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Advances in Molecular Activity of Potential Drugs 3.0

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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 (31 July 2023) | Viewed by 16697

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Special Issue Editor

Prof. Dr. István Zupkó

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Guest Editor

Department of Pharmacodynamics and Biopharmacy, University of Szeged, Szeged, Hungary
Interests: anticancer properties of natural products and their synthetic analogs; antimetastatic activity

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 conditions make it necessary to discover new drugs and refine those already in use. Investigations into new drugs include research on newly synthesized, novel compounds and those isolated from plants or secreted by microorganisms. In addition, discovering the complete 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 therapy. Therefore, efforts spent to elucidate the molecular activity of drugs make sense in the context of extending their application. Furthermore, besides novel chemical entities, combinations that act synergistically can reach the expected therapeutical goal. In all cases, identifying the target is an essential step toward understanding the work of the drug candidate, which is essential in further development.

The Special Issue entitled Advances in Molecular Activity of Potential Drugs aims to cover all these topics of pharmacological research. Therefore, papers related to the broadly understood progress in investigating new compounds, potential drugs, and drugs already used in therapies are invited for submission. In addition, manuscripts that deal with innovative combinations are also welcome. Finally, studies that describe the molecular activities of drugs currently in use and drug candidates are welcome. Review articles that summarize published research will also be appreciated.

We look forward to your contributions, and thank you for them in advance.

Prof. Dr. István Zupkó
Guest Editor

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
drug targets
molecular mechanism of action
cell cycle
stress response
cell lines
model organisms
drug combinations

Published Papers (11 papers)

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Research

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20 pages, 11673 KiB

Open AccessArticle

A Novel Quinazoline Derivative Prevents and Treats Arsenic-Induced Liver Injury by Regulating the Expression of RecQ Family Helicase

by Heping Yang, Min Mo, Langlang Yang, Jia Yu, Jiao Li, Sha Cheng, Baofei Sun, Bixue Xu, Aihua Zhang and Heng Luo

Int. J. Mol. Sci. 2023, 24(21), 15521; https://doi.org/10.3390/ijms242115521 - 24 Oct 2023

Viewed by 876

Abstract

Arsenic is a carcinogenic metalloid toxicant widely found in the natural environment. Acute or prolonged exposure to arsenic causes a series of damages to the organs, mainly the liver, such as hepatomegaly, liver fibrosis, cirrhosis, and even hepatocellular carcinoma. Therefore, it is imperative to seek drugs to prevent arsenic-induced liver injury. Quinazolines are a class of nitrogen heterocyclic compounds with biological and pharmacological effects in vivo and in vitro. This study was designed to investigate the ameliorating effects of quinazoline derivatives on arsenic-induced liver injury and its molecular mechanism. We investigated the mechanism of the quinazoline derivative KZL-047 in preventing and ameliorating arsenic-induced liver injury in vitro by cell cycle and apoptosis. We performed real-time fluorescence quantitative polymerase chain reaction (qPCR) and Western blotting combined with molecular docking. In vivo, the experiments were performed to investigate the mechanism of KZL-047 in preventing and ameliorating arsenic-induced liver injury using arsenic-infected mice. Physiological and biochemical indices of liver function in mouse serum were measured, histopathological changes in liver tissue were observed, and immunohistochemical staining was used to detect changes in the expression of RecQ-family helicases in mouse liver tissue. The results of in vitro experiments showed that sodium arsenite (SA) inhibited the proliferation of L-02 cells, induced apoptosis, blocked the cell cycle at the G1 phase, and decreased the expression of RecQ family helicase; after KZL-047 treatment in arsenic-induced L-02 cells, the expression of RecQ family helicase was upregulated, and the apoptosis rate was slowed, leading to the restoration of the cell viability level. KZL-047 inhibited arsenic-induced oxidative stress, alleviated oxidative damage and lipid peroxidation in vivo, and ameliorated arsenic toxicity-induced liver injury. KZL-047 restored the expression of RecQ family helicase proteins, which is consistent with the results of in vitro studies. In summary, KZL-047 can be considered a potential candidate for the treatment of arsenic-induced liver injury. Full article

(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 3.0)

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21 pages, 7560 KiB

Open AccessArticle

Bortezomib Is Effective in the Treatment of T Lymphoblastic Leukaemia by Inducing DNA Damage, WEE1 Downregulation, and Mitotic Catastrophe

by Rahman Ud Din, Anan Jiao, Yinxia Qiu, Aarmann Anil Mohinani Mohan, Kei-Ching Yuen, Hoi-Tung Wong, Timothy Ming-Hun Wan, Phoebe On-Yi Wong and Chun-Fung Sin

Int. J. Mol. Sci. 2023, 24(19), 14646; https://doi.org/10.3390/ijms241914646 - 27 Sep 2023

Viewed by 1329

Abstract

T lymphoblastic leukemia (T-ALL) is an aggressive haematolymphoid malignancy comprising 15% of acute lymphoblastic leukemia (ALL). Although its prognosis has improved with intensive chemotherapy, the relapse/refractory disease still carries a dismal prognosis. Thus, there is an urgent need to develop novel therapy for T-ALL. Bortezomib, a 26S proteasome inhibitor, is licensed to treat plasma cell myeloma and mantle cell lymphoma. Due to its favorable side effect profile, it is a novel agent of research interest in the treatment of ALL. Despite an increasing number of clinical trials of bortezomib in T-ALL, its detailed mechanistic study in terms of DNA damage, cell cycle, and mitotic catastrophe remains elusive. Moreover, WEE1, a protein kinase overexpressed in ALL and involved in cell-cycle regulation, has been known to be a novel therapeutic target in many cancers. But the role of bortezomib in modulating WEE1 expression in ALL still remains elusive. In this study, we demonstrate the therapeutic efficacy of bortezomib on T-ALL primary samples and cell lines. Our findings reveal that bortezomib treatment induces DNA damage and downregulates WEE1, leading to G2-M cell-cycle progression with damaged DNA. This abnormal mitotic entry induced by bortezomib leads to mitotic catastrophe in T-ALL. In conclusion, our findings dissect the mechanism of action of bortezomib and provide further insights into the use of bortezomib to treat T-ALL. Our findings suggest the possibility of novel combination therapy using proteasome inhibitors together with DNA-damaging agents in the future, which may fill the research gaps and unmet clinical needs in treating ALL. Full article

(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 3.0)

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16 pages, 17039 KiB

Open AccessArticle

Antiproliferative and Antimetastatic Properties of 16-Azidomethyl Substituted 3-O-Benzyl Estrone Analogs

by Seyyed Ashkan Senobar Tahaei, Ágnes Kulmány, Renáta Minorics, Anita Kiss, Zoltán Szabó, Péter Germán, Gábor J. Szebeni, Nikolett Gémes, Erzsébet Mernyák and István Zupkó

Int. J. Mol. Sci. 2023, 24(18), 13749; https://doi.org/10.3390/ijms241813749 - 6 Sep 2023

Viewed by 831

Abstract

Four diastereomers of 16-azidomethyl substituted 3-O-benzyl estradiol (1–4) and their two estrone analogs (16AABE and 16BABE) were tested for their antiproliferative properties against human gynecological cancer cell lines. The estrones were selected for additional experiments based on their outstanding cell growth-inhibiting activities. Both compounds increased hypodiploid populations of breast cancer cells, and 16AABE elicited cell cycle disturbance as evidenced by flow cytometry. The two analogs substantially increased the rate of tubulin polymerization in vitro. 16AABE and 16BABE inhibited breast cancer cells’ migration and invasive ability, as evidenced by wound healing and Boyden chamber assays. Since both estrone analogs exerted remarkable estrogenic activities, as documented by a luciferase reporter gene assay, they can be considered as promising drug candidates for hormone-independent malignancies. Full article

(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 3.0)

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15 pages, 2262 KiB

Open AccessArticle

Microbial Metabolites of 3-n-butylphthalide as Monoamine Oxidase A Inhibitors

by Joanna Gach, Joanna Grzelczyk, Tomasz Strzała, Filip Boratyński and Teresa Olejniczak

Int. J. Mol. Sci. 2023, 24(13), 10605; https://doi.org/10.3390/ijms241310605 - 25 Jun 2023

Viewed by 948

Abstract

Novel compounds with antidepressant activity via monoamine oxidase inhibition are being sought. Among these, derivatives of 3-n-butylphthalide, a neuroprotective lactone from Apiaceae plants, may be prominent candidates. This study aimed to obtain the oxidation products of 3-n-butylphthalide and screen them regarding their activity against the monoamine oxidase A (MAO-A) isoform. Such activity of these compounds has not been previously tested. To obtain the metabolites, we used fungi as biocatalysts because of their high oxidative capacity. Overall, 37 strains were used, among which Penicillium and Botrytis spp. were the most efficient, leading to the obtaining of three main products: 3-n-butyl-10-hydroxyphthalide, 3-n-butylphthalide-11-oic acid, and 3-n-butyl-11-hydroxyphthalide, with a total yield of 0.38–0.82 g per g of the substrate, depending on the biocatalyst used. The precursor–3-n-butylphthalide and abovementioned metabolites inhibited the MAO-A enzyme; the most active was the carboxylic acid derivative of the lactone with inhibitory constant (K_i) < 0.001 µmol/L. The in silico prediction of the drug-likeness of the metabolites matches the assumptions of Lipinski, Ghose, Veber, Egan, and Muegge. All the compounds are within the optimal range for the lipophilicity value, which is connected to adequate permeability and solubility. Full article

(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 3.0)

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17 pages, 47282 KiB

Open AccessArticle

Investigation of Anticancer Properties of Monoterpene-Aminopyrimidine Hybrids on A2780 Ovarian Cancer Cells

by Viktória Nagy, Raji Mounir, Gábor J. Szebeni, Zsolt Szakonyi, Nikolett Gémes, Renáta Minorics, Péter Germán and István Zupkó

Int. J. Mol. Sci. 2023, 24(13), 10581; https://doi.org/10.3390/ijms241310581 - 24 Jun 2023

Cited by 1 | Viewed by 1192

Abstract

The present study aimed to characterize the antiproliferative and antimetastatic properties of two recently synthesized monoterpene-aminopyrimidine hybrids (1 and 2) on A2780 ovary cancer cells. Both agents exerted a more pronounced cell growth inhibitory action than the reference agent cisplatin, as determined by the MTT assay. Tumor selectivity was assessed using non-cancerous fibroblast cells. Hybrids 1 and 2 induced changes in cell morphology and membrane integrity in A2780 cells, as evidenced by Hoechst 33258–propidium iodide fluorescent staining. Cell cycle analysis by flow cytometry revealed substantial changes in the distribution of A2780 ovarian cancer cells, with an increased rate in the subG1 and G2/M phases, at the expense of the G1 cell population. Moreover, the tested molecules accelerated tubulin polymerization in a cell-free in vitro system. The antimetastatic properties of both tested compounds were investigated by wound healing and Boyden chamber assays after 24 and 48 h of incubation. Treatment with 1 and 2 resulted in time- and concentration-dependent inhibition of migration and invasion of A2780 cancer cells. These results support that the tested agents may be worth of further investigation as promising anticancer drug candidates. Full article

(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 3.0)

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18 pages, 3966 KiB

Open AccessArticle

Unraveling Membrane-Disruptive Properties of Sodium Lauroyl Lactylate and Its Hydrolytic Products: A QCM-D and EIS Study

by Negin Gooran, Sue Woon Tan, Bo Kyeong Yoon and Joshua A. Jackman

Int. J. Mol. Sci. 2023, 24(11), 9283; https://doi.org/10.3390/ijms24119283 - 25 May 2023

Cited by 2 | Viewed by 1676

Abstract

Membrane-disrupting lactylates are an important class of surfactant molecules that are esterified adducts of fatty acid and lactic acid and possess industrially attractive properties, such as high antimicrobial potency and hydrophilicity. Compared with antimicrobial lipids such as free fatty acids and monoglycerides, the membrane-disruptive properties of lactylates have been scarcely investigated from a biophysical perspective, and addressing this gap is important to build a molecular-level understanding of how lactylates work. Herein, using the quartz crystal microbalance–dissipation (QCM-D) and electrochemical impedance spectroscopy (EIS) techniques, we investigated the real-time, membrane-disruptive interactions between sodium lauroyl lactylate (SLL)—a promising lactylate with a 12-carbon-long, saturated hydrocarbon chain—and supported lipid bilayer (SLB) and tethered bilayer lipid membrane (tBLM) platforms. For comparison, hydrolytic products of SLL that may be generated in biological environments, i.e., lauric acid (LA) and lactic acid (LacA), were also tested individually and as a mixture, along with a structurally related surfactant (sodium dodecyl sulfate, SDS). While SLL, LA, and SDS all had equivalent chain properties and critical micelle concentration (CMC) values, our findings reveal that SLL exhibits distinct membrane-disruptive properties that lie in between the rapid, complete solubilizing activity of SDS and the more modest disruptive properties of LA. Interestingly, the hydrolytic products of SLL, i.e., the LA + LacA mixture, induced a greater degree of transient, reversible membrane morphological changes but ultimately less permanent membrane disruption than SLL. These molecular-level insights support that careful tuning of antimicrobial lipid headgroup properties can modulate the spectrum of membrane-disruptive interactions, offering a pathway to design surfactants with tailored biodegradation profiles and reinforcing that SLL has attractive biophysical merits as a membrane-disrupting antimicrobial drug candidate. Full article

(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 3.0)

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16 pages, 5945 KiB

Open AccessArticle

Ethyl Gallate Inhibits Bovine Viral Diarrhea Virus by Promoting IFITM3 Expression, Lysosomal Acidification and Protease Activity

by Linlin Zhang, Guanghui Yang, Jun Wang, Jialu Zhang, Keyuan Chen, Xiaoran Xiong, Yaohong Zhu, Chuang Xu and Jiufeng Wang

Int. J. Mol. Sci. 2023, 24(10), 8637; https://doi.org/10.3390/ijms24108637 - 12 May 2023

Viewed by 1604

Abstract

Bovine viral diarrhea virus (BVDV) is a highly contagious viral disease which causes economic losses to the cattle industry. Ethyl gallate (EG) is a phenolic acid derivative which has various potentials to modulate the host response to pathogens, such as via antioxidant activity, antibacterial activity, inhibition of the production of cell adhesion factors, and so on. This study aimed to evaluate if EG influences BVDV infection in Madin-Darby Bovine Kidney (MDBK) cells, and to understand the antiviral mechanism. Data indicated that EG effectively inhibited BVDV infection by co-treatment and post-treatment in MDBK cells with noncytotoxic doses. In addition, EG suppressed BVDV infection at an early stage of the viral life cycle by blocking entry and replication steps but not viral attachment and release. Moreover, EG strongly inhibited BVDV infection by promoting interferon-induced transmembrane protein 3 (IFITM3) expression, which localized to the cytoplasm. The protein level of cathepsin B was significantly reduced by BVDV infection, whereas with treatment with EG, it was significantly enhanced. The fluorescence intensities of acridine orange (AO) staining were significantly decreased in BVDV-infected cells but increased in EG-treated cells. Finally, Western blot and immunofluorescence analyses demonstrated that EG treatment significantly enhanced the protein levels of autophagy markers LC3 and p62. Chloroquine (CQ) significantly increased IFITM3 expression, and Rapamycin significantly decreased it. Thus, EG may regulate IFITM3 expression through autophagy. Our results showed that EG could have a solid antiviral activity on BVDV replication in MDBK cells via increased IFITM3 expression, lysosomal acidification, protease activity, and regulated autophagy. EG might have value for further development as an antiviral agent. Full article

(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 3.0)

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19 pages, 4806 KiB

Open AccessArticle

Experimental Studies on the Thermal Properties and Decomposition Course of a Novel Class of Heterocyclic Anticancer Drug Candidates

by Marta Worzakowska, Małgorzata Sztanke and Krzysztof Sztanke

Int. J. Mol. Sci. 2023, 24(7), 6190; https://doi.org/10.3390/ijms24076190 - 24 Mar 2023

Cited by 1 | Viewed by 1090

Abstract

The experimental studies on the thermal properties and decomposition course of a novel class of potential anticancer drugs (1–5) containing in their heterobicyclic structures the asymmetrical triazine template were performed with the use of differential scanning calorimetry (DSC) and simultaneous thermogravimetry/differential scanning calorimetry (TG/DTG/DSC) coupled online with Fourier transform infrared spectroscopy (FTIR) and quadrupole mass spectrometry (QMS) in inert and oxidizing conditions. All the compounds were thermally characterized in detail for the first time in this article. The DSC studies proved that the melting points of the tested compounds depended on the position and type of the substituent at the phenyl moiety, whereas they did not depend on the furnace atmosphere. All the tested polynitrogenated heterocycles proved to be molecules with high thermal stability in both atmospheres, and most of them (1, 3–5) were more stable in oxidizing conditions, which indicated the formation of a more thermally stable form of the compounds when interacting with oxygen. The simultaneous TG/FTIR/QMS analyses confirmed that their pyrolysis process occurred in one main stage resulting in the emission of volatiles such as NH₃, HNCO, HCN, CO, CO₂, H₂O, NO₂, aromatic amine derivatives, alkenes (for compounds 1–5), and HCl (for the compound 5). On the other hand, the oxidative decomposition process was more complicated and proceeded in two main stages leading to the emission of NH₃, CO₂, CO, HCN, HNCO, H₂O, some aromatics (for compounds 1–5), HCl (for compounds 3–5) as well as the additional volatiles such as N₂, NO₂, NH₂OH, and (CN)₂. The type of the formed volatiles indicated that the decomposition process of the studied heterocycles under the influence of heating was initiated by the radical mechanism. Their decomposition was related to the symmetric cleavage of C–N and C–C bonds (inert conditions) and additional reaction of the volatiles and residues with oxygen (oxidizing conditions). Full article

(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 3.0)

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13 pages, 4272 KiB

Open AccessArticle

Stabilization of the Dimeric State of SARS-CoV-2 Main Protease by GC376 and Nirmatrelvir

by Alessandro Paciaroni, Valeria Libera, Francesca Ripanti, Andrea Orecchini, Caterina Petrillo, Daniela Francisci, Elisabetta Schiaroli, Samuele Sabbatini, Anna Gidari, Elisa Bianconi, Antonio Macchiarulo, Rohanah Hussain, Lucia Silvestrini, Paolo Moretti, Norhan Belhaj, Matteo Vercelli, Yessica Roque, Paolo Mariani, Lucia Comez and Francesco Spinozzi

Int. J. Mol. Sci. 2023, 24(7), 6062; https://doi.org/10.3390/ijms24076062 - 23 Mar 2023

Cited by 3 | Viewed by 2103

Abstract

The main protease (Mpro or 3CLpro) is an enzyme that is evolutionarily conserved among different genera of coronaviruses. As it is essential for processing and maturing viral polyproteins, Mpro has been identified as a promising target for the development of broad-spectrum drugs against coronaviruses. Like SARS-CoV and MERS-CoV, the mature and active form of SARS-CoV-2 Mpro is a dimer composed of identical subunits, each with a single active site. Individual monomers, however, have very low or no catalytic activity. As such, inhibition of Mpro can be achieved by molecules that target the substrate binding pocket to block catalytic activity or target the dimerization process. In this study, we investigated GC376, a transition-state analog inhibitor of the main protease of feline infectious peritonitis coronavirus, and Nirmatrelvir (NMV), an oral, bioavailable SARS-CoV-2 Mpro inhibitor with pan-human coronavirus antiviral activity. Our results show that both GC376 and NMV are capable of strongly binding to SARS-CoV-2 Mpro and altering the monomer-dimer equilibrium by stabilizing the dimeric state. This behavior is proposed to be related to a structured hydrogen-bond network established at the Mpro active site, where hydrogen bonds between Ser1’ and Glu166/Phe140 are formed in addition to those achieved by the latter residues with GC376 or NMV. Full article

(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 3.0)

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Review

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15 pages, 937 KiB

Open AccessReview

Changes in Expression and Function of Placental and Intestinal P-gp and BCRP Transporters during Pregnancy

by Péter Szatmári and Eszter Ducza

Int. J. Mol. Sci. 2023, 24(17), 13089; https://doi.org/10.3390/ijms241713089 - 23 Aug 2023

Cited by 2 | Viewed by 1462

Abstract

ABC transporters are ubiquitous in the human body and are responsible for the efflux of drugs. They are present in the placenta, intestine, liver and kidney, which are the major organs that can affect the pharmacokinetic and pharmacologic properties of drugs. P-gp and BCRP transporters are the best-characterized transporters in the ABC superfamily, and they have a pivotal role in the barrier tissues due to their efflux mechanism. Moreover, during pregnancy, drug efflux is even more important because of the developing fetus. Recent studies have shown that placental and intestinal ABC transporters have great importance in drug absorption and distribution. Placental and intestinal P-gp and BCRP show gestational-age-dependent expression changes, which determine the drug concentration both in the mother and the fetus during pregnancy. They may have an impact on the efficacy of antibiotic, antiviral, antihistamine, antiemetic and oral antidiabetic therapies. In this review, we would like to provide an overview of the pharmacokinetically relevant expression alterations of placental and intestinal ABC transporters during pregnancy. Full article

(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 3.0)

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18 pages, 2653 KiB

Open AccessReview

Melanocortin 1 Receptor (MC1R): Pharmacological and Therapeutic Aspects

by Yoonwoo Mun, Woohyun Kim and Dongyun Shin

Int. J. Mol. Sci. 2023, 24(15), 12152; https://doi.org/10.3390/ijms241512152 - 29 Jul 2023

Cited by 3 | Viewed by 3042

Abstract

Melanocortins play crucial roles in regulating the stress response, inflammation, and skin pigmentation. In this review, we focus on the melanocortin 1 receptor (MC1R), a G protein-coupled receptor primarily known for regulating skin pigmentation and exhibiting anti-inflammatory effects. First, we provide an overview of the structure, signaling pathways, and related diseases of MC1R. Next, we discuss the potential therapeutic use of synthetic peptides and small molecule modulators of MC1R, highlighting the development of various drugs that enhance stability through amino acid sequence modifications and small molecule drugs to overcome limitations associated with peptide characteristics. Notably, MC1R-targeted drugs have applications beyond skin pigmentation-related diseases, which predominantly affect MC1R in melanocytes. These drugs can also be useful in treating inflammatory diseases with MC1R expression present in various cells. Our review underscores the potential of MC1R-targeted drugs to treat a wide range of diseases and encourages further research in this area. Full article

(This article belongs to the Special Issue Advances in Molecular Activity of Potential Drugs 3.0)

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