NNK
Based on 2 publication(s) in Google Scholar
NNK is a nicotine-nitrosated derivative. NNK simultaneously stimulates Bcl2 phosphorylation exclusively at Ser70 and c-Myc at Thr58 and Ser62 through activation of both ERK1/2 and PKCα. NNK induces survival and proliferation of human lung cancer cells. NNK can be used for lung cancer mice model structure.
For research use only. We do not sell to patients.
- Purity: 99.97%
- CAS No.: 64091-91-4
- Formula: C10H13N3O2
- Molecular Weight:207.23
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Storage:Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
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Publications Citing Use of MedChemExpress (MCE) NNK
MoreAll Endogenous Metabolite Isoforms
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Biological Activity
ERK1, ERK2, PKCα, Bcl2, c-Myc [1]
NNK (100 pM; 0-60 min) stimulates activation of PKCα and MAPKs ERK1/2 that directly induce c-Myc phosphorylation[1].
NNK (100 pM; 96 hours) enhances proliferation of cells expressing WT but not AA c-Myc mutant[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:NCI-H82 cells[1]
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Concentration:100 pM
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Incubation Time:0-60 min
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Result:Stimulated activation of PKCα and MAPKs ERK1/2 that directly induced c-Myc phosphorylation.
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Cell Line:H1299 lung cancer cells[1]
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Concentration:100 pM
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Incubation Time:96 hours
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Result:Enhanced proliferation of cells expressing WT but not T58A/S62A c-Myc mutant.
Please do not refer to only one article to determine the experimental conditions. It is recommended to determine the optimal experimental conditions (animal strain, age, dosage, frequency and cycle, detection time and indicators, etc.) through preliminary experiments before the formal experiment.
NNK can be used in animal modeling to create lung tumor models. NNK is absorbed more rapidly from the duodenum than from the stomach in mice and is metabolized in both tissues. Alpha-carbon hydroxylation, which activates NNK, and pyridine N-oxidation, which inactivates NNK, occur more extensively in the duodenum than in the stomach. The rate of carbonyl reduction of NNK in the duodenum is ten times higher[2][4].
Administration: 3.1 mg or 9-9.4 mg (62.4 μg/mL) • add to drinking water
Mice: A/J
Administration: 100 mg/kg in 0.1 mL PBS • i.p. • three doses of NNK on three alternate days
(2) After 16 weeks of treatment with the carcinogens, all the mice were dissected, and their lungs and major organs were fixed in Tellyesniczky for 7 days, then the number of surface adenomas was counted under a dissection microscope.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
| NCT Number | Sponsor | Condition | Start Date |
Phase
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|---|---|---|---|---|
| NCT01329991 | Plexxikon| | 2011-05 | PHASE1 |
Chemical Information
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CAS No. 64091-91-4
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Appearance Solid
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Molecular Weight 207.23
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Formula C10H13N3O2
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Color White to light yellow
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SMILES
O=C(C1=CC=CN=C1)CCCN(C)N=O
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years In solvent -80°C 6 months -20°C 1 month
Publications (2)
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Journal Impact Factor
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Most Recent
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Eur J Pharmacol
2024 Jun 15:973:176511. PMID: 38604545 -
Mol Carcinog
HORMAD1 Polymorphisms Influence Susceptibility to Esophageal Squamous Cell Carcinoma Through Gene-Smoking Interaction. [Abstract]2025 Aug 28. PMID: 40875139
Solvent & Solubility
DMSO : ≥ 62.5 mg/mL (301.60 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
* "≥" means soluble, but saturation unknown.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
For the following dissolution methods, please prepare the working solution directly:
It is recommended to prepare fresh solutions and use them promptly within a short period of time.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 1% CMC-Na/saline water
Solubility: 3.33 mg/mL (16.07 mM); Clear solution; Need ultrasonic and warming and heat to 50°C
Purity & Documentation
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Data Sheet (278 KB)
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SDS (584 KB)
- English - EN (584 KB)
- Français - FR (584 KB)
- Deutsch - DE (584 KB)
- Norwegian - NO (584 KB)
- Español - ES (584 KB)
- Swedish - SV (584 KB)
- Italian - IT (584 KB)
- Portuguese - PT (584 KB)
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Handling Instructions (2659 KB)
References
[1]. Jin Z, et al. Tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone promotes functional cooperation of Bcl2 and c-Myc through phosphorylation in regulating cell survival and proliferation. J Biol Chem. 2004;279(38):40209-40219. [Content Brief]
[2]. Castonguay A, et al. Lung tumorigenicity of NNK given orally to A/J mice: its application to chemopreventive efficacy studies. Exp Lung Res. 1991;17(2):485-499. [Content Brief]
[3]. Ge GZ, et al. Tobacco carcinogen NNK-induced lung cancer animal models and associated carcinogenic mechanisms. Acta Biochim Biophys Sin (Shanghai). 2015 Jul;47(7):477-87. [Content Brief]
[4]. Razani-Boroujerdi S, et al. Early manifestations of NNK-induced lung cancer: role of lung immunity in tumor susceptibility. Am J Respir Cell Mol Biol. 2007 Jan;36(1):13-9. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 4.8256 mL | 24.1278 mL | 48.2556 mL | 120.6389 mL |
| 5 mM | 0.9651 mL | 4.8256 mL | 9.6511 mL | 24.1278 mL | |
| 10 mM | 0.4826 mL | 2.4128 mL | 4.8256 mL | 12.0639 mL | |
| 15 mM | 0.3217 mL | 1.6085 mL | 3.2170 mL | 8.0426 mL | |
| 20 mM | 0.2413 mL | 1.2064 mL | 2.4128 mL | 6.0319 mL | |
| 25 mM | 0.1930 mL | 0.9651 mL | 1.9302 mL | 4.8256 mL | |
| 30 mM | 0.1609 mL | 0.8043 mL | 1.6085 mL | 4.0213 mL | |
| 40 mM | 0.1206 mL | 0.6032 mL | 1.2064 mL | 3.0160 mL | |
| 50 mM | 0.0965 mL | 0.4826 mL | 0.9651 mL | 2.4128 mL | |
| 60 mM | 0.0804 mL | 0.4021 mL | 0.8043 mL | 2.0106 mL | |
| 80 mM | 0.0603 mL | 0.3016 mL | 0.6032 mL | 1.5080 mL | |
| 100 mM | 0.0483 mL | 0.2413 mL | 0.4826 mL | 1.2064 mL |
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