Crystal structure of amikacin

Bau, Robert; Tsyba, Irina

doi:10.1016/s0040-4020(99)00983-7

Cited by 8 publications

(2 citation statements)

References 21 publications

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“…Our group had been successful earlier in using systematic crystallization procedures 9 that have been used widely for the crystallization of macromolecules to obtain crystals of various water-soluble compounds that had never been crystallized before. ,, The idea behind these procedures is to change various crystallization parameters (concentration of sample, concentration of precipitants, nature of solvents, ionic strength, pH, etc.) in a systematic way until optimum conditions for the formation of high-quality crystals are obtained 9b.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure of a Water-Soluble Hexanuclear Silver(I) Nicotinate Cluster Comprised of a “Cyclohexane-Chair”-Type of Framework, Showing Effective Antibacterial and Antifungal Activities: Use of “Sparse Matrix” Techniques for Growing Crystals of Water-Soluble Inorganic Complexes

et al. 2003

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The synthesis of a water-soluble anionic silver 2-mercaptonicotinate complex having effective antibacterial and antifungal properties is described. Its structure has been confirmed to be a hexameric cluster by an X-ray diffraction analysis of a mixed Na(+)/Tris(+) salt (Tris(+) = tris(hydroxymethyl)methylammonium cation). The [Ag(mna)](6)(6-) cluster has a Ag(6)S(6) core and an overall shape of twisted hexagonal cylinder with six sulfur atoms and six silver atoms alternating on a puckered drum-like surface. Each Ag atom is trigonally coordinated by one N and two S ligands. The overall [Ag(mna)](6)(6-).4Na(+).2[(HOCH(2))(3)CNH(3)](+).10H(2)O complex has a layered appearance in the crystal packing diagram, with a [Ag(mna)](6)(-) cluster layer alternating with a solvent layer consisting of sodium atoms, Tris buffer cations, and water molecules. The structure is almost identical to that of a neutral [Ag(Hmna)](6) complex reported earlier. The neutral and charged complexes are both known to possess antimicrobial activities, and some biological properties of these and related compounds are briefly discussed in this paper.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Structure of a Water-Soluble Hexanuclear Silver(I) Nicotinate Cluster Comprised of a “Cyclohexane-Chair”-Type of Framework, Showing Effective Antibacterial and Antifungal Activities: Use of “Sparse Matrix” Techniques for Growing Crystals of Water-Soluble Inorganic Complexes

et al. 2003

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“…There are at least two hypotheses to explain the findings. First, Bau et al described the X-ray crystal structure of amikacin [ 32 ], establishing that the spatial relationship depends on two bifurcated hydrogen (H) bonds that are necessary for the internal conformation of the amikacin molecule. The first H-bond is common with the molecule of kanamycin to control the A/B ring orientation but the second H-bond is required to define the conformational angles around the B/C ring junction.…”

Section: Discussionmentioning

confidence: 99%

Pharmacodynamics of nine generic products of amikacin compared with the innovator in the neutropenic mouse thigh infection model

et al. 2015

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BackgroundPreviously, we validated the mouse thigh infection model to test the therapeutic equivalence of generic antibiotic products. Here, our aim was to compare the in vivo efficacy of amikacin products in clinical use in Colombia using this animal model.ResultsAll except one generic product had the same in vitro potency, judging by the lack of differences on MIC and MBC compared with the innovator. However, eight of nine generic products failed in the neutropenic mouse thigh infection model to achieve the innovator’s maximum effect (Emax ≤ 5.65 for the generics vs. 6.58 log10 CFU/g for the innovator) against Escherichia coli SIG-1, after subcutaneous treatment every 6 h with doses ranging from 1.5 to 3072 mg/kg per day.ConclusionAs we demonstrated previously with other antibiotics such as vancomycin, gentamicin and oxacillin, the generic products of amikacin failed the in vivo efficacy testing. The therapeutic equivalence should be assessed in vivo before clinical approval of generic products.

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