PEGylated methotrexate based micellar conjugates for anticancer chemotherapy

Bansal, DivyaBhargava; Bhadra, D.; Gupta, Umesh; Jain, NK

doi:10.4103/0973-8398.150042

Cited by 2 publications

(5 citation statements)

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“…The clinical uses of MTX showed some disadvantages because of its very short plasma half-life. Therefore, cancer cells may show resistance to this drug in higher doses due to cellular efflux phenomenon; it can also induce dose-dependent side effects in normal cells such as bone marrow, gastrointestinal mucosa, hair, and renal system 16,17 . Thus, conjugation of MTX with some targeting carriers such as modified MNPs could increase the accumulation of drug in tumor cells and lead to reduction of side effects in normal cells and also decrease drug-resistance phenomena in target cells 13 .…”

Section: Quick Response Codementioning

confidence: 99%

“…To obtain methotrexate (MTX) chemical conjugation, MTX (Sigma-Aldrich,Steinheim, Germany) (25 mg, 0.055 mmol) and N, N-dicyclohexylcarbodiimide (DCC) (Alfa Aesar Company, Lancashire, UK) (13 mg, 0.066 mmol) were dissolved in 4 mL dimethyl formamide (DMF) (ratio 1:12) 17 . The reaction solution was stirred overnight at 0°C.…”

Section: Conjugation Of Methotrexate To Fe 3 O 4 -Dpa-peg-nhmentioning

confidence: 99%

“…To synthesize mono-and di-methylester of MTX, first MTX (3.75 mg, 0.00825 mmol) and DCC (3.7 mg, 0.018 mmol) were dissolved in 1 mL DMF (ratio 1:2.2) and reaction solution was stirred overnight at 0C. The precipitate was removed by centrifugation at 5000 rpm (10 min, 4°C) 17 . After that, the supernatant was divided into two parts.…”

Section: Analysis Of Carboxylate Group Activation Of Mtxmentioning

confidence: 99%

“…To this end, carboxyl groups of MTX were activated via DCC in dry DMF and in the absence of N-hydroxysuccinimide for a controlled loading of MTX to Fe 3 O 4 -DPA-PEG-NH 2 17 . MTX was reacted with 1.1 equiv.…”

Section: Fig2: Particle Size Analyser Curve Of Fe 3 O 4 Nps Averagementioning

confidence: 99%

“…of DCC for 18 h at 0°C. The white N, N-dicyclohexylurea was precipitated by centrifugation and then, activated MTX was chemically reacted with nucleophilic amino group of Fe 3 O 4 -DPA-PEG-NH 2 to form Fe 3 O 4 -DPA-PEG-MTX 17 .The MTX loaded MNPs were easily collected by magnetic bead separation system. The UV spectrophotometry of unreacted MTX in 302 nm revealed about 88% loading efficiency of drug onto magnetic nanocarriers.…”

Section: Fig2: Particle Size Analyser Curve Of Fe 3 O 4 Nps Averagementioning

confidence: 99%

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2015

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Magnetic nanocarriers have been used for specific drug delivery to release therapeutic drugs into target cancer cells. We used bifunctional methotrexate (MTX) conjugated magnetic nanoparticles (MNPs) (~37 nm) engineered by dopamine-polyethylene glycol to targeted folate receptor (FR)-positive cancer cells. For this purpose, MTX was chemically loaded on to MNPs with N, Ndicyclohexylcarbodiimide (DCC) in the absence of NHS at 0C. Activation process of MTX was analyzed via synthesis of different MTX methyl esters through HPLC instrument. The HPLC analysis showed that in a selective condition and in the presence of 1.1 equiv. of reactiveagent,-carboxyl group of MTX was more active. Enzymatic release study of MTX demonstrated that the highest rate of drug release was at pH=3.8 with protease enzyme (85.12%). Also, cytotoxicity assay revealed that Fe 3 O 4-DPA-PEG-MTX NPs were able to target over expressed FR cell line (MCF-7) but did not have any effect on FR-negative A549 cells and significantly inhibit them.

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Section: Quick Response Codementioning

confidence: 99%

Section: Conjugation Of Methotrexate To Fe 3 O 4 -Dpa-peg-nhmentioning

confidence: 99%

Section: Analysis Of Carboxylate Group Activation Of Mtxmentioning

confidence: 99%

Section: Fig2: Particle Size Analyser Curve Of Fe 3 O 4 Nps Averagementioning

confidence: 99%

Section: Fig2: Particle Size Analyser Curve Of Fe 3 O 4 Nps Averagementioning

confidence: 99%

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PTS micelles for the delivery of hydrophobic methotrexate

Cerqueira

Noro

Moura

et al. 2019

International Journal of Pharmaceutics

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Polyoxyethanyl-α-tocopheryl sebacate (PTS) is an amphiphilic compound with self-emulsifying properties known to form micelles. In this work, we report the production of PTS micelles for the encapsulation and delivery of a hydrophobic derivative of methotrexate, MTX di-ethylated (MTX-OEt). We optimized the micelles production by testing two different techniques: auxiliary solvent and sonication. Small and homogeneous micelles (≈40 nm) were obtained through the auxiliary solvent method performed at 30°C and using 15 mg/mL of PTS. The produced micelles with the most promising physicochemical properties did not induce cytotoxicity when tested in normal human cells (BJ5ta cells), being considered for the encapsulation of MTX-OEt. This prodrug was achieved by Fisher esterification using ethanol, being isolated in good yield (η = 68%). MTX-OEt was efficiently encapsulated onto the produced micelles which preserved their physicochemical properties. The PTS micelles loaded with MTX-OEt, free MTX-OEt and free unmodified MTX revealed similar biological effect against cancer cells (Caco-2 cells). These results demonstrated that the biological activity of MTX is not altered after modification. The developed PTS micelles revealed a promising intracellular delivery performance with potentiality for cancer therapy.

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PEGylated methotrexate based micellar conjugates for anticancer chemotherapy

Cited by 2 publications

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PTS micelles for the delivery of hydrophobic methotrexate

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