Hydrophobic substituents on isatin derivatives enhance their inhibition against bacterial peptidoglycan glycosyltransferase activity

Lasting Tracking and Rapid Discrimination of Live Gram-Positive Bacteria by Peptidoglycan-Targeting Carbon Quantum Dots

“…In other words, compared with the less negatively charged lipopolysaccharides (Gram-negative bacteria), peptidoglycan (Gram-positive bacteria) could easily bind to cationic amino groups of T-SCQDs. In addition, peptidoglycan is composed of N -acetylglucosamine and N -acetylmuramic acid cross-linked by short peptides. , These structural characteristics endow peptidoglycan with a large number of hydrophobic regions . Hence, the benzopyrrole structure of T-SCQDs enables interaction with the fragments of peptidoglycan by hydrophobic interaction.…”

“…49,50 These structural characteristics endow peptidoglycan with a large number of hydrophobic regions. 51 Hence, the benzopyrrole structure of T-SCQDs enables interaction with the fragments of peptidoglycan by hydrophobic interaction. In addition, abundant hydrophilic groups on the surface of peptidoglycan can also form hydrogen bonds with hydroxyl groups on the surface of T-SCQDs.…”

Rational structural modification of the isatin scaffold to develop new and potent antimicrobial agents targeting bacterial peptidoglycan glycosyltransferase

“…General synthetic procedures of N-4-butylphenyl-5substituent-isatin analogues (compound 1-5) Compound 1 was synthesized and puried by following the reported procedures. 35 For the synthesis of compound 2-5, to the mixture of 1 mM 5-substituent isatin, 1 mM 4-butylphenyl boronic acid, 3 mM triethylamine in 20 mL CH 2 Cl 2 and activated 4Å molecular sieve, 1 mM copper(II) acetate were added, and the mixture was kept stirring until reaction was completed. The solid was then removed and washed by CH 2 Cl 2 (20 mL Â 3).…”

“…Our previous study via high-throughput screening has successfully identied a natural heterocyclic compound, isatin (1H indole-2,3-dione), which is found to be a potential PGT inhibitor aer a simple modication on its N-1 and C-3 positions. 32,35 The 2-site structural modications, however, have not fully utilized the potential pharmacological properties of isatin moiety because its molecular scaffold allows multi-site three-directional structure modications to create additional chemical features to t for a specic purpose. Recent literature have shown that the diverse pharmacological properties of isatin-modied compounds have been identied in many other research areas, 36,37 such as anti-cancer, 38 anti-tubercular, 39 antimalarial, 40 anti-HIV 41 and anti-bacterial 42,43 treatments with good potency.…”

A Mini Review on Isatin, an Anticancer Scaffold with Potential Activities against Neglected Tropical Diseases (NTDs)

“…The synthesized compounds were evaluated in vitro for their lipid II transglycosylation inhibitory effects (IC 50 ) on E. coli PBP1b. Among the synthesized compounds, 103 proved to be most active with an MIC of 6 μg/mL for methicillin-susceptible Staphylococcus aureus (MSSA), methicillin-resistant Staphylococcus aureus (MRSA), and B. subtilis and 12 μg/mL for E. coli ( Figure 17 ) [ 124 ].…”