| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C23H21N5 |
| SMILES | |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
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Compound Overview
N4Py is a bleomycin-mimetic pentadentate ligand that targets intracellular FeII and reversibly chelates a range of transition metals. Its chelates trigger apoptosis through two routes, DNA cleavage via ROS generation and XIAP downregulation via ZnII chelation, though only FeII/FeIII-N4Py shows potent DNA-cleaving activity. A folate conjugate of N4Py targets folate receptors, can undergo intracellular cleavage, and selectively kills FR-positive cancer cells; the ligand can also be used in research on nasopharyngeal epidermoid carcinoma, ovarian cancer, and mammary adenocarcinoma[1][2]. It has a molecular formula of C23H21N5 and a molecular weight of 367.45 g/mol.
Physical & Chemical Properties
| CAS Number | 167695-87-6 |
|---|---|
| Molecular Formula | C23H21N5 |
| Molecular Weight | 367.45 g/mol |
| SMILES | C1(C(C2=CC=CC=N2)N(CC3=CC=CC=N3)CC4=NC=CC=C4)=NC=CC=C1 |
| Signaling Pathway | Apoptosis; Metabolic Enzyme/Protease; Immunology/Inflammation; NF-κB |
| Storage | Please store the product under the recommended conditions in the Certificate of Analysis. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
[2]. Geersing A. Redox-active N4Py-metal complexes in human cell cultures. Groningen: Rijksuniversiteit Groningen, 2017. ISBN 978-90-367-9760-3.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with your institution's chemical hygiene plan.
In Vitro
The complexes that N4Py forms with Fe2+, Fe3+, Cu2+, Mn2+, and Zn2+ differ in spectral and electrochemical properties, and Fe2+-N4Py shows characteristic metal-to-ligand charge transfer absorption[1]. N4Py can give rise to Fe (II)-N4Py and Fe (III)-N4Py, and both efficiently cleave supercoiled pUC18 plasmid DNA under cell-free conditions[1]. In A2780, SKOV3 and OSE-C2 cells, metabolic activity is significantly reduced by Mn (II)-N4Py, Fe (II)-N4Py and Fe (III)-N4Py formed by N4Py, with IC50 values in the range of 5-10 μM[1]. Mn (II)-N4Py, Fe (II)-N4Py and Fe (III)-N4Py also induce significant late apoptotic/necrotic cell death in A2780, SKOV3 and OSE-C2 cells; free N4Py shows the strongest cytotoxicity among them, whereas Cu (II)-N4Py and Zn (II)-N4Py show minimal cytotoxicity[1]. In A2780 cells, hROS production is induced by Mn (II)-N4Py, Fe (II)-N4Py, Fe (III)-N4Py, and Cu (II)-N4Py but not by Zn (II)-N4Py; NAC abrogates the hROS production induced by all of these except Cu (II)-N4Py, and instead enhances the hROS production induced by Cu (II)-N4Py[1].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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