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I. PRODUCTION, ISOLATION AND PHYSICOCHEMICAL PROPERTIES
RAMESH C. PANDEY, MARGARET W. TOUSSAINT, RONALD M. STROSHANE, CHABI C. ...
1981 Volume 34 Issue 11 Pages
1389-1401
Published: 1981
Released on J-STAGE: April 12, 2006
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A new antitumor antibiotic, fredericamycin A (FCRC-A48, NSC-305263), has been isolated from a strain of
Streptomyces griseus (FCRC-48). Based on its unique ultraviolet-visible spectrum, infrared spectrum, proton and carbon-13 nuclear magnetic resonance spectra and mass spectra, it is judged to be a novel acid-base indicator type of compound. Its production, isolation and physicochemical properties are discussed. The isolation, ultraviolet-visible spectrum and some biological properties of two minor components, fredericamycin B and fredericamycin C, are also described.
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II. BIOLOGICAL PROPERTIES
DANA J. WARNICK-PICKLE, KEVIN M. BYRNE, RAMESH C. PANDEY, RICHARD J. W ...
1981 Volume 34 Issue 11 Pages
1402-1407
Published: 1981
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Fredericamycin A is a novel antibiotic produced by a soil isolate of
Streptonryces griseus (FCRC-48).
In vitro, fredericamycin A exhibits antibacterial, antifungal, and cytotoxic activities.
In vivo, fredericamycin A exhibits very good antitumor activity against P388 mouse leukemia as well as the CD8F mammary tumor and marginal activity against B
16 melanoma. Fredericamycin A failed to demonstrate any interaction with DNA and inhibited protein and RNA synthesis preferentially to DNA synthesis in
Bacillus subtilis and P388 cells.
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AKIRA NAKAGAWA, YUZURU IWAI, HIROSHI HASHIMOTO, NOBUKO MIYAZAKI, RUIKO ...
1981 Volume 34 Issue 11 Pages
1408-1415
Published: 1981
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Virantmycin, a novel chlorine-containing antiviral antibiotic, has been isolated from
Streptomyces nitrosporeus No. AM-2722. The active substance in culture broth is isolated as colorless needles by solvent extraction followed by high performance liquid chromatography on silicic acid. The molecular formula is C
19H
26NO3Cl (molecular weight 351) from the elemental analysis and mass spectrum. The antibiotic possesses antifungal activity and potent inhibitory activity against various RNA and DNA viruses.
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SHOJI OMOTO, HIROKO OGINO, SHIGEHARU INOUYE
1981 Volume 34 Issue 11 Pages
1416-1423
Published: 1981
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Four members of globomycin, SF-1902 A
2, A
3, A
4a and A
4b were newly isolated from the culture of
Streptomyces hygroscopicus SF-1902. These minor components shared four amino acids in common and the fifth was either valine or
allo-isoleucine. The fatty acid moiety varied from 3-hydroxy-2-methylheptanoic acid in A
2 to 3-hydroxy-2-methylundecanoic acids in A
4b. The length of alkyl chain greatly affected the antibacterial activity, and maximum activity was shown by the homologue (A
5) possessing the longest alkyl chain.
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I. PRODUCTION, ISOLATION AND CHARACTERIZATION
JIRO ITOH, SHOJI OMOTO, TAKASHI SHOMURA, HIROKO OGINO, KATSUYOSHI IWAM ...
1981 Volume 34 Issue 11 Pages
1424-1428
Published: 1981
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Oligostatins C, D and E, three new antibiotics were found in the culture filtrate of
Streplomyces my.vogenes nov. sp. SF-1130. Their spectral and chemical properties suggested that oligostatins were basic oligosaccharide antibiotics. They exhibited not only antibacterial activity but also strong amylase inhibitory activity.
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II. STRUCTURES OF OLIGOSTATINS C, D AND E
SHOJI OMOTO, JIRO ITOH, HIROKO OGINO, KATSUYOSHI IWAMATSU, NOBUSUKE NI ...
1981 Volume 34 Issue 11 Pages
1429-1433
Published: 1981
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The structures of oligostatins C, D and E were studied spectrometrically and chemically. Oligostatins C, D and E are pseudo-penta, -hexa and -heptasaccharides with a nitrogen containing glycosidic bond. These antibiotics represent a new series of amylase inhibitors of the saturated basic oligosaccharide.
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SYNTHESIS AND ACTIVITY OF 6-O-(3-AMINO-3-DEOXY-α-D-G LUCOPYRANOSYL)- AND 5-O-(β-D-RIBOFURANOSYL)APRAMYCINS
YOSHIO ABE, SUSUMU NAKAGAWA, TAKAYUKI NAITO, HIROSHI KAWAGUCHI
1981 Volume 34 Issue 11 Pages
1434-1446
Published: 1981
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6-
O-(3-Amino-deoxy-α-D-glucopyranosyl)apramycin (
17) was prepared by glycosidation of a suitably blocked 5, 6-dihydroxy derivative (
11) of apramycin with a blocked 3-aminoglucosyl chloride (
15). Ribosylation of the 5-hydroxy-6-
O-tetrahydropyranyl (THP) derivative (
19) of apramycin gave 5-
O-(β-D-ribofuranosyl)apramycin (
24) along with the 6α (
25) and 6β (
26) isomers. Similar reaction with the 6-hydroxy-5-
OS-THP derivative (
20) or
11 gave only
25 and
26, but not
24.
17 was at least as active as apramycin against most Gram-positive and Gram-negative bacteria tested and more active than apramycin against strains producing aminoglycoside-modifying enzymes. Strains of
Pseudomonas aeruginosa were generally less sensitive to
17 than to apramycin.
24 was the most active of the three ribofuranosyl derivatives prepared though it was less active than
17.
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THE PREPARATION AND COUPLING OF 4-ACYLAMINO-α-OXIMINOBENZENEACETIC ACIDS AND 1, 2-DIHYDRO-6-METHYL-α-OXIMINO-2-OXO-3-PYRIDINEACETIC ACID TO 7-AMINOCEPHALOSPORANIC ACID
JOHN M. DOMAGALA, THEODORE H. HASKELL, H. D. HOLLIS SHOWALTER
1981 Volume 34 Issue 11 Pages
1447-1455
Published: 1981
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A series of 4-acylamino-α-oximinobenzeneacetic acids, and 1, 2-dihydro-6-methyl-α-oximino-2-oxo-3-pyridineacetic acid were prepared and coupled to 7-aminocephalosporanic acid and its 3'-(1-methyltetrazol-5-yl)thiolo analogue. Several coupling methods and oxime protecting groups were thoroughly examined. The best coupling procedure employed dimethylchloroformimini um chloride, and the tetrahydropyranyl (THP) group was selected for oxime protection. The cephalosporins prepared were tested and compared to cefuroxime and cefotaxime. The corresponding α-keto acids, and O-methyl oximes were also examined.
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GIULIANO NANNINI, ETTORE PERRONE, DINO SEVERINO, FERRUCCIO CASABUONA, ...
1981 Volume 34 Issue 11 Pages
1456-1468
Published: 1981
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The synthesis and
in vitro activity of 7-vinylenethioacetamido cephalosporins with a tetrazolo-pyridazine at the 3-position are described. These cephalosporins showed good activity against Gram-positive and Gram-negative bacteria. 7-[(Z)-β-Carboxyvinylenethioacetamido]-3-[(tetrazolo[1, 5-b]pyridazin-8-amino-6-yl)-thiomethyl]-3-cephem-4-carboxylic acid (K 13176, 21) was significantly more active
in vitro and
in vivo than cefazolin against Gramnegative bacteria.
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MASATO TODA, MATSUHISA INOUE, SUSUMU MITSUHASHI
1981 Volume 34 Issue 11 Pages
1469-1475
Published: 1981
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The cephalosporin β-lactamase (cephalosporinase) was purified from a strain of
Proteus morganii which showed resistance to cephalosporins. The optimal pH was about 8.5, and the optimal temperature was 40°C. The isoelectric point was 8.7 and the molecular weight was estimated to be about 41, 000 from sodium dodecyl sulfate-acrylamide gel electrophoresis. The enzyme activity was inhibited by cloxacillin, ampicillin, carbenicillin, cefuroxime, cefotaxime, ceftizoxime (FK749), cefinenoxime (SCE-1365), cefoxitin, cefinetazole, YM09330 and moxalactam (6059-S), but not by clavulanic acid or CP-45899. The β-lactamase also hydrolyzed cephaloridine, cefazolin, cephalothin, cephalexin, cefotiam, cefamandole and benzylpenicillin. These results suggest the possibility that the properties of β-lactamases may be characterized by measuring the kinetic parameters of the enzyme toward newly-introduced β-lactam antibiotics and β-lactamase inhibitors.
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IWAO YAMAZAKI, YOSHIHIRO SHIRAKAWA, TAKESHI FUGONO
1981 Volume 34 Issue 11 Pages
1476-1485
Published: 1981
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The renal excretory mechanism of cefmenoxime in rabbits was compared with that of 6 other cephalosporins (cefotaxime, deacetylcefotaxime, cefotiam, cefazolin, cephaloridine, and cefsulodin). The clearance ratios (C
f-Drug/C
Inulin=CR
f) of cefmenoxime (337) and cefazolin (73) were considerably higher than those of the 5 other cephalosporins (0.9-20). When
p-aminohippurate (PAH) was administered concurrently with each of the cephalosporins, the CR
f values of the cephalosporins except for cefsulodin were significantly decreased. These findings indicate that cefmenoxime and the 5 other cephalosporins except cefsulodin are actively incorporated in the proximal tubular cells and secreted into the tubular lumen. In the case of cefotiam and cefsulodin, glomerular filtration tended to exceed urinary excretion with the highest dose of PAH (40 mg/kg/minute), suggesting the possibility of tubular reabsorption of these drugs. On the other hand, glomerular filtration of cefmenoxime and the 4 other cephalosporins did not exceed urinary excretion. The drug concentration ratio of the cortex to medulla indicated that the tubular cell level of cefmenoxime was lower than, higher than, and similar to those of cephaloridine, cefotaxime, and the remaining cephalosporins, respectively. These results demonstrate that the renal excretory mechanism of cefmenoxime is similar to that of cefazolin but not to that of the remaining cephalosporins.
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B. MALEWICZ, E. BOROWSKI, H. M. JENKIN
1981 Volume 34 Issue 11 Pages
1486-1491
Published: 1981
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Trimethylammonium methyl esters (DMS) of polyene macrolides are products of the methylation of native polyene antibiotics with dimethyl sulfate. We isolated individual components of the DMS-aureofacin complex and characterized their toxicity and activity to induce permeability changes in cell membranes. The DMS-aureofacin complex contained five components readily separated by thin-layer chromatography on polygram cellulose plates. DMS-Aureofacin A, a major component of the complex (90%), showed poor selective toxicity between yeast cells and mammalian cells grown in culture. DMS-Aureofacin B (6%) and DMS-aureofacin E (4%) exhibited very high biological activities and differed qualitatively in selective toxicity. DMS-Aureofacin B was much more active for mammalian cells than for yeast cells. In contrast, DMS-aureofacin E was much more active for yeast cells than for mammalian cells. DMS-Aureofacin C and D were present in the complex in only minute quantities which did not permit their biological characterization.
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AKIHIRO YOSHIMOTO, YASUE MATSUZAWA, YOSHIYUKI MATSUSHITA, TOSHIKAZU OK ...
1981 Volume 34 Issue 11 Pages
1492-1494
Published: 1981
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YASUE MATSUZAWA, TOSHIKAZU OKI
1981 Volume 34 Issue 11 Pages
1495-1497
Published: 1981
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IWAO KITAMURA, HIROYASU TOBE, AKIHIRO YOSHIMOTO, TOSHIKAZU OKI, HIROSH ...
1981 Volume 34 Issue 11 Pages
1498-1500
Published: 1981
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R. J. MEHTA, Y. K. OH, R. D. SITRIN, E. A. SHULTIS, Y. K. OH
1981 Volume 34 Issue 11 Pages
1501-1503
Published: 1981
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KANEMASA KATSU, MATSUHISA INOUE, SUSUMU MITSUHASHI
1981 Volume 34 Issue 11 Pages
1504-1506
Published: 1981
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HIROSHI GUSHIMA, SHUNICHI WATANABE, TAKESHI SAITO, TOSHIO SASAKI, HIDE ...
1981 Volume 34 Issue 11 Pages
1507-1512
Published: 1981
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GOTO NAKAMURA, KIMIKO KOBAYASHI, TOSIO SAKURAI, KIYOSHI SONO
1981 Volume 34 Issue 11 Pages
1513-1514
Published: 1981
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WEN-CHIH LIU, VERA SEINER, LORETTA D. DEAN, WILLIAM H. TREJO, PACIFICO ...
1981 Volume 34 Issue 11 Pages
1515-1516
Published: 1981
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NOBUTAKA IMAMURA, KATSUMI KAKINUMA, NOBUO IKEKAWA, HARUO TANAKA, SATOS ...
1981 Volume 34 Issue 11 Pages
1517-1518
Published: 1981
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