Faculty of Pharmacy

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Understanding the Infrared Multiple Photon Dissociation Spectra of Hydrogen‐Tagged Protonated Betaine: Vibrational Confinement Counteracts the Hydrogen Bonding Induced OH Stretching Frequency Downshift
(Wiley, 2025-06-11)
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Pejov, Ljupcho
<jats:p>Finite‐temperature vibrational spectra of protonated betaine and its noncovalently bonded clusters with molecular hydrogen are modeled using Lagrangian dynamics with the atom‐centered density matrix propagation (ADMP) scheme. The focus is put on the O-H stretching mode, which serves as a primary indicator of the type and strength of the noncovalent intermolecular interactions. The computed anharmonic OH stretching vibrational frequency shifts in the case of protonated betaine upon tagging with H<jats:sub>2</jats:sub> at the OH group site at 40 K are in quantitative agreement with the experimental infrared multiple photon dissociation data. The shifts computed from simulations at 4 K contain only the harmonic contributions. It is found that this is a consequence of vibrational confinement of the O-H oscillator caused by the H<jats:sub>2</jats:sub> tagger, which remains close to the vibrating atoms throughout the simulation and counteracts the frequency redshift induced by the weak hydrogen bonding interaction. Changes in the O-H stretching potential, along with a small but observable confinement relaxation at 40 K leads to O-H stretching frequency downshift as compared to 4 K. Application of the two‐trace 2D correlation analysis of the computed vibrational density of states spectra enables a clear distinction between bands of different origin to be made.</jats:p>
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Molecular Hydrogen Acts as a Hydrogen Bond Proton Acceptor: From Protonated Betaine Tagging to the Weakest Hydrogen Bond
(American Chemical Society (ACS), 2024-05-09)
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Pejov, Ljupcho
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Phytoremediation potential of Milk thistle (Silybum marianum) - A sustainable approach to mitigate soil contamination while supporting pharmaceutical applications
(2025-05-27)
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Gjorgjievska, Jovana
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Todorov, Filip
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Stoilkovska Gjorgievska, Veronika
Milk thistle (Silybum marianum) is recognized for its medicinal properties and potential as a phytoremediation agent. [1,2] This study assesses its ability to absorb heavy metals and decontaminate soils while preserving pharmacological efficacy. Soil and plant samples were collected from eight locations in North Macedonia during different vegetative phases. Mechanical and pedological soil analyses were conducted to characterize soil composition, while heavy metal concentrations in soil and plant material were evaluated using ICP-AES. Silymarin content in the plant and seeds was determined via high-performance liquid chromatography (HPLC). The soils exhibited significant variability in heavy metal content. Lead (Pb) levels ranged from 25 to 107 mg/kg, cadmium (Cd) from 0.1 to 1.3 mg/kg, and zinc (Zn) from 14 to 203 mg/kg. Notably, lead and cadmium levels in plant material were below detection limits, confirming minimal accumulation, whereas zinc levels varied significantly, peaking in urban areas. Silymarin content ranged from 0.02% to 0.16% in plant material, with seeds exhibiting higher concentrations (1.14%), demonstrating the plant's resilience and pharmacological viability in contaminated environments. These results highlight the adaptability of milk thistle to diverse soil conditions and its capacity to accumulate metals without compromising silymarin production. By combining phytoremediation with medicinal plant cultivation, milk thistle offers a sustainable approach to mitigating soil contamination while supporting pharmaceutical applications. This study provides critical insights for integrating environmental restoration with the production of high-value medicinal plants.
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Cannabinoid production in various Cannabis sativa L. in vitro cultures
(Springer Nature, 2025-01-02)
Ana Trajkovska;
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Oliver Tusevski;
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Iskra Davkova;
The main goal of this study was to develop an efficient micropropagation protocol for cannabis (Cannabis sativa L.) and to summarize the influence of plant growth regulators on cannabinoid production in various in vitro cultures. Three in vitro culture lines were obtained during cannabis micropropagation and referred to calli, shoots, and plantlets. Shoot multiplication was examined on apical segments isolated from in vitro seedlings and cultivated on solid MS/B5 medium supplemented with various concentrations (0.05-1.0 mg·L− 1) of thidiazuron (TDZ). Callogenesis was induced from leaf explants of seedlings in the presence of 1.0 mg·L− 1 TDZ and 0.5 mg·L− 1 1-naphthaleneacetic acid (NAA), while further biomass production was evaluated upon TDZ (0.5-2.0 mg·L− 1). The shoot regenerative potential was assessed on various concentrations (0.1-1.0 mg·L− 1) of indole-3-butyric acid (IBA). The HPLC-DAD analysis of cannabinoids revealed that cannabidiolic acid (CBDA), cannabidiol (CBD), cannabinol (CBN), ∆9-tetrahydrocannabinol (∆9-THC), and ∆9-tetrahydrocannabinolic acid (∆9-THCA) were the main identified cannabinoids in calli, shoots and regenerated plantlets. The superior production of Δ9-THC was observed in multiple shoots cultured on 0.05 mg·L− 1 TDZ (49.23 mg·g− 1), callus cultures treated with 1.0 mg·L− 1 TDZ (3.92 µg·g− 1), as well in plantlets regenerated on hormone-free medium (80.1 mg·g− 1). The Δ9-THC content in the leaves of 6-month-old regenerated plantlets was significantly higher (1.6-fold) than that of the mother plant. Cannabinoid contents in the inflorescences of the mother plant were higher or even comparable to those observed for acclimatized plantlets. In conclusion, cannabis in vitro cultures could be proposed as promising systems for cannabinoid production.
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Assessment of cytotoxic impact of wild grown Lavandula angustifolia essential oil encapsulated in liposomes and nanoemulsions on DU145 cancer cell line
(Marmara University Press, 2024-12)
Mimoza BASHOLLI-SALIHU
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Aida LOSHAJ-SHALA
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Art ÇUNAKU
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Venesa LUPÇI
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Ufuk BAǦCI
The cytotoxic activity of free and nanoencapsulated essential oil of Lavandula angustifolia (LEO) was evaluated in this study. The aim was to produce different nanoformulations (NF) of LEO to improve the physicochemical properties of NF and the cytotoxic activity of LEO in the DU145 cancer cell line. Essential oil-based liposomes (LEO-Lipoid S100, -Ph 85G, and -Ph 90H) and nanoemulsions (LEO-NE) were prepared by ethanol injection method and high-pressure homogenization, respectively. LEO demonstrates measurable in vitro cytotoxic activity against the DU145 cell line (IC50 75 μg/mL). NE and Ph90H LS significantly enhanced its cytotoxic activity, while LEOLipoid S100 LS and LEO-Ph 85G LS showed no significant difference. LEO-Ph 90H LS and LEO-NE demonstrate stable nanosystems and enhanced cytotoxic potential against the DU-145 cancer cell line, suggesting promising therapeutic benefits for future application. Further studies involving in vivo experiments are necessary to validate and extend these findings.
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ORMOSIL nanoparticles as drug delivery carriers for oxaliplatin: formulation development and characterization
(Springer Science and Business Media LLC, 2024-06-17)
Djurdjic, Beti
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Boev, Ivan
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Geškovski, Nikola
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Development of novel portable NIR spectroscopy process analytical technology (PAT) tool for monitoring the transition of ibuprofen to ibuprofen sodium during wet granulation process
(Elsevier BV, 2024-09-05)
Atanaskova, Elizabeta
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Angelovska, Veronika
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Chachorovska, Marina
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Anevska Stojanovska, Natasha
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Petrushevski, Gjorgji
The aim of this research was to develop a process analytical technology (PAT) tool for monitoring the transformation of the active ingredient ibuprofen into the fast-dissolving salt ibuprofen sodium during the wet granulation process. Two near-infrared (NIR) spectrophotometers, portable and benchtop spectrophotometer, were compared. During the analysis with the built models, both demonstrated comparable accuracy and precision (R2X = 0.995, R2Y = 0.927, Q2 = 0.995, and R2X = 0.990, R2Y = 0.948, Q2 = 0.992, respectively). Considering the applicability, a model based on the portable NIR spectroscopic data was chosen for further development and application as a PAT tool for monitoring different steps during the wet granulation process. The evaluation of the model's predictive capability involved analyzing laboratory trial batches with varying amounts of sodium carbonate, resulting in different concentrations of ibuprofen sodium at the end of the wet granulation process. Subsequently, tablets were manufactured from each trial batch, followed by dissolution analysis. The dissolution rate assays were in good agreement with the NIR-predicted concentrations of ibuprofen sodium at the end of the wet granulation process. Based on the results, the proposed model provides an excellent tool to monitor the ibuprofen acid-salt transformation, to determine the end-point of the reaction, and to efficiently control the wet granulation process.
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FT-NIR models for predicting film quality parameters in titanium dioxide-free tablet coatings
(Elsevier BV, 2025-02-01)
Gorachinov, Filip
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Koviloska, Monika
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Tnokovska, Katerina
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Atanasova, Ana
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Antovska, Packa
This study leverages Fourier Transform Near-Infrared (FT-NIR) spectroscopy to monitor the coating process of pharmaceutical tablets using PVA-based TiO2-free films, with talc and iron oxides as opacifiers. By employing a combination of multivariate analytical techniques, the correlation between film coating progression and film thickness was evaluated. Assessment of coating thickness for different coating levels was performed by optical microscopy. Additionally, using colorimetric analysis by scanner method, the color progression for different coating levels was evaluated and expressed as the a* value from CIELAB color space. The coordinate value a* showed predictable changes with the progression of the coating process and film thickness values, indicating its utility as a robust reference method for quality control and process optimization. The predictive capability of the OPLS models, validated against measured film thickness and the a* value, demonstrated low prediction errors and confirmed the models' effectiveness in distinguishing coating levels and accurately predicting film coating progression. The OPLS model used knowledge-based peaks of interest, which were further confirmed by loading and coefficient plots. The study demonstrated that film thickness, as a destructive, and a* value from CIELAB color space, as a non-destructive reference method for coating progression could be used during a controlled pharmaceutical coating process for product quality assessment and pharmaceutical process endpoint determination.
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3D printed extended-release hydrochlorothiazide tablets
(Elsevier BV, 2025-03-01)
Tasevska, Teodora
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Adamov, Ivana
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Geškovski, Nikola
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Ibrić, Svetlana
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In this study 3D printed tablets (printlets) with extended release of hydrochlorothiazide (HHT) as model active ingredient were designed and developed. Four formulations, F0.1SSE, F1SSE, F0.1DLP and F1DLP, have been manufactured and characterized, using non-typical semi-solid extrusion (SSE) with UV light solidification and digital light processing (DLP) techniques. Obtained rheological studies pointed out to F1SSE and F1DLP as more suitable for SSE and DLP printing, respectively. Photopolymerization process between photopolymer (PEGDA) and photoinitiator (DPPO; 0.1% and 1%) was investigated using FTIR, with PCA modeling utilized to analyze spectral variations over time and estimate crosslinking kinetics. SSE printlets averaged ∼6.5 mm in diameter, ∼3 mm in height and ∼110 mg in mass, while DLP printlets averaged ∼8.5 mm in diameter, ∼2.5 mm in height, with masses of ∼170 mg (F0.1DLP) and ∼220 mg (F1DLP). All four formulations complied to the requirements of European pharmacopeia for uniformity of dosage units of single dose preparations. In vitro release studies indicated extended-release profiles in both 0.1M Hydrochloric acid (HCl) and phosphate buffer pH 6.8 for SSE and DLP printlets. The release kinetics of HHT from the printlets were modeled to fit First order, Higuchi, Korsmeyer-Peppas and Hixson-Crowell equations and the most probable ones were determined based on the R2 values and Akaike information criterion. FTIR and Raman spectroscopic analyses of printlets confirmed the presence of characteristic peaks from both, HHT and excipients, as well as modifications in bonds due to the photopolymeric reaction.
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Differentiation of Cannabis seeds employing digital morphological screening and infrared spectroscopy coupled with multivariate modeling
(Elsevier, 2024-05-01)
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Geškovski, Nikola
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Trajkovska, Ana
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Cultivation of Cannabis for medicinal purposes primarily relies on seed propagation with expected variations in yield, cannabinoid content, growth rate and seed material non-uniformity. This study aims to employ digital methods for morphological analysis and infrared spectroscopy, combining them with multivariate analysis to characterize and differentiate Cannabis seeds. Morphological traits of 100 seeds from both commercial Cannabis specimens and wild-growing local varieties were analyzed using the high-throughput phenotyping software in addition to their collected infrared spectra in the mid-IR region. Subsequently, a chemometrics approach by means of Principal Component Analysis (PCA), Hierarchical Cluster Analysis (HCA), and Partial Least Square-Discriminatory Analysis (PLS-DA) was applied. The statistical indicators of the PLS-DA model (R2X=0.99, R2Y=0.63, Q2=0.64) demonstrate strong predictive capabilities for the differentiation of Cannabis seed specimens based on morphological attributes. The score scatter plot clearly shows a distinct grouping pattern, primarily driven by seed size. Wild-type seeds predominantly cluster into group 1, characterized by smaller diameters, while commercial seeds cluster into group 2. By analysing spectral data, in contrast to the expected differentiation based on secondary metabolites (cannabinoids) in the seeds, differentiation was based on the macronutrient profile with characteristic bands at 3275 cm−1, 2921 cm−1, 2852 cm−1, 1743 cm−1, 1630 cm−1, 1532 cm−1, 1459 cm−1, 1239 cm−1, 1157 cm−1, 1094 cm−1, 1018 cm−1, identified as the most distinctive spectral features. The PCA model (R2X=0.88 and Q2=0.85) was composed of 5 principal components explaining 88% of the spectral variations. The loading plot of the PLS-DA model reveals the distinctive spectral features for both groups (lipid and carbohydrate bands - group 2 samples, protein and water content - group 1 samples). The developed models have the potential for application for rapid screening of quality parameters of Cannabis seeds and their differentiation.

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