Arrhenius parameters for the alkaline hydrolysis of esters in aqueous solution. Part III. Methyl betaine methyl ester

Wright, Margaret Robson

doi:10.1039/j29680000548

Cited by 22 publications

(15 citation statements)

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“…Betaine esters show a strongly pH dependent hydrolysis behavior [10][11][12]17,18], as illustrated in Fig. 1.…”

Section: Dodecyl Betainate/dodecanol/betaine Hydrochloride/ D 2 O Phamentioning

confidence: 99%

Studies on dodecyl betainate in combination with its degradation products or with phosphatidyl choline–phase behavior and hemolytic activity

Lundberg

Ljusberg‐Wahren

Norlin

et al. 2004

Journal of Colloid and Interface Science

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“…Betaine esters show a strongly pH dependent hydrolysis behavior [10][11][12]17,18], as illustrated in Fig. 1.…”

Section: Dodecyl Betainate/dodecanol/betaine Hydrochloride/ D 2 O Phamentioning

confidence: 99%

Studies on dodecyl betainate in combination with its degradation products or with phosphatidyl choline–phase behavior and hemolytic activity

Lundberg

Ljusberg‐Wahren

Norlin

et al. 2004

Journal of Colloid and Interface Science

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“…The release of the attached bacterial cells is dependent on the conversion of cationic pCBMA-1 C2 into zwitterionic pCBMA-1. It is known that the hydrolysis rate of betaine esters is influenced by several factors, such as the length of the spacer between the quaternary amine and the carboxyl groups, [27] the nature of the hydrolyzable group, temperature, [28] and pH value. The majority of polymer chains of the ester group used in this work were hydrolyzed.…”

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confidence: 99%

A Switchable Biocompatible Polymer Surface with Self‐Sterilizing and Nonfouling Capabilities

et al. 2008

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Microbial adhesion onto implanted biomaterials and the subsequent formation of biofilms is one of the major causes of biomedical device failure. The use of antimicrobial and nonfouling coatings are two strategies for the prevention of the attachment and spreading of microorganisms on the surfaces of implantable materials. Antimicrobial surfaces containing covalently linked quaternary ammonium compounds (QACs) have proved to be able to efficiently kill a variety of microorganisms. [1][2][3][4][5][6][7] A major problem with QAC surfaces is the attachment of dead microorganisms remaining on antimicrobial coatings, which can trigger an immune response and inflammation, and block its antimicrobial functional groups. In addition, such antimicrobial coatings can not fulfill the requirements of nonfouling [8] and biocompatibility as implantable biomaterials. Poly(ethylene glycol) (PEG) derivatives [9][10][11][12][13][14] or zwitterionic polymers [15][16][17][18] have been extensively used as nonfouling materials to reduce bacterial attachment and biofilm formation. However, the susceptibility of PEG to oxidation damage has limited its long-term application in complex media. [11,19] We recently showed that zwitterionic materials such as poly(sulfobetaine methacrylate) (pSBMA) were able to dramatically reduce bacterial attachment and biofilm formation [18] and were highly resistant to nonspecific protein adsorption, even from undiluted blood plasma and serum. [20][21][22][23][24] Although zwitterionic coatings can reduce the initial attachment and delay colonization of microbes on surfaces, there is a possibility of introducing pathogenic microbes into the patient during implantation operations and catheter insertions, which results in the failure of implanted devices; the use of antimicrobial agents will then be necessary to eliminate these microbes. Surface-responsive materials have been developed for a broad spectrum of applications, [25] but it is still a great challenge to develop biocompatible materials that have both antimicrobial and nonfouling capabilities. To the best of our knowledge, no such materials have been reported to date.Herein we report a new switchable polymer surface coating, which combines the advantages of both nonfouling and cationic antimicrobial materials and overcomes their disadvantages (Figure 1). In this system, poly(N,N-dimethyl-N-(ethoxycarbonylmethyl)-N-[2'-(methacryloyloxy)ethyl]-ammonium bromide) (pCBMA-1 C2, cationic precursor) on a surface can kill greater than 99.9 % of Escherichia coli K12 in one hour, and 98 % of the dead bacterial cells can be released when the cationic derivatives are hydrolyzed to nonfouling zwitterionic polymers. pCBMA-1 C2 and control coatings were grafted by surface-initiated atom transfer radical polymerization (ATRP) onto a gold surface covered with initiators. The thicknesses of the obtained polymer coatings, as measured by atomic force microscopy (AFM), [26] were 26-32 nm (Table 1).The bactericidal activity of pCBMA-1 C2 surfaces was determined using E. co...

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“…1). Although the increased rate of base-catalyzed hydrolysis of lower esters of this structure has been investigated and is understood to be caused by an inductive effect from the positive charge (5,26), this property does not seem to have been considered in connection with biological (10,27) or recent surface chemical (4,25) studies of compounds of this type. In the present paper, we describe the synthesis of some esters between betaine (trimethylglycine) and long-chain fatty alcohols, their antimicrobial activities, and their rates of hydrolysis.…”

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confidence: 99%

Antimicrobial activity of betaine esters, quaternary ammonium amphiphiles which spontaneously hydrolyze into nontoxic components

Lindstedt

Allenmark

Thompson

et al. 1990

Antimicrob Agents Chemother

115

100

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A series of quaternary ammonium compounds that are esters of betaine and fatty alcohols with hydrocarbon chain lengths of 10 to 18 carbon atoms were tested with respect to antimicrobial activities and rates of hydrolysis. When the tetradecyl derivative was tested against some selected microorganisms, the killing effect was comparable to that of the stable quaternary ammonium compound cetyltrimethylammonium bromide. At higher pH values, both the antimicrobial effect and the rate of hydrolysis of the esters increased. However, whereas at pH 6 greater than 99.99% killing of Salmonella typhimurium was achieved with 5 ,ug/ml in 3 min, the rate of hydrolysis was less than 20% in 18 h. At pH 7, a similar killing effect was achieved in 2 min and 50% hydrolysis occurred in ca. 5 h. Thus, it is possible to exploit the rapid microbicidal effect of the compounds before they hydrolyze. The rate of hydrolysis was reduced by the presence of salt. The bactericidal effect of the betaine esters increased with the length of the hydrocarbon chain of the fatty alcohol moiety up to 18 carbon atoms. Since the hydrolysis products are normal human metabolites, the hydrolysis property may extend the use of these quaternary ammonium compounds as disinfectants and antiseptics for food and body surfaces.The membrane-disruptive and antimicrobial activities of cationic surfactants are well recognized. These agents are often active against a broad range of bacteria and other cells and can also inactive certain viruses (16,29). Because of their high affinity for biological membranes, these agents show a low selectivity and can be damaging to a variety of mammalian cells (17,23,24).Since the time needed to kill microorganisms with cationic surfactants is usually short, it could be expected that side effects in the host might be decreased by the use of substances that are subject to hydrolytic degradation. However, the lifetime of the compounds must be sufficiently long to allow proper inactivation of the undesired microorganisms. The products obtained in the degradation steps should also be significantly less toxic than the original compound and should ideally constitute normal metabolites of the host.To explore the possible use of degradable cationic surfactants, we studied a series of amphiphilic betaine esters (Fig. 1). Although the increased rate of base-catalyzed hydrolysis of lower esters of this structure has been investigated and is understood to be caused by an inductive effect from the positive charge (5, 26), this property does not seem to have been considered in connection with biological (10,27) or recent surface chemical (4, 25) studies of compounds of this type. In the present paper, we describe the synthesis of some esters between betaine (trimethylglycine) and long-chain fatty alcohols, their antimicrobial activities, and their rates of hydrolysis. MATERIALS AND METHODSCompounds investigated. The betaine esters were obtained as chlorides by chloroacetylation of the corresponding longchain alcohol, principally as described by Ho...

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Arrhenius parameters for the alkaline hydrolysis of esters in aqueous solution. Part III. Methyl betaine methyl ester

Cited by 22 publications

References 0 publications

Studies on dodecyl betainate in combination with its degradation products or with phosphatidyl choline–phase behavior and hemolytic activity

Studies on dodecyl betainate in combination with its degradation products or with phosphatidyl choline–phase behavior and hemolytic activity

A Switchable Biocompatible Polymer Surface with Self‐Sterilizing and Nonfouling Capabilities

Antimicrobial activity of betaine esters, quaternary ammonium amphiphiles which spontaneously hydrolyze into nontoxic components

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