18432-95-6

Usage

Uses

Used in Inorganic Chemistry:
DICHLORO(1,10-PHENANTHROLINE)PLATINUM(II) is used as a reactant for the synthesis of mixed-metal complexes incorporating platinum and lanthanide centers. Its ability to form stable complexes with other metal ions makes it a valuable precursor in the preparation of heterometallic systems with potential applications in various areas, such as catalysis, magnetism, and luminescence.
Used in Organometallic Chemistry:
This platinum complex is employed as a reactant in the synthesis of platinum complexes containing a chelating di-fluoro-substituted thiourea ligand. The incorporation of such ligands can enhance the stability, reactivity, and selectivity of the resulting organometallic compounds, which can be further explored for applications in homogeneous catalysis and as potential therapeutic agents.
Used in Supramolecular Chemistry:
DICHLORO(1,10-PHENANTHROLINE)PLATINUM(II) is used as a component in the formation of adducts between ternary Pt(III)-amino acid-aromatic diimine complexes and flavin mononucleotide. These adducts can exhibit unique properties, such as enhanced stability and novel photophysical behaviors, which can be exploited in the development of new supramolecular systems and functional materials.
Used in Catalysis:
This platinum complex serves as a catalyst for the selective synthesis of monoorganotin trihalides. Its ability to facilitate the formation of specific organotin compounds with high selectivity makes it a valuable catalyst in the field of organotin chemistry, which has potential applications in various industries, including polymer synthesis, pharmaceuticals, and materials science.

InChI:InChI=1/C12H8N2.2ClH.Pt/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1;;;/h1-8H;2*1H;/q;;;+2/p-2

Upstream product

• 7647-01-0 hydrogenchloride 
• 10025-99-7 potassium tetrachloroplatinate(II) 
• 5144-89-8 1,10-phenanthroline hydrate 
• 208333-25-9 [(1,10-phenanthroline)PtI(C₆H₅)] 
• 852673-84-8 [(1,10-phenanthroline)PtI(C₆H₄CH₃)] 
• 852673-85-9 [(1,10-phenanthroline)PtI(C₆H₄OCH₃)] 
• 852673-86-0 [(1,10-phenanthroline)PtI(C₆H₄CF₃)] 
• 66-71-7 1,10-Phenanthroline 
• 1314046-47-3 (DMSO)PtCl₂ 
• 1083089-64-8 [Pt(η1-CH2CH2N(CH2CH3)2-κC,κN)(1,10-phenanthroline)]ClO4 

Downstream Products

• 158640-23-4 Pt(1,10-phenanthroline)(C_.tplbond.CC₆H₅)2 
• 220294-68-8 [Pt(1,2-bis(benzylthio)ethylene-1,2-dithiolate)(1,10-phenanthroline)] 
• 200193-90-4 (1,10-phenanthroline)(4-MeO-C₆H₄S)2Pt 
• 200193-88-0 (1,10-phenanthroline)(PhS)2Pt 
• 218292-74-1 (1,10-phenanthroline)(4-NO₂-C₆H₄S)2Pt 
• 200193-92-6 (1,10-phenanthroline)(4-Me₂N-C₆H₄S)2Pt 
• 233587-07-0 cis-[Cp(dppe)Fe-CN-Pt(phen)Cl]SbF₆ 
• 560132-94-7 Pt(1,10-phenanthroline)(p-CCC₆H₄CHO)2 
• 666854-01-9 [Pt(1,10-phenanthroline)(4-(2,2'-dipyridylamino)phenylacetylide)2] 
• 620966-86-1 1,10-phenanthrolinebis(4-cyano-tetrafluorophenylthiolato)platinum(II) 
• 620966-85-0 1,10-phenanthrolinebis(pentafluorophenylthiolato)platinum(II) 
• 1207518-47-5 [Co(I)(1,1,1-tris(diphenylphosphinomethyl)ethane)(μ-η2-C,C':κ2S,S'-acetylenedithiolate)Pt(1,10-phenanthroline)]BPh4 
• 1233766-64-7 cis-[Pt(κ2S,O-2,6-F2C6H3C(O)NC(S)NEt2)(1,10-phenanthroline)]PF6 

Relevant academic research and scientific papers

A comparative study of the effects of platinum (Ii) complexes on β-amyloid aggregation: Potential neurodrug applications

Herein the effects of three platinum complexes, namely (SP-4-2)-(2,2′-bipyridine)dichlorido platinum(II), Pt-bpy, (SP-4-2)-dichlorido(1,10-phenanthroline) platinum(II), Pt-phen, and (SP-4-2)-chlorido(2,2′:6′,2′ ′-terpyridine)platinum(II) chloride, Pt-terpy, on the aggregation of an amyloid model system derived from the C-terminal domain of Aβ peptide (Aβ21–40) were investigated. Thioflavin T (ThT) binding assays revealed the ability of Pt(II) compounds to repress amyloid aggregation in a dose-dependent way, whereas the ability of Aβ21–40 peptide to interfere with ligand field of metal complexes was analyzed through UV-Vis absorption spectroscopy and electrospray ionization mass spectrometry. Spectroscopic data provided micromolar EC50 values and allowed to assess that the observed inhibition of amyloid aggregation is due to the formation of adducts between Aβ21–40 peptide and complexes upon the release of labile ligands as chloride and that they can explore different modes of coordination toward Aβ21–40 with respect to the entire Aβ1–40 polypeptide. In addition, conformational studies through circular dichroism (CD) spectroscopy suggested that Pt-terpy induces soluble β-structures of monomeric Aβ21–40, thus limiting self-recognition. Noticeably, Pt-terpy demonstrated the ability to reduce the cytotoxicity of amyloid peptide in human SH-SY5Y neuroblastoma cells. Presented data corroborate the hypothesis to enlarge the application field of already known metal-based agents to neurodegenerative diseases, as potential neurodrugs.

Synthesis and evaluation of the anticancer activity of [Pt(diimine)(N,N-dibutyl-N′-acylthiourea)]+complexes

Despite the concerted efforts to develop targeted cancer treatments, these therapies are plagued by the rapid development of resistance and serious adverse drug reactions. Based on the wide clinical use and successes of the platinum drugs like cisplatin and oxaliplatin, we investigated the synthesis and potential anticancer efficacy of alternative platinum complexes. A series of nine cationic square planar platinum(ii) complexes were synthesized and characterized and then evaluated for their anticancer activity. The complexes were of the type [Pt(diimine)(Ln-κO,S)]+where diimine is either 1,10-phenanthroline (phen), 5,6-dimethyl-1,10-phenanthroline (dmp) or dipyrido[3,2-f:2′,3′-h]quinoxaline (dpq) and Ln-κO,Srepresenting variousN,N-dibutyl-N′-acylthiourea ligands. The anticancer activity of the synthesised complexes was evaluated against two lung cancer cell lines (A549 and H1975) and a colorectal cancer cell line, HT-29. The 50% inhibitory concentrations (IC50) for the most cytotoxic compounds were determined and the mode of cell death evaluated. The structure-activity relationships indicated that complexes with the 5,6-dimethyl-1,10-phenanthroline variation of the diimine ligand were the most active against the cell lines tested, while the activity of complexes based on the acylthiourea ligand varied between the cell lines. IC50values for the three active platinum complexes were in the low micromolar range for the three cell lines and ranged between 0.68 μM and 2.28 μM. Changes to cell morphology indicate that the active platinum complexes induce cell death by both apoptosis and paraptosis. The complexes were able to induce the nuclear expression of the cyclin-dependent kinase inhibitor, p21, which is an indicator of DNA damage. The collective data indicate that these platinum complexes are valuable lead compounds for further analysis and cancer drug discovery.

Anionic versus neutral Pt(II) complexes: The relevance of the charge for human serum albumin binding

The focus of this work is pointing out the different behavior of two structurally related Pt(II) complexes, the anionic cyclometalated NBu4[(Bzq)Pt(Thio)], 1 and the neutral [(Phen)Pt(Thio)], 2, (Bzq = benzo[h]quinoline, Phen = 1,10-phenantroline, Thio = 1,2-benzenedithiolate), on the interaction with human serum albumin (HSA), a key drug-delivery protein in the bloodstream. Being very limited the number of anionic Pt(II) complexes reported to date, this is a pioneering example of report on a protein-ligand interaction involving a negatively charged platinum compound. The study was carried out by using fluorescence spectroscopy, differential scanning calorimetry and molecular docking simulations. The results revealed a strong binding affinity between the anionic compound and the protein, whereas a weak/moderate binding interaction was highlighted for the neutral one. Comparative studies with site specific ligands (warfarin and ibuprofen), allowed us to identify the protein binding sites of the two compounds. The work aims to shed light on the relevance of the charge in designing new drugs with a favorable binding affinity for HSA, which strongly contributes to influence their pharmacological and toxicological profile.

Platinum(II) Complexes with 1,10-Phenanthroline and Hydrophilic Alkoxyacetate Ligands as Potential Antitumor Agents

Four platinum complexes, formulated as [Pt(phen)(OCOCH2OR)2] (phen=1,10-phenanthroline, R=Me, Et, iPr, or tBu), have been synthesized and well characterized by elemental analysis, IR, 1H-NMR, 13C-NMR and ESI-MS spectroscopy. Replacing chloride groups of the precursor Pt(phen)Cl2 with alkoxyacetate anions greatly improved the aqueous solubility and cytotoxicity of the resulting platinum complexes. The in vitro cytotoxicity study revealed that complexes 1–3 were active in vitro towards four human tumor cell lines, especially complex 1 which exhibited prominent in vitro cytotoxic activity against HCT-116 cell lines comparable to cisplatin and oxaliplatin. Flow cytometry assay indicated that representative complexes 1 and 2 exerted cytotoxicity on HCT-116 cell lines through inducing cell apoptosis and blocking cell cycle progression in the S or G2/M phases. The interaction of representative complexes with pET28a plasmid DNA was tested by agarose gel electrophoresis, which demonstrated that complexes 1 and 2 were capable of distorting plasmid DNA mainly by covalent binding and degradation effect.

Conformational analysis and potential anticancer activity of [Pt(phen)(L1 -κ: S)2] studied by single crystal X-ray diffraction and variable temperature 1H and 195Pt NMR spectroscopy

The mixed-ligand [Pt(phen)(L1-κS)2] complex, in which two N,N-diethyl-N′-1-naphthoylthioureato ligands (L1)- coordinate in an unusual κS-thio/amido mode, crystallises in two solvatomorphs, form I and form II, whose structures have been determined by single crystal X-ray diffraction. These crystals were obtained from tetrahydrofuran and methanol/water respectively showing interesting sandwich (form I) and half-sandwich (form II) intramolecular π-stacking arrangements between the naphthoyl moiety of the acylthioureato ligands and the 1,10-phenanthroline ligand that adopt an anti-conformation above and below the square planar coordination plane. Variable temperature 1H and 195Pt NMR spectroscopy showed that these π-stacking arrangements persist in methanol solution especially at lower temperatures, where significant chemical shift shielding and asymmetry are observed indicating at least 3 conformers at -50 °C. A preliminary study indicates that this new compound may have potential as a new anticancer agent since it is active against the A549 lung cancer cell-line with an IC50 value of 6 ± 0.9 μM.

Photocytotoxic cancer cell-targeting platinum(ii) complexes of glucose-appended curcumin and biotinylated 1,10-phenanthroline

Mixed-ligand platinum(ii) complexes, [Pt(phen)(pacac)](NO3) (1), [Pt(phen)(cur)](NO3) (2), [Pt(bt-phen)(cur)](NO3) (3) and [Pt(phen)(scur)](NO3) (4), where phen is 1,10-phenanthroline, bt-phen is 5-biotin-1,10-p

Cationic olefin complexes of platinum(II): Aspects of availability and reactivity

The series of complexes of formula [PtCl(η2-olefin)(N^N)]+, previously investigated for N^N = N,N,N′,N′-tetramethyl-ethylenediamine (Me4en), has been extended to the case of aromatic diimines 1,10-phenanthroline (phen) and 3,4,7,8-tetramethyl-1,10-phenanthroline (Me4phen) and to a variety of olefins (ethene, propene and styrene). The complexes have been prepared by reaction of the [PtCl3(η2-olefin)]? anions (K[PtCl3(η2-styrene)] reported here for the first time) with N^N in basic methanol. The initial [PtCl{η1-CH2–CH(R′)–OMe}(N^N)] (R′ = Me, Ph) complexes are formed in quantitative yield and as pure Markovnikov isomer. The reaction of the alkoxylic species with non coordinating acids, results in the quantitative formation of the desired cationic π-olefin complexes [PtCl(η2-olefin)(N^N)]+. The phenanthroline ligand confers peculiar properties to the new compounds. In particular, by reaction with triethylamine, [PtCl{η2-CH2[dbnd]CH(Me)}(N^N)]+ species, undergo deprotonation of the olefin and formation of the dimeric species [{PtCl(N^N)}2(μ-η1:η2-CH2CH[dbnd]CH2)]+ which could be isolated and characterized. Interestingly such product in acetonitrile gives a disproportionation with precipitation of [PtCl2(phen)] and formation in solution of the new η3-allyl complex [Pt(η3-C3H5)(phen)]ClO4.

Synthesis, characterization, and cytotoxicity of Pt(IV) complexes containing 1,10-phenanthroline and 2,2′-bipyridine and diaminocyclohexane ligands

Four platinum(IV) complexes containing intercalating ligands [1,10-phenanthroline (phen) and 2,2′-bipyridine (bpy)] and ancillary ligands [(1S,2S)-diaminocyclohexane (SS-DACH) and (1R,2R)-diaminocyclohexane (RR-DACH)] were synthesized and characterized by 1H nuclear magnetic resonance, electrospray ionization mass spectrometry, X-ray crystal structure analysis, elemental analysis, ultraviolet absorption spectroscopy, circular dichroism spectroscopy, and electrochemical analysis. The reactions between [Pt(phen)(SS-DACH)Cl2]2+ and glutathione and Ac-CPFC-NH2 were investigated by high-performance liquid chromatography. [Pt(phen)(SS-DACH)Cl2]2+ was reduced to its corresponding Pt(II) complex [Pt(phen)(SS-DACH)]2+, while glutathione and Ac-CPFC-NH2 were oxidized to glutathione-disulfide and a peptide containing an intramolecular disulfide bond, respectively. The cytotoxicities of the Pt(IV) complexes against a human non-small cell lung cancer cell line (A549) and the corresponding cisplatin-resistant cell line (A549cisR) were evaluated. These Pt(IV) complexes showed a higher activity toward A549 and A549cisR than did cisplatin. Also, the cytotoxicities of the Pt(IV) complexes were higher for A549cisR than for A549 cells. Moreover, the cytotoxicities of the (SS-DACH)-liganded platinum complexes were higher than those of the (RR-DACH)-liganded platinum complexes in either A549 or A549cisR cells. Phen-liganded platinum complexes were more cytotoxic than the bpy-liganded platinum complexes. The cytotoxicities of these Pt(IV) complexes had no correlation with reduction potentials.

The Effect of Drug Loading on Micelle Properties: Solid-State NMR as a Tool to Gain Structural Insight

The present study highlights the importance of understanding the structural changes of micelles induced by drug loading on their physico-chemical properties. A block copolymer with attached fructose, which interacts with GLUT5 receptor, was used and conjugated with a low and a high amount of platinum drugs. Against expectations, the low-loading micelle, despite having a less defined morphology and larger nanoparticle size according to TEM, displays higher cellular uptake and higher toxicity. This behaviour can only be understood when elucidating additional information on the structure of micelles. Extensive solid-state NMR measurements were therefore employed to reveal that the drug loading affected swelling and mobility of core and shell of the micelle. The results obtained from solid-state NMR spectroscopy could explain all the observations on this system. In summary, solid-state NMR spectroscopy is an excellent tool to understand the effects of drug loading on the behavior of micelles.

Reaction between the Pt(II)-complexes and the amino acids of the β-amyloid peptide

Reaction between [Pt(ophen)Cl2] and HIS was monitored and the solvolysis (k1) and Cl/HIS ligand exchange (k2) rate constants obtained. The k1 and k2 were (6.2?±?0.4)?×?10?5?s?1 and 52.8?×?10?2?M?1?s?1, respectively. The corresponding calculated values were 47.5?×?10?5?s?1 and 52.2?×?10?2?M?1?s?1, in agreement with the experiment. Calculations were used to establish the reactivity order for a set of amino acids: MET?～?LYS?～?HIS(ε)?>?GLU?～?ASP?>>?ASN?～?GLN. In spite of the similar reactivity among MET, LYS and HIS, the thermodynamics suggests the reactions with LYS and HIS more favorable than with MET. Therefore, N-containing amino acids should be potential targets of Pt(II)-complexes in β-amyloid.