| Chemical Properties | Back Directory | [storage temp. ]
2-8°C | [solubility ]
DMSO: 2mg/mL, clear | [form ]
Solid | [color ]
White to off-white | [InChIKey]
BELJCNWNXQVJPZ-UHFFFAOYSA-M | [SMILES]
Cl[Pt](N)([N+]1=C2C=CC=CC2=C3C=CC=CC3=C1)N.[O-][N+]([O-])=O |
| Hazard Information | Back Directory | [Uses]
Phenanthriplatin is a monovalent platinum(II)-based complex with a large cytotoxicity against cancer cells[1]. | [Biological Activity]
Phenanthriplatin is a cationic monofunctional DNA-binding platinum (II) complex with significantly greater anticancer activity (IC50 in μM = 0.035/Ntera20.22/A5490.30/HeLa0.59/U2OS0.74/PC30.94/MCF72.02/HT29; 72 hMTT assay) than cisplatinoxaliplatinand pyriplatin. Enhanced cellular uptake due to its hydrophobic phenanthridine ligand as well as more rapid DNA covalent-binding activity both contribute to its superior anticancer efficacy. Phenanthriplatin binds more effectively to 5μ-deoxyguanosine monophosphate than to N-acetyl methioninewhereas pyriplatin reacts equally to both. | [Enzyme inhibitor]
This potent Pt(II) complex (FW = 505.82 g/mol; CAS 1416900-51-0), also known as cis-diamminephenanthridinechloroplatinum(II), penetrates cell membranes either by passive diffusion or carrier-mediated active transport, with the hydrophobic ligand maximizing cellular uptake and making it cytotoxic compared with cisplatin and carbinatoplatin. Its molecular structure was designed with based the X-ray structure of RNA polymerase II (Pol II), when stalled at a monofunctional pyriplatin-DNA adduct. Phenanthriplatin interacts with guanine residues, forming highly potent, monofunctional DNA adducts. While many Pol II elongation complexes stall after successful addition of CTP opposite the phenanthriplatin-dG adduct in an error-free manner, a few slowly undergo error-prone bypass of the phenanthriplatin-dG lesion, a behavior that resembles DNA polymerases that similarly switch from high-fidelity replicative DNA processing (errorfree) to low-fidelity translesion DNA synthesis (error-prone) at DNA damage sites | [References]
[1] Veclani D, et al. Intercalation Ability of Novel Monofunctional Platinum Anticancer Drugs: A Key Step in Their Biological Action. J Chem Inf Model. 2021;61(9):4391-4399. DOI:10.1021/acs.jcim.1c00430 |
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| Company Name: |
Merck KGaA
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| Tel: |
21-20338288 |
| Website: |
www.sigmaaldrich.cn |
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