Intermolecular Bonding of the Antibiotic Diumycin

Kirschbaum, Joel; Slusarchyk, William A.; Weisenborn, Frank L.

doi:10.1002/jps.2600590604

Cited by 15 publications

(3 citation statements)

References 14 publications

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“…For example, repeated preparations of 11 wt % 5′DSCG-3C in water at ambient conditions exhibited different crystalline structures seen under cross polars (Figure 5). [56][57][58][59][60][61] Observation of the peak broadening as the concentration of 5′DSCG is increased in D 2 O is consistent with the formation of liquid crystals as a result of self-association or asembly. 62,63 We discovered that molecules such as 5′-monosodium cromoglycate (5′MSCG) or 5′DSCG-EG 2 , both being water-soluble, exhibited similar peak broadening and upfield chemical shifts in their proton NMR spectra (Figures 6 and 7).…”

Section: Nonamphiphilic Molecular Structure Is Needed For Lcsupporting

confidence: 54%

“…Many pharmacologically active compounds exhibit such self-association. Examples include anesthetics, antipsychotics, and antibiotics. − Observation of the peak broadening as the concentration of 5′DSCG is increased in D 2 O is consistent with the formation of liquid crystals as a result of self-association or asembly. , We discovered that molecules such as 5′-monosodium cromoglycate (5′MSCG) or 5′DSCG-EG 2 , both being water-soluble, exhibited similar peak broadening and upfield chemical shifts in their proton NMR spectra (Figures and ). However, no birefringence or sign of LC phases were observed for either of these molecules at any concentration or temperature.…”

Section: Resultsmentioning

confidence: 76%

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Nonamphiphilic Assembly in Water: Polymorphic Nature, Thread Structure, and Thermodynamic Incompatibility

et al. 2009

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Self-assembly of large quantities of entirely water-soluble molecules is entropically challenging. In this work, we describe the design and synthesis of water-soluble aromatic (dichromonyl) molecules that can form nonamphiphilic assemblies and the so-called chromonic liquid crystal phase in water. We discover a new molecule, 5'DSCG-diviol, that exhibits a large birefringent phase, and we show that the formation of this unique class of nonamphiphilic lyotropic liquid crystal shares enormous similarity to the polymorphism observed for crystal formation. Small-angle neutron scattering (SANS) revealed a concentration-independent rod-shaped assembly at concentrations below and above the formation of liquid crystal phase. Adding a small percentage of monoanionic aromatic molecules to the liquid crystal resulted in the elimination of the liquid crystal phase, but addition of dianionic aromatic molecules retained the liquid crystal phase. Together, these results suggest a new assembly structure for nonamphiphilic molecules in water, which is comprised of long threads of small molecules connected by salt bridges stacked over aromatic groups, with the molecular threads heavily hydrated with solvent water. Furthermore, mixing molecules with different structures can result in new liquid crystalline materials, or in segregation of the molecules into different solvation volumes, each of which contains only one type of molecule. The unusual thermodynamic incompatibility of entirely water-soluble molecules also supports the model of molecular threads, in which two polymer-like assemblies do not mix.

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Section: Nonamphiphilic Molecular Structure Is Needed For Lcsupporting

confidence: 54%

Section: Resultsmentioning

confidence: 76%

Nonamphiphilic Assembly in Water: Polymorphic Nature, Thread Structure, and Thermodynamic Incompatibility

et al. 2009

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“…Vancomycin,ristocetin,ristomycetin (2,28), enduracidin (17), moenomycin, prasinomycin, 11,837 RP (14), macarbomycin (29), and several detergents such as deoxycholate and n-octanol (16) dephosphorylation of C,,-isoprenyl pyrophosphate (25). The penicillins and cephalosporins inhibit transpeptidase and carboxypeptidase activity (2,28).…”

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confidence: 99%

Additional Antibiotic Inhibitors of Peptidoglycan Synthesis

Linnett

Strominger

1973

Antimicrob Agents Chemother

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Diumycin, janiemycin, nisin, and subtilin inhibited peptidoglycan synthesis catalyzed by particulate enzyme systems from Bacillus stearothermophilus and Escherichia coli . All of these, except for nisin, also induced accumulation of the lipid intermediate in peptidoglycan synthesis. Concentrations required for 50% inhibition of peptidoglycan synthesis were less than 0.1 μg/ml for diumycin and in the range of 10 to 100 μg/ml for janiemycin, nisin, and subtilin in both organisms. The discrepancy between the extremely low concentration of diumycin required to inhibit the in vitro system from E. coli and the much higher concentration required to inhibit growth of the organism is noteworthy.

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Chemical and biological aspects of a new family of phosphorus‐containing antibiotics

Slusarchyk¹

1971

Biotech & Bioengineering

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The chemical, physical, and biological properties of a group of phosphorus‐containing antibiotics are reviewed. Included in this family of antibiotics are the following compounds or mixtures of compounds: diumycin, macarbomycin, moenomycin, prasinomycin, 803GRP, 11,837RP, and 19,402RP. Among the aspects discussed are: antimicrobial activity in vitro, long duration of activity, toxicity, use in animal nutrition, cross resistance, mode of action, chemical and physical properties, and degradation studies.

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Intermolecular Bonding of the Antibiotic Diumycin

Cited by 15 publications

References 14 publications

Nonamphiphilic Assembly in Water: Polymorphic Nature, Thread Structure, and Thermodynamic Incompatibility

Nonamphiphilic Assembly in Water: Polymorphic Nature, Thread Structure, and Thermodynamic Incompatibility

Additional Antibiotic Inhibitors of Peptidoglycan Synthesis

Chemical and biological aspects of a new family of phosphorus‐containing antibiotics

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