Negamycin

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MedKoo CAT#: 562711

CAS#: 33404-78-3

Description: Negamycin is a broad-spectrum antibacterial agent. It acts by inhibiting protein synthesis.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-09-28. Prices are subject to change without notice.

Negamycin 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#: 562711
Name: Negamycin
CAS#: 33404-78-3
Chemical Formula: C9H20N4O4
Exact Mass: 248.1485
Molecular Weight: 248.28
Elemental Analysis: C, 43.54; H, 8.12; N, 22.57; O, 25.78


Synonym: Negamycin;

IUPAC/Chemical Name: (2-((3R,5R)-3,6-Diamino-5-hydroxyhexanoyl)-1-methylhydrazino) acetic acid

InChi Key: IKHFJPZQZVMLRH-RNFRBKRXSA-N

InChi Code: InChI=1S/C9H20N4O4/c1-13(5-9(16)17)12-8(15)3-6(11)2-7(14)4-10/h6-7,14H,2-5,10-11H2,1H3,(H,12,15)(H,16,17)/t6-,7-/m1/s1

SMILES Code: O=C(O)CN(C)NC(C[C@H](N)C[C@@H](O)CN)=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).

HS Tariff Code:
2934.99.9001


References

1: Pranke I, Bidou L, Martin N, Blanchet S, Hatton A, Karri S, Cornu D, Costes B, Chevalier B, Tondelier D, Girodon E, Coupet M, Edelman A, Fanen P, Namy O, Sermet-Gaudelus I, Hinzpeter A. Factors influencing readthrough therapy for frequent cystic fibrosis premature termination codons. ERJ Open Res. 2018 Feb 23;4(1). pii: 00080-2017. doi: 10.1183/23120541.00080-2017. eCollection 2018 Jan. PubMed PMID: 29497617; PubMed Central PMCID: PMC5827411.

2: Taguchi A, Hamada K, Shiozuka M, Kobayashi M, Murakami S, Takayama K, Taniguchi A, Usui T, Matsuda R, Hayashi Y. Structure-Activity Relationship Study of Leucyl-3-epi-deoxynegamycin for Potent Premature Termination Codon Readthrough. ACS Med Chem Lett. 2017 Sep 29;8(10):1060-1065. doi: 10.1021/acsmedchemlett.7b00269. eCollection 2017 Oct 12. PubMed PMID: 29057051; PubMed Central PMCID: PMC5642019.

3: Taguchi A, Hamada K, Hayashi Y. Chemotherapeutics overcoming nonsense mutation-associated genetic diseases: medicinal chemistry of negamycin. J Antibiot (Tokyo). 2018 Feb;71(2):205-214. doi: 10.1038/ja.2017.112. Epub 2017 Sep 27. Review. PubMed PMID: 28951602.

4: Cocozaki AI, Altman RB, Huang J, Buurman ET, Kazmirski SL, Doig P, Prince DB, Blanchard SC, Cate JH, Ferguson AD. Resistance mutations generate divergent antibiotic susceptibility profiles against translation inhibitors. Proc Natl Acad Sci U S A. 2016 Jul 19;113(29):8188-93. doi: 10.1073/pnas.1605127113. Epub 2016 Jul 5. PubMed PMID: 27382179; PubMed Central PMCID: PMC4961145.

5: McKinney DC, Basarab GS, Cocozaki AI, Foulk MA, Miller MD, Ruvinsky AM, Scott CW, Thakur K, Zhao L, Buurman ET, Narayan S. Structural Insights Lead to a Negamycin Analogue with Improved Antimicrobial Activity against Gram-Negative Pathogens. ACS Med Chem Lett. 2015 Jul 12;6(8):930-5. doi: 10.1021/acsmedchemlett.5b00205. eCollection 2015 Aug 13. PubMed PMID: 26288696; PubMed Central PMCID: PMC4538447.

6: Hamada K, Taguchi A, Kotake M, Aita S, Murakami S, Takayama K, Yakushiji F, Hayashi Y. Structure-Activity Relationship Studies of 3-epi-Deoxynegamycin Derivatives as Potent Readthrough Drug Candidates. ACS Med Chem Lett. 2015 May 11;6(6):689-94. doi: 10.1021/acsmedchemlett.5b00121. eCollection 2015 Jun 11. PubMed PMID: 26101575; PubMed Central PMCID: PMC4468409.

7: McKinney DC, Bezdenejnih-Snyder N, Farrington K, Guo J, McLaughlin RE, Ruvinsky AM, Singh R, Basarab GS, Narayan S, Buurman ET. Illicit Transport via Dipeptide Transporter Dpp is Irrelevant to the Efficacy of Negamycin in Mouse Thigh Models of Escherichia coli Infection. ACS Infect Dis. 2015 May 8;1(5):222-30. doi: 10.1021/acsinfecdis.5b00027. Epub 2015 Apr 7. PubMed PMID: 27622650.

8: Guo J, Miele EW, Chen A, Luzietti RA, Zambrowski M, Walsky RL, Buurman ET. Pharmacokinetics of the natural antibiotic negamycin. Xenobiotica. 2015;45(7):625-33. doi: 10.3109/00498254.2015.1006301. Epub 2015 Mar 3. PubMed PMID: 25733027.

9: Olivier NB, Altman RB, Noeske J, Basarab GS, Code E, Ferguson AD, Gao N, Huang J, Juette MF, Livchak S, Miller MD, Prince DB, Cate JH, Buurman ET, Blanchard SC. Negamycin induces translational stalling and miscoding by binding to the small subunit head domain of the Escherichia coli ribosome. Proc Natl Acad Sci U S A. 2014 Nov 18;111(46):16274-9. doi: 10.1073/pnas.1414401111. Epub 2014 Nov 3. PubMed PMID: 25368144; PubMed Central PMCID: PMC4246262.

10: Polikanov YS, Szal T, Jiang F, Gupta P, Matsuda R, Shiozuka M, Steitz TA, Vázquez-Laslop N, Mankin AS. Negamycin interferes with decoding and translocation by simultaneous interaction with rRNA and tRNA. Mol Cell. 2014 Nov 20;56(4):541-50. doi: 10.1016/j.molcel.2014.09.021. Epub 2014 Oct 9. PubMed PMID: 25306922; PubMed Central PMCID: PMC4334386.

11: Taguchi A, Hamada K, Kotake M, Shiozuka M, Nakaminami H, Pillaiyar T, Takayama K, Yakushiji F, Noguchi N, Usui T, Matsuda R, Hayashi Y. Discovery of natural products possessing selective eukaryotic readthrough activity: 3-epi-deoxynegamycin and its leucine adduct. ChemMedChem. 2014 Oct;9(10):2233-7. doi: 10.1002/cmdc.201402208. Epub 2014 Jul 9. PubMed PMID: 25044534.

12: Bates RW, Khanizeman RN, Hirao H, Tay YS, Sae-Lao P. A total synthesis of (+)-negamycin through isoxazolidine allylation. Org Biomol Chem. 2014 Jul 21;12(27):4879-84. doi: 10.1039/c4ob00537f. PubMed PMID: 24875354.

13: Pascual-Pascual SI. [Treatment with antisense oligonucleotides in Duchenne's disease]. Rev Neurol. 2012 May 21;54 Suppl 3:S31-9. Review. Spanish. PubMed PMID: 22605630.

14: Taguchi A, Nishiguchi S, Shiozuka M, Nomoto T, Ina M, Nojima S, Matsuda R, Nonomura Y, Kiso Y, Yamazaki Y, Yakushiji F, Hayashi Y. Negamycin analogue with readthrough-promoting activity as a potential drug candidate for duchenne muscular dystrophy. ACS Med Chem Lett. 2012 Jan 2;3(2):118-22. doi: 10.1021/ml200245t. eCollection 2012 Feb 9. PubMed PMID: 24900441; PubMed Central PMCID: PMC4025641.

15: Shiozuka M, Matsuda R. [Therapeutic readthrough strategy for suppression of nonsense mutations in duchenne muscular dystrophy]. Brain Nerve. 2011 Nov;63(11):1253-60. Review. Japanese. PubMed PMID: 22068478.

16: Floquet C, Rousset JP, Bidou L. Readthrough of premature termination codons in the adenomatous polyposis coli gene restores its biological activity in human cancer cells. PLoS One. 2011;6(8):e24125. doi: 10.1371/journal.pone.0024125. Epub 2011 Aug 31. PubMed PMID: 21909382; PubMed Central PMCID: PMC3166079.

17: Hayashi Y, Nishiguchi S, Sydnes MO, Regnier T, Hasegawa JY, Katoh T, Kajimoto T, Node M, Kiso Y. A new synthesis of (+)-negamycin and its derivatives as a potential therapeutic agent for Duchenne muscular dystrophy treatment. Adv Exp Med Biol. 2009;611:137-8. PubMed PMID: 19400128.

18: Hayashi Y, Regnier T, Nishiguchi S, Sydnes MO, Hashimoto D, Hasegawa J, Katoh T, Kajimoto T, Shiozuka M, Matsuda R, Node M, Kiso Y. Efficient total synthesis of (+)-negamycin, a potential chemotherapeutic agent for genetic diseases. Chem Commun (Camb). 2008 May 28;(20):2379-81. doi: 10.1039/b801498a. Epub 2008 Mar 18. PubMed PMID: 18473076.

19: Allamand V, Bidou L, Arakawa M, Floquet C, Shiozuka M, Paturneau-Jouas M, Gartioux C, Butler-Browne GS, Mouly V, Rousset JP, Matsuda R, Ikeda D, Guicheney P. Drug-induced readthrough of premature stop codons leads to the stabilization of laminin alpha2 chain mRNA in CMD myotubes. J Gene Med. 2008 Feb;10(2):217-24. PubMed PMID: 18074402.

20: Schroeder SJ, Blaha G, Moore PB. Negamycin binds to the wall of the nascent chain exit tunnel of the 50S ribosomal subunit. Antimicrob Agents Chemother. 2007 Dec;51(12):4462-5. Epub 2007 Jul 30. PubMed PMID: 17664317; PubMed Central PMCID: PMC2167971.