N-Phthaloylchitosan-g-mPEG design for all-trans retinoic acid-loaded polymeric micelles

Opanasopit, Praneet; Ngawhirunpat, Tanasait; Rojanarata, Theerasak; Choochottiros, Chantiga; Chirachanchai, Suwabun

doi:10.1016/j.ejps.2007.01.002

Cited by 43 publications

(23 citation statements)

References 25 publications

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“…2) Synthesis of polyamide amine containing disulfide linkage (PAA): cystamine bisacrylamide (1.044 g, 4 mmol) and a mixture of phenethylamine and ethanolamine (total 4 mmol, mol ratio: phenethylamine/ethanolamine ¼ 9/1 and 8/ 2) were reacted at 125 C under Ar atmosphere to acquire PAA, which was purified by dissolving in methanol and precipitated in ethyl ether. 3) Synthesis of amphiphilic graft copolymer: typically, a-carboxy-u-methoxy polyethylene glycol (MPEG-COOH, 1.05 g, Mn ¼ 2100, 0.5 mmol of carboxyl, prepared by reacting MPEG with succinic anhydride as described in previous literature [35,36]), DCC (0.124 g, 0.7 mmol), and DMAP (0.061 g, 0.05 mmol) were dissolved in dry DMSO in a 50 mL flame dried flask. Freshly prepared PAA (0.74 g, phenethylamine/ethanolamine ¼ 8/ 2, 0.4 mmol of hydroxyl group) in 10 mL of dry DMSO was added slowly.…”

Section: Synthesis Of Reduction-degradable Amphiphilic Polyamide Aminmentioning

confidence: 99%

Disassemblable micelles based on reduction-degradable amphiphilic graft copolymers for intracellular delivery of doxorubicin

et al. 2010

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Section: Synthesis Of Reduction-degradable Amphiphilic Polyamide Aminmentioning

confidence: 99%

Disassemblable micelles based on reduction-degradable amphiphilic graft copolymers for intracellular delivery of doxorubicin

et al. 2010

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“…PEGylated chitosan nanoparticles have been investigated as carriers for diverse small molecular drugs such as paclitaxel, camptothecin, methotrexate, and all-trans retinoic acid (ATRA) [116][117][118][119][120]. Recently, the effect of PEG conjugation on PTX-loaded N-octyl-sulfate chitosan nanoparticles was investigated by Qu et al [116].…”

Section: Pegylated Chitosan Nanoparticlesmentioning

confidence: 99%

“…All-trans retinoic acid (ATRA), a compound from retinoid class, is an effective drug for the treatment of epithelial and hematological malignancies but it can readily undergo degradation when exposed to light. This could be surmounted by incorporation of ATRA into N-phthalolylchitosan-g-mPEG (PLC-g-mPEG) nanoparticles [117]. The photostability of ATRA in the nanoparticle was signi.cantly improved, when compared to ATRA in ethanol solution.…”

Section: Pegylated Chitosan Nanoparticlesmentioning

confidence: 99%

Chitosan Mediated Targeted Drug Delivery System: A Review

Patel¹,

Patel²,

Patel³

2010

J Pharm Pharm Sci

235

166

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-Chitosan has prompted the continuous movement for the development of safe and effective drug delivery systems because of its unique physicochemical and biological characteristics. The primary hydroxyl and amine groups located on the backbone of chitosan allow for chemical modification to control its physical properties. When the hydrophobic moiety is conjugated to a chitosan molecule, the resulting amphiphile may form self-assembled nanoparticles that can encapsulate a quantity of drugs and deliver them to a specific site of action. Chemical attachment of the drug to the chitosan throughout the functional linker may produce useful prodrugs, exhibiting the appropriate biological activity at the target site. Mucoadhesive and absorption enhancement properties of chitosan increase the in vivo residence time of the dosage form in the gastrointestinal tract and improve the bioavailability of various drugs. The main objective of this review is to provide an insight into various target-specific carriers, based on chitosan and its derivatives. The first part of the review is concerned with the organ-specific delivery system using chitosan and its derivatives. The subsequent section considers the recent developments of drug delivery carriers for cancer therapy with special focus on various targeting strategies. __________________________________________________________________________________________

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“…However, ATRA's hydrophobicity is a limitation. To improve its aqueous solubility, attempts have been made to develop intravenous injectable formulations of ATRA using drug delivery systems such as cyclodextrin complexes (5), liposomes (6), niosomes (7), polymeric micelles (1,8), lipid emulsion (LE; 2,9), microemulsion (10), solid lipid nanoparticles (SLNs; 11), and nanostructured lipid carriers (NLC; 12). Currently, a parenteral liposomal encapsulated-ATRA formulation is being tested in a phase II clinical trial: ATRA-IV® (formerly known as ATRAGEN®, Antigenics Inc.; 6).…”

Section: Introductionmentioning

confidence: 99%

“…The incorporation of ATRA into liposomes has significantly improved the potency and duration of ATRA's activity while reducing the side effects associated with this drug. Most importantly, intravenously administered liposomal encapsulated ATRA could maintain stable plasma concentrations over a prolonged period after multiple dosing in preclinical and clinical models (6). Although liposomal encapsulated ATRA has advantages over the oral formulation, its capacity for drug loading and stability during storage are limited.…”

Section: Introductionmentioning

confidence: 99%

Nanostructured Lipid Carriers (NLC) for Parenteral Delivery of an Anticancer Drug

et al. 2011

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Abstract. The purpose of this research was to formulate nanostructured lipid carriers (NLC) for the parenteral delivery of an anticancer drug, all-trans retinoic acid (ATRA). The ATRA was incorporated into NLC by the de novo emulsification method. The effect of the formulation factor, i.e., type and oil ratio, initial ATRA concentration on physicochemical properties was determined. The anticancer efficacy of ATRA-loaded NLC on HL-60 and HepG2 cells was also studied. NLC was formulated using a blend of solid lipids (cetyl palmitate) and liquid lipids (soybean oil (S), medium-chain triglyceride (M), S/oleic acid (O; 3:1) and M/O (3:1)) at a weight ratio of 1:1. ATRA-loaded NLC had an average size of less than 200 nm (141.80 to 172.95 nm) with a narrow PDI and negative zeta potential that was within an acceptable range for intravenous injection. The results indicated that oleic acid enhanced the ATRAloading capacity of NLC. In vitro ATRA release was only approximately 4.06% to 4.34% for 48 h, and no significant difference in ATRA release rate from all NLC formulations in accordance with the composition of the oil phase. Moreover, no burst release of the drug was observed, indicating that NLC could prolong the release of ATRA. The initial drug concentration affected the photodegradation rate but did not affect the release rate. All ATRA-loaded NLC formulations exhibited the photoprotective property. The cytotoxicity results showed that all ATRA-loaded NLC had higher cytotoxicity than the free drug and HL-60 cells were more sensitive to ATRA than HepG2 cells.

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N-Phthaloylchitosan-g-mPEG design for all-trans retinoic acid-loaded polymeric micelles

Cited by 43 publications

References 25 publications

Disassemblable micelles based on reduction-degradable amphiphilic graft copolymers for intracellular delivery of doxorubicin

Disassemblable micelles based on reduction-degradable amphiphilic graft copolymers for intracellular delivery of doxorubicin

Chitosan Mediated Targeted Drug Delivery System: A Review

Nanostructured Lipid Carriers (NLC) for Parenteral Delivery of an Anticancer Drug

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