Bioorganic Chemistry最新文献

{"title":"Design, synthesis, and in vitro and in vivo anti-drug resistant cervical cancer activity of novel licochalcone A derivatives based on dual targeting of VEGFR-2/P-gp","authors":"Zheng Yang ,&nbsp;Zhengye Liu ,&nbsp;Mourboul Ablise ,&nbsp;Juan Jia ,&nbsp;Aikebaier Maimaiti ,&nbsp;Zhi-Yuan Lv ,&nbsp;Zuohelaguli Mutalipu ,&nbsp;Tong Yan ,&nbsp;Yu Wang ,&nbsp;Aizitiaili Aihaiti ,&nbsp;Jinyao Li ,&nbsp;Zhijian Li ,&nbsp;Shixia Huo","doi":"10.1016/j.bioorg.2025.108639","DOIUrl":"10.1016/j.bioorg.2025.108639","url":null,"abstract":"<div><div>Targeting the VEGF/VEGFR-2 signaling pathway is considered to be an effective strategy for the treatment of cervical cancer, and multidrug resistance in cervical cancer has now been widely demonstrated to be caused by the upregulation of P-gp. This study designed and synthesized a series of novel licochalcone A derivatives using licochalcone A as the lead compound and VEGFR-2 and P-gp as the action targets. The principle of active substructure splicing was employed to design and synthesize a series of novel licochalcone A derivatives and to preliminarily evaluate the in vitro and ex vivo anti-cancer active effects of the target compounds. The results showed that the IC₅₀ values of candidate compound A20 against HeLa and HeLa/DDP cells were 3.19 ± 0.08 and 3.69 ± 0.53 μΜ, respectively, with a resistance index (RI) of 1.16, and there was showed minimal development of resistance. In addition, A20 was able to form a hydrogen bonding force with VEGFR-2 and P-gp, inhibit phosphorylation of VEGFR-2 and downstream PI3K/AKT signaling pathway proteins, induce apoptosis, block cells in the S phase, inhibit invasive migration, inhibit tubulogenesis in HUVEC cells and inhibit efflux of rhodamine 123 in HeLa/DDP cells. In addition, A20 at 200 mg/kg orally had an acceptable safety profile in acute toxicity assays. The antitumor inhibitory effects on tumor growth in the HeLa/DDP cell xenograft tumor model were 70.9 %, 72.2 %, and 89.5 % at 10, 20 and 40 mg/kg orally. These results suggest that A20 may be a potent VEGFR-2 and P-gp inhibitor with potential for treating cisplatin-resistant cervical cancer.</div></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"163 ","pages":"Article 108639"},"PeriodicalIF":4.5,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144178285","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Triple-target small molecule for PRRSV and ASFV infections","authors":"Youle Zheng ,&nbsp;Yanbin Song ,&nbsp;Jin Feng ,&nbsp;Defeng Wen ,&nbsp;Mengyu Chang ,&nbsp;Mengping Song ,&nbsp;Hua Cao ,&nbsp;Min Ling ,&nbsp;Yixin Yu ,&nbsp;Yanfei Tao ,&nbsp;Wentao Li ,&nbsp;Xu Wang","doi":"10.1016/j.bioorg.2025.108637","DOIUrl":"10.1016/j.bioorg.2025.108637","url":null,"abstract":"<div><div>Pigs are vital sources of food and biological products. However, viruses such as porcine reproductive and respiratory syndrome virus (PRRSV) and African swine fever virus (ASFV) pose significant threats to the global swine industry, resulting in substantial financial losses. Currently, there are no available drugs or effective vaccines to combat these viruses. This study presents a small molecule, denoted as C14, which demonstrates promising potential to target porcine CD163, RNA-dependent RNA polymerase (RdRp) of PRRSV, and S273R of ASFV, and exhibits activity against both PRRSV (half maximal effective concentration [EC₅₀] = 0.34 μM) and ASFV (EC₅₀ &lt; 0.1 μM). By employing the strategy of similar topological structure binding properties of protein targets (STSBPT), interactions between C14 and targets were further analysed. The results indicate that the 5-Å regions of C14 within the active pockets of these macromolecular targets exhibit highly similar structural features, which may facilitate the development of antiviral drugs. Chemical synthesis, docking simulations, and antiviral activity assays were further conducted, and it was found that the structure of C14 is devoid of redundant elements, making it a prime candidate as core scaffold for subsequent structural optimization. This study provides a valuable reference for the development of multi-target antiviral drugs against PRRSV and ASFV.</div></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"163 ","pages":"Article 108637"},"PeriodicalIF":4.5,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144169199","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Perylene tetracarboxylic acid-folate conjugated carbon quantum dots for targeted photodynamic therapy of prostate cancer","authors":"Eman Serag ,&nbsp;Sara A. Abdel Gaber ,&nbsp;Ayman A. Abdel-Shafi ,&nbsp;Mohamed E. El-Khouly","doi":"10.1016/j.bioorg.2025.108631","DOIUrl":"10.1016/j.bioorg.2025.108631","url":null,"abstract":"<div><div>This study reports the facile one-pot hydrothermal synthesis of water-soluble perylenetetracarboxylic dianhydride (PTCDA) conjugated carbon quantum dots (Per CDs) and their folate conjugate (PerFACDs), addressing the insolubility of PTCDA, a promising photosensitizer. Both CDs were thoroughly characterized using HRTEM, FTIR, Raman, and XPS techniques. Their singlet oxygen quantum yield (Φ_Δ), zeta potential, absorption and photoluminescence spectra were also studied. Their anti-human prostate cancer activity was tested using PC-3 cells as a model. The mode of cell death was investigated using flow cytometry, and their heamolytic activity and effect on the viability of normal peripheral blood mononuclear cells and were evaluated to assess the safety. The produced CDs were uniform spheres with diameters below 8 nm. At physiological pH, PerCDs exhibited a surface charge of −9 mV, while PerFACDs had −12 mV and a Φ_Δ of 0.22. The biocompatibility and cytotoxicity of the produced CDs were evaluated in vitro normal human fibroblast (HFF-1) cells, and peripheral blood cells. Both PerCDs and PerFACD showed negligible toxicity toward normal cells. To assess selective cytotoxicity, the selectivity index (SI) was calculated under dark conditions, yielding values of 1.47 for PerCDs and 2.4 for PerFACD, indicating significantly enhanced selectivity of PerFACD toward PC3 cells. Upon illumination using monochromatic 520 nm light-emitting diode (1.5 mW/cm²), a total eradication of PC-3 cells was achieved within 60 min of irradiation using Per FA CD that was significantly more potent than Per CDs. Per FA CDs-PDT induced an apoptotic cell death mode at shorter irradiation times and a necrotic one at longer durations. These findings suggest that our synthesized third generation photosensitizer Per CDs and Per FA CD hold promise as safe and effective candidates for targeted PDT of prostate cancer.</div></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"163 ","pages":"Article 108631"},"PeriodicalIF":4.5,"publicationDate":"2025-05-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144169201","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Aurora kinases, emerging critical targets for cancer treatment and related new therapeutic strategies","authors":"Sua Chung ,&nbsp;Ella Sperier ,&nbsp;Kevin Graciano ,&nbsp;Xiaoping Hu ,&nbsp;Hua Guo ,&nbsp;Jia Xu","doi":"10.1016/j.bioorg.2025.108633","DOIUrl":"10.1016/j.bioorg.2025.108633","url":null,"abstract":"<div><div>The Aurora kinases are a family of serine/threonine kinases crucial for regulating mitosis. Overexpression of the Aurora kinases has been reported in multiple cancer types. They play important roles in driving an oncogenic transformation of cancer cells by regulating their survival and proliferation, mainly because of the kinases' mitotic activity. Aurora kinase inhibitors (AKIs) were developed and tested in clinical trials and effectively suppressed many cancer types, suggesting the potential for Aurora kinases as a novel therapeutic target. Aurora kinase inhibition has also been well-documented to enhance chemotherapy effectiveness in various cancers. However, not all cancer types respond to AKIs, and the mechanisms behind the resistance are still elusive. This review will first briefly summarize the gene expression, regulation, and substrates of the Aurora Kinases, describe the function of Aurora kinases in mitosis, and then review the Aurora kinases' oncogenic roles in different cancer types as well as tumorigenesis, including cancer metabolism and anti-tumor immune evasion. In addition, we recapped the recent studies that revealed the critical role of Aurora Kinases in various cancer therapies and discussed the clinical outcomes of AKIs in combination with other types of therapies. Furthermore, we reviewed the current development of a new generation of AKI, such as PROTAC degrader. Further understanding the mechanism underlying the responsiveness of AKIs could help evaluate their effect and improve them as potential therapeutic targets.</div></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"163 ","pages":"Article 108633"},"PeriodicalIF":4.5,"publicationDate":"2025-05-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144169202","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Rationale design, synthesis and antimicrobial activity of benzimidazole-pyridinecarbonitrile conjugates: Insights into ROS-induced oxidative damage and molecular dynamics simulations","authors":"Hayam A. Abd El Salam ,&nbsp;Mostafa I. Abdelglil ,&nbsp;Eman Sabry ,&nbsp;Mohamed Abdelraof ,&nbsp;Sameh Abdelwahed ,&nbsp;Mona A. Gadallah ,&nbsp;Ahmed A. El-Rashedy ,&nbsp;Asmaa Saleh ,&nbsp;Aladdin M. Srour","doi":"10.1016/j.bioorg.2025.108627","DOIUrl":"10.1016/j.bioorg.2025.108627","url":null,"abstract":"<div><div>A new series of Benzimidazole pyridinecarbonitrile scaffolds <strong>4a-r</strong> have been designed and synthesized through a regioselective Michael addition interaction between 2-acetyl <em>N</em>-propyne-benzimidazole (<strong>1</strong>) and ylidenemalononitrile (<strong>2</strong>), facilitated by a freshly prepared sodium methoxide solution. All synthesized derivatives were assessed for their antimicrobial potential on <em>S. aureus</em> (Gram-positive), <em>P. aeruginosa</em> (Gram-negative), as well as <em>C</em><em>.</em> <em>albicans</em> (unicellular fungal). Derivatives <strong>4a</strong>, <strong>4c</strong>, <strong>4f</strong>, <strong>4</strong><strong>l</strong>, <strong>4</strong><strong>m</strong> and <strong>4q</strong> showed promising antimicrobial properties against all the tested MDR pathogens. In particular, compounds <strong>4c</strong>, <strong>4f</strong>, <strong>4</strong><strong>l</strong>, and <strong>4</strong><strong>m</strong> demonstrated brilliant inhibitory activity on <em>C</em><em>.</em> <em>albicans</em> with MIC = 10 <em>μ</em>g/mL each, a 4-fold increase compared to Amphotericin B (MIC = 40 <em>μ</em>g/mL). While compound <strong>4a</strong> presented MIC = 10 <em>μ</em>g/mL compared with ciprofloxacin (MIC = 20 <em>μ</em>g/mL) against MRSA, the MIC recorded by <strong>4c</strong> and <strong>4f</strong> against <em>P. aeruginosa</em> was 20 <em>μg/mL,</em> which equals that of ciprofloxacin. Bacterial lipid peroxidation (LPO) and antibiofilm activity and evaluation of reactive oxygen species (ROS) induced by the most potent derivatives were evaluated, revealing that derivatives <strong>4f</strong> and <strong>4</strong><strong>m</strong> demonstrated the best behavior among the tested compounds. Furthermore, molecular docking and molecular dynamics (MD) simulations validated the stability of compound <strong>4f</strong> within the catalytic binding pocket of the DNA gyrase receptor. The molecules were geometrically optimized using DFT with the B3LYP 6–21 basis set, and their electronic properties were analyzed. The study also encompassed ADME predictions and drug-likeness assessments for the new compounds.</div></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"163 ","pages":"Article 108627"},"PeriodicalIF":4.5,"publicationDate":"2025-05-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144178284","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Design of photoactivatable methylene blue-bufalin conjugate for GPX4-targeted degradation to induce ferroptosis-like death in breast cancer therapy","authors":"Xiaoman Mo ,&nbsp;Junjie Lan ,&nbsp;Yanni Wang ,&nbsp;Hang Zhong ,&nbsp;Huan He ,&nbsp;Zaichang Yang ,&nbsp;Silong Zhang ,&nbsp;Weidong Pan","doi":"10.1016/j.bioorg.2025.108629","DOIUrl":"10.1016/j.bioorg.2025.108629","url":null,"abstract":"<div><div>Bufalin is a potent antitumor agent; however, its high toxicity limits its clinical application. Here, we explored the development of a novel photosensitizer-small molecule conjugate, <strong>MB-Buf</strong>, which combines the photosensitizer methylene blue (MB) with bufalin. The goal is to achieve targeted photodegradation of GPX4 upon light activation. The compound <strong>MB-Buf</strong> integrates the photodynamic properties of MB with the antitumor activity of bufalin. Under light irradiation, it generates reactive oxygen species (ROS), exhibiting photodynamic therapeutic activity, while its toxicity toward normal cells is reduced by 15-fold compared to bufalin alone. In vivo studies using a 4 T1-Luci xenograft mouse model demonstrated that <strong>MB-Buf</strong>, in combination with light irradiation, significantly inhibits tumor growth. These findings support <strong>MB-Buf</strong> as a promising new cancer treatment strategy, offering a potential approach to overcome the limitations of conventional therapies.</div></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"163 ","pages":"Article 108629"},"PeriodicalIF":4.5,"publicationDate":"2025-05-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144169200","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Structure activity relationship of Aristolochic acid analogues: Inhibitory effect on human and rat gonadal 3β-Hydroxysteroid dehydrogenases","authors":"Weijian Zhu ,&nbsp;Zhuoqi Chen ,&nbsp;Shaowei Wang ,&nbsp;Yang Zhu ,&nbsp;Ren-shan Ge","doi":"10.1016/j.bioorg.2025.108630","DOIUrl":"10.1016/j.bioorg.2025.108630","url":null,"abstract":"<div><div><em>Aristolochia</em> species have been used in traditional Chinese medicine for over 1500 years to treat gynecological disorders. Recent pharmacological efforts focus on developing safer aristolochic acid derivatives (AAs) to retain therapeutic efficacy while minimizing toxicity. Human 3β-hydroxysteroid dehydrogenase 2 (h3β-HSD2) catalyzes the formation of precursors for sex hormones and corticosteroids, which play critical role in endocrine disorders such as polycystic ovary syndrome (PCOS) and Cushing's syndrome. This study aimed to evaluate AAs for their inhibitory effects on h3β-HSD2 and compared it with rat testicular 3β-HSD1. The inhibitory strength on h3β-HSD2 was AAB (IC₅₀, 18.31 μM) &gt; aristololactam I (28.52 μM) &gt; AAC (39.73 μM) &gt; AAD (164.76 μM). The inhibitory strength on rat 3β-HSD1 was AAB (IC₅₀, 17.52 μM) &gt; AAI (31.37 μM) &gt; AAC (37.32 μM) &gt; aristolone (89.66 μM). Docking showed that all chemicals bind to NAD⁺-binding site with the mix mode. AAs dose-dependently inhibited P4 synthesis in KGN cells, and ALI showed no cytotoxicity even at 100 μM. Overall, this study identifies AAs as potent inhibitors of h3β-HSD2 and r3β-HSD1, enzymes implicated in the pathophysiology of PCOS and Cushing's syndrome. Safe AAs-based therapeutics for endocrine disorders may be achievable.</div></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"162 ","pages":"Article 108630"},"PeriodicalIF":4.5,"publicationDate":"2025-05-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144134737","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Tipranavir analogs as antiviral agents: Design, synthesis, in vitro, and in silico study of new SARS-CoV-2 main protease inhibitors","authors":"Selwan M. El-Sayed ,&nbsp;Dina I.A. Othman ,&nbsp;Ghada S. Hassan ,&nbsp;Ahmed H.E. Hassan ,&nbsp;Shahenda M. El-Messery ,&nbsp;Ahmed R. El-Sheakh","doi":"10.1016/j.bioorg.2025.108624","DOIUrl":"10.1016/j.bioorg.2025.108624","url":null,"abstract":"<div><div>The current study aims at developing non-peptidic new antiviral hits against main protease (M^pro) of SARS-COV2 using the non-peptidic M^pro inhibitor tipranavir (TPV) as a starting point. <em>In vitro</em> protease inhibition assay of the targeted compounds indicated that compound <strong>6f</strong> and its cyclized triazole analogue <strong>7f</strong> were the most active in the present study with IC₅₀ values of 6.48 and 7.38 μM, respectively. These values were better than the 9.06 μM IC₅₀ value of reference standard; TPV. In general, acylthiosemicarbazide derivatives <strong>6e–g</strong> were more potent than corresponding acylsemicarbazide derivatives <strong>6a–c</strong>. Also, the 4-chlorophenyl combined with either thiosemicabazide or 5-mercaptotriazolyl moieties in the molecules were the best for protease inhibitory activity. Cytotoxicity testing assay suggested that the tested molecules were relatively safe for the normal human lung fibroblast cell line WI-38 with IC₅₀ values that ranged from 48.75 to 399.96 μM. Results of the molecular modeling study were consistent with those of <em>in vitro</em> biological evaluation. Collectively, compounds <strong>6f</strong> and <strong>7f</strong> could be considered as non-peptidic new antiviral hits with protease inhibitory activity for further modifications and development to potent antiviral agents as protease inhibitors.</div></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"163 ","pages":"Article 108624"},"PeriodicalIF":4.5,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144169271","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Modifying the chromophoric ring of betalamic acid in plant pigments. Synthesis and characterization of methylated betalains","authors":"Pedro Martínez-Rodríguez ,&nbsp;Luis Eduardo Contreras-Llano ,&nbsp;Diego José Pagán-López ,&nbsp;María Alejandra Guerrero-Rubio ,&nbsp;José Daniel Lozada-Ramírez ,&nbsp;Samanta Hernández-García ,&nbsp;Fernando Gandía-Herrero","doi":"10.1016/j.bioorg.2025.108623","DOIUrl":"10.1016/j.bioorg.2025.108623","url":null,"abstract":"<div><div>The recent discovery of decarboxylated betalains, derived from dopamine, in nature has expanded the number of chemical modifications possible in these plant pigments. Alternative starting materials in biochemical processes can yield novel molecules with modifications in the betalamic ring. For the first time, a functional group has been incorporated into the betalamic acid structure of betalains, thus creating a novel family of methylated pigments. A synthetic pathway starting from α-methyl-DOPA yields 6-methyl-betalamic acid. The process is enzymatic and kinetic characterization reveals that the formation of 6-methyl-betalamic acid is favored over the formation of 6-methyl-dopaxanthin, as a further condensation reaction can be hindered. Starting from the methylated betalamic acid, a novel family of methylated betalains has been biotechnologically produced comprising ten yellow and violet molecules. The novel compounds were characterized by using HPLC-ESI-Q-TOF-MS, spectrophotometry, and spectrofluorometry. Potential antioxidant capacity was measured using the ORAC assay, demonstrating the molecules' effectiveness against peroxyl radicals, with indoline-6-methyl-betacyanin identified as the most antioxidant. This study shows the venue for the chemical modification of the betalamic ring in pigments and thus represents the beginning of the era of betalain core chemistry. This opens new fields for future research to explore novel structures and their potential bioactive effects.</div></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"162 ","pages":"Article 108623"},"PeriodicalIF":4.5,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144130995","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis and characterization of Fe(II)- and Cr(II)-complexes with isatin-aryl hydrazone ligand as bio-reactive reagents and effective catalysts for styrene epoxidation.","authors":"Mohamed Shaker S. Adam","doi":"10.1016/j.bioorg.2025.108625","DOIUrl":"10.1016/j.bioorg.2025.108625","url":null,"abstract":"<div><div>For the facile preparative description of aryl-hydrazones and their interesting coordination modes, a new aryl-hydrazone derivative (HLhdzh) was formed from the combination of 2,4-dihydroxybenzaldehyde with isatin-hydrazide. HLhdzh coordinated to Fe²⁺ and Cr²⁺ ions to give two new metal(II)-complexes (as Fe(Lhdzh)₂ and Cr(Lhdzh)₂, respectively). Their chemical structure was confirmed with perspective spectroscopic tools, and by measuring their purity <em>via</em> micro-elemental investigations. Against the proliferative progress of human cancer cell lines and the namely prevalent microbial series, the bio-potential of HLhdzh, Fe(Lhdzh)₂, and Cr(Lhdzh)₂ was demonstrated, highlighting the considerable action of the nuclearity in Fe(Lhdzh)₂ and Cr(Lhdzh)₂ compared to that of HLhdzh. Also, the bio-potential of HLhdzh, Fe(Lhdzh)₂, and Cr(Lhdzh)₂ was studied within their interacting process with ctDNA (deoxyribonucleic acid) spectrophotometrically and viscometrically. Their antireflective action against the tumors and microorganisms was successfully reported, within the inhabited zoon areas (against the microbes) and the <em>IC</em>₅₀ concentrations (against the tumors). Assigning the values of Gibbs' free energy and binding constant, the nature of their interacting features was addressed, referring to the presented mono-nuclear ion (nuclearity effect) for modification of their complexes' interaction. For the catalytic oxygenative systems, the homogeneous catalytic potential of Fe(Lhdzh)₂ and Cr(Lhdzh)₂ was evaluated in the oxygenative progress of styrene with H₂O₂ to give styrene<strong>-</strong>epoxide at 85 °C. The yield percentage of styrene<strong>-</strong>epoxide catalyzed by Fe(Lhdzh)₂ or Cr(Lhdzh)₂ was obtained using GC–MS, affording 88 and 85 % after 5 h, respectively. The reactivity variation for each catalyst was attributed to the influence of nuclear nature (synergistic influence), which was supported by a proper mechanism, spectroscopically.</div></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"163 ","pages":"Article 108625"},"PeriodicalIF":4.5,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144169273","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}