ChemMedChem最新文献_第5页

IF 3.6 4区医学

ChemMedChem Pub Date : 2025-02-26 DOI: 10.1002/cmdc.202401017

Michael M. Hann

引用次数: 0

Peptides Corresponding to the Receptor-Binding Domain (RBD) of Several SARS-CoV-2 Variants Of Concern Prevent Recognition of the Human ACE2 Receptor and Consecutive Cell Infections 几种受关注的SARS-CoV-2变体的受体结合域（RBD）对应的肽阻止人类ACE2受体的识别和连续的细胞感染。

IF 3.6 4区医学

ChemMedChem Pub Date : 2025-02-25 DOI: 10.1002/cmdc.202400973

Mandy Schwarze, Alexandra Brakel, Ralf Hoffmann, Andor Krizsan

{"title":"Peptides Corresponding to the Receptor-Binding Domain (RBD) of Several SARS-CoV-2 Variants Of Concern Prevent Recognition of the Human ACE2 Receptor and Consecutive Cell Infections","authors":"Mandy Schwarze, Alexandra Brakel, Ralf Hoffmann, Andor Krizsan","doi":"10.1002/cmdc.202400973","DOIUrl":"10.1002/cmdc.202400973","url":null,"abstract":"New strategies are needed to prevent and control upcoming outbreaks of SARS-CoV-2 infections, independent of vaccination. SARS-CoV-2 binds to the human ACE-2 receptor through the receptor binding domain (RBD) of the spike (S) protein, allowing the virus to enter human cells and begin replication. When peptides corresponding to four regions of RBD containing previously reported ACE-2 interaction sites were explored, the sequence 392 to 421, peptide p392wt, bound strongly to ACE-2 and inhibited wild-type RBD binding to ACE-2. Interestingly, p392 peptides corresponding to mutated sequences from different SARS-CoV-2 VOCs, including the current VOC BA.5 and KP.3, bound less strongly to ACE-2, but showed partially better inhibition of the ACE-2 interaction of all tested RBDs. When studied in a SARS-CoV-2 pseudovirus assay, the p392 peptides showed a good inhibition rate of 98.8±8.1 % at a peptide concentration of ~244 μmol/L, while none of the p392 peptides inhibited antibody binding to the RBD, suggesting that peptide treatment is sufficient in the presence of anti-RBD antibodies. Interestingly these peptides were active in the presence of diluted human serum and non-toxic to human cell lines.","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":"20 7","pages":""},"PeriodicalIF":3.6,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/cmdc.202400973","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143490206","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Structural Insights Into Galectin-3 Recognition of a Selenoglycomimetic. 半乳糖凝集素-3识别硒糖模拟物的结构见解。

IF 3.6 4区医学

ChemMedChem Pub Date : 2025-02-25 DOI: 10.1002/cmdc.202401005

Maria Pia Lenza, Cristina Di Carluccio, Ferran Nieto-Fabregat, Luciano Pirone, Rita Russo, Sonia Di Gaetano, Domenica Capasso, Alessia Stornaiuolo, Alfonso Iadonisi, Michele Saviano, Roberta Marchetti, Emilia Pedone, Alba Silipo

{"title":"Structural Insights Into Galectin-3 Recognition of a Selenoglycomimetic.","authors":"Maria Pia Lenza, Cristina Di Carluccio, Ferran Nieto-Fabregat, Luciano Pirone, Rita Russo, Sonia Di Gaetano, Domenica Capasso, Alessia Stornaiuolo, Alfonso Iadonisi, Michele Saviano, Roberta Marchetti, Emilia Pedone, Alba Silipo","doi":"10.1002/cmdc.202401005","DOIUrl":"10.1002/cmdc.202401005","url":null,"abstract":"Chimera-type galectin-3 (Gal-3) is a β-galactoside-binding protein containing a single conserved carbohydrate-recognition domain, crucial in fibrosis and carcinogenesis. Selenium-based Gal-3 inhibitors have emerged as promising therapeutic agents, particularly for treating neoplastic diseases. Among them, a seleno-digalactoside (SeDG) substituted with a benzyl group at position 3 of both saccharide residues (benzyl 3,3'-seleno-digalactoside, SeDG-Bn), attracted considerable attention for its selectivity and potent inhibitory efficacy against Gal-3. NMR spectroscopy and molecular dynamics simulations were combined to investigate the binding of SeDG-Bn to Gal-3 at the molecular level. This approach revealed the recognized epitope, the binding mode within Gal-3 binding pocket and enabled the generation of a 3D model of the complex. Our findings show that the presence of a single benzyl group establishes hydrophobic contacts with amino acids in Gal-3 β-sheets S2 and S3, crucially enhancing the binding affinity compared to unmodified SeDG. The digalactose backbone orientation in Gal-3 binding site is partially modified by the benzyl group with respect to complexes with lactosamine and SeDG. These results provide valuable insights into the design of more potent and selective inhibitors for Gal-3, potentially contributing to new therapeutic strategies for conditions such as cancer and fibrosis.","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202401005"},"PeriodicalIF":3.6,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143490209","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Discovery of Novel 2-Oxindoles as Compounds with Antiglaucoma Activity. 具有抗青光眼和神经保护活性的新型2-氧吲哚化合物的发现。

IF 3.6 4区医学

ChemMedChem Pub Date : 2025-02-23 DOI: 10.1002/cmdc.202400977

Roman O Eremeev, Alexander M Efremov, Daria V Zakharova, Olga V Beznos, Elena V Sokolova, Konstantin Y Kalitin, Olga Y Mukha, Daria V Vinogradova, Ivan M Veselov, Pavel N Shevtsov, Ludmila G Dubova, Denis A Babkov, Alexander A Spasov, Elena F Shevtsova, Natalia A Lozinskaya

{"title":"Discovery of Novel 2-Oxindoles as Compounds with Antiglaucoma Activity.","authors":"Roman O Eremeev, Alexander M Efremov, Daria V Zakharova, Olga V Beznos, Elena V Sokolova, Konstantin Y Kalitin, Olga Y Mukha, Daria V Vinogradova, Ivan M Veselov, Pavel N Shevtsov, Ludmila G Dubova, Denis A Babkov, Alexander A Spasov, Elena F Shevtsova, Natalia A Lozinskaya","doi":"10.1002/cmdc.202400977","DOIUrl":"10.1002/cmdc.202400977","url":null,"abstract":"Oxindole-based natural indoles analogues retain the rigidity and size of the original indole ring system whilst introducing more 3-dimensionality and potential increased water solubility. We report the first preparation of a diverse series of new melatonin analogues 4, 6, 11, 12 based on 3-hydroxy-2-oxindoles (11) and hydroxy-free 2-oxindoles (4, 6, 12) and evaluated their ability to reduce intraocular pressure as well as their neuroprotective and antioxidant properties. Reductive amination was used to obtain new 5-(benzylamino)-substituted (indolin-3-yl)acetonitriles 11 and (indolin-3-yl)acetic acids 12 with high yields. Compounds 4 a, c, 6 a and 11 a, d, h, j-l demonstrated IOP reduction effect in range 15-27 % similar to the effect of reference compounds melatonin and timolol (12 % and 18 % reduction, respectively). 5-(Benzylamino)-substituted 3-hydroxy-2-oxindoles 11, unlike compounds 4, 6, inhibited lipid peroxidation in range 2.075-13.012 μM. Inhibition of NQO2 associated with antioxidant properties of melatonin was also evaluated for synthesized compounds and it was found that compound 11 h showed the best NQO2 inhibitory activity with an IC50=39 μM (vs. melatonin IC50=64 μM). All synthesized compounds 4, 6, 11, 12 at a concentration of 30 μM do not possess the mitochondrial toxicity. Moreover, no disruption of tubulin polymerization was observed even in the presence of 100 μM of the compounds. Thus, 3-hydroxy-2-oxindole derivatives 11 can be used for drug design of first-in-class antiglaucoma drugs with antioxidant and neuroprotective properties.","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400977"},"PeriodicalIF":3.6,"publicationDate":"2025-02-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143481918","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Cerium(IV)-Catalyzed Allylic Oxidation of 3-Sulfolene: An Efficient Tool for the Synthesis of 4-Substituted Sulfol-2-Enes with Antiproliferative Activity. 铈（IV）催化3-亚砜烯丙基氧化：合成具有抗增殖活性的4-取代2-亚砜烯的有效工具。

IF 3.6 4区医学

ChemMedChem Pub Date : 2025-02-23 DOI: 10.1002/cmdc.202500010

Elżbieta Łastawiecka, Magdalena Mizerska-Kowalska, Adrianna Sławińska-Brych, Karolina Mrozik, Barbara Zdzisińska

{"title":"Cerium(IV)-Catalyzed Allylic Oxidation of 3-Sulfolene: An Efficient Tool for the Synthesis of 4-Substituted Sulfol-2-Enes with Antiproliferative Activity.","authors":"Elżbieta Łastawiecka, Magdalena Mizerska-Kowalska, Adrianna Sławińska-Brych, Karolina Mrozik, Barbara Zdzisińska","doi":"10.1002/cmdc.202500010","DOIUrl":"10.1002/cmdc.202500010","url":null,"abstract":"Cyclic sulfones play an important role in the field of drug discovery and design due to their valuable properties and their broad range of applications. Herein, we report an efficient cerium(IV)-catalyzed allylic oxidation of a simple 3-sulfolene. This process provides a straightforward and facile approach to sulfol-2-en-4-one, a versatile synthetic intermediate. Notably, this study represents the first instance of cerium catalysis employed in allylic oxidation. Furthermore, we demonstrated the transformation of sulfol-2-en-4-one into 4-substituted sulfol-2-enes with therapeutic applications. In silico analysis performed using the SwissAdme tool indicated that the obtained 4-amine (7 a-7 d) and 4-carbamate (9 a and 9 b) derivatives of sulfol-2-en-4-one met the rules imposed on small-molecule drugs. Moreover, these compounds inhibited the proliferation (MTT assay) of colon cancer and osteosarcoma cells. Notably, compounds 7 b and 7 c, which exhibited the best selectivity index (ratio of IC50 calculated for normal and cancer cells), induced cell cycle arrest and apoptosis (flow cytometry analysis). Considering the present results, the cerium-catalyzed allylic oxidation of sulfol-3-ene proves to be an efficient and practical method for synthesizing sulfol-2-en-4-one, a versatile chemical synthon for developing sulfolane derivatives, including those with promising anticancer potential.","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202500010"},"PeriodicalIF":3.6,"publicationDate":"2025-02-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143481910","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Discovery of CCR8 Antagonist IDOR-1136-5177 for the Treatment of Cancer. 发现CCR8拮抗剂IDOR-1136-5177用于治疗癌症。

IF 3.6 4区医学

ChemMedChem Pub Date : 2025-02-23 DOI: 10.1002/cmdc.202400968

Stefan Diethelm, Luboš Remeň, Hamed Aissaoui, Cédric Leroy, Alexia Chavanton-Arpel, Luca Docci, Swen Seeland, François Lehembre, Olivier Corminboeuf

{"title":"Discovery of CCR8 Antagonist IDOR-1136-5177 for the Treatment of Cancer.","authors":"Stefan Diethelm, Luboš Remeň, Hamed Aissaoui, Cédric Leroy, Alexia Chavanton-Arpel, Luca Docci, Swen Seeland, François Lehembre, Olivier Corminboeuf","doi":"10.1002/cmdc.202400968","DOIUrl":"https://doi.org/10.1002/cmdc.202400968","url":null,"abstract":"CCR8 is a GPCR mainly expressed in tumor-infiltrating T-regulatory cells (Treg) and high CCR8 expression is associated with poor prognosis in cancer. CCR8 and its ligand CCL1 may be involved in Treg recruitment, conversion and/or immunosuppressive function. Recently, pharmacological inhibition of CCR8 in mouse models has been reported to result in tumor regression and small molecule inhibitors of CCR8 have entered the clinic. Aiming to find a new class of CCR8 antagonists, a high throughput screen (HTS) of the Idorsia compound library was performed. HTS hits with a promising profile were identified and subsequent characterization revealed hERG as a key parameter that required further optimization. We reasoned that a strategy focused on discrete structural modifications would offer significant potential to reduce hERG inhibition. The lead optimization campaign we report led to the identification of compound 52 (IDOR-1136-5177), a highly potent CCR8 antagonist representing a new chemical class of CCR8 inhibitors with excellent in vitro and in vivo properties.","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400968"},"PeriodicalIF":3.6,"publicationDate":"2025-02-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143481912","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Novel Sulfonamide-Sydnone Hybrids: Complementary Insight into Anti-Inflammatory Action, Anti-SARS-CoV-2 Activity, Human Serum Albumin Interaction, and in silico Analysis. 新型磺胺-突触复合物：抗炎作用、抗sars - cov -2活性、人血清白蛋白相互作用和硅分析的互补见解

IF 3.6 4区医学

ChemMedChem Pub Date : 2025-02-23 DOI: 10.1002/cmdc.202400697

Igor Resendes Barbosa, Mayara Alves Amorim, Vitor Hélio de Souza Oliveira, Eunice André, Guilherme Pereira Guedes, Otávio Augusto Chaves, Carlos Serpa, Natalia Fintelman-Rodrigues, Carolina Q Sacramento, Thiago Moreno L Souza, Carlos Mauricio R Sant'Anna, Aurea Echevarria

{"title":"Novel Sulfonamide-Sydnone Hybrids: Complementary Insight into Anti-Inflammatory Action, Anti-SARS-CoV-2 Activity, Human Serum Albumin Interaction, and in silico Analysis.","authors":"Igor Resendes Barbosa, Mayara Alves Amorim, Vitor Hélio de Souza Oliveira, Eunice André, Guilherme Pereira Guedes, Otávio Augusto Chaves, Carlos Serpa, Natalia Fintelman-Rodrigues, Carolina Q Sacramento, Thiago Moreno L Souza, Carlos Mauricio R Sant'Anna, Aurea Echevarria","doi":"10.1002/cmdc.202400697","DOIUrl":"https://doi.org/10.1002/cmdc.202400697","url":null,"abstract":"Acute lung injury (ALI) is a severe condition often seen in intensive care unit patients. Due to limited treatment options, ALI is linked to high rates of mortality and morbidity. Bacterial and viral infections are significant contributors to ALI. For instance, severe acute respiratory syndrome-coronavirus-2 (SARS-CoV-2) infection can lead to a strong inflammatory response that may progress to ALI, a leading cause of death in COVID-19 cases. Prior research has demonstrated that sulfonamides and sydnones exhibit anti-inflammatory and antiviral properties, which has led us to develop compounds containing both scaffolds. Most of the new sulfonamide-sydnone hybrids are expected to be orally bioavailable based on in silico ADME predictions. They effectively suppressed the development of ALI in lipopolysaccharide (LPS)-challenged mice and inhibited viral replication in Calu-3 cells, with minimal cytotoxicity in non-infected Calu-3 and Vero E6 cells. Molecular docking investigations indicated some possible viral targets for the action of the sydnones, highlighting the possible interaction with non-structural proteins of SARS-CoV-2. Additionally, combined experimental and theoretical studies indicated that the new compounds can strongly interact with human serum albumin, suggesting a possible extended residence time in the human bloodstream.","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400697"},"PeriodicalIF":3.6,"publicationDate":"2025-02-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143481924","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Replacing a Cereblon Ligand by a DDB1 and CUL4 Associated Factor 11 (DCAF11) Recruiter Converts a Selective Histone Deacetylase 6 PROTAC into a Pan-Degrader. 用DDB1和CUL4相关因子11 （DCAF11）招募者替代小脑配体将选择性组蛋白去乙酰化酶6 PROTAC转化为泛降解物。

IF 3.6 4区医学

ChemMedChem Pub Date : 2025-02-20 DOI: 10.1002/cmdc.202500035

Felix Feller, Heiko Weber, Martina Miranda, Irina Honin, Maria Hanl, Finn K Hansen

{"title":"Replacing a Cereblon Ligand by a DDB1 and CUL4 Associated Factor 11 (DCAF11) Recruiter Converts a Selective Histone Deacetylase 6 PROTAC into a Pan-Degrader.","authors":"Felix Feller, Heiko Weber, Martina Miranda, Irina Honin, Maria Hanl, Finn K Hansen","doi":"10.1002/cmdc.202500035","DOIUrl":"10.1002/cmdc.202500035","url":null,"abstract":"Proteolysis-targeting chimeras (PROTACs) have recently gained popularity as targeted protein degradation (TPD) promises to overcome the limitations of occupancy-driven pharmacology. However, most degraders rely on a small number of E3 ligases. In this study, we present the first-in-class histone deacetylase (HDAC) PROTACs recruiting the DDB1- and CUL4- associated factor 11 (DCAF11). We established a synthesis route entirely on solid-phase to prepare a set of eleven degraders. The long and flexible spacer bearing FF2039 (1j) showed significant HDAC1 and 6 degradation in combination with cytotoxicity against the multiple myeloma cell line MM.1S. Further investigations revealed that 1j was also able to degrade HDAC isoforms of class I, IIa and IIb. Compared to our previously published cereblon-recruiting HDAC6 selective PROTAC A6, we succesfully transformed the selective degrader into a pan-HDAC degrader by switching the recruited E3 ligase. A detailed profiling of the anticancer properties of 1j demonstrated its significant antiproliferative activity against both hematological and solid cancer cell lines, driven by cell cycle arrest and apoptosis induction.","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202500035"},"PeriodicalIF":3.6,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143456350","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

An Effective Reaction-Based Virtual Screening Method to Discover New CDK8 Ligands. 一种有效的基于反应的虚拟筛选方法发现新的CDK8配体

IF 3.6 4区医学

ChemMedChem Pub Date : 2025-02-19 DOI: 10.1002/cmdc.202400825

Wei Chen, Hanlin Fang, Huan He, Jing Ping, Jianxin Ge

{"title":"An Effective Reaction-Based Virtual Screening Method to Discover New CDK8 Ligands.","authors":"Wei Chen, Hanlin Fang, Huan He, Jing Ping, Jianxin Ge","doi":"10.1002/cmdc.202400825","DOIUrl":"10.1002/cmdc.202400825","url":null,"abstract":"Cyclin Dependent Kinase 8 (CDK8) is a valuable drug target for cancer suppression. Through an effective reaction-based virtual screening method consisting of pharmacophore modeling, Scifinder database searches, and energy evaluations, a number of new type II CDK8 ligands were discovered with comparable or better binding free energies than the ones reported in literature. In this method, a pharmacophore model, derived from seven crystal structures of CDK8 and type II ligands, was able to catch the key interactions for ligands binding at the ATP binding site of CDK8. This model then was used to screen the results from Scifinder database searches that apply chemical reaction rules in the search cycles, and the output compounds were evaluated and ranked first by a fast energy estimation method and then by the VM2 free energy calculation method. Among the top discovered ligands, three have lower Kd values against CDK8 than a potent reference ligand, and compound F (3-[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]-1-(8-hydroxynaphthalen-1-yl)urea) is the most potent one with an Kd value of 7.5 nM. Compound F has a relatively small molecular structure, receives both strong van der Waals energy and optimized overall electrostatic energy when binding with CDK8, and deserves to be a promising lead compound for further development. This effective virtual screening method and the novel compounds found in this work have implications for CDK8 drug discovery.","PeriodicalId":147,"journal":{"name":"ChemMedChem","volume":" ","pages":"e202400825"},"PeriodicalIF":3.6,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143456347","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Metal-Catalyzed Cross-Coupling for the Synthesis of β-Lactam Drugs and Related Chemical Probes. 金属催化交偶联合成β-内酰胺类药物及相关化学探针。

IF 3.6 4区医学

ChemMedChem Pub Date : 2025-02-18 DOI: 10.1002/cmdc.202400960

Jules Bresson, Katie Burke, Mélanie Ethève-Quelquejeu, Laura Iannazzo, Kevin Cariou

引用次数: 0