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MedKoo Cat#: 206922 | Name: Phenanthriplatin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phenanthriplatin, also known as cis-[Pt(NH3)2-(phenanthridine)Cl]NO3, is a new drug candidate. It belongs to a family of platinum(II)-based agents which includes cisplatin, oxaliplatin and carboplatin. Phenanthriplatin Acts As a Covalent Poison of Topoisomerase II Cleavage Complexes. Phenanthriplatin exhibits significantly greater activity than cisplatin and oxaliplatin. The cellular uptake of phenanthriplatin is substantially greater than that of cisplatin and pyriplatin because of the hydrophobicity of the phenanthridine ligand. Phenanthriplatin binds more effectively to 5'-deoxyguanosine monophosphate than to N-acetyl methionine, whereas pyriplatin reacts equally well with both reagents.

Chemical Structure

Phenanthriplatin
Phenanthriplatin
CAS#1416900-51-0

Theoretical Analysis

MedKoo Cat#: 206922

Name: Phenanthriplatin

CAS#: 1416900-51-0

Chemical Formula: C13H13ClN4O3Pt

Exact Mass: 503.0324

Molecular Weight: 503.81

Elemental Analysis: C, 30.99; H, 2.60; Cl, 7.04; N, 11.12; O, 9.53; Pt, 38.72

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Phenanthriplatin; cis-[Pt(NH3)2-(phenanthridine)Cl]NO3;
IUPAC/Chemical Name
cis-[Pt(NH(3))(2)(phenanthridine)Cl]NO(3)
InChi Key
DPJHXHZDGLFQMM-UHFFFAOYSA-M
InChi Code
InChI=1S/C13H9N.ClH.NO3.2H2N.Pt/c1-2-6-11-10(5-1)9-14-13-8-4-3-7-12(11)13;;2-1(3)4;;;/h1-9H;1H;;2*1H2;/q;;3*-1;+3/p-1
SMILES Code
N[Pt]([N]1=CC2=C(C3=C1C=CC=C3)C=CC=C2)(Cl)N.[O-][N+]([O-])=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Phenanthriplatin was discovered by Professor Stephen J. Lippard at Massachusetts Institute of Technology and is currently being developed by Blend Therapeutics for its potential use in human cancer therapy. Phenanthriplatin is thought to penetrate cell membranes in its ionised form by either passive diffusion or carrier-mediated active transport. The hydrophobic phenanthridine ligand of the drug is thought to maximise its cellular uptake, rendering it more effective and cytotoxic compared with cisplatin. Once it has entered the cell, phenanthriplatin is distributed in a similar manner to other platinum-based anticancer agents, residing primarily in the cell's nucleus. The ultimate target of the drug is nuclear DNA.

Preparing Stock Solutions

The following data is based on the product molecular weight 503.81 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Bruno PM, Liu Y, Park GY, Murai J, Koch CE, Eisen TJ, Pritchard JR, Pommier Y, Lippard SJ, Hemann MT. A subset of platinum-containing chemotherapeutic agents kills cells by inducing ribosome biogenesis stress. Nat Med. 2017 Apr;23(4):461-471. doi: 10.1038/nm.4291. Epub 2017 Feb 27. PubMed PMID: 28263311; PubMed Central PMCID: PMC5520548. 2: Ravera M, Gabano E, Zanellato I, Perin E, Arrais A, Osella D. Polyanionic Biopolymers for the Delivery of Pt(II) Cationic Antiproliferative Complexes. Bioinorg Chem Appl. 2016;2016:2380540. Epub 2016 Sep 28. PubMed PMID: 27774043; PubMed Central PMCID: PMC5059510. 3: Riddell IA, Agama K, Park GY, Pommier Y, Lippard SJ. Phenanthriplatin Acts As a Covalent Poison of Topoisomerase II Cleavage Complexes. ACS Chem Biol. 2016 Nov 18;11(11):2996-3001. Epub 2016 Oct 6. PubMed PMID: 27648475; PubMed Central PMCID: PMC5248983. 4: Riddell IA, Johnstone TC, Park GY, Lippard SJ. Nucleotide Binding Preference of the Monofunctional Platinum Anticancer-Agent Phenanthriplatin. Chemistry. 2016 May 23;22(22):7574-81. doi: 10.1002/chem.201600236. Epub 2016 Apr 25. PubMed PMID: 27111128; PubMed Central PMCID: PMC4884344. 5: Czapar AE, Zheng YR, Riddell IA, Shukla S, Awuah SG, Lippard SJ, Steinmetz NF. Tobacco Mosaic Virus Delivery of Phenanthriplatin for Cancer therapy. ACS Nano. 2016 Apr 26;10(4):4119-26. doi: 10.1021/acsnano.5b07360. Epub 2016 Mar 28. PubMed PMID: 26982250; PubMed Central PMCID: PMC5155116. 6: Zask A, Ellestad GA. Recent Advances in Stereoselective Drug Targeting. Chirality. 2015 Sep;27(9):589-97. doi: 10.1002/chir.22470. Epub 2015 Jun 11. Review. PubMed PMID: 26096879. 7: Johnstone TC, Suntharalingam K, Lippard SJ. Third row transition metals for the treatment of cancer. Philos Trans A Math Phys Eng Sci. 2015 Mar 13;373(2037). pii: 20140185. doi: 10.1098/rsta.2014.0185. Review. PubMed PMID: 25666060; PubMed Central PMCID: PMC4342973. 8: Gregory MT, Park GY, Johnstone TC, Lee YS, Yang W, Lippard SJ. Structural and mechanistic studies of polymerase η bypass of phenanthriplatin DNA damage. Proc Natl Acad Sci U S A. 2014 Jun 24;111(25):9133-8. doi: 10.1073/pnas.1405739111. Epub 2014 Jun 9. PubMed PMID: 24927576; PubMed Central PMCID: PMC4078841. 9: Margiotta N, Savino S, Gandin V, Marzano C, Natile G. Monofunctional platinum(II) complexes with potent tumor cell growth inhibitory activity: the effect of a hydrogen-bond donor/acceptor N-heterocyclic ligand. ChemMedChem. 2014 Jun;9(6):1161-8. doi: 10.1002/cmdc.201402028. Epub 2014 May 2. PubMed PMID: 24799414. 10: Johnstone TC, Lippard SJ. The chiral potential of phenanthriplatin and its influence on guanine binding. J Am Chem Soc. 2014 Feb 5;136(5):2126-34. doi: 10.1021/ja4125115. Epub 2014 Jan 27. PubMed PMID: 24417436; PubMed Central PMCID: PMC3937553. 11: Johnstone TC, Park GY, Lippard SJ. Understanding and improving platinum anticancer drugs--phenanthriplatin. Anticancer Res. 2014 Jan;34(1):471-6. Review. PubMed PMID: 24403503; PubMed Central PMCID: PMC3937549. 12: Johnstone TC, Alexander SM, Lin W, Lippard SJ. Effects of monofunctional platinum agents on bacterial growth: a retrospective study. J Am Chem Soc. 2014 Jan 8;136(1):116-8. doi: 10.1021/ja411742c. Epub 2013 Dec 23. PubMed PMID: 24364388; PubMed Central PMCID: PMC3920743. 13: Kellinger MW, Park GY, Chong J, Lippard SJ, Wang D. Effect of a monofunctional phenanthriplatin-DNA adduct on RNA polymerase II transcriptional fidelity and translesion synthesis. J Am Chem Soc. 2013 Sep 4;135(35):13054-61. doi: 10.1021/ja405475y. Epub 2013 Aug 25. PubMed PMID: 23927577; PubMed Central PMCID: PMC3791135. 14: Park GY, Wilson JJ, Song Y, Lippard SJ. Phenanthriplatin, a monofunctional DNA-binding platinum anticancer drug candidate with unusual potency and cellular activity profile. Proc Natl Acad Sci U S A. 2012 Jul 24;109(30):11987-92. doi: 10.1073/pnas.1207670109. Epub 2012 Jul 6. PubMed PMID: 22773807; PubMed Central PMCID: PMC3409760.