Novel bisstyryl derivatives of bakuchiol: targeting oral cavity pathogens

Mallepally V Reddy; Niranjan Thota; Payare L Sangwan; Pankaj Malhotra; Furqan Ali; Inshad A Khan; Swapandeep S Chimni; Surrinder Koul

doi:10.1016/j.ejmech.2010.03.049

Novel bisstyryl derivatives of bakuchiol: targeting oral cavity pathogens

Mallepally V Reddy, Niranjan Thota, Payare L Sangwan, Pankaj Malhotra, Furqan Ali, Inshad A Khan, Swapandeep S Chimni, Surrinder Koul

Department of Drug Design and Pharmacology

21 Citations (Scopus)

Abstract

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 μg/ml) than bakuchiol and triclosan respectively. These compounds effectively inhibit the biofilm formation of single and multiple species at 2 - 8 × 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.

Original language	English
Journal	European Journal of Medicinal Chemistry
Volume	45
Issue number	7
Pages (from-to)	3125-34
Number of pages	10
ISSN	0223-5234
DOIs	https://doi.org/10.1016/j.ejmech.2010.03.049
Publication status	Published - Jul 2010

Keywords

Anti-Bacterial Agents
Bacteria
Biofilms
Cell Survival
Humans
Microbial Sensitivity Tests
Mouth
Phenols
Stereoisomerism
Structure-Activity Relationship
Styrene
Triclosan
Journal Article
Research Support, Non-U.S. Gov't

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10.1016/j.ejmech.2010.03.049

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title = "Novel bisstyryl derivatives of bakuchiol: targeting oral cavity pathogens",

abstract = "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 μg/ml) than bakuchiol and triclosan respectively. These compounds effectively inhibit the biofilm formation of single and multiple species at 2 - 8 × 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.",

keywords = "Anti-Bacterial Agents, Bacteria, Biofilms, Cell Survival, Humans, Microbial Sensitivity Tests, Mouth, Phenols, Stereoisomerism, Structure-Activity Relationship, Styrene, Triclosan, Journal Article, Research Support, Non-U.S. Gov't",

author = "Reddy, {Mallepally V} and Niranjan Thota and Sangwan, {Payare L} and Pankaj Malhotra and Furqan Ali and Khan, {Inshad A} and Chimni, {Swapandeep S} and Surrinder Koul",

year = "2010",

month = jul,

doi = "10.1016/j.ejmech.2010.03.049",

language = "English",

volume = "45",

pages = "3125--34",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier Masson",

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TY - JOUR

T1 - Novel bisstyryl derivatives of bakuchiol

T2 - targeting oral cavity pathogens

AU - Reddy, Mallepally V

AU - Thota, Niranjan

AU - Sangwan, Payare L

AU - Malhotra, Pankaj

AU - Ali, Furqan

AU - Khan, Inshad A

AU - Chimni, Swapandeep S

AU - Koul, Surrinder

PY - 2010/7

Y1 - 2010/7

N2 - 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 μg/ml) than bakuchiol and triclosan respectively. These compounds effectively inhibit the biofilm formation of single and multiple species at 2 - 8 × 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.

AB - 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 μg/ml) than bakuchiol and triclosan respectively. These compounds effectively inhibit the biofilm formation of single and multiple species at 2 - 8 × 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.

KW - Anti-Bacterial Agents

KW - Bacteria

KW - Biofilms

KW - Cell Survival

KW - Humans

KW - Microbial Sensitivity Tests

KW - Mouth

KW - Phenols

KW - Stereoisomerism

KW - Structure-Activity Relationship

KW - Styrene

KW - Triclosan

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.1016/j.ejmech.2010.03.049

DO - 10.1016/j.ejmech.2010.03.049

M3 - Journal article

C2 - 20427099

SN - 0223-5234

VL - 45

SP - 3125

EP - 3134

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 7

ER -

Novel bisstyryl derivatives of bakuchiol: targeting oral cavity pathogens

Abstract

Keywords

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