2079-00-7 Usage
Description
Blasticidin S is a nucleoside antibiotic produced by Streptomyces griseochromogenes and biosynthesized from cytosine, glucose, arginine, and methionine. It is an antifungal agent with potent activity against various pathogens, including the rice pathogen, Piricularia oryzae. Blasticidin S inhibits protein synthesis and is active against bacteria, tumor cell lines, and nematodes. It has been used as a marker for strain manipulations and is presented as the free base to avoid problems associated with the use of the hydrochloride.
Uses
Used in Agriculture:
Blasticidin S is used as a fungicide for the control of rice blast (Pyricularia oryzae) by foliar application.
Used in Pharmaceutical Industry:
Blasticidin S is used as an antifungal agent with potent activity against various pathogens, making it a valuable asset in the development of treatments for fungal infections.
Used in Research and Development:
Blasticidin S is used as a marker for strain manipulations, aiding researchers in their work with various microorganisms and contributing to advancements in the field of microbiology.
Production Methods
Blasticidin S is produced by Streptomyces griseochromogenes,
and has a wide range of antimicrobial activity (4).
This antibiotic was utilized in the Far East beginning in
1961 against the rice blast pathogen Pyricularia oryzae,
with effective control achieved at rates of 10–40 ppm (4).
Pharmacology
Inhibits protein synthesis both in eukaryotes and in
prokaryotes (5,6). Interacts with ribosomal RNA in large
subunit, interfering with the transpeptidation step.
Inhibits cell-free protein synthesis in P. oryzae and
Escherichia coli.
Metabolic pathway
Several blasticidin S-resistant microorganisms are
found to produce blasticidin S deaminase which
catalyzes the hydrolytic deamination of the cytosine
moiety in blasticidin S to give a non-toxic
deaminohydroxy derivative.
Metabolism
3H-blasticidin S administered to mice was excreted in
the urine and feces within 24 h. Cytomycin and cytosin
were identified as the main metabolites in and on rice
plants, respectively (7). In soil, DT50 < 5 d. Metabolized to
nontoxic deaminohydroxy blasticidin S by Aspergillus sp.
and resistant Bacillus cereus. Novel deaminase and coding
genes, BSD and bsr, were isolated as selectable marker
genes for genetic engineering (8).
Toxicity evaluation
Acute oral LD50 for male rats: 56.8, female rats: 55.9,
male mice: 51.9, and female mice: 60.1 mg/kg. Acute
percutaneous LD50 for rats >500 mg/kg. Eye: severe irritation.
Degradation
Blasticidin-S is obtained as white needle crystals which are very soluble in
water. The compound is stable in the pH range 5-7 but it is unstable under
alkaline conditions. It is readily degraded by sunlight when on the surface
of rice plants with the main degradation product being cytosine (2)
(Yamaguchi et al., 1972) as shown in Scheme 1.
Check Digit Verification of cas no
The CAS Registry Mumber 2079-00-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,7 and 9 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2079-00:
(6*2)+(5*0)+(4*7)+(3*9)+(2*0)+(1*0)=67
67 % 10 = 7
So 2079-00-7 is a valid CAS Registry Number.
InChI:InChI=1/C17H26N8O5/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29)/t9?,10-,13+,14-/m0/s1
2079-00-7Relevant articles and documents
Reevaluation of the final steps in the biosynthesis of blasticidin S by Streptomyces griseochromogenes and identification of a novel self-resistance mechanism
Zhang, Qibo,Cone, Martha C.,Gould, Steven J.,Mark Zabriskie
, p. 693 - 701 (2000)
The final steps in the biosynthesis of the antifungal peptidyl- nucleoside blasticidin S (3) have been revised to include a novel self- resistance mechanism wherein the previously proposed final precursor, demethylblasticidin S (7), is modified with a leucine residue yielding leucyldemethylblasticidin S (10) which exhibits reduced antibiotic activity. Methylation of 10 yields leucylblasticidin S (9) which can be exported from the bacterium and hydrolyzed to 3. Also disclosed is the finding of a blasticidin S N-acetyltransferase activity that may function to detoxify 3 and 7 inadvertently produced prior to export or which gain reentry to the cell. (C) 2000 Elsevier Science Ltd.
SUBSTITUTED SPIROCYCLIC KETOENOLS
-
, (2008/06/13)
The present invention relates to novel substituted spirocyclic ketoenols of the formula (I) in which W, X, Y, Z, A, B, D and G are as defined in the disclosure, to a plurality of processes for their preparation and to their use as pesticides, microbicides and herbicides.
Use of oxabicyclo[2.2.1]heptane derivatives as pesticidal agents
-
, (2008/06/13)
7-oxabicyclo[2.2.1]heptane derivatives of formula (I) in which X, R1, R2, R3 and R4 have the meanings set forth in the specification, are very suitable for controlling undesired microorganisms and animal pests. New 7-oxabicyclo[2.2.1]heptane derivatives of formula (Ia) in which X, R1, R2, R3 and R14 have the meanings set forth in the specification, and a process for the preparation of the new compounds.
Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides(III)
-
, (2008/06/13)
The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 3 to 10, n represents 0, 1 or 2, Y represents sulphur or oxygen, R1 represents halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl and R2 represents hydrogen, halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl, ?except for compounds where R1=alkyl, Y=oxygen and X=hydrogen, and to processes for their preparation and to their use as pesticides.
