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AKIRA ENDO, OSAMU HAYASHIDA, SHIGEO MURAKAWA
1983 Volume 36 Issue 3 Pages
203-207
Published: 1983
Released on J-STAGE: April 12, 2006
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Mutastein, a new inhibitor of glucosyltransferases (GTase) of
Streptococcus mutans, was isolated from cultural broth of
Aspergillus terreus M3328. Mutastein was a heat-stable protein and was sensitive to pronase digestion. In the formation of glucans, that of adhesive water-insoluble glucans of
S. mutans was specifically inhibited by mutastein.
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I. DISCOVERY AND BIOLOGICAL ACTIVITY
D. L. PRUESS, M. KELLETT
1983 Volume 36 Issue 3 Pages
208-212
Published: 1983
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Streptomyces clavuligerus NRRL 3585, a culture which produces a variety of β-lactam antibiotics in the penicillin, cephalosporin and clavam families, was found to produce a new β-lactam antibiotic, Ro 22-5417. The compound, which was neither a substrate for nor inhibitor of several β-lactamases, showed antimicrobial activity in defined minimal medium but little or no inhibitory activity in nutrient-rich medium. The activity was bacteriostatic against
Bacillus species ATCC 27860 and was antagonized by D- and L-methionine, L-cystathionine, L-homocystine and
O-acetyl-L-homoserine but not by L-homoserine, L-aspartate, L-cysteine or other common amino acids, vitamins and nucleosides. Our results are consistent with Ro 22-5417 acting as an inhibitor in methionine biosynthesis.
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II. FERMENTATION, ISOLATION AND STRUCTURE
R. H. EVANS Jr., H. Ax, A. JACOBY, T. H. WILLIAMS, E. JENKINS, J. P. S ...
1983 Volume 36 Issue 3 Pages
213-216
Published: 1983
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The purification of a new antibiotic, Ro 22-5417, was achieved by a variety of preparative column chromatographic methods. The antibiotic was obtained crystalline with an overall recovery of 3% after a 300-fold purification. The structure was determined from proton and
13C NMR spectra to be 3-(7-oxo-l-aza-4-oxabicyclo[3.2.0]hept-3-yl)alanine.
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III. ABSOLUTE STEREOCHEMISTRY
JEAN-CLAUDE MÜLLER, VOLDEMAR TOOME, DAVID L. PRUESS, JOHN F. BLOU ...
1983 Volume 36 Issue 3 Pages
217-225
Published: 1983
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The complete stereostructure of the new antibiotic Ro 22-5417 has been established as 3-[(3
S, 5
S)-7-oxo-1-aza-4-oxabicyclo[3.2.0]hept-3-yl]-L-alanine. This result together with the synthesis of an (3
R, 5
R)-L-analog allowed us to postulate that clavams require the
R-configuration at the ring juncture for β-lactamase inhibitory activity, while the opposite
S-stereochemistry is essential for antifungal activity.
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ISOLATION OF DEOXYPENTALENYLGLUCURON
SHUJI TAKAHASHI, MICHIKO TAKEUCHI, MAMORU ARAI, HARUO SETO, NOBORU OTA ...
1983 Volume 36 Issue 3 Pages
226-228
Published: 1983
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Deoxypentalenylglucuron was isolated from the culture broths of three different strains, such as
Streptomyces omiyaensis, S. albofaciens and
S. viridifaciens. The structure of deoxypentalenylglucuron has been determined by
1H and
13C NMR, mass spectroscopy and by chemical correlation to be an oxidation product of pentalenene 1. Deoxypentalenylglucuron (1) has some antitumor activity against Sarcoma 180 in mice.
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KATSUYOSHI IWAMATSU, SHIGEHARU INOUYE, TAKASHI TSURUOKA, KAZUKO MIZUTA ...
1983 Volume 36 Issue 3 Pages
229-241
Published: 1983
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C-7 and C-3 substituents of a new antibiotic SF-1623 were chemically modified to improve the bioactivity, and substituent effect at C-7 and C-3 was examined on the basis of MIC and ED
50 values against selected bacteria. Among a large number of derivatives, MT-141 possessing 2-D-2-amino-2-carboxyethylthioacetamido residue at C-7 and
N-methyltetrazolylthiomethyl residue at C-3 showed a high order of antibacterial activity
in vitro and especially
in vivo.
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NAOHIKO YASUDA, HISAO IWAGAMI, EIJI NAKANISHI, TERUAKI NAKAMIYA, YUKIO ...
1983 Volume 36 Issue 3 Pages
242-249
Published: 1983
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The synthesis and antibacterial activity of a series of β-lactam antibiotics having a 5-carboxyimidazole-4-carbonyl group attached through an amide linkage to ampicillin, cephaloglycin or their analogs are described. Some compounds of this series were found to possess high activity against
Pseudomonas and other Gram-negative bacteria.
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M. PHILIPPE, B. QUICLET-SIRE, A. M. SEPULCHRE, S. D. GERO, H. LOIBNER, ...
1983 Volume 36 Issue 3 Pages
250-255
Published: 1983
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The synthesis of 1-deaminogentamicin C
2 described here, uses 3, 2′, 6′, 3″-tetrakis-
N-tert-butoxycarbonylgentamicin C
2 (
2) as intermediate.
N-Formylation of
2 followed by per-
O-acetylationn and dehydration furnished the isocyanide
5. Radical-induced deamination of the latter using tri-
n-butylstannane and removal of the protecting groups afforded the target 1-deaminogentamicin C
2 (
7). Its
in vitro antibacterial activity is less than that of the parent gentamicin C
2. The behaviour of
7 towards minoglycoside-inactivating enzymes was also examined; interestingly, it was found to be neither substrate nor inhibitor for such enzymes. These results strongly suggest that the substitution pattern of the 1-position determines the biological properties of the aminoglycoside antibiotics.
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JACK TADANIER, ROBERT HALLAS
1983 Volume 36 Issue 3 Pages
256-266
Published: 1983
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Syntheses of the 3-
O-demethyl-2, 3-di-
epi-fortimicins A and B and the 3-
O-demethyl-3-
epi-fortimicins A and B have been accomplished in processes the key steps of which were solvolyses of 4-
N-acetyl-3-
O-demethyl-3-
O-methanesulfonylfortimicin derivatives. Antibacterial activities of the new antibiotics are reported.
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JACK TADANIER, ROBERT HALLAS, JAMES HOLMS, LESLIE A. FREIBERG, DAVID B ...
1983 Volume 36 Issue 3 Pages
267-275
Published: 1983
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Selective reactions of 3-
O-demethyl-3-
O-methanesulfonyl-4-
N, 5-
O-methylenefortimicin derivatives have been used as the key steps in the syntheses of 3-amino-3-demethoxyfortimicin A and the C-2 epimeric 2-amino-3-
O-demethyl-2-deoxyfortimicins A.
In vitro antibacterial activities of the new fortimicin derivatives are reported.
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TOTAL SYNTHESES OF THE ANTITUMOR ANTIBIOTICS, E- AND Z-TOMAYMYCINS
ZENZABURO TOZUKA, HISASHI TAKASUGI, TAKAO TAKAYA
1983 Volume 36 Issue 3 Pages
276-282
Published: 1983
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The total syntheses of naturally occurring
E-tomaymycin (
1E) and its olefinic geometrical isomer,
Z-tomaymycin (
1Z) are described. The
Z-isomer was found to have the same antibacterial activity as
E-isomer (
1E).
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HARUO IKEDA, MASAHARU INOUE, SATOSHI OMURA
1983 Volume 36 Issue 3 Pages
283-288
Published: 1983
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Three macrolide antibiotic-producing strains, the spiramycin producer
Streptomyces ambofaciens, the tylosin producer
Streptomyces fradiae, and the cirramycin producer
Streptomyces cirratus easily formed protoplasts when treated with lysozyme in hypertonic medium. Each type of protoplast was regenerated to a mycelial form at a frequency of 90 to 100% in regeneration medium supplemented with a plasma expander. In the spiramycin producer
S. ambofaciens and the tylosin producer
S. fradiae, antibiotic productivities of the regenerated progeny were drastically changed. Some regenerated progeny from the three strains gave higher production. One from
S. ambofaciens showed about twice the productivity of the original strain and one obtained after two rounds of protoplast regeneration from
S. fradiae produced about three times as much as the original strain.
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IV. BACTERICIDAL ACTION OF THE COMPONENT VA-2
KATO TANI, TOUTARO YAMAGUCHI
1983 Volume 36 Issue 3 Pages
289-295
Published: 1983
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The action of VA-2, the most active component of antibiotic M-92, against
S. aureus is bactericidal but not bacteriolytic. The bactericidal action is markedly affected by incubation temperature, whether bacterial cells are prolific or resting. The bactericidal kinetics of VA-2 is biphasic, since addition of VA-2 caused rapid and straight decrease in viability curve and reached a plateau after several minutes. The bactericidal activity of VA-2 is blocked by 2, 4-dinitrophenol. Alike to many membrane-active bacteriocins, VA-2 seems to exert its action through two stages.
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HIROMI SAKAMOTO, HISAE KAWAMITSU, MASANAO MIWA, MASAAKI TERADA, TAKASH ...
1983 Volume 36 Issue 3 Pages
296-300
Published: 1983
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The cytotoxic effects of bleomycin on HeLa cells in culture were enhanced by incubation of the cells with benzamide, a potent inhibitor of poly(ADP-ribose) polymerase, at concentrations at which benzamide alone did not show any cytotoxicity. Benzamide plus bleomycin display enhanced therapeutic effects against Ehrlich ascites tumor cells
in vivo. On daily treatment with various doses of bleomycin plus benzamide for 10 days, mice with Ehrlich ascites tumors survived longer than mice on treatment with bleomycin alone.
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KANKI KOMIYAMA, KEN-ICHI EDANAMI, AKIRA TANOH, HIROSHI YAMAMOTO, IWAO ...
1983 Volume 36 Issue 3 Pages
301-311
Published: 1983
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Stubomycin showed direct cytotoxic activity on mammalian cells, yeast, and fungi, and rapid hemolytic activity on mouse erythrocytes. The rate and extent of the cytotoxic and hemolytic activities decreased at lower temperatures. Studies with radioactive precursors revealed that a marginal cytocidal concentration of the antibiotic inhibited synthesis of DNA, RNA, and protein of leukemic cells at almost the same rate. Stubomycin did not show any mutagenicity on mammalian cells and bacteria
i.e. the induction of revertants on six bacterial strains, and chromosomal aberrations, sister chromatid exchanges, and the induction of cells resistant to 6-thioguanine on Chinese hamster cells (DON D-6). The antagonistic effect of various kinds of lipids including phospholipids, cholesterol, olive oil and squalene was studied. Significant antagonism of stubomycin against anti-Saccharomyces cerevisiae activity was observed with phospholipids except for egg lecithin and with cholesterol. The primary action of the antibiotic seems to be to change the cell surface and ultimately the lysis and death of the cells.
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SETSUKO KUNIMOTO, KEIKO MIURA, YOSHIKAZU TAKAHASHI, TOMIO TAKEUCHI, HA ...
1983 Volume 36 Issue 3 Pages
312-317
Published: 1983
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Intracellular levels of 4'-
O-tetrahydropyranyladriamycin (THP) and adriamycin (ADM) were measured by a fluorospectroscopic method, and the former was shown to be taken up by L5178Y cells much faster than ADM; the uptake velocity of THP at 1 μg/ml was calculated to be about 170 times faster than that of ADM. High performance liquid chromatography of cell extracts indicated that THP exists mainly in nuclei intact without hydrolysis. The effect of THP in inhibiting [
3H]thymidine incorporation into DNA also indicated that THP taken up by cells rapidly went to nuclei and inhibited DNA synthesis. Fifty percent inhibition concentrations of THP or ADM on [
3H]-thymidine incorporation during a 60-minute period, 15 minutes after the addition, were 0.1 μg/ ml and 4.2 μg/ml, respectively. Similar results were obtained when L1210 cells were used in place of the L5178Y cells.
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HIROSHI NAKAYAMA, AKIRA SHIMAZU, HARUO SETO, NOBORU OTAKE
1983 Volume 36 Issue 3 Pages
318-320
Published: 1983
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KIMIHIRO WATANABE, TORU OKUDA, KAZUTERU YOKOSE, TAMOTSU FURUMAI, HIROM ...
1983 Volume 36 Issue 3 Pages
321-324
Published: 1983
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ALFREDO AGUILAR, FERNANDO BAQUERO, JOSE L. MARTÍNEZ, CARLOS ASE ...
1983 Volume 36 Issue 3 Pages
325-327
Published: 1983
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LEONARDO M. CAPPELLETTI, ROBERTO SPAGNOLI
1983 Volume 36 Issue 3 Pages
328-330
Published: 1983
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DAISHIRO IKEDA, SHUICHI GOMI, SHINICHI KONDO, HAMAO UMEZAWA
1983 Volume 36 Issue 3 Pages
331-334
Published: 1983
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AKIRA SAKAI, TAKUSABURO EBINA, NAKAO ISHIDA
1983 Volume 36 Issue 3 Pages
335-338
Published: 1983
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DAVID R. WHITE, CLARENCE J. MARING, GARY A. CAIN
1983 Volume 36 Issue 3 Pages
339-342
Published: 1983
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