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HIROSHI TOMODA, SATOSHI OMURA
1990 Volume 43 Issue 10 Pages
1207-1222
Published: October 25, 1990
Released on J-STAGE: April 19, 2006
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YOSUKE SAWADA, MASAMI HATORI, HARUAKI YAMAMOTO, MAKI NISHIO, TAKEO MIY ...
1990 Volume 43 Issue 10 Pages
1223-1229
Published: October 25, 1990
Released on J-STAGE: April 19, 2006
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Pradimicin FA-1 was produced
via directed biosynthesis with substitution of D-serine for D-alanine in the 15-position of pradimicin A. This substitution was achieved by the addition of D-serine to the culture medium of
Actinomadura hibisca P157-2. Likewise, pradimicin FA-2 was co-produced along with pradimicin FA-1 when the pradimicins A and C producing strain,
A. hibisca A2493 was grown in D-serine-supplemented medium. The new pradimicin analogs share a common core structure of 5, 6-dihydrobenzo[
a]naphthacenequinone substituted by D-serine at C-15, but differ in the disaccharide moiety at C-5. Pradimicin FA-1 has an
N-methylamino sugar and D-xylose. Pradimicin FA-2 is the des-
N-methyl analog of pradimicin FA-1. The
in vitro and
in vivo antifungal activity of the analogs was comparable to that of pradimicin A.
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TOSHIKAZU OKI, MASATOSHI KAKUSHIMA, MAKI NISHIO, HIDEO KAMEI, MINORU H ...
1990 Volume 43 Issue 10 Pages
1230-1235
Published: October 25, 1990
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Three
N,
N-dimethyl pradimicins were synthesized by reductive alkylation of pradimicins A, E and FA-2 and evaluated for antifungal activity, water solubility and acute toxicity in mice. They showed
in vitro antifungal activity superior to pradimicin A.
N,
N-Dimethylpradimicins E and FA-2 showed great improvement in water solubility and animal tolerance.
N,
N-Dimethylpradimicin FA-2 was effective in 3 experimental
in vivo fungal infection models.
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GEORG KNÜBEL, LINDA K. LARSEN, RICHARD E. MOORE, IRA A. LEVINE, G ...
1990 Volume 43 Issue 10 Pages
1236-1239
Published: October 25, 1990
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6-Cyano-5-methoxy-12-methylmdolo[2, 3-
a]carbazole and 6-cyano-5-methoxyindolo[2, 3-
a]carbazole are responsible for most of the cytotoxicity and antiviral activity associated with the blue-green alga
Nostoc sphaericum EX-5-1. The compounds are active against HSV II and show weak cytotoxicity against KB and LoVo human carcinoma cell lines.
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R. HAUTZEL, H. ANKE, W. S. SHELDRICK
1990 Volume 43 Issue 10 Pages
1240-1244
Published: October 25, 1990
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Mycenon (C
11H
5Cl
3O
3), a new inhibitor of isocitrate lyase (EC 4.1.3.1) was isolated from the culture broth of a basidiomycete,
Mycena sp. Mycenon is a novel chlorinated benzoquinone derivative which is also active against bacteria and fungi. Malate synthase (EC 4.1.3.2) the second key enzyme of the glyoxylate cycle was not affected by mycenon. Isocitrate lyase preparations from plants, bacteria and fungi were sensitive. The following
Ki-values for mycenon have been determined:
Ricinus communis, 5.2 μM;
Acinetobacter calcoaceticus, 11 μM;
Neurospora crassa, 7.4 μM. The structure of mycenon has been determined by a single crystal X-ray analysis.
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YOSHIHIRO TERUI, RYUJI SAKAZAKI, JUN'ICHI SHOJI
1990 Volume 43 Issue 10 Pages
1245-1253
Published: October 25, 1990
Released on J-STAGE: April 19, 2006
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Structures of a series of new antibiotics, agglomerins A, B, C and D, which are active against a variety of anaerobic bacteria, were determined to be 1-acyl-2, 3-dihydroxy-l, 3-butadiene-l-carboxylic acid, (1→3)-γ-lactones,
i.e., 2-acyl-4-ylidenetetronic acids with different hydrocarbon chains in the acyl group. Their common chromophore exhibited tautomerism in solution. The relationship of their structure to the activity against anaerobes is discussed.
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MICHIKO SAKAMOTO, KEN-ICHI YAMAMOTO, KUNIO ISSHIKI, TOMOYUKI ISHIKURA, ...
1990 Volume 43 Issue 10 Pages
1254-1270
Published: October 25, 1990
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Using PS-5 as starting material, the effects of chemical modification at the C-3 side chain were studied on the antibacterial activity against Gram-positive and Gram-negative bacteria including β-lactamase-producers. Among 35 side chains tested, 4-pyridylthio showed the highest antibacterial activity against the Gram-positive bacteria, and D-cysteinyl against the Gram-negative microbes. In general, compared with acetamidoethylthio in PS-5, basic side chains showed improved antibacterial activity against the staphylococci and pseudomonads, whereas the antibiotic activity against the Gram-negative bacteria decreased with bulky side chains. The introduction of 6-aminopenicillanate and 7-aminocephalosporanate to the C-3 side chain of carbapenem significantly reduced the antibacterial activity against the β-lactamase-producing microbes.
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JOACHIM FIRL, AXEL PROX, PETER LUGER, ROLAND MAIER, EBERHARD WOITUN, K ...
1990 Volume 43 Issue 10 Pages
1271-1277
Published: October 25, 1990
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Dirithromycin (
3) isomerizes upon dissolution in different solvents. From X-ray analysis of V-T 108, an analogue of dirithromycin, and comparative
1H and
13C NMR, and MS data, the isomer of dirithromycin was confirmed to be the C-16-(
S)-epimer. The ratio of the two epimers at equilibrium conditions was approximately 8:2 (
R/
S) in methanol at room temperature.
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SHINTARO NISHIMURA, NOBUYOSHI YASUDA, HIROSHI SASAKI, KAZUO SAKANE, TA ...
1990 Volume 43 Issue 10 Pages
1278-1285
Published: October 25, 1990
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The synthesis and antibacterial activity of several 7β-[l-(2-aminothiazol-4-yl)-l-cyclopropane-carboxyamido]cephem derivatives (
1) are described. The structure-activity relationships of
1 are also presented.
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STEPHEN J. MORRIS, DAVID E. THURSTON, THOMAS G. NEVELL
1990 Volume 43 Issue 10 Pages
1286-1292
Published: October 25, 1990
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An HPLC assay is described that can be used to study the covalent bonding interaction of carbinolamine-containing pyrrolo[2, 1-c][1, 4]benzodiazepines with the model nucleophile thiophenol, in order to evaluate electrophilicity at the C-11-position. Preliminary experiments with anthramycin, tomaymycin and neothramycin show that their reaction with thiophenol follows second-order kinetics, but the ranking order of reactivity (neothramycin > tomaymycin > anthramycin), does not correlate with either
in vitro cytotoxicity or
in vivo antitumour activity. This suggests that other factors such as non-covalent DNA-interaction or drug transport play a more crucial role in biological activity than simple alkylating ability. This assay should, however, prove a useful tool in the study of structure-activity relationships for this series of compounds and provide "C-11-electrophilicity" parameters for use in Hansch analysis and related studies.
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RYQHEI F. TSUJI, MASAKUNI YAMAMOTO, AKITO NAKAMURA, TAKAO KATAOKA, JUN ...
1990 Volume 43 Issue 10 Pages
1293-1301
Published: October 25, 1990
Released on J-STAGE: April 19, 2006
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The immunosuppressive effects of prodigiosin 25-C were studied in comparison with FK506. Both prodigiosin 25-C and FK506 suppressed T cell proliferation in response to concanavalin A (con A) or phytohemagglutinin (PHA) more significantly than that to lipopolysaccharide. However, prodigiosin 25-C inhibited con A-mediated mitogenic response more strongly than PHA-mediated one. FK506 showed no selectivity among those responses. In addition, when higher concentration of con A was used an inhibitory effect of prodigiosin 25-C became more evident whereas that of FK506 became less evident. Furthermore, prodigiosin 25-C affected neither interleukin-2 (IL-2) production nor IL-2 receptor (IL-2R) and transferrin receptor (TF-R) expression
in vitro, though FK506 extensively inhibited IL-2 production and significantly suppressed IL-2R and TF-R expression.
When comparing the effects of prodigiosin 25-C and FK506
in vivo by injecting antigens of different nature to a mouse, prodigiosin 25-C selectively inhibited cytotoxic T lymphocyte (CTL) activity induced by an allogenic mastocytoma, P815, without affecting production of antibody against a thymus dependent (TD) antigen, sheep red blood cell (SRBC). On the contrary, FK506 significantly inhibited both CTL induction and the antibody production. When
Brucella abortus, a thymus independent (TI) antigen, and SRBC were simultaneously challenged to a mouse, neither prodigiosin 25-C nor FK506 affected antibody production against the TI antigen while the effect on the TD antigen were the same as described above. The present results revealed the unique immunosuppressive property of prodigiosin 25-C which was different from that of FK506.
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KAZUKIYO YAMAOKA, KUNITOMO WATANABE, YOSHINORI MUTO, NAOKI KATOH, KAZU ...
1990 Volume 43 Issue 10 Pages
1302-1306
Published: October 25, 1990
Released on J-STAGE: April 19, 2006
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We described plasmid mediated transfer of resistance to β-lactam antibiotics between
Bacteroides fragilis strains. Ampicillin-resistance was transferred from
B. fragilis strain GAI-10150 to a
B. fragilis strain JC-101 with a frequency of 10
-6/input donor by a filter mating technique. A common plasmid band, named pBFKW1, was found in both the donor and the transconjugants. The plasmid was purified by an ethidium bromide-CsCl ultracentrifugation. The molecular size of the plasmid pBFKW1 which seemed to encode the β-lactam resistance and β-lactamase production was estimated
ca. 40 kb by the analysis of endonuclease digest. Substrate profile of the enzymes derived from the donor and a transconjugant were of cephalosporinase character.
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KEITH R. FOX
1990 Volume 43 Issue 10 Pages
1307-1315
Published: October 25, 1990
Released on J-STAGE: April 19, 2006
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The interaction between UK63052, a novel derivative of the quinomycin group of bifunctional intercalating antibiotics, with DNA has been investigated by footprinting techniques and the results compared with echinomycin. UK63Q52 binds strongly but reversibly to DNA and decreases the gel mobility of most DNA fragments, although the mobility of bent kinetoplast DNA is increased. The drug binds selectively to the dinucleotide CpG though not all such sequences present good binding sites. Binding is best when CG is surrounded by AT base pairs. UK63052 and echinomycin have different effects on DNA structure as assessed by changes in the sensitivity to modification by diethylpyrocarbonate. The results are interpreted by suggesting that substitutions on the chromophores affect the precise details of DNA recognition.
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MICHIHIKO KOBAYASHI, NORIYUKI YANAKA, TORU NAGASAWA, HIDEAKI YAMADA
1990 Volume 43 Issue 10 Pages
1316-1320
Published: October 25, 1990
Released on J-STAGE: April 19, 2006
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Using resting cells of
Rhodococcus rhodochrous J1, in which a large amount of nitrilase is induced, a simple and efficient bioconversion process for the production of pyrazinoic acid, an antimycobacterial agent, through catalysis by a nitrilase was developed. The reaction conditions for production of pyrazinoic acid were optimized. Under optimum conditions, 3.5 M cyanopyrazine was converted to pyrazinoic acid, with a molar conversion yield of 100%. The highest yield achieved corresponded to 434 g of pyrazinoic acid per liter of reaction mixture. The synthesized pyrazinoic acid was isolated and identified physico-chemically.
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KEIKO NAKAGAWA, AKIO TORIKATA, KAZUO SATO, YOSHIHISA TSUKAMOTO
1990 Volume 43 Issue 10 Pages
1321-1328
Published: October 25, 1990
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Microorganisms were screened for their ability to modify milbemycin A
4 (
la). Many strains, mostly actinomycetes and zygomycetes, were found to convert milbemycin A
4 (
la) to one or more new products. Among these products, M-l, M-2, and M-3 were obtained using
Amycolata autotrophica subsp.
amethystina ATCC 35204, and were identified as 30-hydroxymilbemycin A
4 (
1b), 26, 30-dihydroxymilbemycin A
4 (
Ic), and milbemycin A
4 30-oic acid (
1d), respectively. Other milbemycins and LL-F28249α (
7a) also underwent 30-hydroxylation by the microorganism. 22, 23-Dihydroavermectin B
1a (
8a) was not hydroxylated at any position by
A. autotrophica subsp.
amethystina ATCC 35204, but a corresponding hydroxyl product at the C-30 position was obtained using
Amycolatopsis mediterranei IFO 13415.
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HIROHARU MORI, SHINJI FUNAYAMA, YOHEI SUDO, KANKI KOMIYAMA, SATOSHI OM ...
1990 Volume 43 Issue 10 Pages
1329-1331
Published: October 25, 1990
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ADRIENNE L. TÖKÉS
1990 Volume 43 Issue 10 Pages
1332-1333
Published: October 25, 1990
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RAMIN FAGHIH, MARK BUYTENDORP, RICHARD STEPHENS, DWIGHT HARDY, JAKE PL ...
1990 Volume 43 Issue 10 Pages
1334-1336
Published: October 25, 1990
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CHENG-JUN MO, KAZUO SHIN-YA, KAZUO FURIHATA, KEIKO FURIHATA, AKIRA SHI ...
1990 Volume 43 Issue 10 Pages
1337-1340
Published: October 25, 1990
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KEN-ICHI KIMURA, SHOJI NAKAYAMA, NOBORU NAKAJIMA, MAKOTO YOSHIHAMA, NO ...
1990 Volume 43 Issue 10 Pages
1341-1343
Published: October 25, 1990
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YOSHINORI YAMASHITA, YUTAKA SAITOH, KATSUHIKO ANDO, KEIICHI TAKAHASHI, ...
1990 Volume 43 Issue 10 Pages
1344-1346
Published: October 25, 1990
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DEREK J. HOOK, JOSEPH J. YACOBUCCI, SEAN O'CONNOR, MIKE LEE, ED KERNS, ...
1990 Volume 43 Issue 10 Pages
1347-1348
Published: October 25, 1990
Released on J-STAGE: April 19, 2006
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