The Structure of Anthramycin

Leimgruber, W.; Batcho, Andrew D.; Schenker, F.

doi:10.1021/ja00952a051

Cited by 133 publications

(48 citation statements)

References 3 publications

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“…In this communication, the isolation, characterization and structural elucidation of mazethramycin and its derivatives are reported. The structure of mazethramycin has been confirmed to be an N-methyl derivative of anthramycinl, 2) Mazethramycin (I) was produced in a shaking culture of the strain ME561-L4 at 27°C in a medium containing 2.5% glycerol, 0.5% meat extract, 0.5% Polypepton, 1.0% yeast extract, 0.2% NaCl, 0.05% MgSO4 • 7H2O, 0.05% K2HPO4 and 0.32% CaCO3 adjusted to pH 7.4. After 96-hour cultivation, the cultured broth (3.53 liters) was filtered.…”

Section: The Journal Of Antibiotics Mazethramycin a New Member Of Anmentioning

confidence: 92%

Mazethramycin, a new member of anthramycin group antibiotics.

Kunimoto¹,

Masuda²,

Kanbayashi³

et al. 1980

J. Antibiot.

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Section: The Journal Of Antibiotics Mazethramycin a New Member Of Anmentioning

confidence: 92%

Mazethramycin, a new member of anthramycin group antibiotics.

Kunimoto¹,

Masuda²,

Kanbayashi³

et al. 1980

J. Antibiot.

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“…The observation that NBZDs are present in human brain samples stored since 1940 [30], when benzodiazepines were not yet synthesized, clearly indicates that NBZDs do not derive from environmental pollution by synthetic benzodiazepines, which entered the market only in 1959. Several attempts to find out the endogenous biosynthetic pathways of NBZD production have been made [31][32][33][34]. However, an endogenous biochemical pathway of NBZDs has not yet been identified in mammalian cells [33] while it has been found that microorganisms like Streptomyces and Penicillium can synthesize molecules like anthramycin and cyclopeptine, respectively, both containing the basic 1,4-benzodiazepine structure [35].…”

Section: Natural Benzodiazepinesmentioning

confidence: 99%

Management of Hepatic Encephalopathy: Role of Rifaximin

Zeneroli

Avallone²,

Corsi³

et al. 2005

Chemotherapy

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Hepatic encephalopathy (HE) is a neuropsychiatric syndrome, which develops in patients with acute or chronic liver failure. It is widely accepted to be due to impairment of hepatic clearance of toxic products from the gut such as ammonia. Accumulation of ammonia induces a glutamate neurotoxicity leading to an increased tone of the γ-aminobutyric acid A (GABA-A) receptor system in the brain which results in HE. Factors either increasing the ammonia levels (protein load, constipation, sepsis, or gastrointestinal bleeding) or potentiating the functional activity of the GABAergic system [natural benzodiazepine-like compounds (NBZDs) or exogenous benzodiazepines] may act as precipitating factors of HE. NBZDs are present in trace amounts in the blood of normal subjects and have been found to be increased in the blood of patients with liver cirrhosis, with or without HE. These compounds may derive either from the diet since they have been found in plants, vegetables and animals or from gut bacteria. The observation that intestinal bacterial flora is involved in the production of both primary agent of HE (ammonia) and precipitating factors (NBZDs) suggests that the use of nonabsorbable antibiotics such as rifaximin may be useful in preventing episodes of HE in patients with liver cirrhosis.

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“…Anthramycin was isolated as a pure substance and its chemical structure was confirmed by synthesis (Leimgruber, Stefanovic, Schenker, Karr & Berger, 1965;Leimgruber, Batcho & Schenker, 1965). The antibiotic has ant|tumor and antiprotozoal activity.…”

Section: Introductionmentioning

confidence: 99%

Structural investigations of mode of action of drugs. II. Molecular structure of anthramycin methyl ether monohydrate

Arora¹

1979

Acta Crystallogr Sect B

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The crystal and molecular structure of CxTHt9N304. H20, an ant|tumor agent, has been determined using X-ray diffraction. The space group is orthorhombic, P2~ 2 ~ 21. The cell dimensions, measured on a diffractometer, are a = 7.984 (1), b = 13.495 (3), c = 16.200 (3) A, and Z = 4. The structure was solved by direct methods and refined by anisotropic least squares to an R index of 0.050. The 1,4-diazepine ring has a boat conformation while the five-membered pyrrole ring is a flattened envelope. The stereochemistry at C(12) and C (13) is trans. There are one intramolecular and five intermolecular hydrogen bonds. One interesting feature is the involvement of the methoxy O atom in hydrogen bonding. A Kendrewmodels study indicates that the anthramycin molecule is most probably covalently bound at C(11) to DNA through N(2) of guanine in the wide groove and also O(1) of the anthramycin molecule may be involved in hydrogen bonding to sugar O atoms.

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The Structure of Anthramycin

Cited by 133 publications

References 3 publications

Mazethramycin, a new member of anthramycin group antibiotics.

Mazethramycin, a new member of anthramycin group antibiotics.

Management of Hepatic Encephalopathy: Role of Rifaximin

Structural investigations of mode of action of drugs. II. Molecular structure of anthramycin methyl ether monohydrate

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