Targeted antitumoral dehydrocrotonin nanoparticles with L-ascorbic acid 6-stearate

Frungillo, Lucas; Martins, Dorival; Teixeira, Sérgio R.; Anazetti, Maristela Conti; Melo, Patrı́cia da Silva; Durán, Nélson

doi:10.1002/jps.21760

Cited by 10 publications

(11 citation statements)

References 34 publications

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“…Similar cytotoxic activity against tumor cells was reported using polymeric nanoparticles containing the antitumor compound transdehydrocrotonin (DHC) and L-ascorbic acid 6-stearate (ASC-S), which was taken up more easily by tumor cells than by normal ones [27]. ASC-S-DHC nanoparticles were prepared by the nanoprecipitation method, in which PLGA, DHC, and ASC-S dissolved in acetone were added to an aqueous solution containing Pluronic F68 and polyvinyl alcohol (PVA).…”

Section: Introductionmentioning

confidence: 64%

Drug Nanoparticle Formulation Using Ascorbic Acid Derivatives

Moribe

Limwikrant

Higashi

et al. 2011

Journal of Drug Delivery

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Drug nanoparticle formulation using ascorbic acid derivatives and its therapeutic uses have recently been introduced. Hydrophilic ascorbic acid derivatives such as ascorbyl glycoside have been used not only as antioxidants but also as food and pharmaceutical excipients. In addition to drug solubilization, drug nanoparticle formation was observed using ascorbyl glycoside. Hydrophobic ascorbic acid derivatives such as ascorbyl mono- and di-n-alkyl fatty acid derivatives are used either as drugs or carrier components. Ascorbyl n-alkyl fatty acid derivatives have been formulated as antioxidants or anticancer drugs for nanoparticle formulations such as micelles, microemulsions, and liposomes. ASC-P vesicles called aspasomes are submicron-sized particles that can encapsulate hydrophilic drugs. Several transdermal and injectable formulations of ascorbyl n-alkyl fatty acid derivatives were used, including ascorbyl palmitate.

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Section: Introductionmentioning

confidence: 64%

Drug Nanoparticle Formulation Using Ascorbic Acid Derivatives

Moribe

Limwikrant

Higashi

et al. 2011

Journal of Drug Delivery

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“…The increased biological activity of violacein loaded in nanoparticles has been demonstrated in previous works either with tumoral cells 26 or Staphylococci strains 27 and the addition of derivatives of ascorbic acid on external surface of nanoparticles had been shown to increase the efficiency of dehydrocrotonin loaded in PLGA nanoparticles with a protein mediated uptake mechanism and a shunt of cell death mechanism to receptor-mediated pathways. 29 However, an unexpected observation was reached, since free ascorbic acid exhibits a buffering effect in violacein-mediated toxicity, while the addition of ascorbic acid on the external surface of PLGA nanoparticles loading violacein actually promotes an improvement of the toxicity of this compound. This suggests a differential cell death mechanism between free violacein and NP-AA-violacein.…”

Section: Discussionmentioning

confidence: 99%

“…Cells were used in the exponential growth phase at passage 15-30. To assess cell viability, the cells were seeded (3.10 5 cells.mL -1 ) in 96 well plates and incubated with different concentrations of free or nanoparticle-loaded violacein for 72 hours, as previously described. 29 In all experiments with encapsulated violacein, the final concentration of nanoparticles was maintained constant by addition of a complementary amount of blank. Cell viability was determined by MTT reduction assay and the inhibitory concentration for 50% of the cells (IC 50 ) was standardized as a 26 In order to verify whether free ascorbic acid has any buffering effect in free violacein-mediated toxicity, cells were exposed to free violacein at IC 50 values and a concentration of ascorbic acid equivalent to the total amount of this compound recovered from NP-AA.…”

Section: Cytotoxicity Assays Cell Culturesmentioning

confidence: 99%

“…However, efforts to create drug carriers with derivatives of ascorbic acid to avoid undesirable oxidation processes and to improve the shelf-life of ascorbic acid on nanoparticles are being carried out and showed promising results with polymeric nanoparticles carrying another antitumoral compound, dehydrocrotonin. 29 Complementary studies on toxicity of such complexes against normal cells and in vivo evaluations should be carried out to further characterize the pharmacological potential of this system.…”

Section: Dovepressmentioning

confidence: 99%

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Antitumoral activity of L-ascorbic acid-poly-D,L-(lactide-co-glycolide) nanoparticles containing violacein

Martins

Frungillo²,

Anazzetti³

et al. 2010

IJN

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It has been demonstrated that tumoral cells have a higher uptake of ascorbic acid compared to normal cells. This differential characteristic can be used as a way to improve the specificity of antitumoral compounds if combined with polymeric drug delivery systems. The aim of this study was to prepare, characterize and evaluate the antitumoral activity of poly-D,L-(lactide-co-glycolide) 50:50 loading the antitumoral compound violacein and capped with L-ascorbic acid. Nanoparticles were prepared using the nanoprecipitation method and morphologically characterized by scanning electron microscopy (SEM). The average diameter and Zeta potential were determined by photon correlation spectroscopy method (PCS), and assays were carried out to determine the content of ascorbic acid and in vitro drug release kinetics. The antitumoral activity of this system was also evaluated against HL-60 cells by tetrazolium reduction assay. Nanoparticles with size distribution between 300-400 nm and strong negative outer surface (-40 mV) were obtained by this method. Analysis of ascorbic acid content showed that this compound was mainly localized on the external surface of nanoparticles. Violacein loading efficiency was determined as 32% ± 1% and this drug was gradually released from nanoparticles at different rates depending on the composition of the release media. In addition, this system was observed to be 2 × more efficient as an antitumoral compared with free violacein.

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“…The inhibition by L‐AS of the growth of murine leukemia p388D1 cell line can approach 90% at the level of 10 µg mL −1 . Besides, the L‐AS can be severed as the carriers of dehydrocrotonin (DHC) nanoparticles and the formed nanoparticles enhance the antitumoral activity of DHC …”

Section: Introductionmentioning

confidence: 99%

Environmentally benign downstream process for the enzymatic production of 6‐O‐L‐ascorbyl stearate

Luhong

2015

J of Chemical Tech & Biotech

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BACKGROUND: The current processes used to produce 6-O-L-ascorbyl stearate are mature but far from environmentally benign. Even in the enzymatic process, a water-washing step is still indispensable, forming a large amount of waste water. The aim of this study is to improve understanding of the behavior of the reaction mixture formed during enzymatic synthesis of ascorbyl stearate and create a novel product purification method omitting the water-washing step. RESULTS: Adding hot methyl stearate (65 ∘ C) will liquefy the solidified mixture composed of 6-O-L-ascorbyl stearate, L-ascorbic acid and methyl stearate, the filtrate of almost pure methyl stearate could be reused, and the cake gained could be washed and recrystallized from ethyl acetate at 4 ∘ C to gain the pure 6-O-L-ascorbyl stearate. The single recovery rate of 6-O-L-ascorbyl stearate is 66.0%, the purity of it is 99.8% detected by LC/MS. CONCLUSION: Taking advantage of the phase behavior and the solubility differences of 6-O-L-ascorbyl stearate, L-ascorbic acid and methyl stearate in ethyl acetate at different temperatures, it is possible to produce 6-O-L-ascorbyl stearate in an environment-friendly way. The process developed in this study is easy to scale up and suitable for the synthesis of similar 6-O-L-ascorbyl derivatives of other fatty acids, such as palmitic acid.

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Targeted antitumoral dehydrocrotonin nanoparticles with L-ascorbic acid 6-stearate

Cited by 10 publications

References 34 publications

Drug Nanoparticle Formulation Using Ascorbic Acid Derivatives

Drug Nanoparticle Formulation Using Ascorbic Acid Derivatives

Antitumoral activity of L-ascorbic acid-poly-D,L-(lactide-co-glycolide) nanoparticles containing violacein

Environmentally benign downstream process for the enzymatic production of 6‐O‐L‐ascorbyl stearate

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