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Advances in Molecular Activity of Potential Drugs 2.0

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Molecular Pharmacology".

Deadline for manuscript submissions: closed (15 January 2023) | Viewed by 28567

Special Issue Editors


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Guest Editor
Institute of Genetics and Microbiology, University of Wroclaw, 50-137 Wrocław, Poland
Interests: fungi; yeast; cell lines; cell cycle; cellular response to stress (plants, prokaryotic, and eukaryotic organisms); environmental research; mitochondria; genomics; proteome; genetic adaptations to interactions in the environment
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Guest Editor
Institute of Pharmaceutical Chemistry, University of Szeged (SZTE), Szeged, Hungary
Interests: beta-amino acids; aminodiols; heterocyclic chemistry; drug design and synthesis; chiral catalysts; terpenoids
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

An aging population; the appearance of new cancers and viral, bacterial, or fungal diseases; and insufficiently effective methods of treating existing diseases make it necessary to discover new drugs and to refine those that are already in use. Investigations into new drugs include research on both newly synthesized, novel compounds and those isolated from plants or secreted by microorganisms. Discovering the full molecular mechanisms of drugs or potential drugs is extremely important in terms of improving the quality of treatment and predicting the side effects of long-term treatment. The many years that have been spent searching for the molecular activity of drugs make sense in the context of extending their application. It is also important to look for drugs that work synergistically. In research on the molecular activity of drugs and potential drugs, both model organisms and cell lines are applied, which help us to obtain many valuable results in a relatively short time.

We are thus putting together a Special Issue entitled Advances in Molecular Activity of Potential Drugs. We invite papers that are related to the broadly understood progress in the field of investigating new compounds, potential drugs, and drugs that are already used in therapies. We encourage you to submit works carried out on model organisms, cell lines, animals, and as part of clinical trials. Research showing new molecular activities of already-used drugs, as well as on compounds that are potential drugs, are welcome. It is also important in this field of research to search for synergisms to find compounds that, when used together, act strongly and more efficiently in the therapy. Review articles summarizing published research are also very valuable for drawing conclusions and searching for further methods of research.
We look forward to your contributions and thank you for them in advance.

Dr. Magdalena Cal
Prof. Dr. Zsolt Szakonyi
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. There is an Article Processing Charge (APC) for publication in this open access journal. For details about the APC please see here. Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

 

Keywords

  • potential drugs
  • drugs
  • molecular mechanism of action
  • cell cycle
  • stress response
  • cell lines
  • model organisms
  • clinical tests
  • diseases

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Published Papers (10 papers)

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Research

Jump to: Review

20 pages, 2168 KiB  
Article
First Synthesis of DBU-Conjugated Cationic Carbohydrate Derivatives and Investigation of Their Antibacterial and Antifungal Activity
by Fruzsina Demeter, Patrik Török, Alexandra Kiss, Richárd Kovásznai-Oláh, Zsuzsa Máthéné Szigeti, Viktória Baksa, Fruzsina Kovács, Noémi Balla, Ferenc Fenyvesi, Judit Váradi, Anikó Borbás and Mihály Herczeg
Int. J. Mol. Sci. 2023, 24(4), 3550; https://doi.org/10.3390/ijms24043550 - 10 Feb 2023
Cited by 1 | Viewed by 1926
Abstract
The emergence of drug-resistant bacteria and fungi represents a serious health problem worldwide. It has long been known that cationic compounds can inhibit the growth of bacteria and fungi by disrupting the cell membrane. The advantage of using such cationic compounds is that [...] Read more.
The emergence of drug-resistant bacteria and fungi represents a serious health problem worldwide. It has long been known that cationic compounds can inhibit the growth of bacteria and fungi by disrupting the cell membrane. The advantage of using such cationic compounds is that the microorganisms would not become resistant to cationic agents, since this type of adaptation would mean significantly altering the structure of their cell walls. We designed novel, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)-derived amidinium salts of carbohydrates, which may be suitable for disturbing the cell walls of bacteria and fungi due to their quaternary ammonium moiety. A series of saccharide-DBU conjugates were prepared from 6-iodo derivatives of d-glucose, d-mannose, d-altrose and d-allose by nucleophilic substitution reactions. We optimized the synthesis of a d-glucose derivative, and studied the protecting group free synthesis of the glucose-DBU conjugates. The effect of the obtained quaternary amidinium salts against Escherichia coli and Staphylococcus aureus bacterial strains and Candida albicans yeast was investigated, and the impact of the used protecting groups and the sugar configuration on the antimicrobial activity was analyzed. Some of the novel sugar quaternary ammonium compounds with lipophilic aromatic groups (benzyl and 2-napthylmethyl) showed particularly good antifungal and antibacterial activity. Full article
(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 2.0)
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18 pages, 10278 KiB  
Article
Novel Erlotinib–Chalcone Hybrids Diminish Resistance in Head and Neck Cancer by Inducing Multiple Cell Death Mechanisms
by József Murányi, Cintia Duró, Bianka Gurbi, István Móra, Attila Varga, Krisztina Németh, József Simon, Miklós Csala and Antal Csámpai
Int. J. Mol. Sci. 2023, 24(4), 3456; https://doi.org/10.3390/ijms24043456 - 9 Feb 2023
Cited by 2 | Viewed by 2091
Abstract
In a search for novel therapeutic options for head and neck squamous cell carcinomas (HNSCCs) generally treated with limited therapeutic success, we synthesized a series of novel erlotinib–chalcone molecular hybrids with 1,2,3-triazole and alkyne linkers and evaluated them for their anticancer activity on [...] Read more.
In a search for novel therapeutic options for head and neck squamous cell carcinomas (HNSCCs) generally treated with limited therapeutic success, we synthesized a series of novel erlotinib–chalcone molecular hybrids with 1,2,3-triazole and alkyne linkers and evaluated them for their anticancer activity on Fadu, Detroit 562 and SCC-25 HNSCC cell lines. Time- and dose-dependent cell viability measurements disclosed a significantly increased efficiency of the hybrids compared to the 1:1 combination of erlotinib and a reference chalcone. The clonogenic assay demonstrated that hybrids eradicate HNSCC cells in low micromolar concentrations. Experiments focusing on potential molecular targets indicate that the hybrids trigger the anticancer effect by a complementary mechanism of action that is independent of the canonical targets of their molecular fragments. Confocal microscopic imaging and real-time apoptosis/necrosis detection assay pointed to slightly different cell death mechanisms induced by the most prominent triazole- and alkyne-tethered hybrids (6a and 13, respectively). While 6a featured the lowest IC50 values on each of the three HNSCC cell lines, in Detroit 562 cells, this hybrid induced necrosis more markedly compared to 13. The therapeutic potential indicated by the observed anticancer efficacy of our selected hybrid molecules validates the concept of development and justifies further investigation to reveal the underlying mechanism of action. Full article
(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 2.0)
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18 pages, 1547 KiB  
Article
Stereoselective Synthesis and Antiproliferative Activities of Tetrafunctional Diterpene Steviol Derivatives
by Dorottya Bai, Zsuzsanna Schelz, Dóra Erdős, Anna K. Kis, Viktória Nagy, István Zupkó, György T. Balogh and Zsolt Szakonyi
Int. J. Mol. Sci. 2023, 24(2), 1121; https://doi.org/10.3390/ijms24021121 - 6 Jan 2023
Cited by 4 | Viewed by 1939
Abstract
A new family of diterpene-type aminotriol derivatives has been synthesised from stevioside in a stereoselective manner. The key intermediate spiro-epoxide was prepared through the methyl ester of the allilyc diol derived from steviol. The oxirane ring was opened with primary and secondary amines, [...] Read more.
A new family of diterpene-type aminotriol derivatives has been synthesised from stevioside in a stereoselective manner. The key intermediate spiro-epoxide was prepared through the methyl ester of the allilyc diol derived from steviol. The oxirane ring was opened with primary and secondary amines, providing a versatile library of aminotriols. The corresponding primary aminotriol was formed by palladium-catalysed hydrogenation, and an N,O-heterocyclic compound was synthesised in a regioselective reaction. All new compounds were characterised by 1D- and 2D-NMR techniques and HRMS measurements. In our in vitro investigations, we found that the aromatic N-substituted derivatives exhibited high inhibition of cell growth on human cancer cell lines (HeLa, SiHa, A2780, MCF-7 and MDA-MB-231). The antiproliferative activities were assayed by the MTT method. Furthermore, the introduction of an additional hydroxy group slightly increased the biological activity. The drug-likeness of the compounds was assessed by in silico and experimental physicochemical characterisations, completed by kinetic aqueous solubility and in vitro intestinal-specific parallel artificial membrane permeability assay (PAMPA-GI) measurements. Full article
(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 2.0)
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15 pages, 1707 KiB  
Article
Metabolomic and Proteomic Changes in Candida albicans Biofilm in Response to Zosteric Acid Treatment
by Cristina Cattò, Laura Corte, Luca Roscini, Gianluigi Cardinali, Federica Villa and Francesca Cappitelli
Int. J. Mol. Sci. 2022, 23(22), 14067; https://doi.org/10.3390/ijms232214067 - 15 Nov 2022
Cited by 3 | Viewed by 2020
Abstract
Zosteric acid (ZA) is a secondary metabolite of the seagrass Zostera marina, with antibiofilm activity against fungi. Information concerning its mechanisms of action is lacking and this limits the development of more potent derivatives based on the same target and activity structure. The [...] Read more.
Zosteric acid (ZA) is a secondary metabolite of the seagrass Zostera marina, with antibiofilm activity against fungi. Information concerning its mechanisms of action is lacking and this limits the development of more potent derivatives based on the same target and activity structure. The aim of this work was to investigate the ZA mode of action by analyzing the metabolic status of Candida albicans biofilm and its protein expression profile upon ZA treatment. Fourier-Transform Infrared Spectroscopy confirmed that ZA modified the metabolomic response of treated cells, showing changes in the spectral regions, mainly related to the protein compartment. Nano Liquid Chromatography–High-Resolution Mass Spectrometry highlighted that 10 proteins were differentially expressed in the C. albicans proteome upon ZA treatment. Proteins involved in the biogenesis, structure and integrity of cell walls as well as adhesion and stable attachment of hyphae were found downregulated, whereas some proteins involved in the stress response were found overexpressed. Additionally, ZA was involved in the modulation of non-DNA-based epigenetic regulatory mechanisms triggered by reactive oxygen species. These results partially clarified the ZA mechanism of action against fungi and provided insight into the major C. albicans pathways responsible for biofilm formation. Full article
(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 2.0)
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17 pages, 1955 KiB  
Article
Metabolomics Analysis Revealed Significant Metabolic Changes in Brain Cancer Cells Treated with Paclitaxel and/or Etoposide
by Ahlam M. Semreen, Leen Oyoun Alsoud, Waseem El-Huneidi, Munazza Ahmed, Yasser Bustanji, Eman Abu-Gharbieh, Raafat El-Awady, Wafaa S. Ramadan, Mohammad A.Y. Alqudah, Mohd Shara, Ahmad Y. Abuhelwa, Nelson C. Soares, Mohammad H. Semreen and Karem H. Alzoubi
Int. J. Mol. Sci. 2022, 23(22), 13940; https://doi.org/10.3390/ijms232213940 - 11 Nov 2022
Cited by 7 | Viewed by 2422
Abstract
Cancer of the central nervous system (CNS) is ranked as the 19th most prevalent form of the disease in 2020. This study aims to identify candidate biomarkers and metabolic pathways affected by paclitaxel and etoposide, which serve as potential treatments for glioblastoma, and [...] Read more.
Cancer of the central nervous system (CNS) is ranked as the 19th most prevalent form of the disease in 2020. This study aims to identify candidate biomarkers and metabolic pathways affected by paclitaxel and etoposide, which serve as potential treatments for glioblastoma, and are linked to the pathogenesis of glioblastoma. We utilized an untargeted metabolomics approach using the highly sensitive ultra-high-performance liquid chromatography-electrospray ionization quadrupole time-of-flight mass spectrometry (UHPLC-ESI-QTOF-MS) for identification. In this study, 92 and 94 metabolites in U87 and U373 cell lines were profiled, respectively. The produced metabolites were then analyzed utilizing t-tests, volcano plots, and enrichment analysis modules. Our analysis revealed distinct metabolites to be significantly dysregulated (nutriacholic acid, L-phenylalanine, L-arginine, guanosine, ADP, hypoxanthine, and guanine), and to a lesser extent, mevalonic acid in paclitaxel and/or etoposide treated cells. Furthermore, both urea and citric acid cycles, and metabolism of polyamines and amino acids (aspartate, arginine, and proline) were significantly enriched. These findings can be used to create a map that can be utilized to assess the antitumor effect of paclitaxel and/or etoposide within the studied cancer cells. Full article
(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 2.0)
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23 pages, 3394 KiB  
Article
Synthesis and Anticancer and Antiviral Activities of C-2′-Branched Arabinonucleosides
by Miklós Bege, Alexandra Kiss, Ilona Bereczki, Jan Hodek, Lenke Polyák, Gábor Szemán-Nagy, Lieve Naesens, Jan Weber and Anikó Borbás
Int. J. Mol. Sci. 2022, 23(20), 12566; https://doi.org/10.3390/ijms232012566 - 19 Oct 2022
Cited by 5 | Viewed by 1976
Abstract
d-Arabinofuranosyl-pyrimidine and -purine nucleoside analogues containing alkylthio-, acetylthio- or 1-thiosugar substituents at the C2’ position were prepared from the corresponding 3’,5’-O-silylene acetal-protected nucleoside 2’-exomethylenes by photoinitiated, radical-mediated hydrothiolation reactions. Although the stereochemical outcome of the hydrothiolation depended on the structure [...] Read more.
d-Arabinofuranosyl-pyrimidine and -purine nucleoside analogues containing alkylthio-, acetylthio- or 1-thiosugar substituents at the C2’ position were prepared from the corresponding 3’,5’-O-silylene acetal-protected nucleoside 2’-exomethylenes by photoinitiated, radical-mediated hydrothiolation reactions. Although the stereochemical outcome of the hydrothiolation depended on the structure of both the thiol and the furanoside aglycone, in general, high d-arabino selectivity was obtained. The cytotoxic effect of the arabinonucleosides was studied on tumorous SCC (mouse squamous cell) and immortalized control HaCaT (human keratinocyte) cell lines by MTT assay. Three pyrimidine nucleosides containing C2’-butylsulfanylmethyl or -acetylthiomethyl groups showed promising cytotoxicity at low micromolar concentrations with good selectivity towards tumor cells. SAR analysis using a methyl β-d-arabinofuranoside reference compound showed that the silyl-protecting group, the nucleobase and the corresponding C2’ substituent are crucial for the cell growth inhibitory activity. The effects of the three most active nucleoside analogues on parameters indicative of cytotoxicity, such as cell size, division time and cell generation time, were investigated by near-infrared live cell imaging, which showed that the 2’-acetylthiomethyluridine derivative induced the most significant functional and morphological changes. Some nucleoside analogues also exerted anti-SARS-CoV-2 and/or anti-HCoV-229E activity with low micromolar EC50 values; however, the antiviral activity was always accompanied by significant cytotoxicity. Full article
(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 2.0)
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19 pages, 6098 KiB  
Article
Combined PARP and Dual Topoisomerase Inhibition Potentiates Genome Instability and Cell Death in Ovarian Cancer
by Inken Flörkemeier, Julia S. Hillmann, Jörg P. Weimer, Jonas Hildebrandt, Nina Hedemann, Christoph Rogmans, Astrid Dempfle, Norbert Arnold, Bernd Clement and Dirk O. Bauerschlag
Int. J. Mol. Sci. 2022, 23(18), 10503; https://doi.org/10.3390/ijms231810503 - 10 Sep 2022
Cited by 4 | Viewed by 2912
Abstract
Although ovarian cancer is a rare disease, it constitutes the fifth leading cause of cancer death among women. It is of major importance to develop new therapeutic strategies to improve survival. Combining P8-D6, a novel dual topoisomerase inhibitor with exceptional anti-tumoral properties in [...] Read more.
Although ovarian cancer is a rare disease, it constitutes the fifth leading cause of cancer death among women. It is of major importance to develop new therapeutic strategies to improve survival. Combining P8-D6, a novel dual topoisomerase inhibitor with exceptional anti-tumoral properties in ovarian cancer and compounds in preclinical research, and olaparib, a PARP inhibitor targeting DNA damage repair, is a promising approach. P8-D6 induces DNA damage that can be repaired by base excision repair or homologous recombination in which PARP plays a major role. This study analyzed benefits of combining P8-D6 and olaparib treatment in 2D and 3D cultures with ovarian cancer cells. Measurement of viability, cytotoxicity and caspase activity were used to assess therapy efficacy and to calculate the combination index (CI). Further DNA damage was quantified using the biomarkers RAD51 and γH2A.X. The combinational treatment led to an increased caspase activity and reduced viability. CI values partially show synergisms in combinations at 100 nM and 500 nM P8-D6. More DNA damage accumulated, and spheroids lost their membrane integrity due to the combinational treatment. While maintaining the same therapy efficacy as single-drug therapy, doses of P8-D6 and olaparib can be reduced in combinational treatments. Synergisms can be seen in some tested combinations. In summary, the combination therapy indicates benefits and acts synergistic at 100 nM and 500 nM P8-D6. Full article
(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 2.0)
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24 pages, 1920 KiB  
Article
Stereoselective Synthesis and Application of Gibberellic Acid-Derived Aminodiols
by Zein Alabdeen Khdar, Tam Minh Le, Zsuzsanna Schelz, István Zupkó and Zsolt Szakonyi
Int. J. Mol. Sci. 2022, 23(18), 10366; https://doi.org/10.3390/ijms231810366 - 8 Sep 2022
Cited by 1 | Viewed by 1779
Abstract
A series of gibberellic acid-based aminodiols was designed and synthesized from commercially available gibberellic acid. Exposure of gibberellic acid to hydrochloric acid under reflux conditions resulted in aromatization followed by rearrangement to form allo-gibberic acid. The key intermediate, ethyl allo-gibberate, was prepared according [...] Read more.
A series of gibberellic acid-based aminodiols was designed and synthesized from commercially available gibberellic acid. Exposure of gibberellic acid to hydrochloric acid under reflux conditions resulted in aromatization followed by rearrangement to form allo-gibberic acid. The key intermediate, ethyl allo-gibberate, was prepared according to literature methods. Epoxidation of key intermediate and subsequent ring-opening of the corresponding epoxide with different nucleophiles resulted in N-substituted aminodiols. The regioselective ring closure of N-benzyl-substituted aminodiol with formaldehyde was also investigated. All aminodiol derivatives were well characterized using modern spectroscopic techniques and evaluated for their antiproliferative activity against a panel of human cancer cell lines. In addition, structure–activity relationships were examined by assessing substituent effects on the aminodiol systems. The results indicated that aminodiols containing aromatic rings on their nitrogen substituents displayed significant cytotoxic effects. Among these agents, N-naphthylmethyl-substituted aminodiols were found to be the most potent candidates in this series. One of these molecules exhibited a modest cancer selectivity determined by non-cancerous fibroblast cells. A docking study was also made to exploit the observed results. Full article
(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 2.0)
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20 pages, 4930 KiB  
Article
Microtube Array Membrane Encapsulated Cell Therapy: A Novel Platform Technology Solution for Treatment of Alzheimer’s Disease
by Shu-Mei Chen, Tsung-Chin Hsu, Chee-Ho Chew, Wan-Ting Huang, Amanda Lin Chen, Yung-Feng Lin, Sabiha Eddarkaoui, Luc Buee and Chien-Chung Chen
Int. J. Mol. Sci. 2022, 23(12), 6855; https://doi.org/10.3390/ijms23126855 - 20 Jun 2022
Cited by 4 | Viewed by 2941
Abstract
Alzheimer’s disease is the most frequent form of dementia in aging population and is presently the world’s sixth largest cause of mortality. With the advancement of therapies, several solutions have been developed such as passive immunotherapy against these misfolded proteins, thereby resulting in [...] Read more.
Alzheimer’s disease is the most frequent form of dementia in aging population and is presently the world’s sixth largest cause of mortality. With the advancement of therapies, several solutions have been developed such as passive immunotherapy against these misfolded proteins, thereby resulting in the clearance. Within this segment, encapsulated cell therapy (ECT) solutions that utilize antibody releasing cells have been proposed with a multitude of techniques under development. Hence, in this study, we utilized our novel and patented Microtube Array Membranes (MTAMs) as an encapsulating platform system with anti-pTau antibody-secreting hybridoma cells to study the impact of it on Alzheimer’s disease. In vivo results revealed that in the water maze, the mice implanted with hybridoma cell MTAMs intracranially (IN) and subcutaneously (SC) showed improvement in the time spent the goal quadrant and escape latency. In passive avoidance, hybridoma cell loaded MTAMs (IN and SC) performed significantly well in step-through latency. At the end of treatment, animals with hybridoma cell loaded MTAMs had lower phosphorylated tau (pTau) expression than empty MTAMs had. Combining both experimental results unveiled that the clearance of phosphorylated tau might rescue the cognitive impairment associated with AD. Full article
(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 2.0)
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Review

Jump to: Research

18 pages, 1621 KiB  
Review
Caffeic Acid and Diseases—Mechanisms of Action
by Nela Pavlíková
Int. J. Mol. Sci. 2023, 24(1), 588; https://doi.org/10.3390/ijms24010588 - 29 Dec 2022
Cited by 48 | Viewed by 7547
Abstract
Caffeic acid belongs to the polyphenol compounds we consume daily, often in the form of coffee. Even though it is less explored than caffeic acid phenethyl ester, it still has many positive effects on human health. Caffeic acid can affect cancer, diabetes, atherosclerosis, [...] Read more.
Caffeic acid belongs to the polyphenol compounds we consume daily, often in the form of coffee. Even though it is less explored than caffeic acid phenethyl ester, it still has many positive effects on human health. Caffeic acid can affect cancer, diabetes, atherosclerosis, Alzheimer’s disease, or bacterial and viral infections. This review focuses on the molecular mechanisms of how caffeic acid achieves its effects. Full article
(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 2.0)
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