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.


Chemical Structure

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Bactobolin
CAS# 72615-20-4

Theoretical Analysis

MedKoo Cat#: 341067
Name: Bactobolin
CAS#: 72615-20-4
Chemical Formula: C14H20Cl2N2O6
Exact Mass: 382.07
Molecular Weight: 383.222
Elemental Analysis: C, 43.88; H, 5.26; Cl, 18.50; N, 7.31; O, 25.05

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 383.22 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

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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.

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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.

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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.