New diarylcyclopentenone enantiomers and biphenyl derivatives from the fungus Talaromyces adpressus
Bioorg Chem. 2024 Mar 9;146:107280. doi: 10.1016/j.bioorg.2024.107280. Online ahead of print.ABSTRACTTen new compounds, including three pairs of diarylcyclopentenone enantiomers (±) talaromycesins A-C (1-3) and four biphenyl derivatives talaromycesins D-G (4-7), along with four known compounds (8-11), were isolated from the fungus Talaromyces adpressus. Their structures were determined by analyses of extensive NMR spectroscopic and HRESIMS data, and their absolute configurations were elucidated by the dimolybdenum tetraacetate [Mo2(AcO)4]-induced ECD spectra, X-ray crystallographic studies, and ECD calculations. These new...
Source: Bioorganic Chemistry - March 13, 2024 Category: Chemistry Authors: Meijia Zheng Yongqi Li Hong Liao Chenxi Zhou Qin Li Chunmei Chen Weiguang Sun Yonghui Zhang Hucheng Zhu Source Type: research
Novel chiral matrine derivatives as potential antitumor agents: Design, synthesis and biological evaluation
In this study, we designed and synthesized a novel chiral matrine derivative. Their cytotoxicity against three types of tumor cells was assessed. Comparing the newly synthesized derivatives to the parent matrine, most compounds exhibited significantly enhanced inhibitory effects on cancer cells. Among them, Q12 exhibited the highest activity, with IC50 values of 8.31 μM against rat glioma cells C6, 6.3 μM against human liver cancer cells HepG2 and 7.14 μM against human gastric cancer cells HGC-27, meanwhile showing low toxicity. Based on IC50 values, we constructed a preliminary structure-activity relationship (SAR). Co...
Source: Bioorganic Chemistry - March 13, 2024 Category: Chemistry Authors: Gan Qiu Fan Li Jamal A H Kowah Junwei Xie Qingfeng Long Lisheng Wang Xu Liu Source Type: research
New diarylcyclopentenone enantiomers and biphenyl derivatives from the fungus Talaromyces adpressus
Bioorg Chem. 2024 Mar 9;146:107280. doi: 10.1016/j.bioorg.2024.107280. Online ahead of print.ABSTRACTTen new compounds, including three pairs of diarylcyclopentenone enantiomers (±) talaromycesins A-C (1-3) and four biphenyl derivatives talaromycesins D-G (4-7), along with four known compounds (8-11), were isolated from the fungus Talaromyces adpressus. Their structures were determined by analyses of extensive NMR spectroscopic and HRESIMS data, and their absolute configurations were elucidated by the dimolybdenum tetraacetate [Mo2(AcO)4]-induced ECD spectra, X-ray crystallographic studies, and ECD calculations. These new...
Source: Bioorganic Chemistry - March 13, 2024 Category: Chemistry Authors: Meijia Zheng Yongqi Li Hong Liao Chenxi Zhou Qin Li Chunmei Chen Weiguang Sun Yonghui Zhang Hucheng Zhu Source Type: research
Novel chiral matrine derivatives as potential antitumor agents: Design, synthesis and biological evaluation
In this study, we designed and synthesized a novel chiral matrine derivative. Their cytotoxicity against three types of tumor cells was assessed. Comparing the newly synthesized derivatives to the parent matrine, most compounds exhibited significantly enhanced inhibitory effects on cancer cells. Among them, Q12 exhibited the highest activity, with IC50 values of 8.31 μM against rat glioma cells C6, 6.3 μM against human liver cancer cells HepG2 and 7.14 μM against human gastric cancer cells HGC-27, meanwhile showing low toxicity. Based on IC50 values, we constructed a preliminary structure-activity relationship (SAR). Co...
Source: Bioorganic Chemistry - March 13, 2024 Category: Chemistry Authors: Gan Qiu Fan Li Jamal A H Kowah Junwei Xie Qingfeng Long Lisheng Wang Xu Liu Source Type: research
Antimicrobial properties of triazolato terpyridine Pd(II) and Pt(II) complexes formed by [3+2] cycloaddition coupling reaction
Bioorg Chem. 2024 Mar 6;146:107262. doi: 10.1016/j.bioorg.2024.107262. Online ahead of print.ABSTRACTModern classes of antimicrobials are crucial because most drugs in development today are basically antibiotic derivatives. Even though a large number of metal-based compounds have been studied as antimicrobial agents, relatively few studies have examined the antimicrobial properties of Pd(II) and Pt(II) compounds. The [3+2] cycloaddition reactions of [M(N3)L]PF6 (M = Pd(II) and Pt(II); L = 4'-(2-pyridyl)-2,2':6',2″-terpyridine) with 4,4,4-trifluoro-2-butynoic acid ethyl ester gave the corresponding triazolate complexes. T...
Source: Bioorganic Chemistry - March 11, 2024 Category: Chemistry Authors: Ahmed M Mansour Krzysztof Radacki Gamal A E Mostafa Essam A Ali Ola R Shehab Source Type: research
Antimicrobial properties of triazolato terpyridine Pd(II) and Pt(II) complexes formed by [3+2] cycloaddition coupling reaction
Bioorg Chem. 2024 Mar 6;146:107262. doi: 10.1016/j.bioorg.2024.107262. Online ahead of print.ABSTRACTModern classes of antimicrobials are crucial because most drugs in development today are basically antibiotic derivatives. Even though a large number of metal-based compounds have been studied as antimicrobial agents, relatively few studies have examined the antimicrobial properties of Pd(II) and Pt(II) compounds. The [3+2] cycloaddition reactions of [M(N3)L]PF6 (M = Pd(II) and Pt(II); L = 4'-(2-pyridyl)-2,2':6',2″-terpyridine) with 4,4,4-trifluoro-2-butynoic acid ethyl ester gave the corresponding triazolate complexes. T...
Source: Bioorganic Chemistry - March 11, 2024 Category: Chemistry Authors: Ahmed M Mansour Krzysztof Radacki Gamal A E Mostafa Essam A Ali Ola R Shehab Source Type: research
Discovery of indoleninyl-pyrazolo[3,4-b]pyridines as potent chemotherapeutic agents against colorectal cancer cells
Bioorg Chem. 2024 Mar 2;146:107256. doi: 10.1016/j.bioorg.2024.107256. Online ahead of print.ABSTRACTA new series of indolenines decorated with pyrazolo[3,4-b]pyridines were designed and synthesized in up to 96% yield from the acid-catalyzed cyclocondensation of 1,3-dialdehydes with 3-aminopyrazoles. X-ray crystallography on a representative derivative, 5n, revealed two close to planar conformations whereby the N-atom of the pyridyl residue was syn or anti to the pyrrole-N atom in the two independent molecules of the asymmetric unit. The computational and DNA binding data suggest that 5n is a strong DNA intercalator with t...
Source: Bioorganic Chemistry - March 9, 2024 Category: Chemistry Authors: Nur Husnaini Basir Abdul Qaiyum Ramle Min Phin Ng Chun Hoe Tan Edward R T Tiekink Kae Shin Sim Wan Jefrey Basirun Melati Khairuddean Source Type: research
Trisarcglaboids A and B, two cytotoxic lindenane sesquiterpenoid trimers with a unique polymerization mode isolated from Sarcandra glabra
Bioorg Chem. 2024 Mar 4;146:107259. doi: 10.1016/j.bioorg.2024.107259. Online ahead of print.ABSTRACTTrisarcglaboids A and B (1 and 2), representing the first example of lindenane sesquiterpenoid trimers repolymerized based on the classical [4 + 2] type dimer, together with known biogenic precursors chlorahololide D (3) and sarcandrolide A (4), were identified as chemical components of the root of Sarcandra glabra. The novel trimeric lindenane sesquiterpenoid skeletons, including their absolute configurations, were characterized using MS, NMR, ECD, and X-ray single crystal diffraction. The proposed Diels-Alder cycloadditio...
Source: Bioorganic Chemistry - March 9, 2024 Category: Chemistry Authors: Danyang Zhang Zhiqi Xiao Nan Wang An Huang Jie Wen Lingyi Kong Jun Luo Source Type: research
Identifying eleven new ferroptosis inhibitors as neuroprotective agents from FDA-approved drugs
In this study, we identified ferroptosis inhibitors as neuroprotective agents from US Food and Drug Administration (FDA)-approved drugs. 1176 drugs have been screened against erastin-induced ferroptosis in HT22 cells, resulting in 89 ferroptosis inhibitors. Among them, 26 drugs showed significant activity with EC50 below10 μM. The most active ferroptosis inhibitor is lumateperone tosylate at nanomolar level. 11 drugs as ferroptosis inhibitors were not reported previously. Further mechanistic studies revealed that their mechanisms of actions involve free radical scavenging, Fe2+ chelation, and 15-lipoxygenase inhibition. N...
Source: Bioorganic Chemistry - March 9, 2024 Category: Chemistry Authors: Qingyun Tan Deyin Wu Yating Lin Haopeng Ai Jun Xu Huihao Zhou Qiong Gu Source Type: research
Unlocking InhA: Novel approaches to inhibit Mycobacterium tuberculosis
Bioorg Chem. 2024 Mar 5;146:107250. doi: 10.1016/j.bioorg.2024.107250. Online ahead of print.ABSTRACTMultidrug-resistant tuberculosis continues to pose a health security risk and remains a public health emergency. Antimicrobial resistance result from treatment regimens that are both insufficient and incomplete leading to the emergence of multidrug-resistant tuberculosis, extensively drug-resistant tuberculosis and totally drug-resistant tuberculosis. The impact of tuberculosis on the people suffering from HIV (Human immunodeficiency virus infection) have resulted in the increased research efforts in designing and discovery...
Source: Bioorganic Chemistry - March 9, 2024 Category: Chemistry Authors: Simranpreet K Wahan Gaurav Bhargava Viney Chawla Pooja A Chawla Source Type: research
Discovery of indoleninyl-pyrazolo[3,4-b]pyridines as potent chemotherapeutic agents against colorectal cancer cells
Bioorg Chem. 2024 Mar 2;146:107256. doi: 10.1016/j.bioorg.2024.107256. Online ahead of print.ABSTRACTA new series of indolenines decorated with pyrazolo[3,4-b]pyridines were designed and synthesized in up to 96% yield from the acid-catalyzed cyclocondensation of 1,3-dialdehydes with 3-aminopyrazoles. X-ray crystallography on a representative derivative, 5n, revealed two close to planar conformations whereby the N-atom of the pyridyl residue was syn or anti to the pyrrole-N atom in the two independent molecules of the asymmetric unit. The computational and DNA binding data suggest that 5n is a strong DNA intercalator with t...
Source: Bioorganic Chemistry - March 9, 2024 Category: Chemistry Authors: Nur Husnaini Basir Abdul Qaiyum Ramle Min Phin Ng Chun Hoe Tan Edward R T Tiekink Kae Shin Sim Wan Jefrey Basirun Melati Khairuddean Source Type: research
Trisarcglaboids A and B, two cytotoxic lindenane sesquiterpenoid trimers with a unique polymerization mode isolated from Sarcandra glabra
Bioorg Chem. 2024 Mar 4;146:107259. doi: 10.1016/j.bioorg.2024.107259. Online ahead of print.ABSTRACTTrisarcglaboids A and B (1 and 2), representing the first example of lindenane sesquiterpenoid trimers repolymerized based on the classical [4 + 2] type dimer, together with known biogenic precursors chlorahololide D (3) and sarcandrolide A (4), were identified as chemical components of the root of Sarcandra glabra. The novel trimeric lindenane sesquiterpenoid skeletons, including their absolute configurations, were characterized using MS, NMR, ECD, and X-ray single crystal diffraction. The proposed Diels-Alder cycloadditio...
Source: Bioorganic Chemistry - March 9, 2024 Category: Chemistry Authors: Danyang Zhang Zhiqi Xiao Nan Wang An Huang Jie Wen Lingyi Kong Jun Luo Source Type: research
Identifying eleven new ferroptosis inhibitors as neuroprotective agents from FDA-approved drugs
In this study, we identified ferroptosis inhibitors as neuroprotective agents from US Food and Drug Administration (FDA)-approved drugs. 1176 drugs have been screened against erastin-induced ferroptosis in HT22 cells, resulting in 89 ferroptosis inhibitors. Among them, 26 drugs showed significant activity with EC50 below10 μM. The most active ferroptosis inhibitor is lumateperone tosylate at nanomolar level. 11 drugs as ferroptosis inhibitors were not reported previously. Further mechanistic studies revealed that their mechanisms of actions involve free radical scavenging, Fe2+ chelation, and 15-lipoxygenase inhibition. N...
Source: Bioorganic Chemistry - March 9, 2024 Category: Chemistry Authors: Qingyun Tan Deyin Wu Yating Lin Haopeng Ai Jun Xu Huihao Zhou Qiong Gu Source Type: research
Unlocking InhA: Novel approaches to inhibit Mycobacterium tuberculosis
Bioorg Chem. 2024 Mar 5;146:107250. doi: 10.1016/j.bioorg.2024.107250. Online ahead of print.ABSTRACTMultidrug-resistant tuberculosis continues to pose a health security risk and remains a public health emergency. Antimicrobial resistance result from treatment regimens that are both insufficient and incomplete leading to the emergence of multidrug-resistant tuberculosis, extensively drug-resistant tuberculosis and totally drug-resistant tuberculosis. The impact of tuberculosis on the people suffering from HIV (Human immunodeficiency virus infection) have resulted in the increased research efforts in designing and discovery...
Source: Bioorganic Chemistry - March 9, 2024 Category: Chemistry Authors: Simranpreet K Wahan Gaurav Bhargava Viney Chawla Pooja A Chawla Source Type: research
Discovery of indoleninyl-pyrazolo[3,4-b]pyridines as potent chemotherapeutic agents against colorectal cancer cells
Bioorg Chem. 2024 Mar 2;146:107256. doi: 10.1016/j.bioorg.2024.107256. Online ahead of print.ABSTRACTA new series of indolenines decorated with pyrazolo[3,4-b]pyridines were designed and synthesized in up to 96% yield from the acid-catalyzed cyclocondensation of 1,3-dialdehydes with 3-aminopyrazoles. X-ray crystallography on a representative derivative, 5n, revealed two close to planar conformations whereby the N-atom of the pyridyl residue was syn or anti to the pyrrole-N atom in the two independent molecules of the asymmetric unit. The computational and DNA binding data suggest that 5n is a strong DNA intercalator with t...
Source: Bioorganic Chemistry - March 9, 2024 Category: Chemistry Authors: Nur Husnaini Basir Abdul Qaiyum Ramle Min Phin Ng Chun Hoe Tan Edward R T Tiekink Kae Shin Sim Wan Jefrey Basirun Melati Khairuddean Source Type: research
