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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/30 15:35:00」(JST)

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Anisomycin, also known as flagecidin is an antibiotic produced by Streptomyces griseolus which inhibits protein synthesis. Partial inhibition of DNA synthesis occurs at anisomycin concentrations that effect 95% inhibition of protein synthesis.^[2] Anisomycin can activate stress-activated protein kinases, MAP kinase and other signal transduction pathways.

Anisomycin is inactive against bacteria.

Pharmacology

Anisomycin interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.

Anisomycin is also mentioned as a potential psychiatric drug, as it may inhibit the consolidation of new context-specific long-term memories.".,^[3] as well as long time consolidated memories rendered labile through reactivation.^[4]

Injection of anisomycin into the hippocampus has been proposed for selective removal of memories.^[5]

Biosynthesis

Despite anisomycin's wide usage as a protein biosynthesis inhibitor, there have been few studies centered around the biosynthesis of anisomycin. One study by Butler in 1965 proposed possible precursors to this natural product. Fermentation of Streptomyces with labeled amino acids was followed by a degradation of the radioactive anisomycin and deacetylanisomycin products to determine the locations of the labeled carbons. Although its pyrrolidine-based structure suggests that it is derived from proline, the results from the experiments indicated that tyrosine, glycine, methionine, and acetate are the primary precursors for the biosynthesis of anisomycin. Tyrosine and, to a limited degree, phenylalanine, contribute to C-2 of the pyrrolidine ring. Methionine is likely responsible for the methylation of the hydroxyl group on the aromatic ring as S-adenosylmethionine (SAM). Glycine or acetate account for C-4 and C-5 on the pyrrolidine ring. It was noted that deacetylanisomycin was a prominent product in the first few days of fermentation, suggesting that acetylation of the C-3 hydroxyl group by acetyl Co-A is the final step in the biosynthesis of anisomycin. The source of the nitrogen within the ring and C-3 were undetermined. However, C-3 is not likely to be provided by the carboxylic acid group of tyrosine because tracking of radioactivity indicated that tyrosine undergoes decarboxylation during fermentation.^[6]

Other uses

Anisomycin is used as a component of Martin Lewis agar, an in vitro diagnostic product which is used extensively in the United States for the selective isolation of Neisseria gonorrhoeae and Neisseria meningitidis.^[1]

References

^ ^a ^b Anisomycin from Sigma Aldrich
^ Grollman, Arthur P. (1967). "Inhibitors of protein biosynthesis. II. Mode of action of anisomycin". The Journal of Biological Chemistry 242 (13): 3226–33. PMID 6027796.
^ Barrientos, Ruth M; O'Reilly, Randall C; Rudy, Jerry W (2002). "Memory for context is impaired by injecting anisomycin into dorsal hippocampus following context exploration". Behavioural Brain Research 134 (1–2): 299–306. doi:10.1016/S0166-4328(02)00045-1. PMID 12191817.
^ Debiec et al, Neuron, 2002. PMID 12408854
^ Wang, S.-H.; Ostlund, SB; Nader, K; Balleine, BW (2005). "Consolidation and Reconsolidation of Incentive Learning in the Amygdala". Journal of Neuroscience 25 (4): 830–5. doi:10.1523/JNEUROSCI.4716-04.2005. PMID 15673662.
^ Butler, K. (1966). "Anisomycin. II.1 Biosynthesis of Anisomycin". The Journal of Organic Chemistry 31 (1): 317–20. doi:10.1021/jo01339a503. PMID 5900818.

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1. レジオネラ感染の臨床症候および診断 clinical manifestations and diagnosis of legionella infection

English Journal

RNA and protein synthesis is required for Ancylostoma caninum larval activation.

Dryanovski DI, Dowling C, Gelmedin V, Hawdon JM.SourceLaboratory of Nematode Biology, Department of Microbiology, Immunology, and Tropical Medicine, The George Washington University Medical Center, 2300 I St. NW, Washington, DC 20037, USA.
Veterinary parasitology.Vet Parasitol.2011 Jun 30;179(1-3):137-43. Epub 2011 Feb 26.
The developmentally arrested infective larva of hookworms encounters a host-specific signal during invasion that initiates the resumption of suspended developmental pathways. The resumption of development during infection is analogous to recovery from the facultative arrested dauer stage in the free
PMID 21354706

Development of JNK2-Selective Peptide Inhibitors That Inhibit Breast Cancer Cell Migration.

Kaoud TS, Mitra S, Lee S, Taliaferro J, Cantrell M, Linse KD, Van Den Berg CL, Dalby KN.SourceDivision of Medicinal Chemistry, ‡Division of Pharmacology and Toxicology, and §Pharm D Program, College of Pharmacy, The University of Texas at Austin , Austin, Texas 78712, United States.
ACS chemical biology.ACS Chem Biol.2011 Jun 17;6(6):658-66. Epub 2011 Apr 5.
Despite their lack of selectivity toward c-Jun N-terminal kinase (JNK) isoforms, peptides derived from the JIP (JNK Interacting Protein) scaffolds linked to the cell-penetrating peptide TAT are widely used to investigate JNK-mediated signaling events. To engineer an isoform-selective peptide inhibit
PMID 21438496

Japanese Journal

Stress-activated mitogen-activated protein kinases c-Jun NH 2-terminal kinase and p38 target Cdc25B for degradation

Uchida Sanae,Yoshioka Katsuji,Kizu Ryoichi,Nakagama Hitoshi,Matsunaga Tsukasa,Ishizaka Yukihito,Poon Randy Y. C.,Yamashita Katsumi
Cancer Research 69(16), 6438-6444, 2009-08-15
… Nongenotoxic stress induced by anisomycin caused rapid degradation of Cdc25B as well as Cdc25A. … Cdc25B with Ser101 mutated to alanine was refractory to anisomycin-induced degradation, and cells expressing such mutant Cdc25B proteins were able to override the anisomycin-induced G2 arrest. …
NAID 120001613724

A Survey of Synthetic and Natural Phytotoxic Compounds and Phytoalexins as Potential Antimalarial Compounds(Pharmacology)

BAJSA Joanna,SINGH Kshipra,NANAYAKKARA Dhammika,DUKE Stephen Oscar,RIMANDO Agnes Mamaril,EVIDENTE Antonio,TEKWANI Babu Lal
Biological & pharmaceutical bulletin 30(9), 1740-1744, 2007-09-01
… Endothall, anisomycin, and cerulenin had sufficient antiplasmodial action to be considered as new lead antimalarial structures. …
NAID 110006380260

Establishment and Characterization of Rat Dental Epithelial Derived Ameloblast-Lineage Clones(CELL AND TISSUE ENGINEERING)

Abe Kaori,Miyoshi Keiko,Muto Taro,Ruspita Intan,Horiguchi Taigo,Nagata Toshihiko,Noma Takafumi
Journal of bioscience and bioengineering 103(5), 479-485, 2007-05-25
… To examine the roles of MAPK signals, we compared the effects of anisomycin and sodium salicylate on the expression of tooth-related differentiation markers. … Both anisomycin and sodium salicylate induced amelogenin, Abcg2, and Bmp4 mRNA and down-regulated p75NGFR mRNA. … On the other hand, ALP, ectodin, Bmp2 and Fgf8 mRNA were up-regulated only by anisomycin. …
NAID 110006278733

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リンク元

「レジオネラ属」

Anisomycin^[1]
Names
	IUPAC name (2R,3S,4S)-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidin-3-yl acetate
	Other names Flagecidin
Identifiers
CAS Registry Number	22862-76-6
ChEBI	CHEBI:338412
ChEMBL	ChEMBL423192
ChemSpider	29260
	InChI InChI=1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m0/s1 ; Key: YKJYKKNCCRKFSL-BFHYXJOUSA-N ; InChI=1/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m0/s1; Key: YKJYKKNCCRKFSL-BFHYXJOUBQ ;
Jmol-3D images	Image
PubChem	31549
	SMILES O=C(O[C@@H]1[C@@H](NC[C@H]1O)Cc2ccc(OC)cc2)C ;
UNII	6C74YM2NGI
Properties
Chemical formula	C14H19NO4
Molar mass	265.31 g/mol
Melting point	139 to 143 °C (282 to 289 °F; 412 to 416 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

　　[★]

英: Legionella
同: Legionella属、レジオネラ
関: レジオネラ科 Legionellaceae、グラム陰性桿菌

特徴

ヒト呼吸器感染症原因菌となる水中の好気性グラム陰性桿菌の一属
グラム陰性桿菌
グラム染色されにくい　→　ヒメネス染色、アクリジンオレンジ染色
BCYE-α寒天培地
細胞内増殖性　(細胞内寄生性細菌と同じ, 結核菌、チフス菌、リステリア菌)

レジオネラ症の代表的菌種レジオネラ属菌

Legionella pneumophila serotype 1　← 最も頻度が高い
Legionella pneumophila serotype 6
Legionella pneumophila other
Legionella micdadei
Legionella bozemanii
Legionella dumffii
Legionella gormanii
Legionella longbeachae
Legionella others

培養

標準的な選択培地：buffered charcoal yeast extract agar(BCYE agar) supplemented with polymyxin, anisomycin, vancomycin, and dyes

レジオネラ属による感染症

レジオネラ症

レジオネラ肺炎：4類感染症

治療

[Anisomycin-1] Anisomycin from Sigma Aldrich

[2] Grollman, Arthur P. (1967). "Inhibitors of protein biosynthesis. II. Mode of action of anisomycin". The Journal of Biological Chemistry 242 (13): 3226–33. PMID 6027796.

[3] Barrientos, Ruth M; O'Reilly, Randall C; Rudy, Jerry W (2002). "Memory for context is impaired by injecting anisomycin into dorsal hippocampus following context exploration". Behavioural Brain Research 134 (1–2): 299–306. doi:10.1016/S0166-4328(02)00045-1. PMID 12191817.

[4] Debiec et al, Neuron, 2002. PMID 12408854

[5] Wang, S.-H.; Ostlund, SB; Nader, K; Balleine, BW (2005). "Consolidation and Reconsolidation of Incentive Learning in the Amygdala". Journal of Neuroscience 25 (4): 830–5. doi:10.1523/JNEUROSCI.4716-04.2005. PMID 15673662.

[6] Butler, K. (1966). "Anisomycin. II.1 Biosynthesis of Anisomycin". The Journal of Organic Chemistry 31 (1): 317–20. doi:10.1021/jo01339a503. PMID 5900818.

匿名

検索

案内

案内

anisomycin

Wikipedia preview

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Contents

Pharmacology

Biosynthesis

Other uses

See also

References

UpToDate Contents

English Journal

Japanese Journal

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★リンクテーブル★

「レジオネラ属」

特徴

レジオネラ症の代表的菌種レジオネラ属菌

培養

レジオネラ属による感染症

治療

匿名

検索

案内

anisomycin

Wikipedia preview

wiki en

Contents

Pharmacology

Biosynthesis

Other uses

See also

References

UpToDate Contents

English Journal

Japanese Journal

Related Links

Related Pictures

★リンクテーブル★

「レジオネラ属」

特徴

レジオネラ症の代表的菌種 レジオネラ属菌

培養

レジオネラ属による感染症

治療

レジオネラ症の代表的菌種レジオネラ属菌