Molecules

12 pages, 2444 KB

Open AccessArticle

Discovery of Primaquine–Indole Carboxamides with Cancer-Cell-Selective Antiproliferative Activity

by Benjamin H. Peer, Jeremiah O. Olugbami, Dipak T. Walunj and Adegboyega K. Oyelere

Molecules 2025, 30(19), 3988; https://doi.org/10.3390/molecules30193988 (registering DOI) - 4 Oct 2025

Indole carboxylic acids are endogenous tryptophan metabolites that have demonstrated a variety of bioactivities, including anticancer effects. Specifically, indole acetic acid (IAA) elicits anticancer activity when combined with ultraviolet B or reactive oxygen species (ROS) generators. Primaquine (PQ) is an approved drug which [...] Read more.

Indole carboxylic acids are endogenous tryptophan metabolites that have demonstrated a variety of bioactivities, including anticancer effects. Specifically, indole acetic acid (IAA) elicits anticancer activity when combined with ultraviolet B or reactive oxygen species (ROS) generators. Primaquine (PQ) is an approved drug which elicits antimalarial activity through ROS generation. We investigated the effects of ICA, IAA, PQ, their combination and PQ–indole carboxamide conjugates on the viability of selected cancer cell lines. We identified PQ–indole carboxamide 2 which elicited more potent antiproliferative effects than PQ and ICA/PQ combination. Our data revealed that compound 2 derived a significant part of its antiproliferative effect from ROS generation. Full article

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18 pages, 564 KB

Open AccessReview

Dictyopterenes A, B, C, and D from Marine Algae

by Igor Jerković, Anja Golemac Lipovac, Dina Balaić and Stela Jokić

Molecules 2025, 30(19), 3987; https://doi.org/10.3390/molecules30193987 (registering DOI) - 4 Oct 2025

Abstract

The review is focused on dictyopterenes A, B, C, and D found in marine algae, covering their (a) distribution; (b) methods of isolation and identification; (c) absolute configuration; and (d) biosynthesis considerations. Dictyopterenes A and B are usually present in high amounts in [...] Read more.

The review is focused on dictyopterenes A, B, C, and D found in marine algae, covering their (a) distribution; (b) methods of isolation and identification; (c) absolute configuration; and (d) biosynthesis considerations. Dictyopterenes A and B are usually present in high amounts in Dictyopteris spp. Dictyopterene A was found to be abundant in D. prolifera, D. undulata, D. latiscula, D. polypodioides, and D. membranacea. Dictyopterene B (hormosirene) was found as the major compound in D. plagiogramma, D. australis, Hormosira banksii, D. potatorum, D. willana, D. antarctica, Xiphophora chondrophylla, X. gladiata, Scytosiphon lomentaria, Colpomenia peregrina, and Haplospora globosa. Dictyopterene C (dictyotene) was a major compound in D. undulata, D. prolifera, D. membranacea, Gomphonema parvulum, Amphora veneta, Phaeodactylum tricornutum, and D. vermicularis. Dictyopterene D (ectocarpene) was present in Ectocarpus siliculosus, Analipus japonicus, D. prolifera, D. undulata, and Sargassum linifolium. The following enantiomers were found: (1S,2R)-dictyopterene A, (1R,2R)-dictyopterene B, (1S,2S)-dictyopterene B, (1S,2R)-dictyopterene B, (R)-dictyopterene C, and (S)-dictyopterene D. In marine algae, C₁₁-hydrocarbons are derived from C₂₀ polyunsaturated fatty acids by the oxidative cleavage via, e.g., 9-hydroperoxyicosa-(5Z,7E,11Z,14Z,17Z)-pentaenoic acid. An alternative biosynthetic pathway for dictyopterene A and B via the proposed intermediates (S)-dictyoprolenols was considered by oxidative cleavage of hydroperoxyicosatetraenoic acid. Full article

(This article belongs to the Special Issue 5th Anniversary of Section Flavours and Fragrances and 30th Anniversary of Molecules)

29 pages, 7409 KB

Open AccessArticle

Coupled Impact of Anthocyanin and Mineral Concentrations in Cranberry Juice on Gut Microbiota and Function Modulation: A First Demonstration

by Eva Revellat, Joanie Dupont-Morissette, Thibault V. Varin, Geneviève Pilon, André Marette and Laurent Bazinet

Molecules 2025, 30(19), 3986; https://doi.org/10.3390/molecules30193986 (registering DOI) - 4 Oct 2025

Abstract

Cranberry juice (CJ), a natural source of anthocyanins, may provide additional health benefits when enriched, as anthocyanins have been shown to influence gut microbiota composition. This study investigated the effects of varying anthocyanin and mineral concentrations in CJ on gut microbiota in mice. [...] Read more.

Cranberry juice (CJ), a natural source of anthocyanins, may provide additional health benefits when enriched, as anthocyanins have been shown to influence gut microbiota composition. This study investigated the effects of varying anthocyanin and mineral concentrations in CJ on gut microbiota in mice. Using electrodialysis with filtration membranes (EDFM), five CJ samples with different anthocyanin/mineral enrichment levels (0/0, −31/−85%, −19/−70%, 26/−32%, and 44/−60%) were produced and administered to C57BL/6J mice for four weeks. Gut microbiota composition was analyzed via 16S rRNA sequencing, and inflammation was determined in macroscopic observations of intestinal tissues. While α and β diversity remained unchanged, differential abundance analysis revealed that gut microbiota changes were influenced by anthocyanin and mineral concentrations. Synergistic trends were observed for Colidextribacter and Oscillibacter (increasing with both compounds) and for Turicibacter, Romboutsia, Enterorhabdus, and Bifidobacterium (decreasing with both compounds). Antagonistic trends emerged for Dubosiella, Acetatifactor, A2, Ruminococcus, and Intestinimonas (decreasing with anthocyanins and increasing with minerals), and the reverse was found for Ligilactobacillus. The most significant microbiota shifts occurred with the −31/−85% CJ, suggesting a strong effect of its low anthocyanin and mineral content. But further analysis is needed to assess their metabolic effects and impact on intestinal health. Full article

(This article belongs to the Special Issue Analyses and Applications of Phenolic Compounds in Food—2nd Edition)

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12 pages, 623 KB

Open AccessArticle

Analysis of Thymoquinone Content in Black Cumin Seeds Using Near-Infrared Reflectance Spectroscopy

by Óscar Ballesteros and Leonardo Velasco

Molecules 2025, 30(19), 3985; https://doi.org/10.3390/molecules30193985 (registering DOI) - 4 Oct 2025

Abstract

Thymoquinone (TMQ) is the main therapeutic constituent in black cumin (Nigella sativa L.) seeds. Conventional quantification by high-performance liquid chromatography (HPLC) is accurate but unsuitable for large-scale screening. This study evaluated the potential of near-infrared reflectance spectroscopy (NIRS) as a rapid and [...] Read more.

Thymoquinone (TMQ) is the main therapeutic constituent in black cumin (Nigella sativa L.) seeds. Conventional quantification by high-performance liquid chromatography (HPLC) is accurate but unsuitable for large-scale screening. This study evaluated the potential of near-infrared reflectance spectroscopy (NIRS) as a rapid and non-destructive alternative. A multi-year dataset of 780 seed samples was analyzed, and robust calibration models were developed using modified partial least squares regression. Independent validation of a two-year calibration equation using samples from a third year yielded a high predictive performance (r² = 0.85; SEP = 1.18 mg g ¹). Adding part of the samples from the third year to the calibration contributed to further improvement in the prediction of the remaining samples, demonstrating the benefits of continuous equation updates. The calibration equation proved effective for selecting genotypes with high TMQ content, particularly when expanded with samples from the third year. Spectral analysis identified key wavelengths associated with TMQ content, with wavelengths around 2106 nm and 2254 nm being the most relevant. This work demonstrates the applicability of NIRS for rapid phenotyping of TMQ content in black cumin seeds. Full article

(This article belongs to the Topic Research on Natural Products of Medical Plants)

15 pages, 2055 KB

Open AccessArticle

Natural Biological Properties Inherited from Native Endemic Flora in Honeys from Lake Ranco Area of Southern Chile: A Botanical and Physicochemical Approach

by Enrique Mejías, Carlos Gómez, Pablo Díaz and Tatiana Garrido

Molecules 2025, 30(19), 3984; https://doi.org/10.3390/molecules30193984 (registering DOI) - 4 Oct 2025

Abstract

Chile boasts a rich variety of native endemic melliferous flora, recognized internationally for the excellent taste and biological properties of its honeys. While honey production occurs across various regions, the southern zone, particularly near native rainforests, yields highly valued honeys that often lack [...] Read more.

Chile boasts a rich variety of native endemic melliferous flora, recognized internationally for the excellent taste and biological properties of its honeys. While honey production occurs across various regions, the southern zone, particularly near native rainforests, yields highly valued honeys that often lack comprehensive analytical characterization. This study was focused on seven apiaries near Lake Ranco in the Los Rios Region, collecting two honey samples from each location over two consecutive harvesting seasons, totaling 20 samples. Key parameters analyzed included botanical origin, total carbohydrates, glucose/fructose ratio, total phenolic compounds, antioxidant/antiradical activity and 5-hydroxymethylfurfural (HMF) content. The results indicated a significant influence of three native species, Eucryphia cordifolia, Caldcluvia paniculata, and Weinmannia trichosperma, on the antioxidant activity of the honeys. The physicochemical parameters measured, along with the concentration and activity of the compounds responsible for this activity, establish a very characteristic pattern for the monofloral honeys of these three species. This information could serve as a foundation for constructing a map to help differentiate Chilean honeys based on their natural biological attributes helpful for consumer health, generating distinctive profiles that would contribute to accurately guaranteeing their geographical origin and, consequently, increase their specific value. Full article

(This article belongs to the Special Issue Bee Product Chemistry: Identification and Characterization of Natural Compounds, 2nd Edition)

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13 pages, 939 KB

Open AccessArticle

Cucurbitane Glycosides from Siraitia Grosvenorii and Their Hepatoprotective Activities

by Jia-Nan Mao, Hua-Xue Huang, Qing-Ling Xie, Guang-Yu Chen, Juan-Jiang Wu, Ying Deng, Shuang Zhan, Zhi Peng, Xu-Dong Zhou and Wei Wang

Molecules 2025, 30(19), 3983; https://doi.org/10.3390/molecules30193983 (registering DOI) - 4 Oct 2025

Abstract

Siraitia grosvenorii (S. grosvenorii), a traditional medicine food homology plant, serves both dietary and medicinal purposes and is increasingly exploited for its bioactivities in pharmaceuticals and nutritional value. In this research, fifteen glycosides including three new cucurbitane-type triterpenoid glycosides named Luohanguosides [...] Read more.

Siraitia grosvenorii (S. grosvenorii), a traditional medicine food homology plant, serves both dietary and medicinal purposes and is increasingly exploited for its bioactivities in pharmaceuticals and nutritional value. In this research, fifteen glycosides including three new cucurbitane-type triterpenoid glycosides named Luohanguosides A–C (1–3) and twelve known ones (4–15) have been isolated from the aqueous extract of fresh S. grosvenorii fruits. A comprehensive analysis of 1D, 2D-NMR, HRESIMS techniques along with some other spectroscopic methods led to the elucidation of their chemical structures. Further investigation focused on the hepatoprotective activities of compounds 1–15. It turned out that compounds 1, 5, and 10 exhibited significant hepatoprotective activities compared to bicyclol under the same concentration (20 μM), providing scientific support for further research on S.grosvenorii products for their preventive potential of hepatic diseases. Full article

36 pages, 1373 KB

Open AccessReview

From Plants to Protection: Cardiorenal Benefits in Non-Diabetic Chronic Kidney Disease and Heart Failure

by Dan Claudiu Măgureanu, Raluca Maria Pop, Ioana Corina Bocsan, Maria Adriana Neag, Angela Cozma, Antonia Mihaela Levai, Veronica Sanda Chedea and Anca Dana Buzoianu

Molecules 2025, 30(19), 3982; https://doi.org/10.3390/molecules30193982 (registering DOI) - 4 Oct 2025

Abstract

Non-diabetic chronic kidney disease (ND-CKD) refers to the progressive and irreversible decline in kidney function occurring in the absence of diabetes mellitus—a distinction that sets it apart from the more prevalent diabetic CKD. While diabetic nephropathy remains the leading cause of CKD globally, [...] Read more.

Non-diabetic chronic kidney disease (ND-CKD) refers to the progressive and irreversible decline in kidney function occurring in the absence of diabetes mellitus—a distinction that sets it apart from the more prevalent diabetic CKD. While diabetic nephropathy remains the leading cause of CKD globally, ND-CKD encompasses a heterogeneous group of etiologies, including hypertensive nephrosclerosis, glomerulonephritis, and interstitial nephritis. Its incidence and prevalence are steadily increasing, particularly in aging populations, and are often underrecognized. Importantly, ND-CKD is not a benign entity; it independently contributes to systemic inflammation, oxidative stress, and metabolic dysregulation, which in turn amplify cardiovascular risk. Among the most severe complications is heart failure (HF), a complex syndrome arising from structural and functional impairments in cardiac performance. Despite ongoing advancements in HF management, mortality remains unacceptably high, ranging from 2–3% at 30 days to up to 50–75% over five years. Standard pharmacologic therapies frequently fall short in halting disease progression and may provoke undesirable side effects. This therapeutic gap has spurred growing interest in natural compounds with multi-targeted effects. Bioactive molecules such as arjunolic acid, kaempferol, luteolin, and resveratrol have shown anti-inflammatory and antioxidant properties that may offer dual benefits for both renal and cardiac function. By modulating shared molecular pathways—including those involved in inflammation, oxidative damage, and cellular dysfunction—these agents hold promise as adjunctive treatments in ND-CKD complicated by heart failure. Full article

(This article belongs to the Special Issue Natural Compounds for Disease and Health, 3rd Edition)

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Graphical abstract

12 pages, 934 KB

Open AccessArticle

Derivative-Based Non-Target Identification of DNA-Reactive Impurities with Fragment Ion Filtering

by Dongmei Zhang, Baojian Hang, Yiran Zhang, Pengfei You, Feng Shi and Liping Gong

Molecules 2025, 30(19), 3981; https://doi.org/10.3390/molecules30193981 (registering DOI) - 4 Oct 2025

Abstract

DNA direct reactive impurities (DDRIs) can react with nucleophilic sites of DNA, leading to mutations. The control strategies outlined in International Council for Harmonisation of Technical Requirements for Pharmaceuticals for Human Use (ICH) M7 are based on the known compound structure of DDRIs. [...] Read more.

DNA direct reactive impurities (DDRIs) can react with nucleophilic sites of DNA, leading to mutations. The control strategies outlined in International Council for Harmonisation of Technical Requirements for Pharmaceuticals for Human Use (ICH) M7 are based on the known compound structure of DDRIs. Non-target screening of DDRIs in drugs is still challenging due to the diversity of the species and the poor stability. In this study, a derivatization reagent including a reactive group and report group was designed to screen DDRIs. Based on the electrophilic theory of chemical carcinogenesis, an amine reagent was used as a reactive group to interact with DDRIs. Two derivatization reagents, p-methoxyaniline and p-methoxybenzoyl-β-alaninamide, were employed, each containing different chromatographic modification groups to mitigate matrix effects. The derivatization products were analyzed by ultra-high-performance liquid chromatography coupled to high-resolution mass spectrometry (UPLC-HRMS). Non-target screening for DDRIs was achieved by product ions filtering of the report group. Full article

(This article belongs to the Special Issue (Mass Spectrometric) Non Target Screening–Techniques and Strategies: Volume II)

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13 pages, 5074 KB

Open AccessArticle

Interface Engineering of ZnO-Decorated ZnFe₂O₄ for Enhanced CO₂ Reduction Performance

by Congyu Cai, Yufeng Sun, Yulan Xiao, Weiye Zheng, Minhui Pan and Weiwei Wang

Molecules 2025, 30(19), 3980; https://doi.org/10.3390/molecules30193980 (registering DOI) - 4 Oct 2025

Abstract

Photocatalytic conversion of CO₂ to hydrocarbon fuels offers a promising pathway for sustainable renewable energy production. In this study, a ZnO/ZnFe₂O₄ composite featuring a Type-II heterojunction was synthesized through a facile one-step hydrothermal approach, significantly enhancing visible-light-driven CO₂ [...] Read more.

Photocatalytic conversion of CO₂ to hydrocarbon fuels offers a promising pathway for sustainable renewable energy production. In this study, a ZnO/ZnFe₂O₄ composite featuring a Type-II heterojunction was synthesized through a facile one-step hydrothermal approach, significantly enhancing visible-light-driven CO₂ reduction activity. The optimized catalyst exhibits CH₄ and CO production rates that are 3.3 and 4.9 times higher, respectively, than those of pristine ZnFe₂O₄ over 6 h. This significant enhancement in photocatalytic performance is attributed to the Type-II band alignment, which not only broadens light absorption but also greatly promotes efficient charge separation. It is corroborated by a series of experimental evidence: a two-fold enhancement in photocurrent response, a 15.1% reduction in PL intensity, decreased electrochemical impedance, and an extended charge carrier lifetime. Furthermore, in situ FTIR spectroscopy confirms that the heterojunction facilitates the formation of key intermediates (specifically *COOH and HCOO⁻). This study highlights the importance of precise interface design based on a Type-II heterojunction in heterostructured composite catalysts and provides mechanistic insights for developing highly efficient CO₂ photoreduction systems. Full article

(This article belongs to the Section Materials Chemistry)

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18 pages, 2325 KB

Open AccessArticle

Synthesis of Silver Nanoparticles by Using Quercus Robur Knopper Gall Extracts

by Vlatka Gvozdić, Zvonimir Užarević, Elvira Kovač Andrić, Vlatko Galić, Lidija Kalinić, Martina Jakovljević Kovač, Ivan Ćorić, Klara Kirchbauer, Domagoj Vidosavljević and Valentina Pavić

Molecules 2025, 30(19), 3979; https://doi.org/10.3390/molecules30193979 (registering DOI) - 4 Oct 2025

Abstract

Galls of the Cynipidae, such as the Knopper gall, are abnormal plant outgrowths induced by insect activity. These structures not only protect the developing larvae but also alter the biochemical properties of host plant tissues. In this study, we report the green synthesis [...] Read more.

Galls of the Cynipidae, such as the Knopper gall, are abnormal plant outgrowths induced by insect activity. These structures not only protect the developing larvae but also alter the biochemical properties of host plant tissues. In this study, we report the green synthesis of silver nanoparticles (AgNPs) using ethanolic extracts of Quercus robur Knopper galls. AgNPs were synthesized via reduction of AgNO₃ and characterized using ATR-FTIR analysis, UV-Vis spectrophotometry, powder X-ray diffraction (PXRD), and transmission electron microscopy (TEM). The UV-Vis analysis showed a strong surface plasmon resonance (SPR) peak at 418 nm. A face-centered cubic (fcc) crystalline structure with an average crystallite size of about 12 nm was verified by PXRD patterns. TEM imaging revealed well-dispersed spherical nanoparticles, consistent with the size obtained via PXRD. ATR-FTIR analysis indicated the involvement of polyphenolic and protein-related functional groups in reduction and stabilization. The synthesized AgNPs exhibited strong growth inhibition capacity against B. subtilis and S. aureus, and moderate capacity against E. coli and P. aeruginosa. These findings highlight the potential of Knopper gall extract as a sustainable source for the eco-friendly synthesis of biologically active nanoparticles. Full article

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26 pages, 2439 KB

Open AccessReview

The Biologically Active Compounds in Fruits of Cultivated Varieties and Wild Species of Apples

by Alexander A. Shishparenok, Anastasiya N. Shishparenok, Heather A. Harr, Valentina A. Gulidova, Eugene A. Rogozhin and Alexander M. Markin

Molecules 2025, 30(19), 3978; https://doi.org/10.3390/molecules30193978 (registering DOI) - 4 Oct 2025

Abstract

Insufficient fruit intake is a major contributor to the development of non-communicable diseases, as the global average of daily fruit consumption remains far below the recommended levels. Apples are among the most widely consumed fruits worldwide, making them an ideal target for nutritional [...] Read more.

Insufficient fruit intake is a major contributor to the development of non-communicable diseases, as the global average of daily fruit consumption remains far below the recommended levels. Apples are among the most widely consumed fruits worldwide, making them an ideal target for nutritional enhancement. Enhancing the content of health-promoting compounds within apples offers a practical way to increase bioactive intake without requiring major dietary changes. This review evaluates which of the 41 biologically active compounds considered in this article can reach physiologically relevant intake levels at the current average daily consumption of cultivated and wild apples. Comparative analysis shows that wild apples consistently contain higher concentrations of phenolic compounds and organic acids than cultivated varieties, in some cases by more than tenfold. At the average daily fruit intake of 121.8 g, wild species provide effective doses of epicatechins, anthocyanins, chlorogenic acid, and malic acid. In contrast, cultivated apples reach this level only for chlorogenic acid. Notably, less than 50 g of wild apple is sufficient to supply physiologically relevant amounts of several polyphenols. These findings highlight the potential of wild apple species as donors of bioactive compounds and provide a framework for breeding future apple cultivars that combine consumer appeal with enhanced health benefits. Full article

(This article belongs to the Special Issue Nutritional Properties and Sensory Analysis of Food)

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7 pages, 204 KB

Open AccessEditorial

Food Chemistry and Bioactive Compounds in Relation to Health

by Leontina Grigore-Gurgu, Elena Enachi and Iuliana Aprodu

Molecules 2025, 30(19), 3977; https://doi.org/10.3390/molecules30193977 (registering DOI) - 4 Oct 2025

Abstract

Bioactive compounds present in food are essential factors in maintaining optimal health, through their ability to modulate physiological processes, reduce oxidative stress, and contribute to the prevention of chronic diseases related to aging [...] Full article

(This article belongs to the Special Issue Food Chemistry and Bioactive Compounds in Relation to Health)

12 pages, 2020 KB

Open AccessArticle

Molecular-Genetic Research of Rhodococcus rhodochrous IEGM 1362, an Active (–)-Isopulegol Biotransformer

by Polina Y. Maltseva, Natalia A. Plotnitskaya and Irina B. Ivshina

Molecules 2025, 30(19), 3976; https://doi.org/10.3390/molecules30193976 - 3 Oct 2025

Abstract

The present study aimed to identify genes encoding enzymes involved in the biotransformation of monoterpenoid (–)-isopulegol by Rhodococcus rhodochrous IEGM 1362. This strain is able to transform (–)-isopulegol with formation of two novel metabolites with promising antitumor and analeptic activities. Cell fractions of [...] Read more.

The present study aimed to identify genes encoding enzymes involved in the biotransformation of monoterpenoid (–)-isopulegol by Rhodococcus rhodochrous IEGM 1362. This strain is able to transform (–)-isopulegol with formation of two novel metabolites with promising antitumor and analeptic activities. Cell fractions of rhodococci and specific inhibitor of cytochrome P450-dependent oxygenase activity were used to establish the localization and type of biotransformation enzymes. The expression of nine CYP450 genes selected by bioinformatics analysis was analyzed by quantitative real-time PCR (qRT-PCR). Selection of optimal reference genes for normalization of qRT-PCR results was performed using BestKeeper, Normfinder, geNorm, Delta CT, and RefFinder algorithms. As a result of these studies, the role of CYP450 enzyme complexes in the biotransformation of (–)-isopulegol was confirmed, and their cytoplasmic localization was established. The genes encoding DNA gyrase subunit B (gyrB) and protein translocase subunit A (secA) were selected as the most stable reference genes. The induced expression of the gene encoding CYP450 hydroxylase in the presence of (–)-isopulegol was determined. The obtained data allow us to identify the specific CYP450 enzyme involved in (–)-isopulegol biotransformation by R. rhodochrous IEGM 1362 and lay the foundation for further studies of molecular and genetic mechanisms of monoterpenoid biotransformation. Full article

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14 pages, 7499 KB

Open AccessArticle

Design and Color Prediction of Anthracene-Based Dyes Based on Quantum Chemical Calculations

by Yanyi Li, Jiahao Zhang, Mei Bai, Hao Li, Zengbo Ke and Chunsheng Zhou

Molecules 2025, 30(19), 3975; https://doi.org/10.3390/molecules30193975 - 3 Oct 2025

Abstract

We systematically investigated the parent anthracene (abbreviated as en-1, C₁₄H₁₀) and three N,N′-disubstituted derivatives: the 1,5-diethylanthracene (en-2, C₁₈H₁₈), the 1,5-divinylanthracene (en-3, C₁₈H₁₄), and the 1,5-diphenylanthracene (en-4, C₂₆ [...] Read more.

We systematically investigated the parent anthracene (abbreviated as en-1, C₁₄H₁₀) and three N,N′-disubstituted derivatives: the 1,5-diethylanthracene (en-2, C₁₈H₁₈), the 1,5-divinylanthracene (en-3, C₁₈H₁₄), and the 1,5-diphenylanthracene (en-4, C₂₆H₁₈), using a rigorous density functional theory (DFT)/time-dependent density functional theory (TD-DFT) approach. Following full geometric optimization and frequency validation (no imaginary frequencies), frontier molecular orbital analysis revealed an inverse correlation between conjugation extent and the HOMO-LUMO energy gap. Electrostatic potential (ESP) analysis further indicated a progressive increase in surface potential variance upon substitution, reflecting charge redistribution. TD-DFT calculations yielded vertical excitation wavelengths of 438 nm, 441 nm, 464 nm, and 496 nm for en-1, en-2, en-3, and en-4, respectively. Complementary color theory predicts visual colors of yellow, yellow, red, and orange for these compounds based on their absorption characteristics. This work establishes a closed-loop “computation-spectra-color” model for anthracene-based dyes, providing a transferable design paradigm for novel functional pigments with high molar extinction coefficients. Full article

(This article belongs to the Section Physical Chemistry)

15 pages, 2053 KB

Open AccessArticle

Detection of Biomarker Clusterin in SERS Immunoassays on Al Foil After Substrate Selection and Assay Optimization with Fluorescently Labeled Antibodies

by Saule Mergenbayeva, Xeniya Terzapulo and Rostislav Bukasov

Molecules 2025, 30(19), 3974; https://doi.org/10.3390/molecules30193974 - 3 Oct 2025

Abstract

Clusterin plays an important role in carcinogenesis and serves as an important diagnostic biomarker of various clinical conditions. This work describes an application of a surface-enhanced Raman scattering (SERS)-based immunoassay using Al foil substrate that has the potential for the detection of clusterin. [...] Read more.

Clusterin plays an important role in carcinogenesis and serves as an important diagnostic biomarker of various clinical conditions. This work describes an application of a surface-enhanced Raman scattering (SERS)-based immunoassay using Al foil substrate that has the potential for the detection of clusterin. We first optimized the parameters of the assay using anti-human IgG/human IgG (hIgG) as a model antibody/antigen system using various substrates based on Au film, Si, Al tape and Al foil. Among the tested substrates, Al foil exhibited better performance, when assay of human IgG on Al foil demonstrated a detection limit of 2 pM and a semi logarithmic trend range from 10 pM to 1000 pM. Afterwards, the same SERS immunoassay method was implemented for detection of clusterin and resulted in a good semi-logarithmic calibration line with a high R² value of 0.99, which was obtained in the range from 1 ng/mL to 1000 ng/mL. The low detection limit for clusterin antigen was found to be 3 ng/mL, which is better than most LODs for clusterin reported in the literature and also nearly 4 orders of magnitude lower than possible concentrations of clusterin in human blood. Moreover, the assay requires a relatively low volume of sample (10 μL). Overall, the assay performance demonstrates the significant potential of SERS on Al foil as a low-cost/high-availability substrate for sensing and biosensing, including detection of cancer biomarkers. Full article

(This article belongs to the Section Analytical Chemistry)

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18 pages, 5815 KB

Open AccessArticle

Solvent-Responsive Luminescence of an 8-Hydroxyquinoline-Modified 1H-Imidazo[4,5-f][1,10]phenanthroline Ligand and Its Cu(I) Complexes: Excited-State Mechanisms and Structural Effects

by Zhenqin Zhao, Siyuan Liu, Shu Cui, Yichi Zhang, Ziqi Jiang and Xiuling Li

Molecules 2025, 30(19), 3973; https://doi.org/10.3390/molecules30193973 - 3 Oct 2025

Abstract

Understanding how solvents influence the luminescence behavior of Cu(I) complexes is crucial for designing advanced optical sensors. This study reports the synthesis, structures and photophysical investigation of an 8-hydroxyquinoline-functionalized 1H-imidazo[4,5-f][1,10]phenanthroline ligand, ipqH₂, and its four Cu(I) complexes [...] Read more.

Understanding how solvents influence the luminescence behavior of Cu(I) complexes is crucial for designing advanced optical sensors. This study reports the synthesis, structures and photophysical investigation of an 8-hydroxyquinoline-functionalized 1H-imidazo[4,5-f][1,10]phenanthroline ligand, ipqH₂, and its four Cu(I) complexes with diphosphine co-ligands. Photoluminescence studies demonstrated distinct solvent-dependent excited-state mechanisms. In DMSO/alcohol mixtures, free ipqH₂ exhibited excited-state proton transfer (ESPT) and enol-keto tautomerization, producing dual emission at about 447 and 560 nm, while the complexes resisted ESPT due to hydrogen bond blocking by PF₆⁻ anions and Cu(I) coordination. In DMSO/H₂O, aggregation-caused quenching (ACQ) and high-energy O–H vibrational quenching dominated, but complexes 1 and 2 showed a significant red-shifted emission (569–574 nm) with high water content due to solvent-stabilized intra-ligand charge transfer and metal-to-ligand charge transfer ((IL+ML)CT) states. In DMSO/DMF, hydrogen bond competition and solvation-shell reorganization led to distinct responses: complexes 1 and 3, with flexible bis[(2-diphenylphosphino)phenyl]ether (POP) ligands, displayed peak splitting and (IL + ML)CT redshift emission (501 ⟶ 530 nm), whereas complexes 2 and 4, with rigid 9,9-dimethyl-4,5-bis(diphenylphosphino)-9H-xanthene (xantphos), showed weaker responses. The flexibility of the diphosphine ligand dictated DMF sensitivity, while the coordination, the hydrogen bonds between PF₆⁻ anions and ipqH₂, and water solubility governed the alcohol/water responses. This work elucidates the multifaceted solvent-responsive mechanisms in Cu(I) complexes, facilitating the design of solvent-discriminative luminescent sensors. Full article

(This article belongs to the Special Issue Influence of Solvent Molecules in Coordination Chemistry)

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19 pages, 7612 KB

Open AccessArticle

Co-Exposure to Glyphosate and Polyethylene Microplastic Affects Their Toxicity to Chlorella vulgaris: Implications for Algal Health and Aquatic Risk

by Magdalena Podbielska, Małgorzata Kus-Liśkiewicz, Dariusz Płoch and Ewa Szpyrka

Molecules 2025, 30(19), 3972; https://doi.org/10.3390/molecules30193972 - 3 Oct 2025

Abstract

Polyethylene microplastics (PE-MPs) and glyphosate (GLY) are widespread aquatic contaminants, but their combined effects on microalgae remain poorly understood. This study assessed the individual and joint toxicity of GLY and PE-MPs to the model microalga Chlorella vulgaris. Acute (3-day) and chronic (7-day) [...] Read more.

Polyethylene microplastics (PE-MPs) and glyphosate (GLY) are widespread aquatic contaminants, but their combined effects on microalgae remain poorly understood. This study assessed the individual and joint toxicity of GLY and PE-MPs to the model microalga Chlorella vulgaris. Acute (3-day) and chronic (7-day) exposures were performed using GLY at 1–40 mg/L, alone or combined with PE-MPs (10 mg/L). A four-parameter log-logistic (4PL) model was applied to estimate median effect concentrations (EC₅₀). After 72 h, the EC₅₀ values were 9.77 mg/L for the GLY single system and 2.31 mg/L for the GLY-PE combined system, confirming enhanced toxicity in combined exposures. Co-exposure reduced pigment levels (chlorophyll a, chlorophyll b, and carotenoids) by up to 65% and significantly increased oxidative stress markers, including reactive oxygen species production and malondialdehyde accumulation, compared with single treatments. Antioxidant enzymes (superoxide dismutase and catalase) showed concentration- and time-dependent responses, indicating activation of cellular defense mechanisms. Scanning Electron Microscopy revealed PE-induced aggregation and structural damage to algal cells, particularly at higher GLY concentrations. These findings demonstrate that PE-MPs can amplify the toxic effects of GLY on microalgae and highlight the need for further studies at environmentally relevant concentrations and with different polymer types. Full article

(This article belongs to the Special Issue Chemical Analysis of Pollutant in the Environment)

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28 pages, 1515 KB

Open AccessArticle

Engineering PVA-CNF-MOF Composite Films for Active Packaging: Enhancing Mechanical Strength, Barrier Performance, and Stability for Fresh Produce Preservation

by Sergio Carrasco, Juan Amaro-Gahete, Eduardo Espinosa, Almudena Benítez, Francisco J. Romero-Salguero and Alejandro Rodríguez

Molecules 2025, 30(19), 3971; https://doi.org/10.3390/molecules30193971 - 3 Oct 2025

Abstract

Food waste is a global challenge, with nearly 40% of food discarded annually, leading to economic losses, food insecurity, and environmental harm. Major factors driving spoilage include microbial contamination, enzymatic activity, oxidation, and excessive ethylene production. Active packaging offers a promising solution by [...] Read more.

Food waste is a global challenge, with nearly 40% of food discarded annually, leading to economic losses, food insecurity, and environmental harm. Major factors driving spoilage include microbial contamination, enzymatic activity, oxidation, and excessive ethylene production. Active packaging offers a promising solution by extending shelf life through the selective absorption or release of specific substances. In this study, polyvinyl alcohol (PVA) films incorporating metal-organic frameworks (MOFs) were prepared via solvent casting to enhance their mechanical and barrier properties. Five MOFs (HKUST-1, MIL-88A, BASF-A520, UiO-66, and MOF-801) were embedded in the PVA matrix and analyzed for their physical, mechanical, and optical characteristics. The incorporation of TEMPO-oxidized cellulose nanofibers (CNF) improved MOF dispersion, significantly strengthening film performance. Among the formulations, PVA-CNF-MOF-801 exhibited the best performance, with a 130% increase in tensile strength, a 50% reduction in water vapor permeability, and a 168% improvement in UV protection compared with neat PVA films. Ethylene adsorption tests with climacteric fruits confirmed that CNF-containing films retained ethylene more effectively than those without CNFs, although the differences among the MOFs were minimal. These results highlight the potential of PVA-CNF-MOF composite films as sustainable active packaging materials, providing an effective strategy to reduce food waste and its environmental impact. Full article

(This article belongs to the Special Issue Lignocellulosic Biomass III)

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13 pages, 3420 KB

Open AccessArticle

Design, Synthesis and Herbicidal Activity of 1,2,4-Oxadiazole Compounds as Novel Light-Dependent Protochlorophyllide Oxidoreductase Inhibitors

by Xiao Hu, Jing Miao, Yiyi Tian, Wennan Luo, Jixian Shang, Ruiyuan Liu and Huizhe Lu

Molecules 2025, 30(19), 3970; https://doi.org/10.3390/molecules30193970 - 3 Oct 2025

Abstract

Light-dependent protochlorophyllide oxidoreductase (LPOR, E.C.1.3.1.33) plays a crucial role in the biosynthesis of chlorophyll in plants. Therefore, inactivating LPOR can hinder the production of chlorophyll to achieve the effect of weed control. In this research, utilizing an active substructure splicing method, 20 new [...] Read more.

Light-dependent protochlorophyllide oxidoreductase (LPOR, E.C.1.3.1.33) plays a crucial role in the biosynthesis of chlorophyll in plants. Therefore, inactivating LPOR can hinder the production of chlorophyll to achieve the effect of weed control. In this research, utilizing an active substructure splicing method, 20 new 1,2,4-oxadiazole compounds targeting LPOR were synthesized. Among them, compounds 5j, 5k and 5q exhibited superior inhibitory efficacy in greenhouse herbicidal trials. In vitro enzyme activity assays indicated that 5q significantly inhibited Arabidopsis thaliana LPOR (AtLPOR), with an IC₅₀ value of 17.63 μM. Furthermore, compound 5q exhibited superior crop safety and holds potential application prospects for weed management in cotton. Molecular docking and dynamic simulations were employed to elucidate the binding mode and molecular mechanism of 5q with AtLPOR. These experimental and theoretical results indicate that 5q is a promising candidate for the development of novel herbicides targeting LPOR. Full article

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