Novel bisstyryl derivatives of bakuchiol: targeting oral cavity pathogens.
Novel bisstyryl derivatives of bakuchiol using Heck coupling reaction as the key step were synthesized and screened against a panel of six oral cavity pathogens for their antimicrobial activity. Four compounds (9-12) showed two to fourfold and four to eightfold better activity (MIC 0.25-16 microg/ml) than bakuchiol and triclosan respectively. These compounds effectively inhibit the biofilm formation of single and multiple species at 2 - 8 x MICs. 4- and 4'-Hydroxy/methoxy styryl moieties of the bakuchiol derivatives play a pivotal role towards the activity as established in the SAR studies. Mechanism of action studies revealed microbial membrane structure disruption as the probable mode of action of these compounds.
Reddy
Mallepally V
MV
Department of Bioorganic Chemistry, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu Tawi 180001, India.
Thota
Niranjan
N
Sangwan
Payare L
PL
Malhotra
Pankaj
P
Ali
Furqan
F
Khan
Inshad A
IA
Chimni
Swapandeep S
SS
Koul
Surrinder
S
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000166:cytology / Q000187:drug effects*; D018441:Biofilms / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D009055:Mouth / Q000382:microbiology*; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D020058:Styrene / Q000737:chemistry*; D014260:Triclosan / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D010636:Phenols; D020058:Styrene; D014260:Triclosan; C012765:bakuchiol