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YASUSHI TAKAGI, CHIKARA KOMURO, TSUTOMU TSUCHIYA, SUMIO UMEZAWA, MASA ...
1981 Volume 34 Issue 1 Pages
1-4
Published: 1981
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The titled compounds have been prepared and their antibacterial activities were described.
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FRANCIS R. PFEIFFER, THOMAS W. KU, DAVID C. PETERSON
1981 Volume 34 Issue 1 Pages
5-12
Published: 1981
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trans-4-Aminocyclohexanol-2'-amino-α-D-glucopyranosides were prepared which are derivatives of neamine having the 3-amino and 5 and 6 hydroxyl groups of the 2-deoxystreptamine ring replaced with hydrogen. The 2'-amino-α-glycosides were synthesized by the method of LEMIEUX using a chloro nitroso dimer of a glucal and appropriately substituted cyclohexanols. Reductive deblocking of the intermediate 2-oximino derivatives afforded paromamine and neamine analogues. Two examples of 2'-amino-α-glycosides with ring-opened variations of the 2-deoxystreptamine aglycone are described. None of the compounds exhibited better
in vitro antibacterial activity than neamine when compared against Gram-positive and Gram-negative bacteria.
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TAMIO FUJIWARA, EIJI RONDO
1981 Volume 34 Issue 1 Pages
13-15
Published: 1981
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Four 2-deoxystreptamine (DOS) related compounds including S-11-P, isolated as an intermediate of DOS biosynthesis, were supplemented to the culture of a DOS- mutant of Bacillus circulans. Among the tested aminocyclitol compounds, S-11-P alone was converted to DOS. Addition of other aminocyclitols neither produced antibiotic nor inhibited the incorporation of S-11-P and DOS into butirosins. By these facts, S-11-P was confirmed clearly to be an intermediate of DOS biosynthesis.
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1. SYNTHESIS OF 4-AMINOSPECTINOMYCINS
R. MAIER, E. WOITUN, A. REUTER, W. REUTER, B. WETZEL
1981 Volume 34 Issue 1 Pages
16-21
Published: 1981
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Preparation of 4-dihydro-4-deoxy-4(
R)-aminospectinomycin (
4a) and 4-dihydro-4-deoxy-4(
S)-aminospectinomycin (
4b) is described.
4a shows antibiotic activity comparable to spectinomycin,
4b is devoid of activity.
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2. DERIVATIVES OF 4-DIHYDRO-4-DEOXY-4(R)-AMINOSPECTINOMYCIN
E. WOITUN, R. MAIER, B. WETZEL, W. REUTER, U. LECHNER
1981 Volume 34 Issue 1 Pages
22-27
Published: 1981
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Acyl derivatives 5
a-
jand alkyl derivatives 7a-r of 4-dihydro-4-deoxy-4(
R)-aminospectinomycin (
1a) were prepared and tested for antibacterial activity. Only acyl compounds derived from long chain aliphatic acids or amino acids showed activity
In vitro, but were inactive when tested
In vitro. All alkyl derivatives were active
In vitro.
In vitrohowever only the short chain derivatives 7a-c were active. Compound
7b showed higher activity than spectinomycin.
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J. MAZERSKI, H. WOJCIECHOWSKA, W. ZGODA, B. WOYNAROWSKA, E. BOROWSKI
1981 Volume 34 Issue 1 Pages
28-33
Published: 1981
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Methods for the synthesis of esters and amides of edeine A were developed and a number of derivatives of this type was obtained and characterized. The antimicrobial activities of the derivatives are comparable to the activity of the native antibiotic and indicate that the presence of free carboxyl group in edeine is not essential for its biological activity.
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U. VALCAVI, A. BRANDT, G. B. CORSI, F. MINOJA, G. PASCUCCI
1981 Volume 34 Issue 1 Pages
34-39
Published: 1981
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New tetracycline analogs modified at position 5, 6 and 2 were synthetized. The 5-deoxy- 5-oxo-derivatives, 2a and 3a, were obtained by DMSO/acetic anhydride oxidation of doxycycline (2) and methacycline (3), respectively; the 6-demethyl-6-hydroxymethyl-6-alpha-hydroxyoxytetracycline (3b) by methacycline oxidation with the KClO
3/OsO
4 system and the 6-hydroxyanhydrooxytetracycline (4) treating 3b with periodic acid. The 2-ethoxycarbonyl-2-decarboxamidodoxycycline (2b), was synthetized by treating doxycycline nitrile (2c) with EtOH and anhydrous HCl, 2-thiocarboxamide-2-decarboxamidodoxycycline (2d) by reaction of doxycycline with P2Sg in dioxane and 2-aminomethyl-2-decarboxamidodoxycycline (2e) by RANEY-Nickel reduction of 2d. All the synthetized compounds proved to be almost inactive on agar plates both on Gram-positive and Gram-negative bacteria.
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2. CEPHALOSPORIN DERIVATIVES
R. E. BAMBURY, E. H. W. BÖHME, N. W. BRAKE, M. L. EDWARDS, R. C. ...
1981 Volume 34 Issue 1 Pages
40-46
Published: 1981
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Three cephalosporin derivatives were prepared from 1, 4-dihydro-4-oxypyridine-1-acetic acid. These were the 7-aminocephalosporanic acid (7-ACA) derivative and the compounds with 5-methyl-1, 3, 4-thiadiazol-2-thiol and 1-methyl-1, 2, 3, 4-tetrazole-5-thiol at C-3 of the cephalosporin nucleus. The antibacterial activity of the 7-ACA derivative was comparable to cephalothin, and that of the other two derivatives was comparable to cefazolin. The 7-ACA derivative, compared to cephalothin, was significantly less metabolized, was less protein bound, and had a longer half life.
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I. NORMAL PHASE HPLC FOR MONITORING FERMENTATION AND PURIFICATION PROCESSES
TATSUO OGASAWARA, SHINJI GOTO, SHUNRO MORI, TOSHIKAZU OKI
1981 Volume 34 Issue 1 Pages
47-52
Published: 1981
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A normal phase high performance liquid chromatographic method is presented for the separation and quantitative determination of aclacinomycin A (ACM) and its related compounds classified as anthracycline antibiotics. The sensitive, reliable and reproducible chromatography was achieved on a μ-Porasil column with a mobile phase consisting of chloroform - methanol - acetic acid - water - triethylamine (68: 20: 10: 2: 0.01, v/v). By use of MA144 Ml, one of the ACM analogues, as an internal standard, selectivity of the HPLC method could be retained by virtue of the adjustment of the detecting wavelength to 436 nm. The HPLC method was applicable to monitoring the fermentation and purification processes.
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II. REVERSE PHASE HPLC DETERMINATION OF ACLACINOMYCIN A AND ITS METABOLITES IN BIOLOGICAL FLUIDS USING FLUORESCENCE DETECTION
TATSUO OGASAWARA, YOSHIRO MASUDA, SHINJI GOTO, SHUNRO MORI, TOSHIKAZU ...
1981 Volume 34 Issue 1 Pages
52-56
Published: 1981
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A sensitive, simple and selective reverse phase high performance liquid chromatographic method was applied to the determination of aclacinomycin A (ACM) and its metabolites in plasma. The chromatography was performed on a microparticulate phenethyl derivative of silica using a mobile phase of acetonitrile-0.03 M ammonium formate buffer (pH 5.0), (50:50, v/v) and monitoring with fluorescence detector (excitation 435 nm-emission 505 nm). High reproducibility and linear calibration curves were obtained from 20 ng/ml to 100 ng/ml of ACM and its metabolites in plasma by use of internal standard methods.
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III. ISOLATION AND IDENTIFICATION OF AN EARLY AROMATIC ANSAMYCINPRECURSOR CONTAINING THE SEVEN-CARBON AMINO STARTER-UNIT AND THREE INITIAL ACETATE/PROPIONATE-UNITS OF THE ANSA CHAIN
ORESTE GHISALBA, HERMANN FUHRER, WILHELM J. RICHTER, SERGE MOSS
1981 Volume 34 Issue 1 Pages
58-63
Published: 1981
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A number of rifamycin non-producing UV-mutants derived from
Nocardia mediterranei strains N813 (rifamycin B producer) and A10
1) (
aro-mutant excreting shikimate derived from strain N813) were found to accumulate an identical complex of aromatic components instead of rifamycin B. The main component of this aromatic complex, product P8/1-OG, was isolated from six of these
P--mutant strains and identified spectroscopically as a very early precursor in the biosynthesis of rifamycins.
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IV. IDENTIFICATION OF 3-AMINO-5-HYDROXYBENZOIC ACID AS A DIRECT PRECURSOR OF THE SEVEN-CARBON AMINO STARTER-UNIT
ORESTE GHISALBA, JAKOB NÜESCH
1981 Volume 34 Issue 1 Pages
64-71
Published: 1981
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3-Amino-5-hydroxybenzoic acid was investigated for its ability to induce rifamycin biosynthesis in an appropriate mutant of
Nocardia mediterranei and identified as a direct precursor of the seven-carbon amino starter-unit for the biosynthesis of ansamycins. A model for the biosynthesis of different types of ansamycins is presented and discussed.
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CHARACTERISTICS OF THE IgE ANTIBODIES FOR PENICILLINS AND CEPHALOSPORINS IN RATS
OSAMU SHIHO, KANJI TSUCHIYA
1981 Volume 34 Issue 1 Pages
72-78
Published: 1981
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Rats immunized with sulbenicillin-ovalbumin (SBPC-OvA) in combination with aluminum hydroxide (alum) and thimerosal-killed
Bordetella pertussis produced high levels of anti-SBPC antibodies. Anti-SBPC antibodies were first detected on day 8, reaching the maximum titer on day 12 and rapidly declined thereafter. Anti-SBPC sera obtained on day 13 were sulfhydryllabile and heat-labile. The optimal latent period in the passive cutaneous anaphylaxis (PCA) reaction was 60-72 hours. These results indicate that anti-SBPC antibodies were IgE antibodies. Sprague-Dawley (SD), Wister and F344 rats were equally productive of anti-SBPC antibodies, while SD rats were more productive of anti-cephaloridine (CER) antibodies than Wister and F344 rats did. In SD rats, the IgE antibodies for penicillin G (PCG), ampicillin (ABPC) and SBPC were more easily produced than the IgE antibodies for CER, cefazolin (CEZ) and cephacetrile (CEC).
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ANTIGENIC SPECIFICITY OF RAT ANTI-PENICILLIN-OvA IgE SERA
OSAMU SHIHO, YASUSHI NAKAGAWA, KANJI TSUCHIYA
1981 Volume 34 Issue 1 Pages
79-83
Published: 1981
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Sprague Dawley (SD) rats were immunized with various penicillin-ovalbumin (OvA) in combination with aluminum hydroxide (alum) and thimerosal-killed
Bordetella pertussis for the purpose of obtaining rat anti-penicillin IgE sera. In the rat 60-hour passive cutaneous anaphylaxis (PCA) reaction and the hapten inhibition test, a weak cross reaction between penicillin G (PCG) and ampicillin (ABPC) was observed, but no cross reaction was observed between sulbenicillin (SBPC) and other penicillins. Rat anti-6-formamidopenicillanic acid (FPC) IgE serum reacted with PCG-bovine gamma globulin (BGG), ABPC-BGG and SBPC-BGG, but FPC-BGG did not react with rat anti-PCG, anti-ABPC and anti-SBPC IgE sera and the PCA reaction between anti-FPC IgE sera and FPC-BGG was inhibited by FPC, PCG, ABPC and SBPC. These results indicate that the antigenic active sites of PCG, ABPC and SBPC are limited to the acyl side chain moiety of penicillins, while the antigenic active site of FPC is confined to the penicilloyl moiety of the penicillin.
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ANTIGENIC SPECIFICITY OF RAT ANTI-CEPHALOSPORIN-OvA IgE SERA
OSAMU SHIHO, KANJI TSUCHIYA
1981 Volume 34 Issue 1 Pages
84-89
Published: 1981
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Sprague Dawley (SD) rats were immunized with various cephalosporin- and penicillinovalbumin (OvA) in combination with aluminum hydroxide (alum) and thimerosal-killed
Bordetella pertussis. Anti-cephalosporin IgE antibody production was inferior to anti-penicillin IgE antibody production. Cefsulodin (CFS), sulbenicillin (SBPC) and α-sulfophenyl acetic acid (SPAA) cross-reacted with each other but did not react with cephaloridine (CER), cefazolin (CEZ) and penicillin G (PCG). CER and PCG slightly cross-reacted with each other but did not cross-react with the others tested. Anti-CFS and anti-SBPC IgE sera were related specifically to the SPAA moiety.
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RUTH KOREN, HEDVA BERCOVITZ, HAMAO UMEZAWA, WERNER E. G. MÜLLER
1981 Volume 34 Issue 1 Pages
90-94
Published: 1981
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Bestatin is an inhibitor of cell surface-associated aminopeptidase B and leucine aminopeptidase. This microbial product simulates the role of serum as an activator of uridine uptake in quiescent BHK cells. The compound significantly stimulates the incorporation of labelled thymidine into the acid-insoluble fraction of serum-starved Nil 8 cells in the presence of low concentration of serum. The possible mechanisms of these interactions are discussed.
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MASAAKI ISHIZUKA, TOMIO TAKEUCHI, HAMAO UMEZAWA
1981 Volume 34 Issue 1 Pages
95-102
Published: 1981
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Diketocoriolin B (DKC), at a very low dose (0.1μg/mouse) or in a low concentration (0.01 ng/culture) augmented antibody formation to sheep red blood cells (SRBC)
in vivo and
in vitro. The addition of DKC to spleen cell cultures 24-48 hours after the start of the culture showed the strongest effect. The stimulatory effect was not influenced by the elimination of macrophages. DKC also augmented antibody formation in T cell-depleted spleen cell cultures and in cultures of spleen cells of athyrnic mice. The treatment of spleen cells with DKC at 37°C or 4°C for 30 minutes before the start of the culture enhanced antibody formation to SRBC. Both treatments of macrophage-rich and lymphocyte-rich cells with DKC enhanced antibody formation.
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N. KARDOS, A. EICHHOLZ, C. P. SCHAFFNER
1981 Volume 34 Issue 1 Pages
103-113
Published: 1981
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Binding of aminocyclitol antibiotics to intestinal and kidney brush border membranes has been studied
in vitro by means of vesicular preparations. The binding is rapid, reversible, specific, saturable and has a high affinity. To both tissues, gentamicin and sisomicin bind to a single binding site or receptor. These antibiotics demonstrate increased binding under conditions of increasing pH. Membrane binding disappears when the vesicle proteins are denatured with TCA. A significant reduction in aminocyclitol binding after treatment of vesicles with papain indicates that a portion of the binding receptor protein is exposed to the outer surface of the brush border membrane. The accumulated evidence suggests that the nature of the binding mechanism is not a simple electrostatic interaction between the antibiotic's charged amino groups and the polyanions of the membrane. Alternatively, a specific membrane structure is required for binding whose characteristics reflect a drug-receptor interaction. Receptor binding is characterized as being saturable, reversible, and specific; all of which have been demonstrated for aminocyclitols and brush border membranes.
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MASATO TODA, TORO IKEUCHI, MASAZOT AJIMA, MATSUHISAIN OUE, SUSUMUM ITS ...
1981 Volume 34 Issue 1 Pages
114-117
Published: 1981
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CATHERINE A. PRICE, EVA MARIA LYNCH, BETTY ANNE BOWIE, DAVID J. NEWMAN
1981 Volume 34 Issue 1 Pages
118
Published: 1981
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BRUCE B. JARVIS, JACOB O. MIDIWO, TULEY DESILVA, EUGENE P. MAZZOLA
1981 Volume 34 Issue 1 Pages
120-121
Published: 1981
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R. SCHLEGEL, H. THRUM, J. ZIELINSKI, E. BOROWSKI
1981 Volume 34 Issue 1 Pages
122-123
Published: 1981
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KAZUO TORI, KATSUYA TOKURA, YOHKO YOSHIMURA, YOSHIHIRO TERUI, KEI OKAB ...
1981 Volume 34 Issue 1 Pages
124-129
Published: 1981
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NOBORU OTAKE, TAKESHI OGITA, YUKIO MIYAZAKI, HIROSHI YONEHARA, R. D. M ...
1981 Volume 34 Issue 1 Pages
130-131
Published: 1981
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