3-deazaneplanocin A (DZNeP) HCl

Catalog No.S7120 Synonyms: NSC 617989 HCl

3-deazaneplanocin A (DZNeP) HCl Chemical Structure

Molecular Weight(MW): 298.73

3-deazaneplanocin A (DZNeP)HCl, an analog of adenosine, is a competitive inhibitor of S-adenosylhomocysteine hydrolase with Ki of 50 pM in a cell-free assay.

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Cited by 19 Publications

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Biological Activity

Description 3-deazaneplanocin A (DZNeP)HCl, an analog of adenosine, is a competitive inhibitor of S-adenosylhomocysteine hydrolase with Ki of 50 pM in a cell-free assay.
Features Carbocyclic analog of adenosine, and acts as anti-tumor and anti-virus inhibitor of EZH2.
Targets
S-adenosylhomocysteine hydrolase [1]
()
50 pM(Ki)
In vitro

3-Deazaneplanocin A (1.0 μM) results in a significant increase in accumulation of cells in the G0/G1 phase (58.5%) with a concomitant decrease in the number of cells in S phase (35.2%) and G2/M phases (6.3%) of the cell cycle of human acute myeloid leukemia OCI-AML3 cells. 3-Deazaneplanocin A (1.0 μM) induces apoptosis in OCI-AML3 (~50%) and HL-60 cells (~50%), and a more than 90% reduction in colony growth at 48 hr. 3-Deazaneplanocin A depletes EZH2 levels, and inhibits trimethylation of lysine 27 on histone H3 in the HL-60 and OCI-AML3 cells and in primary AML cells. 3-Deazaneplanocin A treatment induces p16, p21, p27, and FBXO32 while depleting cyclin E and HOXA9 levels. 500 nM 3-Deazaneplanocin A induces differentiation of HL-60 to CD11b+ cell by nearly 3-folds time at 48 h. [2] 3-Deazaneplanocin A has excellent activity against several viral types. 3-Deazaneplanocin A is activity against vesicular stomatitis in L929 cells, parainfluenza 3 in H.Ep-2, vaccinia and yellow fever viruses in vero cells with IC50 of 0.2, 3.6, 2.1 and 2.9 μg/mL, respectively. [3] 3-Deazaneplanocin A displays a strongly and uniformly leishmanistatic effect on American Leishmania (L mexicana and L brasiliensis) strains in the study with average ID50 of 96 ng/mL, but shows no inhibition against the several T. cruzi and T. rangeli strains tested with concentrations up to 10 μg/mL. At a dose of 200 ng/mL, 3-Deazaneplanocin A inhibits S-adenosyl-L-3H-methylmethionine and 3-thymidine incorporation by promastigotes after four days. At a dose of 100 ng/mL, 3-Deazaneplanocin A eliminates approximately 56% of the L mexicana and L brasiliensis from infected human macrophages. [4]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
human HCT116 cells NFyyNoREgXSxdH;4bYPDqGG|c3H5 NInQdYc4OiCq MmD3R5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gTGNVOTF4IHPlcIx{KGG|c3Xzd4VlKGG|IHnubIljcXSrb36gc4Yh[2WubDDwdo9tcW[ncnH0bY9vKGGodHXyJFczKGi{czDifUB{fWyob4Loc4RidWmwZTDCJIF{e2G7LDDJR|UxRTBwMk[g{txONg>? NUPoe5VbOjZyMUC1PFU>
human MDA-MB-231 cells NGHBTolEgXSxdH;4bYPDqGG|c3H5 MWm3NkBp NYnvd5pwS3m2b4TvfIlkcXS7IHHnZYlve3RiaIXtZY4hVUSDLV3CMVI{OSClZXzsd{Bie3Onc4Pl[EBieyCrbnjpZol1cW:wIH;mJINmdGxicILvcIln\XKjdHnvckBi\nSncjC3NkBpenNiYomgd5Vt\m:{aH;kZY1qdmViQjDhd5Nige,:jDDJR|UxRTBwMzFOwG0v NWnRfVF3OjZyMUC1PFU>
human SKHEP1 cells M3;hWWN6fG:2b4jpZ:Kh[XO|YYm= MmHrO|IhcA>? NH3CfFZEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBUU0iHUEGgZ4VtdHNiYYPz[ZN{\WRiYYOgbY5pcWKrdHnvckBw\iClZXzsJJBzd2yrZnXyZZRqd25iYX\0[ZIhPzJiaILzJIJ6KHO3bH\vdohw\GGvaX7lJGIh[XO|YYmsJGlEPTB;MD63NkDPxE1w MYWyOlAyODV6NR?=
human SNU638 cells NE\TZopEgXSxdH;4bYPDqGG|c3H5 NFezNYU4OiCq NIH1[WlEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBUVlV4M{igZ4VtdHNiYYPz[ZN{\WRiYYOgbY5pcWKrdHnvckBw\iClZXzsJJBzd2yrZnXyZZRqd25iYX\0[ZIhPzJiaILzJIJ6KHO3bH\vdohw\GGvaX7lJGIh[XO|YYmsJGlEPTB;MD65NUDPxE1w NVzINpZ4OjZyMUC1PFU>
human A549 cells M121VWN6fG:2b4jpZ:Kh[XO|YYm= Mk\QO|IhcA>? MUnDfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDBOVQ6KGOnbHzzJIF{e2W|c3XkJIF{KGmwaHnibZRqd25ib3[gZ4VtdCCycn;sbYZmemG2aX;uJIFnfGW{IEeyJIhzeyCkeTDzeYxnd3Kqb3ThcYlv\SCEIHHzd4F6NCCLQ{WwQVEvPCEQvF2u MnmxNlYxOTB3OEW=
human PC3 cells NFPhd|BEgXSxdH;4bYPDqGG|c3H5 MkS0O|IhcA>? MXTDfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDQR|Mh[2WubIOgZZN{\XO|ZXSgZZMhcW6qaXLpeIlwdiCxZjDj[YxtKHC{b3zp[oVz[XSrb36gZYZ1\XJiN{KgbJJ{KGK7IIP1cIZwemixZHHtbY5mKEJiYYPzZZktKEmFNUC9PU4{QSEQvF2u NUXkWYltOjZyMUC1PFU>

... Click to View More Cell Line Experimental Data

Assay
Methods Test Index PMID
Western blot
EZH2 / H3K27me3; 

PubMed: 27223261     


DZNep decreased the expression of EZH2 and H3K27me3 in osteosarcoma cells in a dose-dependent manner.

Suz12 / H3K4me3 / H3K36me2; 

PubMed: 23001792     


A marked decrease in H3K27me3 levels in DZNep treated HT29 and SW480 cells compared to untreated controls. While the effect of DZNep was relatively specific for H3K27me3 inhibition in HT29 cells, DZNep also reduced H3K4me3 and H3K36me2 marks in SW480 cells. As reported by others, DZNep treatment caused a decrease in Suz12 protein levels in SW480 cells, whereas Suz12 protein level was unaffected in HT29 cells

TGFBR1 / TGFBR2 / Smad3; 

PubMed: 28373289     


DZNep decreased TGFBR1 and TGFBR2 but not Smad3 protein levels in a dose-dependent fashion in pancreatic cancer. 

EED / p21 / p-RB / p27 / p-CDC2; 

PubMed: 26579445     


Relative protein expression levels affected by DZNep in HCT116 cells. The cells were treated with 5 μmol/L DZNep for 72 h before being subjected to immunoblot assay.

HOXA6 / HOXB3 / HOXC4 / HOXD13; 

PubMed: 26812882     


Western blot analysis showed that both DZNep and EPZ005687 reduced EZH2 expression and H3K27me3 levels. 

p-JNK / JNK / p-p38 / p38 / p-ERK / ERK / p-IκB-α / IκB-α; 

PubMed: 28744016     


DZNep reduced MAPK pathway activation by IL-1β. Primary chondrocytes were treated or not with DZNep (1 µM) in the presence of IL-1β (1ng/mL) for 0min, 5min or 10min. Afer treatment, proteins were extracted, and levels of P-JNK and JNK, P-p38 and p38, P-ERK and ERK, P-IκB-α and IκB-α were determined in cells by western blotting.

27223261 23001792 28373289 26579445 26812882 28744016
Immunofluorescence
α-tubulin; 

PubMed: 27226494     


Representative confocal microscopy images of oocytes with DZNep or GSK343 treatment. The oocytes presented with a typical barrel-shaped spindle and well-aligned chromosomes on the metaphase plate not only in DZNep or GSK343 treated group but also in the control group. Spindle was recognized by α-tubulin (green) and DNA was recognized by PI (Propidium iodide, red). Scale bar = 4 μm.

F-actin / Paxillin; 

PubMed: 23826380     


DZNep treatment impaired actin cytoskeleton and caused cell shrinkage in MHCC97L cells. Stress fiber was stained with FITC-conjugated phalloidin and focal adhesions were stained with anti-paxillin antibody. Nuclei were counterstained with DAPI. Mock-treated cells showed organized bundles of stress fibers and well attached paxillin. DZNep-treated cells shrank and lost proper actin cytoskeleton network.

EZH2 / Mst1; 

PubMed: 24499724     


Co-IF staining of EZH2 and MST1 protein in C4–2 cells treated with DMSO or 5 µM DZNep for 72h in serum-fed growth conditions. Alexa Fluor 488 stained MST1 (green), Alexa Fluor 568 stained EZH2 (red), and DAPI stained cell nuclei (blue). Magnification is 20x. Micrographs are representative of multiple images from two independent experiments.

27226494 23826380 24499724
Growth inhibition assay
Cell viability; 

PubMed: 27223261     


DZNep inhibited osteosarcoma cell proliferation. Cells were treated with DZNep at the indicated concentrations. The relative sensitivity of each line to DZNep was determined by the MTT assay.

27223261
In vivo 3-Deazaneplanocin A shows antileukemia activity in vivo. 3-Deazaneplanocin A (1 mg/kg) significantly prolongs survival of mice implanted with AML cells with a median survival of 43 days compared with control group (36 days), which can be further improved by co-treatment with 10 mg/kg pan-HDAC inhibitor (HDI) panobinostat (52 days, median survival). [2] 3-Deazaneplanocin A at the doses of 8 mg/kg shows in vivo antiviral activity against vaccinia virus in a mouse tailpox assay with median of 0.0 poxftail (84% protection). [3] 3-Deazaneplanocin A at the doses ranging from 0.5 to 1.5 mg/kg/day, significantly reduced development of cutaneous leishmanial infection produced in inbred BALB/c mice by L. b. guyanensis inoculation. [4] 3-Deazaneplanocin A induces massively increased interferon-α production in Ebola virus-infected mice. 3-Deazaneplanocin A (s.c. injection of 2 mg/kg postinfection) prevents death in mice infected with 1000 pfu (30 000 LD50) of mouse-adapted EBO-Z. Treatment with 3-Deazaneplanocin A on day 1 reduces mean serum viral titers on day 2 by 100-fold and on day 3 by 100 000-fold, compared with placebo controls, and results in a mean serum IFN-α level of 1420 pg/mL on day 2 and 1830 pg/mL on day 3. [5]

Protocol

Kinase Assay:

[6]

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S-adenosylhomocysteine hydrolase activity assay:

The reaction mixture used for assay of AdoHcyase contains, in a final volume of 0.5 mL, 50 mM potassium phosphate (pH 7.6), 5 mM dithiothreitol, 1 mM EDTA, 10% glycerol, and the enzyme. L-[8- 14C]AdoHcy is used as substrate and 5 units of calf intestinal adenosine deaminase are included. The reaction is stopped by the addition of 100 μL of 5 M formic acid, and the reaction mixture is then poured onto a column (0.8×2.5 cm) of SP-Sephadex C-25, previously equilibrated in 0.1 M formic acid. Each test tube is rinsed with 0.5 mL of 0.1 M formic acid. [14C]Inosine formed is eluted from the column by 3.5 mL of 0.1 M formic acid into a scintillation vial. The radioactivity is determined after the addition of 10 mL of scintillation fluid. The amount of enzyme used is about 105 pU, or 75 ng of the purified enzyme. One unit is the amount of enzyme needed to form 1 pmol of product in 1 min at 37 ℃.
Cell Research:

[2]

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  • Cell lines: Human acute myeloid leukemia HL-60
  • Concentrations: ~1 μM
  • Incubation Time: 2 days
  • Method:

    Cells are treated with the indicated concentrations of 3-Deazaneplanocin A for 48 hours. After the designated treatments, cells are harvested and washed twice with PBS, and approximately 500 cells are plated in complete Methocult and cultured for 7 to 10 days at 37 ℃ in a 5% CO2 environment. Cells are dyed with crystal violet, and relative colony density is determined by solubilizing the crystal violet dye in 10% acetic acid followed by measurement of absorbance at 450 nm.


    (Only for Reference)
Animal Research:

[2]

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  • Animal Models: Human acute myeloid leukemia xenografts HL-60
  • Formulation: --
  • Dosages: 1 mg/kg
  • Administration: initiated on day 7 and administered twice per week (Tuesday-Thursday) intraperitoneally for 2 weeks
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 52 mg/mL (174.07 mM)
Water 52 mg/mL (174.07 mM)
Ethanol Insoluble
In vivo Add solvents to the product individually and in order(Data is from Selleck tests instead of citations):
Saline
For best results, use promptly after mixing.
30mg/mL

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 298.73
Formula

C12H14N4O3.HCl

CAS No. 120964-45-6
Storage powder
in solvent
Synonyms NSC 617989 HCl

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Histone Methyltransferase Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID