Faculty of Pharmacy

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Mid-infrared spectroscopy as process analytical technology tool for estimation of THC and CBD content in Cannabis flowers and extracts
(Elsevier BV, 2021-04-15)
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Stefov, Stefan
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Huck, Christian W
Tetrahydrocannabinol (THC) and cannabidiol (CBD) are the most notable Cannabis components with pharmacological activity and their content in the plant flowers and extracts are considered as critical quality parameters. The new Medical Cannabis industry needs to adopt the quality standards of the pharmaceutical industry, however, the variability of phytocannabinoids content in the plant material often exerts an issue in the inconsistency of the finished product quality parameters. Sampling problems and sample representativeness is a major limitation in the end-point testing, particularly when the expected variation of the product quality parameters is high. Therefore, there is an obvious need for the introduction of Process Analytical Technology (PAT) for continuous monitoring of the critical quality parameters throughout the production processes. Infrared spectroscopy is a promising analytical technique that is consistent with the PAT requirements and its implementation depends on the advances in instrumentation and chemometrics that will facilitate the qualitative and quantitative aspects of the technique. Our present work aims in highlighting the potential of mid-infrared (MIR) spectroscopy as PAT in the quantification of the main phytocannabinoids (THC and CBD), considered as critical quality/material parameters in the production of Cannabis plant and extract. A detailed assignment of the bands related to the molecules of interest (THC, CBD) was performed, the spectral features of the decarboxylation of native flowers were identified, and the specified bands for the acid forms (THCA, CBDA) were assigned and thoroughly explained. Further, multivariate models were constructed for the prediction of both THC and CBD content in extract and flower samples from various origins, and their prediction ability was tested on a separate sample set. Savitskzy-Golay smoothing and the second derivative of the native MIR spectra (1800-400 cm-1 region) resulted in best-fit parameters. The PLS models presented satisfactory R2Y and RMSEP of 0.95 and 3.79% for THC, 0.99 and 1.44% for CBD in the Cannabis extract samples, respectively. Similar statistical indicators were noted for the Partial least-squares (PLS) models for THC and CBD prediction of decarboxylated Cannabis flowers (R2Y and RMSEP were 0.99 and 2.32% for THC, 0.99 and 1.33% for CBD respectively). The VIP plots of all models demonstrated that the THC and CBD distinctive band regions bared the highest importance for predicting the content of the molecules of interest in the respected PLS models. The complexity of the sample (plant tissue or plant extract), the variability of the samples regarding their origin and horticultural maturity, as well as the non-uniformity of the plant material and the flower-ATR crystal contact (in the case of Cannabis flowers) were governing the accuracy descriptors. Taking into account the presented results, ATR-MIR should be considered as a promising PAT tool for THC and CBD content estimation, in terms of critical material and quality parameters for Cannabis flowers and extracts.
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Novel development of lipid-based formulations: Improved wettability and homogeneous API solid dispersion visualised via near-infrared hyperspectral imaging
(Elsevier BV, 2025-11)
Atanaskova, Elizabeta
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Poms, Johannes
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Wolfgang, Matthias
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Alva, Carolina
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Mussner, Nadia
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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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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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