Nucleozin
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MedKoo CAT#: 326797

CAS#: 341001-38-5

Description: Nucleozin is an antivirus agent. Nucleozin targets influenza A nucleoprotein (NP), a multifunctional, RNA-binding protein necessary for virus replication. Nucleozin is effective in fighting H1N1, H3N2, and H5N1 flu virus strains by inducing the formation of NP aggregates and antagonizing its nuclear accumulation, leading to cessation of viral replication.

Chemical Structure

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Nucleozin
CAS# 341001-38-5
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326797
Name: Nucleozin
CAS#: 341001-38-5
Chemical Formula: C21H19ClN4O4
Exact Mass: 426.11
Molecular Weight: 426.857
Elemental Analysis: C, 59.09; H, 4.49; Cl, 8.30; N, 13.13; O, 14.99

Price and Availability

Size Price Availability Quantity
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 425 Ready to ship
200mg USD 650 Ready to ship
500mg USD 1350 Ready to ship
1g USD 2150 Ready to ship
2g USD 3450 Ready to ship
5g USD 6950 Ready to ship
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Synonym: Nucleozin

IUPAC/Chemical Name: 1-(2-Chloro-4-nitrophenyl)-4-[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]-piperazine

InChi Key: OWXBJAPOSQSWAO-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H19ClN4O4/c1-14-19(20(23-30-14)15-5-3-2-4-6-15)21(27)25-11-9-24(10-12-25)18-8-7-16(26(28)29)13-17(18)22/h2-8,13H,9-12H2,1H3

SMILES Code: O=C(N1CCN(C2=CC=C([N+]([O-])=O)C=C2Cl)CC1)C3=C(C)ON=C3C4=CC=CC=C4

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: Nucleozin, a potent inhibitor of influenza A virus infection, induces the formation of nucleoprotein (NP) aggregates and antagonizes its nuclear accumulation, leading to cessation of viral replication.
In vitro activity: To test if nucleozin blocked onward transport from the RE, images of living virus-infected cells containing GFP-NP-tagged RNPs, as well as RFP-Rab11 were acquired. A549 cells were transfected with GFP-NP and RFP-Rab11, infected with PR8 virus or mock infected 12 h later, and imaged at 8 hpi. The effect of adding nucleozin was then tested. In mock-infected cells, drug addition had little apparent effect, in terms of both the overall localization patterns of GFP-NP and RFP-Rab11 (Fig. 4A) and their movement in time-lapse movies (see min 4.5 to 29 of Movie S1). However, when the drug was added to infected cells, the result was a dramatic loss of the small, highly mobile GFP-NP- and RFP-Rab11-positive bodies, which were replaced by increasingly large cytoplasmic aggregates that still contained both proteins but that in many cases collapsed back onto the perinuclear region (Fig. 4C; see Movie S3). High-magnification movies of vRNP-decorated vesicles moving in the cytoplasm of infected cells showed that they were highly mobile and that while there were apparently continual interactions among them, these were transient (see Fig. S3A [white arrowheads] and Movie S4 in the supplemental material). However, in the presence of nucleozin, interacting vesicular structures tended to remain attached over time, thus forming large agglomerations. (see Fig. S3B [white arrowheads] and Movie S5). Thus, nucleozin exerts a general block to cytoplasmic transport of RNP-Rab11 complexes by sticking vRNPs and their associated transport machinery together, most likely via NP-NP interactions. Reference: J Virol. 2013 Apr; 87(8): 4694–4703. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3624347/
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 22.0 51.63

Preparing Stock Solutions

The following data is based on the product molecular weight 426.86 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: 1. Amorim MJ, Kao RY, Digard P. Nucleozin targets cytoplasmic trafficking of viral ribonucleoprotein-Rab11 complexes in influenza A virus infection. J Virol. 2013 Apr;87(8):4694-703. doi: 10.1128/JVI.03123-12. Epub 2013 Feb 13. PMID: 23408618; PMCID: PMC3624347.
In vitro protocol: 1. Amorim MJ, Kao RY, Digard P. Nucleozin targets cytoplasmic trafficking of viral ribonucleoprotein-Rab11 complexes in influenza A virus infection. J Virol. 2013 Apr;87(8):4694-703. doi: 10.1128/JVI.03123-12. Epub 2013 Feb 13. PMID: 23408618; PMCID: PMC3624347.
In vivo protocol: TBD

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1: Pang B, Cheung NN, Zhang W, Dai J, Kao RY, Zhang H, Hao Q. Structural Characterization of H1N1 Nucleoprotein-Nucleozin Binding Sites. Sci Rep. 2016 Jul 11;6:29684. doi: 10.1038/srep29684. PubMed PMID: 27404920; PubMed Central PMCID: PMC4939526.

2: Lai KK, Cheung NN, Yang F, Dai J, Liu L, Chen Z, Sze KH, Chen H, Yuen KY, Kao RY. Identification of Novel Fusion Inhibitors of Influenza A Virus by Chemical Genetics. J Virol. 2015 Dec 16;90(5):2690-701. doi: 10.1128/JVI.02326-15. PubMed PMID: 26676787; PubMed Central PMCID: PMC4810722.

3: Lin MI, Su BH, Lee CH, Wang ST, Wu WC, Dangate P, Wang SY, Huang WI, Cheng TJ, Lin OA, Cheng YS, Tseng YJ, Sun CM. Synthesis and inhibitory effects of novel pyrimido-pyrrolo-quinoxalinedione analogues targeting nucleoproteins of influenza A virus H1N1. Eur J Med Chem. 2015 Sep 18;102:477-86. doi: 10.1016/j.ejmech.2015.08.016. Epub 2015 Aug 13. PubMed PMID: 26310893.

4: Antony H, Schaeffer PM. A GFP-tagged nucleoprotein-based aggregation assay for anti-influenza drug discovery and antibody development. Analyst. 2013 Oct 21;138(20):6073-80. doi: 10.1039/c3an01041d. Epub 2013 Aug 19. PubMed PMID: 23961535.

5: Amorim MJ, Kao RY, Digard P. Nucleozin targets cytoplasmic trafficking of viral ribonucleoprotein-Rab11 complexes in influenza A virus infection. J Virol. 2013 Apr;87(8):4694-703. doi: 10.1128/JVI.03123-12. Epub 2013 Feb 13. PubMed PMID: 23408618; PubMed Central PMCID: PMC3624347.

6: Hung HC, Liu CL, Hsu JT, Horng JT, Fang MY, Wu SY, Ueng SH, Wang MY, Yaw CW, Hou MH. Development of an anti-influenza drug screening assay targeting nucleoproteins with tryptophan fluorescence quenching. Anal Chem. 2012 Aug 7;84(15):6391-9. doi: 10.1021/ac2022426. Epub 2012 Jul 10. PubMed PMID: 22712523.

7: Cheng H, Wan J, Lin MI, Liu Y, Lu X, Liu J, Xu Y, Chen J, Tu Z, Cheng YS, Ding K. Design, synthesis, and in vitro biological evaluation of 1H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents targeting virus nucleoprotein. J Med Chem. 2012 Mar 8;55(5):2144-53. doi: 10.1021/jm2013503. Epub 2012 Feb 27. PubMed PMID: 22332894.

8: Shen YF, Chen YH, Chu SY, Lin MI, Hsu HT, Wu PY, Wu CJ, Liu HW, Lin FY, Lin G, Hsu PH, Yang AS, Cheng YS, Wu YT, Wong CH, Tsai MD. E339...R416 salt bridge of nucleoprotein as a feasible target for influenza virus inhibitors. Proc Natl Acad Sci U S A. 2011 Oct 4;108(40):16515-20. doi: 10.1073/pnas.1113107108. Epub 2011 Sep 19. PubMed PMID: 21930946; PubMed Central PMCID: PMC3189076.

9: Su CY, Cheng TJ, Lin MI, Wang SY, Huang WI, Lin-Chu SY, Chen YH, Wu CY, Lai MM, Cheng WC, Wu YT, Tsai MD, Cheng YS, Wong CH. High-throughput identification of compounds targeting influenza RNA-dependent RNA polymerase activity. Proc Natl Acad Sci U S A. 2010 Nov 9;107(45):19151-6. doi: 10.1073/pnas.1013592107. Epub 2010 Oct 25. PubMed PMID: 20974907; PubMed Central PMCID: PMC2984200.

10: Kao RY, Yang D, Lau LS, Tsui WH, Hu L, Dai J, Chan MP, Chan CM, Wang P, Zheng BJ, Sun J, Huang JD, Madar J, Chen G, Chen H, Guan Y, Yuen KY. Identification of influenza A nucleoprotein as an antiviral target. Nat Biotechnol. 2010 Jun;28(6):600-5. doi: 10.1038/nbt.1638. Epub 2010 May 30. PubMed PMID: 20512121.