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Merck
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SML2811

Sigma-Aldrich

Phenanthriplatin

>97% (NMR)

Synonyme(s) :

(SP-4-3)-Diamminechlorido(phenanthridine)platinum(II) nitrate, PhenPt, cis-[Pt(NH3)2(phenanthridine)Cl]NO3

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About This Item

Formule empirique (notation de Hill):
C13H15ClN4O3Pt
Numéro CAS:
1416900-51-0
Poids moléculaire :
505.81
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Essai

>97% (NMR)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

Cl[Pt](N)([N+]1=C2C=CC=CC2=C3C=CC=CC3=C1)N.[O-][N+]([O-])=O

Clé InChI

BELJCNWNXQVJPZ-UHFFFAOYSA-M

Actions biochimiques/physiologiques

Phenanthriplatin is a cationic monofunctional DNA-binding platinum (II) complex with significantly greater anticancer activity (IC50 in μM = 0.035/Ntera2, 0.22/A549, 0.30/HeLa, 0.59/U2OS, 0.74/PC3, 0.94/MCF7, 2.02/HT29; 72 h, MTT assay) than cisplatin, oxaliplatin, and 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 5′-deoxyguanosine monophosphate than to N-acetyl methionine, whereas pyriplatin reacts equally to both.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

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Certificats d'analyse (COA)

Lot/Batch Number
0000093365
0000101069

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Amit A Vernekar et al.
Journal of the American Chemical Society, 140(12), 4279-4287 (2018-03-20)
Efficient loading of drugs in novel delivery agents has the potential to substantially improve therapy by targeting the diseased tissue while avoiding unwanted side effects. Here we report the first systematic study of the loading mechanism of phenanthriplatin and its
Matthew W Kellinger et al.
Journal of the American Chemical Society, 135(35), 13054-13061 (2013-08-10)
Transcription inhibition by platinum anticancer drugs is an important component of their mechanism of action. Phenanthriplatin, a cisplatin derivative containing phenanthridine in place of one of the chloride ligands, forms highly potent monofunctional adducts on DNA having a structure and
Daniele Veclani et al.
Journal of the American Chemical Society, 140(43), 14024-14027 (2018-09-07)
The monofunctional platinum drug phenanthriplatin (phenPt) blocks the replication of cancer cells even if it reacts with only one guanine base. However, there is still insufficient experimental data to improve its cytotoxicity and all previously proposed chemical modifications of the
Jerry D Monroe et al.
PloS one, 13(3), e0192505-e0192505 (2018-03-08)
Unlike cisplatin, which forms bifunctional DNA adducts, monofunctional platinum(II) complexes bind only one strand of DNA and might target cancer without causing auditory side-effects associated with cisplatin treatment. We synthesized the monofunctional triamine-ligated platinum(II) complexes, Pt(diethylenetriamine)Cl, [Pt(dien)Cl]+, and Pt(N,N-diethyldiethylenetriamine)Cl, [Pt(Et2dien)Cl]+
Wen Zhou et al.
Chemical communications (Cambridge, England), 54(22), 2788-2791 (2018-02-28)
A trans-DDP based monofunctional phenanthridine Pt(ii) complex was synthesized and characterized. Its anticancer activity was studied in vitro on a panel of human cancer cell lines and mouse intestinal cancer organoids. This complex displays significant antitumor properties, with a different
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