Synthesis and Physicochemical Characterization of the Impurities of Pemetrexed Disodium, an Anticancer Drug

Michalak, Olga; Gruza, Mariusz; Witkowska, Anna; Bujak, Iwona; Cmoch, Piotr

doi:10.3390/molecules200610004

Cited by 10 publications

(6 citation statements)

References 19 publications

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“…Chemical shifts are reported in ppm relative to DMSO (δ = 2.5 ppm) and HDO (δ = 4.8 ppm). Chemical shifts for PTX [ 30 ] and CDs in D 2 O [ 31 ], and DMSO [ 32 ] are consistent with the literature data.…”

Section: Methodssupporting

confidence: 82%

Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies

Ceborska

Zimnicka

Kowalska

et al. 2017

Beilstein J. Org. Chem.

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The complexation of the antifolate pemetrexed (PTX) with native cyclodextrins was studied. This process, along with the findings gathered for the structurally related folic acid was treated as a model for exploiting host–guest interactions of this class of guest molecules in the gas phase, in solution and in the solid state. Mass spectrometry was employed for the investigation of the architecture and relative gas-phase stabilities of these supramolecular complexes. The mode of complexation was further tracked by 1D and 2D NMR proving the formation of the exclusion-type complex with α-CD and pseudorotaxane inclusion-type complexes with β-, and γ-CDs. UV–vis titrations at pH 7.4 gave association constants for the obtained complexes. The stability of the complexes increases in the series: α-CD/PTX < γ-CD/PTX << β-CD/PTX. The association of PTX with a monomer cyclodextrin equivalent – methyl α-D-glucopyranoside – was investigated for a deeper understanding of the type of host–guest interactions. Solid state studies of PTX/CDs were performed using FTIR–ATR and Raman spectroscopy techniques.

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Section: Methodssupporting

confidence: 82%

Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies

Ceborska

Zimnicka

Kowalska

et al. 2017

Beilstein J. Org. Chem.

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“…At this frequency offset, as shown in the color-coded CEST parametric map (Figure f), a marked CEST contrast can be appreciated between PemFE and the control molecule (C12FE). We therefore speculate this CEST signal arises from the aromatic primary amine’s exchangeable proton on the Pem (∼10 ppm using 1 H NMR spectrometry). It is noteworthy that, as a result of the fast exchange rate, the CEST peak at 5.2 ppm is broadened and the exact offset to obtain the “peak” CEST effect was observed to be slightly shifted (ranging from 5.0 to 5.4 ppm) for samples measured at different solution pH or using different saturation power (Figures S7).…”

Section: Resultsmentioning

confidence: 97%

One-Component Supramolecular Filament Hydrogels as Theranostic Label-Free Magnetic Resonance Imaging Agents

Lock

Li²,

Mao

et al. 2017

ACS Nano

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Gadolinium (Gd)-based compounds and materials are the most commonly used magnetic resonance imaging (MRI) contrast agents in the clinic; however, safety concerns associated with their toxicities in the free ionic form have promoted the development of new generations of metal-free contrast agents. Here we report a supramolecular strategy to convert an FDA-approved anticancer drug, Pemetrexed (Pem), to a molecular hydrogelator with inherent chemical exchange saturation transfer (CEST) MRI signals. The rationally designed drug–peptide conjugate can spontaneously associate into filamentous assemblies under physiological conditions and consequently form theranostic supramolecular hydrogels for injectable delivery. We demonstrated that the local delivery and distribution of Pem–peptide nanofiber hydrogels can be directly assessed using CEST MRI in a mouse glioma model. Our work lays out the foundation for the development of drug-constructed theranostic supramolecular materials with an inherent CEST MRI signal that enables noninvasive monitoring of their in vivo distribution and drug release.

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“…Recently, BDO has been found to be converted to 3-butene-1-ol (BTO) through selective dehydration over metal oxide catalysts such as CeO 2 [5] and ZrO 2 [6][7][8]. BTO is a valuable intermediate due to the presence of a reactive double bond and hydroxyl group; it can be used in the synthesis of heterocyclic drugs such as multidrug resistant compounds, anti-HIV drugs, and antiproliferative agents [9][10][11][12]. Therefore, BDO catalytic selective dehydration to BTO has attracted increasing attention with regards to exploiting a high value-added downstream derivative of BDO [13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

1,4-Butanediol Selective Dehydration to 3-Butene-1-ol over Ca–Zr–Sn Composite Oxide Catalysts

Dong

Yang

et al. 2022

Catalysts

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Ca–Zr–Sn composite oxides catalysts for 1,4-butanediol (BDO) selective dehydration to 3-butene-1-ol (BTO) are synthesized by impregnation and co-precipitation in the present work. The results show that Ca–Zr–Sn catalysts prepared from co-precipitation by using NaOH-Na2CO3 mixing alkali solution as precipitant exhibit an excellent catalytic property for BDO dehydration to BTO. For instance, Ca–Zr–Sn oxide with Ca/Zr and Sn/Zr molar ratio of 0.68 and 0.28 calcined at 650 °C gives a BDO conversion and BTO selectivity of about 97% and 82%, respectively, and exhibits no deactivation during 1000 h scale-up experimental testing. X-ray diffraction results indicate that catalytic active centers for BDO dehydration to BTO are from Ca0.15Zr0.85O crystal phase. NH3- and CO2-temperature programmed desorption prove that the surface of obtained catalysts can provide a large amount of acid and base sites simultaneously. FT-IR spectra of pyridine-adsorbed samples show that acid sites on the surface of Ca–Zr–Sn oxide catalyst mainly exist in a state of Lewis acid, which activates terminal -OH groups of BDO molecule through complexing. The activated -OH interacts with β-H activated on base sites O2− anions relative to Ca species, thereby the CH2=CH- bonds are produced through dehydration to form BTO.

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Synthesis and Physicochemical Characterization of the Impurities of Pemetrexed Disodium, an Anticancer Drug

Cited by 10 publications

References 19 publications

Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies

Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies

One-Component Supramolecular Filament Hydrogels as Theranostic Label-Free Magnetic Resonance Imaging Agents

1,4-Butanediol Selective Dehydration to 3-Butene-1-ol over Ca–Zr–Sn Composite Oxide Catalysts

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