Methotrexate - CAS 59-05-2
Catalog number: 59-05-2
Molecular Formula:
Molecular Weight:
Methotrexate is a Folic acid antagonist. It is used as a antineoplastic and antirheumatic.
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Yellow Solid
N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic Acid; (+)-Amethopterin; 4-Amino-N10-methylpteroylglutamic Acid; 4-Amino-N10-methylfolic Acid; Antifolan; CL 14377; EMT 25299; Emtexate; Ledertrexate; MTX; L-Metatrexan; Methylaminopte
Melting Point:
>188°C (dec.)
1. Direct measurement of drug–enzyme interactions by atomic force microscopy; dihydrofolate reductase and methotrexate
Shellie M. Rigby-Singleton, Stephanie Allen, Martyn C. Davies, Clive J. Roberts, Saul J. B. Tendler * and Philip M. Williams. J. Chem. Soc., Perkin Trans. 2, 2002, 1722–1727
High-resolution crystal structures of the enzyme–inhibitor complex have also been elucidated. In particular, the inhibitor methotrexate (MTX) has been studied extensively over the last half century (Fig. 1b). Methotrexate upon binding to DHFR inhabits the same hydrophobic binding site as folate. Demonstrating a higher binding affinity for DHFR than folate, methotrexate acts as a competitive inhibitor of DHFR. When bound, methotrexate adopts an inverse orientation compared to that of folate, but retains the same hydrogen bonding geometry as the enzyme–substrate complex. The binding site is configured of the αB helix (residues 24–32,lc (Lactobacillus casei )), a loop (49–57,lc which forms a part of the active site) connecting the αC helix (43–48,lc) to the βC sheet (58–62,lc), and a 9 to 23,lc residue loop (connecting the βA sheet and the αB helix).
2. An algorithm to determine the mechanism of drug distribution in lipid-core nanocapsule formulations
Catiuscia P. Oliveira, Cristina G. Venturini, Adriana R. Pohlmann*. Soft Matter, 2013, 9, 1141–1150
METHOTREXATE DIETHYL ESTER (3). DMAP (6 mg, 0.4 mmol), as the catalyst, was added to a solution of methotrexate (2) (455 mg, 1 mmol) in ethanol (30 mL). After 10 min under magnetic stirring, DCC (416mg, 2mmol) was added at 0 ℃ to activate the acid functions. The coupling reaction was then carried out at 40 ℃ for 90 h. The medium was evaporated under reduced pressure at 35 ℃ and the residue was dispersed in dichloromethane (30 mL). The product was isolated by filtering the byproduct (dicyclohexylurea). The filtrate was washed with NaHCO3 saturated aqueous solution, dried with anhydrous Na2SO4, and evaporated under reduced pressure. The raw product was purified by preparative column chromatography using silica gel 60 (70–230 mesh) as the stationary phase and chloroform and methanol (99 : 1 v/v) using traces of ammonium hydroxide as the eluent. A yellow solid was obtained in 70% yield. The chemical identity of diethyl (2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)-amino]-pentanedioate was confirmed by 1H NMR.
3. The selective interaction between N-isobutyryl-cysteine enantiomers and L-methotrexate
Cui Chen, Liju Guo, Dongmei Guo, Ya Chen, Qinghong Wang and Yingzi Fu*. Anal. Methods,2014, 6, 7789–7792
In summary, two configurations of NIBC enantiomer modified gold electrodes were used to interact with L-methotrexate. A larger current difference was obtained from the L-NIBC interface; the current difference of over 500 mA indicated an obvious enantioselective reaction between L-methotrexate and the NIBC enantiomers. This provides useful information for investigating the physical and chemical properties of methotrexate.
4. A simple N,N’-dicyclohexylurea adduct of β-alanine can self-assemble to generate nano-morphological versatility in response to different environmental conditions
Sudeshna Kar, Bo-Hong Huang, Kung-Wei Wu, Chi-Rung Lee* and Yian Tai*. Soft Matter,2014, 10,8075–8082
The design and construction of nano-vesicles from the self-assembling peptide and pseudo peptides are being considered as excellent vehicles for the encapsulation and carrying drugs and other bioactive molecules into the living systems due to their enhanced biocompatibility and exceptional adaptability for targeted delivery, but the entrapment capability of stable nano-vesicles generated from single amino acid based molecules is yet to be explored. Thus, we investigated the efficiency of the “Boc-b-Ala–N,N’-dicyclohexylurea” based nano-vesicles to encapsulate the anti-cancer drug methotrexate (MTX). The fluorescence microscopic image of the drug-loaded nano-vesicles clearly depicts the encapsulation of the MTX drug by the vesicles (Fig. 6(a)). Moreover, the entrapped drug can be released easily by simple addition of a biocompatiblemetal salt, such as KCl, into the drug-loaded vesicles, which was confirmed by the fluorescence microscopic image (Fig. 6(b)). This encapsulation–releasing process is further confirmed by fluorescence emission study (Fig. 6(c)). The fluorescence of the MTX drug is found to drop enormously after its encapsulation in the nano-vesicles.
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