Nybomycin

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

MedKoo CAT#: 562406

CAS#: 26326-47-6

Description: Nybomycin is an anti-microbial agent against Mycobacterium smegmatis and Mycobacterium bovis BCG,. It act by binding DNA and inducing a unique morphological change to mycobacterial bacilli leading the bacterial cell death.


Price and Availability

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Nybomycin 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#: 562406
Name: Nybomycin
CAS#: 26326-47-6
Chemical Formula: C16H14N2O4
Exact Mass: 298.0954
Molecular Weight: 298.29
Elemental Analysis: C, 64.42; H, 4.73; N, 9.39; O, 21.45


Synonym: Nybomycin; NSC-613948; NSC 613948; NSC613948;

IUPAC/Chemical Name: 8-(Hydroxymethyl)-6,11-dimethyl-4H-(1,3)oxazolo(5,4,3-ij)pyrido(3,2-g)quinoline-4,10(11H)-dione

InChi Key: HKMUGCUFXWTNSP-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H14N2O4/c1-8-3-13(21)18-7-22-16-14-11(5-10(8)15(16)18)9(6-19)4-12(20)17(14)2/h3-5,19H,6-7H2,1-2H3

SMILES Code: O=C1N2C3=C(OC2)C4=C(C(CO)=CC(N4C)=O)C=C3C(C)=C1


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: Morimoto Y, Baba T, Sasaki T, Hiramatsu K. Apigenin as an anti-quinolone-resistance antibiotic. Int J Antimicrob Agents. 2015 Dec;46(6):666-73. doi: 10.1016/j.ijantimicag.2015.09.006. Epub 2015 Oct 22. PubMed PMID: 26526895.

2: Arai M, Kamiya K, Pruksakorn P, Sumii Y, Kotoku N, Joubert JP, Moodley P, Han C, Shin D, Kobayashi M. Anti-dormant mycobacterial activity and target analysis of nybomycin produced by a marine-derived Streptomyces sp. Bioorg Med Chem. 2015 Jul 1;23(13):3534-41. doi: 10.1016/j.bmc.2015.04.033. Epub 2015 Apr 17. PubMed PMID: 25934225.

3: Parkinson EI, Bair JS, Nakamura BA, Lee HY, Kuttab HI, Southgate EH, Lezmi S, Lau GW, Hergenrother PJ. Deoxynybomycins inhibit mutant DNA gyrase and rescue mice infected with fluoroquinolone-resistant bacteria. Nat Commun. 2015 Apr 24;6:6947. doi: 10.1038/ncomms7947. PubMed PMID: 25907309; PubMed Central PMCID: PMC4421842.

4: Adelmann S, Baldhoff T, Koepcke B, Schembecker G. Selection of operating parameters on the basis of hydrodynamics in centrifugal partition chromatography for the purification of nybomycin derivatives. J Chromatogr A. 2013 Jan 25;1274:54-64. doi: 10.1016/j.chroma.2012.11.031. Epub 2012 Dec 12. PubMed PMID: 23290339.

5: Hiramatsu K, Igarashi M, Morimoto Y, Baba T, Umekita M, Akamatsu Y. Curing bacteria of antibiotic resistance: reverse antibiotics, a novel class of antibiotics in nature. Int J Antimicrob Agents. 2012 Jun;39(6):478-85. doi: 10.1016/j.ijantimicag.2012.02.007. Epub 2012 Apr 23. PubMed PMID: 22534508.

6: Pope JA Jr, Nelson RA, Schaffner CP, Rosen RT, Pandey RC. Applications of thin layer chromatography, high performance liquid chromatography and mass spectrometry in the fermentation and isolation of the antibiotic nybomycin. J Ind Microbiol. 1990 Sep;6(1):61-9. PubMed PMID: 1369285.

7: Nadzan AM, Rinehart KL Jr. Nybomycin. 9. Synthetic and biosynthetic incorporation of 15N as a means of assigning the 13C nuclear magnetic resonance spectrum of nybomycin 1,2. J Am Chem Soc. 1977 Jul 6;99(14):4647-54. PubMed PMID: 874227.

8: Nadzan AM, Rinehart KL Jr. Letter: Nybomycin. 8. Biosynthetic origin of the central ring carbons studied by 13C-labeled substrates. J Am Chem Soc. 1976 Aug 4;98(16):5012-4. PubMed PMID: 950425.

9: Forbis RM, Rinehart KL Jr. Nybomycin. VII. Preparative routes to nybomycin and deoxynybomycin. J Am Chem Soc. 1973 Jul 25;95(15):5003-13. PubMed PMID: 4741283.

10: Knöll WM, Huxtable RJ, Rinehart KL Jr. Nybomycin. VI. Incorporation of acetate- 13 C, acetate- 14 C, and methionine- 14 C. J Am Chem Soc. 1973 Apr 18;95(8):2703-4. PubMed PMID: 4694531.

11: Forbis RM, Rinehart KL Jr. Nybomycin. V. Total synthesis of nybomycin. J Antibiot (Tokyo). 1971 May;24(5):326-7. PubMed PMID: 5581353.

12: Forbis RM, Rinehart KL Jr. Nybomycin. IV. Total synthesis of deoxynybomycin. J Am Chem Soc. 1970 Nov 18;92(23):6995-6. PubMed PMID: 5483075.

13: Rinehart KL Jr, Leadbetter G, Larson RA, Forbis RM. Nybomycin. 3. A revised structure. J Am Chem Soc. 1970 Nov 18;92(23):6994-5. PubMed PMID: 5483074.

14: BROCK TD, SOKOLSKI WT. Biological studies on the antibiotic, nybomycin. Antibiot Chemother (Northfield). 1958 Dec;8(12):631-6. PubMed PMID: 24545057.

15: EBLE TE, BOYACK GA, LARGE CM, DEVRIES WH. Nybomycin: isolation, properties, and derivatives. Antibiot Chemother (Northfield). 1958 Dec;8(12):627-30. PubMed PMID: 24545056.

16: Strelitz F, Flon H, Asheshov IN. NYBOMYCIN, A NEW ANTIBIOTIC WITH ANTIPHAGE AND ANTIBACTERIAL PROPERTIES. Proc Natl Acad Sci U S A. 1955 Sep 15;41(9):620-4. PubMed PMID: 16589716; PubMed Central PMCID: PMC528149.