Surface-Chemical Studies on Chlorhexidine and Related Compounds: II. Interactions with Monomolecular-Film Systems

Fisher, Richard G.; Quintana, Ronald P.

doi:10.1177/00220345750540013001

Cited by 17 publications

(9 citation statements)

References 12 publications

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“…In a different context, Fisher and Quintana have argued that alkyl substituent lengths longer than ethyl are important in facilitating binding to and penetration of stearic acid monolayers, which these authors analogize to intact dental plaques (8). The present work, which shows the greater bactericidal abilities of MB-1, MB-4, and WB-2 than WB-3 and WB-4, is consistent with this view, but does not establish it convincingly.…”

Section: Resultscontrasting

confidence: 49%

Structural Requirements of Guanide, Biguanide, and Bisbiguanide Agents for Antiplaque Activity

Tanzer

Slee

Kamay

1977

Antimicrob Agents Chemother

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The bactericidal efficacy of 16 guanide, biguanide, and bisbiguanide agents was studied in vitro against intact preformed plaques of four oral (plaqueforming) microorganisms: Streptococcus mutans, S. sanguis, Actinomyces viscosus, and A. naeslundii. The activities of these agents were examined in relation to their molecular configurations. These studies indicated that the bisand biguanide configurations are important for efficacy, as is the length of the alkyl side chain. No structural moiety determined efficacy by itself. Furthermore, the activities of these agents were studied to determine the minimal conditions (concentration, duration, and frequency) of treatment required for likely clinical efficacy. At least six agents were judged to have equal or greater efficacy than the reference agent, chlorhexidine digluconate. A plaque bactericidal index was derived for the most potent agents, and comparison to the bactericidal properties of chlorhexidine was expressed as a chlorhexidine coefficient.

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Section: Resultscontrasting

confidence: 49%

Structural Requirements of Guanide, Biguanide, and Bisbiguanide Agents for Antiplaque Activity

Tanzer

Slee

Kamay

1977

Antimicrob Agents Chemother

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“…In their study, leakage occurred if the terminal groups were six carbons long but not for those three carbons long. In our series of bisbiguanide agents, no agent contained terminal groups of fewer than six carbons, so all would be capable of membrane penetration by the mechanism proposed by Fisher and Quintana (1975). All agents had some activity, although those with long terminal groups were not active if their bridge lengths were fewer than six carbons.…”

Section: Discussionmentioning

confidence: 89%

“…Hence, there appear to be steric limitations to the range in which activity could be retained by maintaining the hydrophilic-lipophilic balance of the molecule. Fisher and Quintana (1975) proposed a mechanism of damage to monomolecular film systems by chlorhexidine. In their proposal, bridge length is important.…”

Section: Discussionmentioning

confidence: 99%

“…Furthermore, increasing the methylene bridge to ten carbons made the agent as active as or more active than the agents of lower lipophilicity (agent 6 compared to agents 7-9). Fisher and Quintana (1975) also postulated that the terminal alkyl chains of biguanides are important to activity by penetrating the hydrophobic region of the film after the biguanide group has attached to the anionic surface, again allowing leakage through the film. In their study, leakage occurred if the terminal groups were six carbons long but not for those three carbons long.…”

Section: Discussionmentioning

confidence: 99%

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Structural Determinants of Activity of Chlorhexidine and Alkyl Bisbiguanides Against the Human Oral Flora

Baker¹,

Coburn

Genco³

et al. 1987

J Dent Res

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We assayed chlorhexidine and a series of its analogues, in which the chlorophenyl terminal substituents were replaced with alkyl chains, for their in vitro antimicrobial activity against the Gram-negative and Gram-positive oral bacteria. Changes in antimicrobial activity were correlated with changes in agent structure for identification of structural criteria which may be important in the optimization of agent activity. Chlorhexidine showed substantial antimicrobial activity against the Gram-negative as well as the Gram-positive oral bacteria. The alkyl agents were comparable with chlorhexidine in their activity against Bacteroides gingivalis and Bacteroides intermedius, black-pigmented Gram-negative obligate anaerobes associated with periodontal disease in adults. Alkyl agents alexidine, heptihexidine (1,6-bis-n-heptylbiguanidohexane), hexoctidine (1,8-bis-n-hexylbiguanidoctane), and hexhexidine (1,6-bis-n-hexylbiguanidohexane), as well as chlorhexidine, were active against Actinobacillus actinomycetemcomitans, a Gram-negative organism associated with localized juvenile periodontitis. Hexidecidine (1,10-bis-n-hexylbiguanidodecane) and heptoctidine (1,8-bis-n-heptylbiguanidooctane) were more active, and hexhexidine was as active as chlorhexidine against Fusobacterium nucleatum, also associated with periodontal disease. Seven of the agents were more active than chlorhexidine against Actinomyces species. All test agents were active against Streptococcus mutans, a Gram-positive coccus associated with dental caries. Hexidecidine had activity equal to that of chlorhexidine when evaluated against the entire battery of organisms. Analysis of structure-activity relationships revealed that alkyl chains could replace chlorophenyl groups with retention or improvement of antimicrobial activity.(ABSTRACT TRUNCATED AT 250 WORDS)

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“…The drug may be inactivated while adsorbed to the tooth since we found that plaque is able to form on the teeth even at high drug concentrations. The model proposed by Fisher and Quintana (1975) for the mode of action of the bisbiguanides can provide a possible mechanism for this inactivation. These authors indicate that the guanylguanidine groups are important in the disruption of the bacterial membrane.…”

Section: Discussionmentioning

confidence: 99%

Alkyl‐bisbiguanides as in vitro inhibitors of bacterial growth and dental plaque formation

Baker

Coburn

Genco

et al. 1979

J of Periodontal Research

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Nine anllogues of chlorhexidine, including Alexidine, in which the p‐chloroophenyl group had bneen replaced by straight or branched alkyl chains were found to be substantive ot saliva coated enamel. These alkyl bisbiguanides were also found to be antimicrobial in a tube dilution assay and tn prevent the formation of plaque in an in vitro plaque assay. Each of these compounds was found to be equal to or greater than chlorhexidine in antimicrobial or plaque inhibition activity against the periodontal organisms, Actinomyces viscosus and A. naeslundii. Against the cariogenic organism, Streptococcus mutans, each of these compounds was active but none had more active than several of the other analogues.

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Surface-Chemical Studies on Chlorhexidine and Related Compounds: II. Interactions with Monomolecular-Film Systems

Cited by 17 publications

References 12 publications

Structural Requirements of Guanide, Biguanide, and Bisbiguanide Agents for Antiplaque Activity

Structural Requirements of Guanide, Biguanide, and Bisbiguanide Agents for Antiplaque Activity

Structural Determinants of Activity of Chlorhexidine and Alkyl Bisbiguanides Against the Human Oral Flora

Alkyl‐bisbiguanides as in vitro inhibitors of bacterial growth and dental plaque formation

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