Synthesis of riccardin D derivatives as potent antimicrobial agents.
We describe the synthesis and biological evaluation of riccardin D derivatives, a novel class of antimicrobial molecules. Structural diversification of these derivatives was achieved by introducing hydroxy, methoxy, and bromine into the aromatic rings of riccardin D. The antimicrobial evaluation of these compounds was performed as in vitro assays against clinically isolated bacteria and fungi. The introduction of bromine atom into the arene B of riccardin D led to several strongly active antibacterial compounds with a MIC value ranging from 0.5 to 4μg/mL for Staphylococcus aureus, both methicillin-sensitive and -resistant strains. Antifungal tests found compound 34 was the most potent molecule with a MIC value of 2μg/mL against Candida albicans. This initial biological evaluation suggests that these novel molecules merit further investigation as potential antimicrobial agents.
National Glycoengineering Research Center, Shandong University, Jinan 250012, PR China; School of Pharmaceutical Sciences, Shandong University, Jinan 250012, PR China.
Bin
B
Sun
School of Pharmaceutical Sciences, Shandong University, Jinan 250012, PR China.
Ming
M
Zhang
School of Pharmaceutical Sciences, Shandong University, Jinan 250012, PR China.
Ying
Y
Li
School of Pharmaceutical Sciences, Shandong University, Jinan 250012, PR China.
Qing-Wen
QW
Hu
School of Pharmaceutical Sciences, Shandong University, Jinan 250012, PR China.
Hong-Bo
HB
Zheng
School of Pharmaceutical Sciences, Shandong University, Jinan 250012, PR China.
Wen-Qiang
WQ
Chang
National Glycoengineering Research Center, Shandong University, Jinan 250012, PR China; School of Pharmaceutical Sciences, Shandong University, Jinan 250012, PR China. Electronic address: louhongxiang@sdu.edu.cn.
Hong-Xiang
HX
Lou
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D005658:Fungi / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010647:Phenyl Ethers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D010647:Phenyl Ethers; D013267:Stilbenes; C547185:riccardin D
Anti-MRSA; Anti-fungal; Antimicrobial; Bisbibenzyl; Derivatives