The chemistry of biguanides

Kurzer, Frederick; Pitchfork, Ernest D.

doi:10.1007/bfb0050853

Cited by 31 publications

(21 citation statements)

References 211 publications

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“…Assuming that the positive charge in the monoprotonated biguanide is completely delocalized over the four -NH 2 groups, it might be expected that the N(00) lone pair of electrons would still be able to function as an acceptor in a hydrogen bond. The apparently low affinity of N(00) in BgH ÷ for coordination with H observed here may reflect the large difference between the first and second dissociation constants (Kurzer & Pitchfork, 1968):…”

mentioning

confidence: 75%

Biguanide hydrochloride

Ernst¹

1977

Acta Crystallogr B Struct Sci

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mentioning

confidence: 75%

Biguanide hydrochloride

Ernst¹

1977

Acta Crystallogr B Struct Sci

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“…Conventional antimicrobial susceptibility testing by the spread plate method was conducted as described previously (8 (11). The same reaction in different solvents (DMF and water) also was not successful, though in DMF a very small amount of the acrylate monomer VI was produced.…”

Section: Methodsmentioning

confidence: 99%

New polymeric biocides: synthesis and antibacterial activities of polycations with pendant biguanide groups

Ikeda¹,

Yamaguchi²,

Tazuke³

1984

Antimicrob Agents Chemother

191

142

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Acrylate monomers with pendant biguanide groups were successfully synthesized, and their homopolymers and copolymers were prepared with acrylamide. These cationic disinfectants of polymeric forms exhibited high antibacterial activity against gram-positive bacteria, whereas they were less active against gram-negative bacteria. It was found that the activity of the polymeric disinfectants was much higher than that of the monomeric species, and the difference in activity between the polymers and the monomers was discussed on the basis of their contributions to each elementary process of the lethal action.

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“…The general family of compounds that includes biguanide (1) has been known for over 100 years (1)(2)(3). 3 Members of the family have important applications as medicines, as ligands in coordination chemistry, as bases, and as precursors for the synthesis of various heterocyclic compounds (4).…”

Section: Introductionmentioning

confidence: 99%

Hydrogen-bonded networks in crystals built from bis(biguanides) and their salts

Lebel¹,

Maris²,

Wuest³

2006

Can. J. Chem.

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Biguanide groups and biguanidinium cations incorporate multiple sites that can donate or accept hydrogen bonds. To assess their ability to associate and to direct the formation of extended hydrogen-bonded networks, we examined the structure of crystals of four compounds in which two neutral biguanide groups or the corresponding cations are attached to the 1,4-and 1,3-positions of phenylene spacers. As expected, all four structures incorporate extensive networks of hydrogen bonds and reveal other reliable features. In particular, (1) neutral biguanide groups favor a roughly planar conformation with an intramolecular hydrogen bond, and they associate as hydrogen-bonded pairs, (2) despite coulombic repulsion, biguanidinium cations can also associate as hydrogen-bonded pairs, and (3) the 1,3-phenylenebis(biguanidinium) dication favors a pincerlike conformation that allows chelation of suitable counterions. However, the precise patterns of hydrogen bonding in the structures vary substantially, limiting the usefulness of biguanide and biguanidinium as groups for directing supramolecular assembly. Résumé :Des groupes biguanide et des cations biguanidinium incorporent de multiples sites qui peuvent donner ou accepter des liaisons hydrogène. Dans le but d'évaluer la capacité d'associer et de diriger la formation de réseaux étendus de liaisons hydrogène, on a étudié la structure cristalline de quatre composés dans lesquels deux groupes biguanide neutres, ou les cations correspondants, sont attachés aux positions 1,4-et 1,3-de groupes phénylènes. Comme prévu, les quatre structures permettent d'incorporer des réseaux de liaisons hydrogène et mettent en évidence d'autres caracté-ristiques fiables. En particulier, 1) les groupes biguanide neutres favorisent une conformation pratiquement plane avec une liaison hydrogène intramoléculaire et s'associent sous la forme de paires réunies par des liaisons hydrogène, 2) malgré une répulsion coulombique, les cations biguanidinium peuvent aussi former des paires associées par des liaisons hydrogène et 3) le dication phénylène-1,3-bis(biguanidinium) favorise une conformation en forme de pince qui permet d'effectuer une chélation avec des contre-ions appropriés. Toutefois, les régimes précis des liaisons hydrogène varient d'une façon substantielle, ce qui limite l'utilité des groupes biguanide et biguanidinium comme unités pouvant orienter un assemblage supramoléculaire.

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The chemistry of biguanides

Cited by 31 publications

References 211 publications

Biguanide hydrochloride

Biguanide hydrochloride

New polymeric biocides: synthesis and antibacterial activities of polycations with pendant biguanide groups

Hydrogen-bonded networks in crystals built from bis(biguanides) and their salts

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