Structural Characterization of Biocidal Oligoguanidines

Feiertag, Petra; Albert, Martin; Ecker-Eckhofen, Eva-M.; Hayn, Gertraud; Hönig, Helmut; Oberwalder, Hanns Wolf; Saf, Robert; Schmidt, Andreas; Schmidt, Oskar; Topchiev, Dmitrij

doi:10.1002/marc.200390085

Cited by 40 publications

(34 citation statements)

References 12 publications

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“…Apart from the ammonium groups, the iminium structures are another common form of the cationic groups, like pyridinium, [22][23][24][25] imidazolium 26,27 and guanidinium salts. 28,29 The difference between ammonium and iminium groups is that the positive charges of the latter ones are delocalized evenly through the π bonds or aromatic conjugated systems, which may influence their adsorptive ability to membrane. For example, Yang and coworkers investigated the antimicrobial activity of polymers bearing different iminium groups (pyridinium and imidazolium groups) and quaternary ammonium group (Table 1).…”

Section: Monomer Designsmentioning

confidence: 99%

Antimicrobial cationic polymers: from structural design to functional control

Yang

Cai

Huang

et al. 2017

Polym J

215

174

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Antimicrobial cationic polymers mainly contain two functional components: the cationic groups and the hydrophobic groups. The antimicrobial activity is influenced by the type, amount, location and distribution of these two components. This review summarizes the designs and syntheses of antimicrobial cationic polymers by controlling the above two factors. It involves the structural designs from primary to secondary structures, from covalent to noncovalent syntheses and from bulk to surface. Furthermore, it will discuss how to advance structural designs toward functional controls for optimizing the antimicrobial performances and biocompatibility of antimicrobial cationic polymers. It is anticipated that this review will provide some guidelines for developing molecular engineering of antimicrobial cationic polymers with tailor-made structures and functions.

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Section: Monomer Designsmentioning

confidence: 99%

Antimicrobial cationic polymers: from structural design to functional control

Yang

Cai

Huang

et al. 2017

Polym J

215

174

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“…ATPase) resulting in cytoplasmic membrane disruption (4,5). Akacid-medical-formulation (AMF) (Poly-[2-(2-ethoxy)-ethoxyethyl)-guanidinium-chloride]) is a novel oligoguanidine that is prepared by polycondensation of equimolar amounts of guanidine hydrochloride and 1,2-bis(2-aminoethoxy)ethane and exerts its biocidal activity against airborne and surface microorganisms including bacteria, viruses, fungi, and molds (6).…”

Section: Introductionmentioning

confidence: 99%

Akacid-medical-formulation, a novel biocidal oligoguanidine with antitumor activity reduces S-phase in prostate cancer cell lines through the Erk 1/2 mitogen-activated protein kinase pathway

Neuwirt

Müller²,

Cavarretta³

et al. 2006

Int J Oncol

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Abstract. Oligomeric guanidines are highly efficient biocides against a broad spectrum of microorganisms. However, their antitumor effects have not been studied so far. We investigated an antiproliferative effect of Akacid-medical-formulation (AMF), a member of the oligoguanidine family of biocides, against solid cancer cell lines and primary cells by measuring [3 H]-thymidine incorporation. Additionally, we examined cell cycle distribution in two AMF-sensitive prostate cancer cell lines (DU-145, LNCaP) using flow cytometry. Finally, the influence of AMF on cell cycle regulatory molecules and intracellular kinase cascade-related signaling molecules was assessed. We found that AMF has variable antiproliferative effects on all tested cells. In DU-145 and LNCaP cells, flow cytometric studies showed a reduction of S-phase with a maximum extent of 24 and 58%, respectively. This was associated with a decrease in expression of cyclin D1, cyclindependent kinases 2 and 4, while having varying effects on expression of cyclin E and p27. Additionally, reduced phosphorylation of Erk1 and Erk2 was found, whereas expression of phospho-Akt1 remained unchanged. Herein we report for the first time that AMF exerts potent antiproliferative activity against various malignant cell lines, including those of prostate. We therefore recommend further investigation of the anticancer activity of this biocidal oliguanidine.

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“…and diamines provided complex mixtures of linear and cyclic oligoguanidines between 540 and 1250 MW and their MICs were determined against several microorganisms [76,77]. An average MW of 800 afforded as good or better activities than Vantocil, a standard disinfectant, while lower MWs and the use of longer diamine chains or guanidinium carbonate salts resulted in decreased activity [76].…”

Section: Oligoguanidines-polycondensation Of Guanidinium Salts (Chlormentioning

confidence: 99%

Infectious disease: Connecting innate immunity to biocidal polymers

Gabriel

Som

Madkour

et al. 2007

Materials Science and Engineering: R: Reports

253

258

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Infectious disease is a critically important global healthcare issue. In the U.S. alone there are 2 million new cases of hospital-acquired infections annually leading to 90,000 deaths and 5 billion dollars of added healthcare costs. Couple these numbers with the appearance of new antibiotic resistant bacterial strains and the increasing occurrences of community-type outbreaks, and clearly this is an important problem. Our review attempts to bridge the research areas of natural host defense peptides (HDPs), a component of the innate immune system, and biocidal cationic polymers. Recently discovered peptidomimetics and other synthetic mimics of HDPs, that can be short oligomers as well as polymeric macromolecules, provide a unique link between these two areas. An emerging class of these mimics are the facially amphiphilic polymers that aim to emulate the physicochemical properties of HDPs but take advantage of the synthetic ease of polymers. These mimics have been designed with antimicrobial activity and, importantly, selectivity that rivals natural HDPs. In addition to providing some perspective on HDPs, selective mimics, and biocidal polymers, focus is given to the arsenal of biophysical techniques available to study their mode of action and interactions with phospholipid membranes. The issue of lipid type is highlighted and the important role of negative curvature lipids is illustrated. Finally, materials applications (for instance, in the development of permanently antibacterial surfaces) are discussed as this is an important part of controlling the spread of infectious disease.

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Structural Characterization of Biocidal Oligoguanidines

Cited by 40 publications

References 12 publications

Antimicrobial cationic polymers: from structural design to functional control

Antimicrobial cationic polymers: from structural design to functional control

Akacid-medical-formulation, a novel biocidal oligoguanidine with antitumor activity reduces S-phase in prostate cancer cell lines through the Erk 1/2 mitogen-activated protein kinase pathway

Infectious disease: Connecting innate immunity to biocidal polymers

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