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(Synonyms: 德夸菌素; Angustmycin A) 目录号 : GC60747

A nucleoside analog and GMP synthase inhibitor

Decoyinine Chemical Structure

Cas No.:2004-04-8

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产品描述

Decoyinine is a nucleoside analog and a reversible and non-competitive inhibitor of GMP synthase (IC50 = 17.3 ?M).1 It reduces intracellular levels of GMP, GDP, and GTP, induces sporulation, and inhibits growth and cell wall synthesis in B. subtilis.2,3,4 It also reverses inhibition of aerial mycelium formation in Streptomyces grown in the presence of excess nutrients.5

1.Nakamura, J., and Lou, L.Biochemical characterization of human GMP synthetaseJ. Biol. Chem.270(13)7347-7353(1995) 2.Uratani, B., Lopez, J.M., and Freese, E.Effect of decoyinine on peptidoglycan synthesis and turnover in Bacillus subtilisJ. Bacteriol.154(1)261-268(1983) 3.Zain-ul-abedin, Lopez, J.M., and Freese, E.Induction of bacterial differentiation by adenine- and adenosine-analogs and inhibitors of nucleic acid synthesisNucleos. Nucleot.2(3)257-274(1983) 4.Bai, U., Lewandoski, M., Dubnau, E., et al.Temporal regulation of the Bacillus subtilis early sporulation gene spo0FJ. Bacteriol.172(9)5432-5439(1990) 5.Ochi, K.A decrease in GTP content is associated with aerial mycelium formation in Streptomyces MA406-A-1J. Gen. Microbiol.132(2)299-305(1986)

Chemical Properties

Cas No. 2004-04-8 SDF
别名 德夸菌素; Angustmycin A
Canonical SMILES C=C(O1)[C@@H](O)[C@@H](O)[C@]1(CO)N2C=NC3=C(N)N=CN=C32
分子式 C11H13N5O4 分子量 279.25
溶解度 DMSO: soluble 储存条件 Store at -20°C
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1 mM 3.581 mL 17.9051 mL 35.8102 mL
5 mM 0.7162 mL 3.581 mL 7.162 mL
10 mM 0.3581 mL 1.7905 mL 3.581 mL
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Research Update

Decoyinine Induced Resistance in Rice against Small Brown Planthopper Laodelphax striatellus

Insects 2022 Jan 17;13(1):104.PMID:35055947DOI:10.3390/insects13010104.

Induced resistance against SBPH via microbial pesticides is considered as an eco-friendly and promising management approach. In this study, the induced resistance against SBPH in rice seedling by a new potential microbial pesticide, Decoyinine (DCY), a secondary metabolite produced by Streptomyces hygroscopicus, was evaluated to investigate the effects of DCY on SBPH's biological and population parameters along with defense-related physiological and biochemical indices in rice against SBPH feeding. We found that DCY has potential to improve rice resistance and significantly reduced the fecundity of SBPH. Laboratory results revealed that DCY treated rice significantly changed SBPH's fecundity and population life table parameters. The concentrations of hydrogen peroxide (H2O2), soluble sugars and malondialdehyde (MDA) were significantly lower in DCY treated rice plants against SBPH infestation at 24, 48 and 96 hours post infestation (hpi), respectively. The concentrations of antioxidant enzymes, catalase (CAT) was significantly higher at 72 hpi, while super oxidase dismutase (SOD) and peroxidase (POD) concentrations were recorded higher at 96 hpi. The concentrations of synthases enzymes, phenyl alanine ammonia-lyase (PAL) was higher at 48 hpi, whereas polyphenol oxidase (PPO) concentration was maximum at 72 hpi against SBPH infestation. The results imply that DCY has unique properties to enhance rice resistance against SBPH by stimulating plant defensive responses. Microbial pesticides may be developed as an alternative to chemical pest control.

Effect of Decoyinine on the regulation of alpha-amylase synthesis in Bacillus subtilis

J Bacteriol 1987 Dec;169(12):5867-9.PMID:3119574DOI:10.1128/jb.169.12.5867-5869.1987.

Decoyinine, an inhibitor of GMP synthetase, allows sporulation in Bacillus subtilis to initiate and proceed under otherwise catabolite-repressing conditions. The effect of Decoyinine on alpha-amylase synthesis in B. subtilis, an event which exhibits regulatory features resembling sporulation initiation, was examined. Decoyinine did not overcome catabolite repression of alpha-amylase synthesis in a wild-type strain of B. subtilis but did cause premature and enhanced synthesis in a mutant strain specifically blocked in catabolite repression of alpha-amylase synthesis. Decoyinine had no effect on alpha-amylase enzymatic activity. Thus, it appears that the catabolite control mechanisms governing alpha-amylase synthesis and sporulation in B. subtilis differ in their responses to Decoyinine and hence must consist at least partially of separate components.

Effect of Decoyinine on peptidoglycan synthesis and turnover in Bacillus subtilis

J Bacteriol 1983 Apr;154(1):261-8.PMID:6403504DOI:10.1128/jb.154.1.261-268.1983.

The sporulation of Bacillus subtilis can be induced in the presence of amino acids and glucose by partially depriving the cells of guanine nucleotides. This can be achieved, e.g., by the addition of Decoyinine, a specific inhibitor of GMP synthetase. To determine the effect of this and other inhibitors on cell wall synthesis, we measured in their presence the incorporation of acetylglucosamine into acid-precipitable material. The rate of wall synthesis decreased by 50% within 5 min after Decoyinine addition; this decrease was prevented by the presence of guanosine. A comparison with the effects of other inhibitors of cell wall synthesis indicated that Decoyinine inhibited the final portion of the cell wall biosynthetic pathway, i.e., after the steps inhibited by bacitracin or vancomycin. Decoyinine addition also prevented cellular autolysis and cell wall turnover. It is not known whether these two effects of Decoyinine on cell wall synthesis are causally related.

Induction of Bacillus subtilis sporulation by Decoyinine and the concomitant disappearance of ppGpp in vegetative cells

J Biochem 1982 Mar;91(3):1089-92.PMID:6804450DOI:10.1093/oxfordjournals.jbchem.a133759.

Sporulation of Bacillus subtilis, growing exponentially in the presence of rapidly metabolizable nutrients, was induced by addition of Decoyinine (an antibiotic inhibitor of GMP synthesis), and intracellular amounts of ppGpp were determined after 2 M formic acid extraction by polyethyleneimine (PEI)-cellulose thin-layer chromatography. Consequently, it was found that the ppGpp in vegetative cells abruptly disappeared after the addition of Decoyinine. This indicates that the disappearance of ppGpp is closely correlated to the initiation of B. subtilis sporulation.

Biology of Two-Spotted Spider Mite ( Tetranychus urticae): Ultrastructure, Photosynthesis, Guanine Transcriptomics, Carotenoids and Chlorophylls Metabolism, and Decoyinine as a Potential Acaricide

Int J Mol Sci 2023 Jan 15;24(2):1715.PMID:36675229DOI:10.3390/ijms24021715.

Two-Spotted Spider Mites (TSSMs, Tetranychus urticae Koch 1836 (Acari: Tetranychidae)) is one of the most important pests in many crop plants, and their feeding activity is based on sucking leaf cell contents. The purpose of this study was to evaluate the interaction between TSSMs and their host Lima bean (Phaseolus lunatus) by analyzing the metabolomics of leaf pigments and the transcriptomics of TSSM guanine production. We also used epifluorescence, confocal laser scanning, and transmission electron microscopies to study the morphology and structure of TSSMs and their excreta. Finally, we evaluated the potential photosynthetic ability of TSSMs and the activity and content of Ribulose-1,5-bisphosphate Carboxylase/Oxigenase (RubisCO). We found that TSSMs express several genes involved in guanine production, including Guanosine Monophosphate Synthetase (GMPS) and Decoyinine (DCY), a potential inhibitor of GMPS, was found to reduce TSSMs proliferation in infested Lima bean leaves. Despite the presence of intact chloroplasts and chlorophyll in TSSMs, we demonstrate that TSSMs do not retain any photosynthetic activity. Our results show for the first time the transcriptomics of guanine production in TSSMs and provide new insight into the catabolic activity of TSSMs on leaf chlorophyll and carotenoids. Finally, we preliminary demonstrate that DCY has an acaricidal potential against TSSMs.