Bactobolin

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

MedKoo CAT#: 341067

CAS#: 72615-20-4

Description: Bactobolin is a biochemical.


Price and Availability

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Bactobolin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 341067
Name: Bactobolin
CAS#: 72615-20-4
Chemical Formula: C14H20Cl2N2O6
Exact Mass: 382.0698
Molecular Weight: 383.222
Elemental Analysis: C, 43.88; H, 5.26; Cl, 18.50; N, 7.31; O, 25.05


Synonym: Bactobolin; Y 12278; Y-12278; Y12278.

IUPAC/Chemical Name: Propanamide, 2-amino-N-(3-(dichloromethyl)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl)-, (3S-(3alpha,4alpha(R*),4abeta,5beta,6a

InChi Key: RBCHRRIVFAIGFI-RGBMRXMBSA-N

InChi Code: InChI=1S/C14H20Cl2N2O6/c1-4(17)11(22)18-10-8-7(5(19)3-6(20)9(8)21)12(23)24-14(10,2)13(15)16/h4,6,8-10,13,19-21H,3,17H2,1-2H3,(H,18,22)/t4-,6+,8-,9-,10+,14-/m0/s1

SMILES Code: C1=2[C@H]([C@@H](NC(=O)[C@@H](N)C)[C@](OC1=O)(C(Cl)Cl)C)[C@@H](O)[C@@H](CC2O)O


Technical Data

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).

Harmonized System Code:
293490


References

1: Evans KC, Benomar S, Camuy-Vélez LA, Nasseri EB, Wang X, Neuenswander B, Chandler JR. Quorum-sensing control of antibiotic resistance stabilizes cooperation in Chromobacterium violaceum. ISME J. 2018 Jan 26. doi: 10.1038/s41396-018-0047-7. [Epub ahead of print] PubMed PMID: 29374267.

2: Wong RR, Kong C, Lee SH, Nathan S. Detection of Burkholderia pseudomallei toxin-mediated inhibition of protein synthesis using a Caenorhabditis elegans ugt-29 biosensor. Sci Rep. 2016 Jun 7;6:27475. doi: 10.1038/srep27475. PubMed PMID: 27273550; PubMed Central PMCID: PMC4895344.

3: Ojini I, Gammie A. Rapid Identification of Chemoresistance Mechanisms Using Yeast DNA Mismatch Repair Mutants. G3 (Bethesda). 2015 Jul 21;5(9):1925-35. doi: 10.1534/g3.115.020560. PubMed PMID: 26199284; PubMed Central PMCID: PMC4555229.

4: Amunts A, Fiedorczuk K, Truong TT, Chandler J, Peter Greenberg E, Ramakrishnan V. Bactobolin A binds to a site on the 70S ribosome distinct from previously seen antibiotics. J Mol Biol. 2015 Feb 27;427(4):753-5. doi: 10.1016/j.jmb.2014.12.018. Epub 2015 Jan 3. PubMed PMID: 25562208; PubMed Central PMCID: PMC4332689.

5: Chandler JR, Truong TT, Silva PM, Seyedsayamdost MR, Carr G, Radey M, Jacobs MA, Sims EH, Clardy J, Greenberg EP. Bactobolin resistance is conferred by mutations in the L2 ribosomal protein. MBio. 2012 Dec 18;3(6). pii: e00499-12. doi: 10.1128/mBio.00499-12. PubMed PMID: 23249812; PubMed Central PMCID: PMC3529544.

6: Chandler JR, Heilmann S, Mittler JE, Greenberg EP. Acyl-homoserine lactone-dependent eavesdropping promotes competition in a laboratory co-culture model. ISME J. 2012 Dec;6(12):2219-28. doi: 10.1038/ismej.2012.69. Epub 2012 Jul 5. PubMed PMID: 22763647; PubMed Central PMCID: PMC3504959.

7: Carr G, Seyedsayamdost MR, Chandler JR, Greenberg EP, Clardy J. Sources of diversity in bactobolin biosynthesis by Burkholderia thailandensis E264. Org Lett. 2011 Jun 17;13(12):3048-51. doi: 10.1021/ol200922s. Epub 2011 May 26. PubMed PMID: 21615115; PubMed Central PMCID: PMC3111747.

8: Seyedsayamdost MR, Chandler JR, Blodgett JA, Lima PS, Duerkop BA, Oinuma K, Greenberg EP, Clardy J. Quorum-sensing-regulated bactobolin production by Burkholderia thailandensis E264. Org Lett. 2010 Feb 19;12(4):716-9. doi: 10.1021/ol902751x. PubMed PMID: 20095633; PubMed Central PMCID: PMC2821070.

9: Adachi H, Nishimura Y. Synthesis and biological activity of bactobolin glucosides. Nat Prod Res. 2003 Aug;17(4):253-7. PubMed PMID: 12822903.

10: Adachi H, Nishimura Y, Takeuchi T. Synthesis and activities of bactobolin derivatives having new functionality at C-3. J Antibiot (Tokyo). 2002 Jan;55(1):92-8. PubMed PMID: 11918072.

11: Ishizuka M. [Action and molecular targets of anti cancer agents from microbial products]. Jpn J Antibiot. 1999 Feb;52(2):174-5. Japanese. PubMed PMID: 10221183.

12: Kawada M, Amemiya M, Ishizuka M, Takeuchi T. Differential induction of apoptosis in B16 melanoma and EL-4 lymphoma cells by cytostatin and bactobolin. Jpn J Cancer Res. 1999 Feb;90(2):219-25. PubMed PMID: 10189893.

13: Adachi H, Nishimura Y, Kondo S, Takeuchi T. Synthesis and activity of 3-epi-actinobolin. J Antibiot (Tokyo). 1998 Feb;51(2):202-9. PubMed PMID: 9544942.

14: Adachi H, Usui T, Nishimura Y, Kondo S, Ishizuka M, Takeuchi T. Synthesis and activities of bactobolin derivatives based on the alteration of the functionality at C-3 position. J Antibiot (Tokyo). 1998 Feb;51(2):184-8. PubMed PMID: 9544940.

15: Ishigaki Y, Sato T, Song DL, Hayashi K, Aoyagi T. Suppression of experimental autoimmune myasthenia gravis with new immunosuppressants: 15-deoxyspergualin and actinobolin. J Neurol Sci. 1992 Oct;112(1-2):209-15. PubMed PMID: 1469434.

16: Nishimura Y, Kondo S, Takeuchi T. Syntheses and activities of some bactobolin derivatives. J Antibiot (Tokyo). 1992 May;45(5):735-41. PubMed PMID: 1624375.

17: Ishizuka M. [Immunomodulation by antitumor antibiotics]. Gan To Kagaku Ryoho. 1986 Mar;13(3 Pt 2):697-700. Japanese. PubMed PMID: 3963840.

18: Umezawa H. [Secondary microbial metabolites with potentials for antineoplastic actions: antineoplastic antibiotics and immunopotentiators]. Gan To Kagaku Ryoho. 1983 Apr;10(4 Pt 2):1071-86. Review. Japanese. PubMed PMID: 6191672.

19: Hori M, Suzukake K, Ishikawa C, Asakura H, Umezawa H. Biochemical studies on bactobolin in relation to actinobolin. J Antibiot (Tokyo). 1981 Apr;34(4):465-8. PubMed PMID: 7196909.

20: Munakata T, Okumoto T. Some structure-activity relationships for bactobolin analogs in the treatment of mouse leukemia P388. Chem Pharm Bull (Tokyo). 1981 Mar;29(3):891-4. PubMed PMID: 7249163.