SML2811
Phenanthriplatin
>97% (NMR)
Synonym(s):
(SP-4-3)-Diamminechlorido(phenanthridine)platinum(II) nitrate, PhenPt, cis-[Pt(NH3)2(phenanthridine)Cl]NO3
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5 MG
CZK 2,750.00
25 MG
CZK 11,100.00
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5 MG
CZK 2,750.00
25 MG
CZK 11,100.00
About This Item
Empirical Formula (Hill Notation):
C13H15ClN4O3Pt
CAS Number:
Molecular Weight:
505.81
UNSPSC Code:
12352200
NACRES:
NA.77
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Quality Level
Assay
>97% (NMR)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
2-8°C
SMILES string
Cl[Pt](N)([N+]1=C2C=CC=CC2=C3C=CC=CC3=C1)N.[O-][N+]([O-])=O
InChI key
BELJCNWNXQVJPZ-UHFFFAOYSA-M
Biochem/physiol Actions
Cationic monofunctional DNA-binding platinum (II) complex with significantly greater anticancer activity than cisplatin, oxaliplatin, and pyriplatin.
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.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
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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
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
Ali A Almaqwashi et al.
Journal of the American Chemical Society, 141(4), 1537-1545 (2019-01-03)
Phenanthriplatin, a monofunctional anticancer agent derived from cisplatin, shows significantly more rapid DNA covalent-binding activity compared to its parent complex. To understand the underlying molecular mechanism, we used single-molecule studies with optical tweezers to probe the kinetics of DNA-phenanthriplatin binding
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
Ga Young Park et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(30), 11987-11992 (2012-07-10)
Monofunctional platinum(II) complexes of general formula cis-[Pt(NH(3))(2)(N-heterocycle)Cl]Cl bind DNA at a single site, inducing little distortion in the double helix. Despite this behavior, these compounds display significant antitumor properties, with a different spectrum of activity than that of classic bifunctional
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