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Folate receptor-targeted thiol-maleimide clicked chitosan/carboxymethyl cellulose nanoparticles for cisplatin delivery in oral carcinoma

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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES 2025年 290卷 138976页

作者： Patrojanasophon, Prasopchai Singpanna, Kanokwan Rojanarata, Theerasak Opanasopit, Praneet ngawhirunpat, tanasait Pengnam, Supusson Pornpitchanarong, Chaiyakarn Silpakorn Univ Fac Pharm Pharmaceut Dev Green Innovat Grp PDGIG Nakhon Pathom 73000 Thailand Silpakorn Univ Fac Pharm Res & Innovat Ctr Adv Therapy Med Prod Nakhon Pathom 73000 Thailand

This study aimed to develop cisplatin (CDDP)-loaded folic acid (FA)-decorated nanoparticles (NPs) as targeted drug carrier towards overexpressed folate receptors on the oral carcinoma cell line (KB cells). The FA-conjugated thiolated succinyl chitosan (FA-SH-SCS) and maleimide-grafted-carboxymethyl cellulose (CMC-MAL) were synthesized and acquired in the preparation of NPs via thiol-maleimide click reaction. The physicochemical characteristics, drug loading, and drug release of the FA-decorated NPs (FA-NPs) were examined. Also, the in vitro biocompatibility, cellular uptake, and cell death mechanism were investigated. Relatively spherical NPs with negative charge were obtained with a size of approximately 200 nm. The formation of FA-NPs through click reaction was confirmed by the pH change and Ellman's assay. The release of CDDP from the FA-NPs was influenced by the acidic tumor environment. The FA-NPs were non-toxic to the normal cells. Furthermore, FANPs improved the cellular uptake of CDDP in oral carcinoma cells through specific recognition of folate receptors by FA-NPs. The delivery of CDDP by FA-NPs to the KB cell induced the apoptotic cell death pathway. Therefore, FA-NPs presented the potential to be effective nanocarriers for CDDP delivery in the treatment of oral cancer via active targeting approach.

关键词： Cisplatin Folate receptor Polymeric nanoparticle Thiol-maleimide click chemistry Oral carcinoma cell

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Development of a green and rapid ethanol-based HPLC assay for aspirin tablets and feasibility evaluation of domestically produced bioethanol in Thailand as a sustainable mobile phase

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GREEN PROCESSING AND SYNTHESIS 2025年第1期14卷

作者： Thanayutsiri, Thana Mantadilok, Siwa Sapsin, Jiradet Tungwattanaviboon, Thada Wongwatanasin, Jetsada Opanasopit, Praneet ngawhirunpat, tanasait Rojanarata, Theerasak Silpakorn Univ Fac Pharm Sanam Chandra Palace Campus Nakhon Pathom 73000 Thailand Silpakorn Univ Fac Pharm Pharmaceut Dev Green Innovat Grp PDGIG Nakhon Pathom 73000 Thailand Thai Ethanol Mfg Assoc Bangkok 10400 Thailand

Despite the growing trend of using ethanol as a greener alternative to hazardous solvents like methanol and acetonitrile in high-performance liquid chromatography (HPLC) analysis, no ethanol-based assay has been developed for aspirin tablets, nor has the potential of domestically produced bioethanol as a mobile phase been explored - until now. This study introduces a novel ethanol-based HPLC assay for aspirin and assesses the feasibility of using locally produced bioethanol. The optimized method, featuring a 40% (v/v) ethanol-water mobile phase adjusted to pH 3.6 with glacial acetic acid, with a 15-cm C18 column at 40 degrees C and UV detection at 237 nm, successfully separated aspirin and its degradation product, salicylic acid, in 5 min. It demonstrated excellent linearity (0.1-0.6 mgmL(-1), r(2) = 0.9997), sensitivity (LOD = 0.01 mgmL(-1), LOQ = 0.03 mgmL(-1)), accuracy, and precision, with no interference from excipients. The method's performance on commercial aspirin tablets aligned with official pharmacopoeial methods. In a case study using fuel-grade bioethanol (>99.5% purity) derived from sugarcane molasses or cassava from local manufacturers in Thailand, chromatographic and analytical results matched those obtained with imported ethanol, validating its effectiveness. This innovative approach not only reduces costs and dependence on imported solvents but also supports local bio-circular-green economies and promotes greener, more sustainable analytical practices.

关键词： ethanol HPLC aspirin domestic sustainability

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Chitosan-gold nanoparticles: A trend of skin permeation enhancement effect in animal and human skin model

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JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY 2025年 105卷

作者： Singpanna, Kanokwan Suriyaamporn, Phuvamin Pornpitchanarong, Chaiyakarn ngawhirunpat, tanasait Li, S. Kevin Opanasopit, Praneet Silpakorn Univ Fac Pharm Pharmaceut Dev Green Innovat Grp PDGIG Nakhon Pathom 73000 Thailand Silpakorn Univ Fac Pharm Res & Innovat Ctr Adv Therapy Med Prod Nakhon Pathom 73000 Thailand Univ Cincinnati James L Winkle Coll Pharm Div Pharmaceut Sci Cincinnati OH 45267 USA

The skin constitutes a significant challenge to drug absorption. Despite its convenience, the physiological properties of skin create a formidable barrier to drug transport. Therefore, drug formulations designed for skin delivery must overcome these obstacles to achieve therapeutic efficacy. The present study evaluated the effect of gold nanoparticles on animal and human skin models. Chitosan-capped gold nanoparticles (CS-AuNPs) and citrate-stabilized gold nanoparticles (Ci-AuNPs) were synthesized through a chemical transformation approach. CS-AuNPs and Ci-AuNPs exhibit a relatively spherical shape and a nano-sized dimension, with diameters of 62.82 + 4.05 nm and 27.58 + 0.37 nm, respectively. The zeta potential of the CS-AuNPs indicates positivity, measuring +37.50 + 0.10 mV, while the Ci-AuNPs exhibit a negative potential of -17.63 + 0.98 mV. The study on skin permeation in pig skin demonstrated that using CS-AuNPs resulted in a superior enhancement of the permeation of sodium fluorescein (NaFI) compared to Ci-AuNPs. To verify the effectiveness of CS-AuNPs in enhancing skin permeation, excised human skin was employed as the most realistic model available. The findings suggested that CS-AuNPs exhibited a notable enhancement in the permeation of NaFI through excised human skin. Additionally, the confocal laser scanning microscope (CLSM) study revealed that using CS-AuNPs could enhance the accumulation of NaFI in excised human skin. The finding suggests that CS-AuNPs have demonstrated significant potential as a skin permeation enhancer for small polar compounds. Therefore, their efficacy in this regard makes them a promising candidate for further exploration in skin permeation enhancement.

关键词： Chitosan Gold nanoparticles Transdermal delivery Sodium fluorescein Skin enhancer

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Artificial intelligence-driven hydrogel microneedle patches integrating 5-fluorouracil inclusion complex-loaded flexible pegylated liposomes for enhanced non-melanoma skin cancer treatment

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INTERNATIONAL JOURNAL OF PHARMACEUTICS 2025年 669卷 125072页

作者： Suriyaamporn, Phuvamin Pornpitchanarong, Chaiyakarn Charoenying, Thapakorn Dechsri, Koranat ngawhirunpat, tanasait Opanasopit, Praneet Pamornpathomkul, Boonnada Silpakorn Univ Fac Pharm Dept Ind Pharm Pharmaceut Dev Green Innovat Grp PDGIG Nakhon Pathom Thailand Silpakorn Univ Fac Pharm Res & Innovat Ctr Adv Therapy Med Prod Nakhon Pathom 73000 Thailand

The current study focused on the development of crosslinked hydrogel microneedle patches (cHMNs) incorporating 5-FU-hydroxypropyl beta-cyclodextrin inclusion complex-loaded flexible PEGylated liposomes (5-FUHP(3CD-loaded FP-LPs) to enhance treatment efficacy and reduce drug toxicity. The research utilized artificial intelligence (AI) algorithms to design, optimize, and evaluate the cHMNs. Various AI models were assessed for accuracy, with metrics such as root mean square error and coefficient of determination guiding the selection of the most effective formulation. The physicochemical and mechanical properties, swelling behavior, in vitro skin permeation, and safety of the chosen cHMNs were tested. The results demonstrated that the 5-FU-HP(3CD-loaded FP-LPs, stabilized with limonene, had an optimal particle size of 36.23 f 2.42 nm, narrow size distribution, and zeta potential of -10.24 f 0.37 mV, with high encapsulation efficiency. The cHMNs exhibited a conical needle shape with sufficient mechanical strength to penetrate the stratum corneum up to approximately 467.87 f 65.12 mu m. The system provided a high skin permeation rate of 41.78 f 4.26% and significant drug accumulation in the skin. Additionally, the formulation was proven safe in cell culture while effectively inhibiting cancer growth and promoting apoptosis. This study highlights the potential of AI-enhanced cHMNs for delivering 5-FUHP(3CD-loaded FP-LPs transdermally, offering a promising new treatment avenue for non-melanoma skin cancers.

关键词： 5-Fluorouracil PEGylated liposomes Hydrogel microneedle Artificial intelligence Non-melanoma skin cancers

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Effect of liposomal fluidity on skin permeation of sodium fluorescein entrapped in liposomes

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INTERNATIONAL JOURNAL OF NANOMEDICINE 2015年 10卷 4581-4592页

作者： Subongkot, Thirapit ngawhirunpat, tanasait Burapha Univ Fac Pharmaceut Sci Dept Pharmaceut Technol Chon Buri Thailand Silpakorn Univ Fac Pharm Dept Pharmaceut Technol Muang 73000 Nakhon Pathom Thailand

The purpose of this study was to investigate the effect of ultradeformable liposome components, Tween 20 and terpenes, on vesicle fluidity. The fluidity was evaluated by electron spin resonance spectroscopy using 5-doxyl stearic acid and 16-doxyl stearic acid as spin labels for phospholipid bilayer fluidity at the C5 atom of the acyl chain near the polar head group (hydrophilic region) and the C16 atom of the acyl chain (lipophilic region), respectively. The electron spin resonance study revealed that Tween 20 increased the fluidity at the C5 atom of the acyl chain, whereas terpenes increased the fluidity at the C16 atom of the acyl chain of the phospholipid bilayer. The increase in liposomal fluidity resulted in the increased skin penetration of sodium fluorescein. Confocal laser scanning microscopy showed that ultradeformable liposomes with terpenes increase the skin penetration of sodium fluorescein by enhancing hair follicle penetration.

关键词： ultradeformable liposomes terpenes fluidity electron spin resonance spectroscopy confocal laser scanning microscopy

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Development of a novel microemulsion for oral absorption enhancement of all-trans retinoic acid

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INTERNATIONAL JOURNAL OF NANOMEDICINE 2017年 12卷 5585-5599页

作者： Subongkot, Thirapit ngawhirunpat, tanasait Burapha Univ Fac Pharmaceut Sci Dept Pharmaceut Technol Chon Buri 20131 Thailand Silpakorn Univ Fac Pharm Dept Pharmaceut Technol Amphoe Muang Nakhon Pathom Thailand

This study was aimed to develop a novel microemulsion that contained oleth-5 as a surfactant to enhance the oral absorption of all-trans retinoic acid (ATRA). The prepared microemulsion was evaluated for its particle size, shape, zeta potential, in vitro release, in vitro intestinal absorption, intestinal membrane cytotoxicity and stability. The obtained microemulsion was spherical in shape with a particle size of < 200 nm and a negative surface charge. The in vitro release of the ATRA-loaded microemulsion was best fit with the zero-order model. This microemulsion significantly improved the intestinal absorption of ATRA. Confocal laser scanning microscopy analysis using a fluorescent dye-loaded microemulsion also confirmed the intestinal absorption result. The intestinal membrane cytotoxicity of the ATRA-loaded microemulsion did not differ from an edible oil (fish oil). Stability testing showed that the ATRA-loaded microemulsion was more stable at 25 degrees C than 40 degrees C

关键词： microemulsion all-trans retinoic acid oral absorption enhancement oleth-5 fish oil

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Preparation and Evaluation of Differently Sulfonated Styrene-Divinylbenzene Cross-linked Copolymer Cationic Exchange Resins as Novel Carriers for Drug Delivery

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AAPS PHARMSCITECH 2009年第2期10卷 641-648页

作者： Akkaramongkolporn, Prasert ngawhirunpat, tanasait Opanasopit, Praneet Silpakorn Univ Dept Pharmaceut Technol Fac Pharm Nakhon Pathom 73000 Thailand

The differently sulfonated styrene-divinylbenzene cross-linked copolymer cationic exchange resins were prepared by oil-in-water polymerization and varied degrees of sulfonation. Several characteristics of the obtained resins were evaluated, i.e., Fourier transform infrared spectra, the ion-exchange capacity, microscopic morphology, size, and swelling. The resin characteristics were altered in relation to the degree of sulfonation, proving that differently sulfonated resins could be prepared. The behavior of chlorpheniramine (CPM) loading and in vitro release in the USP simulated gastric (SGF) and intestinal fluids (SIF) of the obtained resins were also evaluated. The CPM loaded in the resinates (drug-loaded resins) increased with the increasing degree of sulfonic group and hence the drug binding site in the employed resins. The CPM release was lower from the resins with the higher degree of sulfonic group due to the increase in the diffusive path depth. The CPM release was obviously lower in SGF than SIF because CPM, a weak base drug, ionized to a greater extent in SGF and then preferred binding with rather than releasing from the resins. In conclusion, the differently sulfonated resins could be utilized as novel carriers for drug delivery.

关键词： cationic exchange resin chlorpheniramine maleate different sulfonation drug loading drug release oil-in-water polymerization

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Fast, facile and ethidium bromide-free assay based on the use of adsorption indicator for the estimation of polyethylenimine to nucleic acid ratio of complete polyplex assembly for gene delivery

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TALANTA 2013年 115卷 241-245页

作者： Plianwong, Samarwadee Opanasopit, Praneet ngawhirunpat, tanasait Rojanarata, Theerasak Silpakorn Univ Pharmaceut Dev Green Innovat Grp PDGIG Fac Pharm Nakhon Pathom 73000 Thailand

A new method was developed for the estimation of polyethylenimine (PEI) to nucleic acid ratio at which the polyplex was completely formed. The assay relied on the attraction of dichlorofluoresceinate dye to adsorb on self-assembling particles as counterions, as induced by the surface charge of the polyplex which became positive once PEI associated equivalently with nucleic acid. This phenomenon resulted in the appearance of pink colored pellets of the polyplex after centrifugation. By the other means, sodium hydroxide solution might be added to free the adsorbed dye into the solution, producing conspicuous green fluorescence under UV light (366 nm). The assay was well applied to the polyplex formulations of PEI and plasmid DNA or siRNA with satisfactory detectability and gave the results in agreement with those from gel retardation method and zeta potential analysis. Importantly, the proposed method required no sophisticated instruments, time-consuming gel electrophoresis, carcinogenic ethidium bromide as well as costly dyes and the analysis could be accomplished within less than 10 min. Hence, it was a fast, facile, cost-effective and safe-for-operator alternative method, suited for the investigation of the optimal PEI to nucleic acid ratio for gene delivery. (C) 2013 Elsevier B.V. All rights reserved.

关键词： Polyethylenimine Nucleic acid Ratio Polyplex Dichlorofluorescein Surface charge

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Ninhydrin reaction on thiol-reactive solid and its potential for the quantitation of D-penicillamine

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TALANTA 2010年第2期82卷 444-449页

作者： Rojanarata, Theerasak Opanasopit, Praneet ngawhirunpat, tanasait Saehuan, Choedchai Silpakorn Univ Fac Pharm Dept Pharmaceut Chem Nakhon Pathom 73000 Thailand Naresuan Univ Fac Allied Hlth Sci Dept Med Technol Phitsanulok 65000 Thailand

While aminothiols produce weak purple-colored reactions with ninhydrin, we demonstrate for the first time that this color could be intensely developed. Using a D-penicillamine paradigm, adsorption of this compound via a disulfide bond onto thiol-reactive solid prior to ninhydrin reaction allowed spectrophotometrical monitoring of the supernatant at 570 nm. Compared with off-solid method, this approach expanded the linear concentration range to 50-600 mu g mL(-1) and enhanced the sensitivity so that D-penicillamine with the concentrations of less than 100 mu g mL(-1) could be accurately quantitated by using a second-order polynomial calibration curve. Additionally, this assay was unaffected by disulfide adduct interference, highlighting its potential for the analysis of D-penicillamine as well as other aminothiols. (C) 2010 Elsevier B.V. All rights reserved.

关键词： Ninhydrin Thiol-reactive solid Penicillamine Aminothiol

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Lysozyme-immobilized electrospun PAMA/PVA and PSSA-MA/PVA ion-exchange nanofiber for wound healing

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PHARMACEUTICAL DEVELOPMENT AND TECHNOLOGY 2015年第8期20卷 976-983页

作者： Tonglairoum, Prasopchai ngawhirunpat, tanasait Rojanarata, Theerasak Opanasopit, Praneet Silpakorn Univ Pharmaceut Dev Green Innovat Grp Fac Pharm Nakhon Pathom 73000 Thailand

This research was aimed to develop the lysozyme immobilized ion-exchange nanofiber mats for wound healing. To promote the healing process, the PSSA-MA/PVA and PAMA ion-exchange nanofiber mats were fabricated to mimic the extracellular matrix structure using electrospinning process followed by thermally crosslinked. Lysozyme was immobilized on the ion-exchane nanofibers by an adsorption method. The ion-exchange nanofibers were investigated using SEM, FTIR and XRPD. Moreover, the lysozyme-immobilized ion-exchange nanofibers were further investigated for lysozyme content and activity, lysozyme release and wound healing activity. The fiber diameters of the mats were in the nanometer range. Lysozyme was gradually absorbed into the PSSA-MA/PVA nanofiber with higher extend than that is absorbed on the PAMA/PVA nanofiber and exhibited higher activity than lysozyme-immobilized PAMA/PVA nanofiber. The total contents of lysozyme on the PSSA-MA/PVA and PAMA/PVA nanofiber were 648 and 166 mg/g, respectively. FTIR and lysozyme activity results confirmed the presence of lysozyme on the nanofiber mats. The lysozyme was released from the PSSA-MA/PVA and PAMA/PVA nanofiber in the same manner. The lysozyme-immobilized PSSA-MA/PVA nanofiber mats and lysozyme-immobilized PAMA/PVA nanofiber mats exhibited significantly faster healing rate than gauze and similar to the commercial antibacterial gauze dressing. These results suggest that these nanofiber mats could provide the promising candidate for wound healing application.

关键词： Immobilize ion-exchange lysozyme nanofiber mats wound healing

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