotoxic 1,2,4-oxadiazole marine metabolite
Manzo, Emiliano,Pagano, Dario,Carbone, Marianna,Ciavatta, M. Letizia,Gavagnin, Margherita
, p. 220 - 228 (2013/02/23)
Phidianidine B (1), a natural 1,2,4-oxadiazole linking both an indole system and an aminoalkyl guanidine group that has been recently reported from a marine mollusk, has been synthesized in seven steps (14% total yield). The synthetic procedure, which is based on the coupling of 3-indolacetic acid methyl ester and the amino-alkyl hydroxy guanidine intermediate 2, opportunely prepared, is of general application and allows the synthesis of analogues with either different alkyl chain length or substitution on the indole ring. ARKAT-USA, Inc.
