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MedKoo Cat#: 584205 | Name: Bicyclomycin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Bicyclomycin
Bicyclomycin
CAS#38129-37-2

Theoretical Analysis

MedKoo Cat#: 584205

Name: Bicyclomycin

CAS#: 38129-37-2

Chemical Formula: C12H18N2O7

Exact Mass: 302.1114

Molecular Weight: 302.28

Elemental Analysis: C, 47.68; H, 6.00; N, 9.27; O, 37.05

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Synonym
Bicyclomycin; Bicozamycin
IUPAC/Chemical Name
Pyridine, 4,4'-(iminodimethylene)di-, citrate (1:1)
InChi Key
WOUDXEYYJPOSNE-DSRXWYFFSA-N
InChi Code
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
SMILES Code
O=C(C(NC1=O)([C@H](O)C(C)(O)CO)OCC2)N[C@]1(O)C2=C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 302.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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. 11: Weber TP, Widger WR, Kohn H. Metal-1,4-dithio-2,3-dihydroxybutane chelates: novel inhibitors of the Rho transcription termination factor. Biochemistry. 2003 Aug 5;42(30):9121-6. PubMed PMID: 12885245. 12: Park Hg HG, Zhang X, Widger WR, Kohn H. Role of the C(1) Triol Group in Bicyclomycin: Synthesis and Biochemical and Biological Properties. J Org Chem. 1996 Nov 1;61(22):7750-7755. PubMed PMID: 11667730. 13: Chandraprakash D, Seshasayee AS. Inhibition of factor-dependent transcription termination in Escherichia coli might relieve xenogene silencing by abrogating H-NS-DNA interactions in vivo. J Biosci. 2014 Mar;39(1):53-61. PubMed PMID: 24499790. 14: Kamiya T, Maeno S, Hashimoto M, Mine Y. Bicyclomycin, a new antibiotic. II. Structural elucidation and acyl derivatives. J Antibiot (Tokyo). 1972 Oct;25(10):576-81. PubMed PMID: 4648312. 15: Someya A, Tanaka K, Tanaka N. Morphological changes of Escherichia coli induced by bicyclomycin. Antimicrob Agents Chemother. 1979 Jul;16(1):87-91. PubMed PMID: 383016; PubMed Central PMCID: PMC352794. 16: Hussein R, Lee TY, Lim HN. Quantitative characterization of gene regulation by Rho dependent transcription termination. Biochim Biophys Acta. 2015 Aug;1849(8):940-54. doi: 10.1016/j.bbagrm.2015.05.003. Epub 2015 May 14. PubMed PMID: 25982507. 17: Washburn RS, Marra A, Bryant AP, Rosenberg M, Gentry DR. rho is not essential for viability or virulence in Staphylococcus aureus. Antimicrob Agents Chemother. 2001 Apr;45(4):1099-103. PubMed PMID: 11257021; PubMed Central PMCID: PMC90430. 18: Santillán A Jr, Park Hg HG, Zhang X, Lee OS, Widger WR, Kohn H. Role of the [4.2.2] Bicyclic Unit in Bicyclomycin: Synthesis, Structure, Chemical, Biochemical, and Biological Properties. J Org Chem. 1996 Nov 1;61(22):7756-7763. PubMed PMID: 11667731. 19: Magyar A, Zhang X, Abdi F, Kohn H, Widger WR. Identifying the bicyclomycin binding domain through biochemical analysis of antibiotic-resistant rho proteins. J Biol Chem. 1999 Mar 12;274(11):7316-24. PubMed PMID: 10066795. 20: Fonseca EL, Marin MA, Encinas F, Vicente AC. Full characterization of the integrative and conjugative element carrying the metallo-β-lactamase bla SPM-1 and bicyclomycin bcr1 resistance genes found in the pandemic Pseudomonas aeruginosa clone SP/ST277. J Antimicrob Chemother. 2015 Sep;70(9):2547-50. doi: 10.1093/jac/dkv152. Epub 2015 Jun 20. PubMed PMID: 26093374.