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Bicyclomycin

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names：
Pyridine, 4,4'-(iminodimethylene)di-, citrate (11)
CAS號(hào)：
38129-37-2
MDL Number：
MF(分子式)： C12H18N2O7 MW(分子量)： 302.283
EINECS: Reaxys Number:
Pubchem ID: Brand:BIOFOUNT

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中文別名	Bicyclomycin
英文別名	Bicyclomycin; Bicozamycin
CAS號(hào)	38129-37-2
Inchi	InChI=1S/C12H18N2O7/c1-6-3-4-21-12(7(16)10(2,19)5-15)9(18)13-11(6,20)8(17)14-12/h7,15-16,19-20H,1,3-5H2,2H3,(H,13,18)(H,14,17)/t7-,10?,11+,12?/m1/s1
InchiKey	WOUDXEYYJPOSNE-DSRXWYFFSA-N
分子式 Formula	C12H18N2O7
分子量 Molecular Weight	302.283
溶解度Solubility
性狀	Solid powder
儲(chǔ)藏條件 Storage conditions	Dry, dark and store at 0-4℃ for short term (days to weeks) or -20℃ for long term (Store correctly 2-3years).

產(chǎn)品說(shuō)明	Bicyclomycin(CAS:38129-37-2):僅限應(yīng)用于工業(yè)或者科學(xué)研究過(guò)程中非醫(yī)療目的，不應(yīng)用于人類或動(dòng)物的臨床診斷以及治過(guò)程療，該產(chǎn)品非藥用，非食用。
Introduction	Bicyclomycin (Bicozamycin) is a broad spectrum antibiotic active against Gram-negative bacteria and the Gram-positive bacterium, Micrococcus luteusn that was isolated from Streptomyces sapporonesis and Streptomyces aizumenses in 1972. It belongs to a class of naturally occurring 2,5-diketopiperazines, that are among the most numerous of all the naturally occurring peptide antibiotics. This clinically useful antibiotic is rapidly absorbed in man when given intramuscularly, has low toxicity and has been used to treat diarrhea in humans and bacterial diarrhea in calves and pigs.
Application1
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[1]Tran L, van Baarsel JA, Washburn RS, Gottesman ME, Miller JH. Single-gene deletion mutants of Escherichia coli with altered sensitivity to bicyclomycin, an inhibitor of transcription termination factor Rho. J Bacteriol. 2011 May;193(9):2229-35. doi: 10.1128/JB.01463-10. Epub 2011 Feb 25. PubMed PMID: 21357484; PubMed Central PMCID: PMC3133090.

[2]Weber TP, Widger WR, Kohn H. The Mg2+ requirements for rho transcription termination factor: catalysis and bicyclomycin inhibition. Biochemistry. 2002 Oct 15;41(41):12377-83. PubMed PMID: 12369827.

[3] Tanaka N, Iseki M, Miyoshi T, Aoki H, Imanaka H. Mechanism of action of bicyclomycin. J Antibiot (Tokyo). 1976 Feb;29(2):155-68. PubMed PMID: 776917.

[4] Someya A, Iseki M, Tanaka N. Active groups of bicyclomycin and the reaction with thiols. J Antibiot (Tokyo). 1979 Apr;32(4):402-7. PubMed PMID: 38239.

[5] Pedrolli D, Langer S, Hobl B, Schwarz J, Hashimoto M, Mack M. The ribB FMN riboswitch from Escherichia coli operates at the transcriptional and translational level and regulates riboflavin biosynthesis. FEBS J. 2015 Aug;282(16):3230-42. doi: 10.1111/febs.13226. Epub 2015 Feb 27. PubMed PMID: 25661987.

6: Malik M, Li L, Zhao X, Kerns RJ, Berger JM, Drlica K. Lethal synergy involving bicyclomycin: an approach for reviving old antibiotics. J Antimicrob Chemother. 2014 Dec;69(12):3227-35. doi: 10.1093/jac/dku285. Epub 2014 Jul 31. PubMed PMID: 25085655; PubMed Central PMCID: PMC4228776.7: Santillán A Jr, Zhang X, Hardesty J, Widger WR, Kohn H. Role of the C(6)-hydroxy group in bicyclomycin: synthesis, structure, and chemical, biochemical, and biological properties. J Med Chem. 1998 Mar 26;41(7):1185-94. PubMed PMID: 9544218.8: Riba I, Gaskell SJ, Cho H, Widger WR, Kohn H. Evidence for the location of bicyclomycin binding to the Escherichia coli transcription termination factor Rho. J Biol Chem. 1998 Dec 18;273(51):34033-41. PubMed PMID: 9852059.9: Müller BW, Zak O, Kump W, Tosch W, Wacker O. Semisynthetic bicyclomycin derivatives: preparation and antibacterial evaluation. J Antibiot (Tokyo). 1979 Jul;32(7):689-705. PubMed PMID: 541264.10: Xu Y, Johnson J, Kohn H, Widger WR. ATP binding to Rho transcription termination factor. Mutant F355W ATP-induced fluorescence quenching reveals dynamic ATP binding. J Biol Chem. 2003 Apr 18;278(16):13719-27. Epub 2003 Jan 27. PubMed PMID: 12551938.1

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