Dayenny L D'Amato, Isabela A A Bessa, Ana Beatriz C Souza, Lucas Mendes-Monteiro, Ronaldo Mohana-Borges, Diego Allonso, Carolina B P Ligiero, Célia Machado Ronconi
The Zika virus (ZIKV) is a global health threat due to its rapid spread and severe health implications, including congenital abnormalities and neurological complications. Differentiating ZIKV from other arboviruses such as dengue virus (DENV) is crucial for effective diagnosis and treatment. This study presents the development of a biosensor for detecting the ZIKV non-structural protein 1 (NS1) using gold nanoparticles (AuNPs) functionalized with monoclonal antibodies employing dynamic light scattering (DLS). The biosensor named ZINS1-mAb-AuNP exhibited specific binding to the ZIKV NS1 protein, demonstrating high colloidal stability indicated by a hydrodynamic diameter (DH) of 140 nm, detectable via DLS. In the absence of the protein, the high ionic strength medium caused particle aggregation. This detection method showed good sensitivity and specificity, with a limit of detection (LOD) of 0.96 µg mL-1, and avoided cross-reactivity with DENV2 NS1 and SARS-CoV-2 spike proteins. The ZINS1-mAb-AuNP biosensor represents a promising tool for the early and accurate detection of ZIKV, facilitating diagnostic and treatment capabilities for arboviral infections.
{"title":"Zika Virus NS1 Protein Detection Using Gold Nanoparticle-Assisted Dynamic Light Scattering.","authors":"Dayenny L D'Amato, Isabela A A Bessa, Ana Beatriz C Souza, Lucas Mendes-Monteiro, Ronaldo Mohana-Borges, Diego Allonso, Carolina B P Ligiero, Célia Machado Ronconi","doi":"10.1002/asia.202400826","DOIUrl":"https://doi.org/10.1002/asia.202400826","url":null,"abstract":"<p><p>The Zika virus (ZIKV) is a global health threat due to its rapid spread and severe health implications, including congenital abnormalities and neurological complications. Differentiating ZIKV from other arboviruses such as dengue virus (DENV) is crucial for effective diagnosis and treatment. This study presents the development of a biosensor for detecting the ZIKV non-structural protein 1 (NS1) using gold nanoparticles (AuNPs) functionalized with monoclonal antibodies employing dynamic light scattering (DLS). The biosensor named ZINS1-mAb-AuNP exhibited specific binding to the ZIKV NS1 protein, demonstrating high colloidal stability indicated by a hydrodynamic diameter (DH) of 140 nm, detectable via DLS. In the absence of the protein, the high ionic strength medium caused particle aggregation. This detection method showed good sensitivity and specificity, with a limit of detection (LOD) of 0.96 µg mL-1, and avoided cross-reactivity with DENV2 NS1 and SARS-CoV-2 spike proteins. The ZINS1-mAb-AuNP biosensor represents a promising tool for the early and accurate detection of ZIKV, facilitating diagnostic and treatment capabilities for arboviral infections.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":null,"pages":null},"PeriodicalIF":3.5,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102574","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Small molecule-responsive tags for targeted protein degradation are valuable tools for fundamental research and drug target validation. Here, we show that genetically incorporated unnatural amino acids bearing a strained alkene or alkyne functionality can act as a minimalist tag for targeted protein degradation. Specifically, we observed the degradation of strained alkene- or alkyne-containing kinases and E2 ubiquitin-conjugating enzymes upon treatment with hydrophobic tetrazine conjugates. The extent of the induced protein degradation depends on the identity of the target protein, unnatural amino acid, and tetrazine conjugate, as well as the site of the unnatural amino acid in the target protein. Mechanistic studies revealed proteins undergo proteasomal degradation after tetrazine tethering, and the identity of tetrazine conjugates influences the dependence of ubiquitination on protein degradation. This work provides an alternative approach for targeted protein degradation and mechanistic insight, facilitating the future development of more effective targeted protein degradation strategies.
{"title":"Selective Protein Degradation through Tetrazine Ligation of Genetically Incorporated Unnatural Amino Acids.","authors":"Jinghao Chen, Gaocan Dai, Shixiang Duan, Yang Huang, Yi-Lin Wu, Zhiyong Xie, Yu-Hsuan Tsai","doi":"10.1002/asia.202400824","DOIUrl":"https://doi.org/10.1002/asia.202400824","url":null,"abstract":"<p><p>Small molecule-responsive tags for targeted protein degradation are valuable tools for fundamental research and drug target validation. Here, we show that genetically incorporated unnatural amino acids bearing a strained alkene or alkyne functionality can act as a minimalist tag for targeted protein degradation. Specifically, we observed the degradation of strained alkene- or alkyne-containing kinases and E2 ubiquitin-conjugating enzymes upon treatment with hydrophobic tetrazine conjugates. The extent of the induced protein degradation depends on the identity of the target protein, unnatural amino acid, and tetrazine conjugate, as well as the site of the unnatural amino acid in the target protein. Mechanistic studies revealed proteins undergo proteasomal degradation after tetrazine tethering, and the identity of tetrazine conjugates influences the dependence of ubiquitination on protein degradation. This work provides an alternative approach for targeted protein degradation and mechanistic insight, facilitating the future development of more effective targeted protein degradation strategies.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":null,"pages":null},"PeriodicalIF":3.5,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102571","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The interplay of ESIPT+TICT mechanisms in 1,8-naphthalimide-hydroxyquinoline (NQ-OH) molecular rotor were reported for the near-IR 'turn-on' emission (λmax 600 nm) and ratiometric (A405nm/A345nm) absorbance-based detection of Al3+ ions in aqueous medium and live cells which were supported by NMR, IR and CV techniques. The limit of detection (LOD) for Al3+ ions is 100 nM and 14.57 nM. The self-assembled spherical aggregates of NQ-OH transformed into cuboidal aggregates upon coordination with Al3+ ions supported by microscopic and dynamic light scattering (DLS) techniques. The complex NQ-OH+Al3+ was further used for the secondary detection of F- ions in aqueous medium via displacement approach with LOD as low as 2.67 nM. A deeper study revealed that the NQ-OH is a solvatochromic dye. Probably, the NQ-OH either in the aggregated state or in the coordination state with Al3+ ions, showed an increase in the emission intensity at 600 nm due to inhibition of the ESIPT process and trigger of the TICT process. We have demonstrated the utility of NQ-OH for the detection of Al3+ ions and NQ-OH+Al3+ complex for the detection of F- ions in MCF7 live cells. We have also discussed the molecular docking studies of NQ-OH with acetylcholinesterase enzyme.
{"title":"ESIPT+TICT-based Near-IR Detection of Al3+ and F- in Live Cells: Molecular Docking with Acetylcholinesterase.","authors":"Sanjeev Kumar, Sheikh Showkat, Satinder Kaur, Satwinderjeet Kaur, Prakash Chander Mishra, Prabhpreet Singh","doi":"10.1002/asia.202400678","DOIUrl":"https://doi.org/10.1002/asia.202400678","url":null,"abstract":"<p><p>The interplay of ESIPT+TICT mechanisms in 1,8-naphthalimide-hydroxyquinoline (NQ-OH) molecular rotor were reported for the near-IR 'turn-on' emission (λmax 600 nm) and ratiometric (A405nm/A345nm) absorbance-based detection of Al3+ ions in aqueous medium and live cells which were supported by NMR, IR and CV techniques. The limit of detection (LOD) for Al3+ ions is 100 nM and 14.57 nM. The self-assembled spherical aggregates of NQ-OH transformed into cuboidal aggregates upon coordination with Al3+ ions supported by microscopic and dynamic light scattering (DLS) techniques. The complex NQ-OH+Al3+ was further used for the secondary detection of F- ions in aqueous medium via displacement approach with LOD as low as 2.67 nM. A deeper study revealed that the NQ-OH is a solvatochromic dye. Probably, the NQ-OH either in the aggregated state or in the coordination state with Al3+ ions, showed an increase in the emission intensity at 600 nm due to inhibition of the ESIPT process and trigger of the TICT process. We have demonstrated the utility of NQ-OH for the detection of Al3+ ions and NQ-OH+Al3+ complex for the detection of F- ions in MCF7 live cells. We have also discussed the molecular docking studies of NQ-OH with acetylcholinesterase enzyme.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":null,"pages":null},"PeriodicalIF":3.5,"publicationDate":"2024-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102565","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Panchromatic dyes have been highly useful in the realm of optical devices. Here, we report that panchromatic dyes with heterohelicenes have been successfully synthesized using a donor-acceptor strategy. Our synthesis resulted in the creation of π-extended aza[5]helicene oligomers with butadiyne linkages, which displayed bathochromically shifted absorption and emission spectra. The solvent-dependent optical measurements revealed the intramolecular charge transfer characteristic of these molecules, and theoretical calculations described the biased molecular orbitals on the azahelicene units that generated the charge-transfer characteristic. Encouraged by these results, we also prepared donor-acceptor-donor dyads using azahelicenes and dimide derivatives, resulting in panchromatic absorbing characteristics covering the range from 250 nm to 800 nm. Theoretical calculations showed the presence of mixed charge-transfer transitions and localized transitions on the azahelicene units, which led to a broad light-absorbing property covering the near IR region. Additionally, we conducted measurements of circular dichroism and circularly polarized luminescence for the obtained products. The g-values were reduced by oligomerization, indicating that the lowest energy transitions were allowed in nature.
全色染料在光学设备领域非常有用。在此,我们报告了利用供体-受体策略成功合成了含有杂环烯的全色染料。我们的合成方法产生了具有丁二炔连接的π-扩展氮杂[5]螺旋烯低聚物,它们显示了浴色偏移的吸收和发射光谱。依赖溶剂的光学测量显示了这些分子的分子内电荷转移特性,理论计算则描述了产生电荷转移特性的氮杂环烯单元上的偏置分子轨道。受到这些结果的鼓舞,我们还利用氮杂环己烯和二酰胺衍生物制备了供体-受体-供体二元化合物,从而获得了覆盖 250 纳米到 800 纳米范围的全色吸收特性。理论计算显示,在氮杂环己烯单元上存在混合电荷转移跃迁和局部跃迁,从而产生了覆盖近红外区域的广泛光吸收特性。此外,我们还对获得的产物进行了圆二色性和圆偏振发光测量。低聚后 g 值降低,表明自然界允许最低能量的转变。
{"title":"Donor-acceptor-donor Dyads with Electron-rich π-Extended Azahelicenes to Panchromatic Absorbing Dyes.","authors":"Satoru Hiroto, Moeko Chujo","doi":"10.1002/asia.202400830","DOIUrl":"https://doi.org/10.1002/asia.202400830","url":null,"abstract":"<p><p>Panchromatic dyes have been highly useful in the realm of optical devices. Here, we report that panchromatic dyes with heterohelicenes have been successfully synthesized using a donor-acceptor strategy. Our synthesis resulted in the creation of π-extended aza[5]helicene oligomers with butadiyne linkages, which displayed bathochromically shifted absorption and emission spectra. The solvent-dependent optical measurements revealed the intramolecular charge transfer characteristic of these molecules, and theoretical calculations described the biased molecular orbitals on the azahelicene units that generated the charge-transfer characteristic. Encouraged by these results, we also prepared donor-acceptor-donor dyads using azahelicenes and dimide derivatives, resulting in panchromatic absorbing characteristics covering the range from 250 nm to 800 nm. Theoretical calculations showed the presence of mixed charge-transfer transitions and localized transitions on the azahelicene units, which led to a broad light-absorbing property covering the near IR region. Additionally, we conducted measurements of circular dichroism and circularly polarized luminescence for the obtained products. The g-values were reduced by oligomerization, indicating that the lowest energy transitions were allowed in nature.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":null,"pages":null},"PeriodicalIF":3.5,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102563","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The field of electrogenerated chemiluminescence (ECL) biosensing has witnessed remarkable growth, emphasizing the need for precise detection of biomarkers. The synthesis approach of peptide-based signal probe with high recognition ability and high ECL efficiency is a significant issue in the ECL biosensing. Here, a heavily labeled signal probe was synthesized for ECL peptide-based biosensing tactic by using a new aldehyde bearing cyclometalated Ir(III) complex ([Ir(bt)2(bpy-CHO)PF6 (bt =2-phenylbenzothiazole, bpy-CHO=4'-methyl-[2,2'-bipyridine]-4-carbaldehyde, denoted as Ir1) as ECL signal reagent and streptavidin (SA) as carrier protein. One ECL peptide-based biosensing method was exemplified for the detection of matrix metalloproteinase 2 (MMP-2) by using Ir1 labeled SA (SA-Ir1) as heavily labeled signal probe and biotinylated peptide as molecular recognition substrate. MMP-2 was sensitively detected in the range from 5 to 100 ng/mL with a detection limit of 1.5 ng/mL. Importantly, two detection modes differing in the order of cleavage recognition by MMP-2 and signal transduction with SA-Ir1 were compared for the first time. First cleavage and second signal transduction were proposed to be beneficial to sensitive detection of target, which provides some ideas for biomarker diagnostics in disease screening at an early stage.
{"title":"Heavily Labeled Signal Probe for Electrogenerated Chemiluminescence Peptide-based Biosensing of Matrix Metalloproteinase 2.","authors":"Danyang Zhang, Manping Qian, Xiaolin Yang, Chengxiao Zhang, Honglan Qi","doi":"10.1002/asia.202400743","DOIUrl":"https://doi.org/10.1002/asia.202400743","url":null,"abstract":"<p><p>The field of electrogenerated chemiluminescence (ECL) biosensing has witnessed remarkable growth, emphasizing the need for precise detection of biomarkers. The synthesis approach of peptide-based signal probe with high recognition ability and high ECL efficiency is a significant issue in the ECL biosensing. Here, a heavily labeled signal probe was synthesized for ECL peptide-based biosensing tactic by using a new aldehyde bearing cyclometalated Ir(III) complex ([Ir(bt)2(bpy-CHO)PF6 (bt =2-phenylbenzothiazole, bpy-CHO=4'-methyl-[2,2'-bipyridine]-4-carbaldehyde, denoted as Ir1) as ECL signal reagent and streptavidin (SA) as carrier protein. One ECL peptide-based biosensing method was exemplified for the detection of matrix metalloproteinase 2 (MMP-2) by using Ir1 labeled SA (SA-Ir1) as heavily labeled signal probe and biotinylated peptide as molecular recognition substrate. MMP-2 was sensitively detected in the range from 5 to 100 ng/mL with a detection limit of 1.5 ng/mL. Importantly, two detection modes differing in the order of cleavage recognition by MMP-2 and signal transduction with SA-Ir1 were compared for the first time. First cleavage and second signal transduction were proposed to be beneficial to sensitive detection of target, which provides some ideas for biomarker diagnostics in disease screening at an early stage.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":null,"pages":null},"PeriodicalIF":3.5,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102566","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Lvqi Jiang, Zhongquan Lin, Shuaishuai Liang, Wen-Bin Yi
Organofluorine compounds have consistently demonstrated practical applications in the life sciences due to the fascinating properties imparted by the fluorine substituents. In recent years, significant advancements have been made in the synthesis of N-fluoroalkyl carbonyl and sulfonyl compounds. This review offers a current overview of the various synthetic routes for N-fluoroalkyl amides/sulfonamides and their transformation to new unexplored N-fluoroalkyl carbonyl/sulfonyl derivatives, categorized into three parts based on the different fluoroalkyl groups.
{"title":"Recent Advances in the Synthesis of N-fluoroalkyl Amides/Sulfonamides and Their Carbonyl/Sulfonyl Derivatives.","authors":"Lvqi Jiang, Zhongquan Lin, Shuaishuai Liang, Wen-Bin Yi","doi":"10.1002/asia.202400909","DOIUrl":"https://doi.org/10.1002/asia.202400909","url":null,"abstract":"<p><p>Organofluorine compounds have consistently demonstrated practical applications in the life sciences due to the fascinating properties imparted by the fluorine substituents. In recent years, significant advancements have been made in the synthesis of N-fluoroalkyl carbonyl and sulfonyl compounds. This review offers a current overview of the various synthetic routes for N-fluoroalkyl amides/sulfonamides and their transformation to new unexplored N-fluoroalkyl carbonyl/sulfonyl derivatives, categorized into three parts based on the different fluoroalkyl groups.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":null,"pages":null},"PeriodicalIF":3.5,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102569","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tripti Mishra, Antara Goswami, Aman Bajpai, Sudipta Basu
In recent years, impairing mitochondria in cancer cells gained attention as alternative cancer therapy. In this context, non-steroidal anti-inflammatory (NSAID) drugs are interesting candidates to damage mitochondria in cancer cells. However, routing NSAIDs specifically into the mitochondria remained a major challenge and less explored. Herein, we have synthesized a small library of Meclofenamic acid and Naproxen derivatives having ester and amide linkage with substituted triphenylphosphonium cations for mitochondria targeting. Screening in cervical cancer (HeLa), breast cancer (MFF7) and colon cancer (HCT-116) cells revealed a Meclofenamic acid derivative having ester linkage with tri (4-methoxyphenyl) phosphonium cation (8A3) which induced mitochondrial damage through mitochondrial outer membrane permeabilization (MOMP) followed by generation of reactive oxygen species (ROS) in the HCT-116 cells. This 8A3-mediated mitochondrial impairment triggered apoptosis by inhibiting Cox-2, reduction in Bcl-2/Bcl-xl expression and Caspase-3/9 cleavage leading to remarkable HCT-116 cell death. This novel mitochondrion targeted Meclofenamic acid derivative has the potential to be used as a chemical biology tool to understand the role of NSAIDs in mitochondria towards cancer therapy.
{"title":"Detouring NSAID into mitochondria to induce apoptosis in cancer cells.","authors":"Tripti Mishra, Antara Goswami, Aman Bajpai, Sudipta Basu","doi":"10.1002/asia.202400732","DOIUrl":"https://doi.org/10.1002/asia.202400732","url":null,"abstract":"<p><p>In recent years, impairing mitochondria in cancer cells gained attention as alternative cancer therapy. In this context, non-steroidal anti-inflammatory (NSAID) drugs are interesting candidates to damage mitochondria in cancer cells. However, routing NSAIDs specifically into the mitochondria remained a major challenge and less explored. Herein, we have synthesized a small library of Meclofenamic acid and Naproxen derivatives having ester and amide linkage with substituted triphenylphosphonium cations for mitochondria targeting. Screening in cervical cancer (HeLa), breast cancer (MFF7) and colon cancer (HCT-116) cells revealed a Meclofenamic acid derivative having ester linkage with tri (4-methoxyphenyl) phosphonium cation (8A3) which induced mitochondrial damage through mitochondrial outer membrane permeabilization (MOMP) followed by generation of reactive oxygen species (ROS) in the HCT-116 cells. This 8A3-mediated mitochondrial impairment triggered apoptosis by inhibiting Cox-2, reduction in Bcl-2/Bcl-xl expression and Caspase-3/9 cleavage leading to remarkable HCT-116 cell death. This novel mitochondrion targeted Meclofenamic acid derivative has the potential to be used as a chemical biology tool to understand the role of NSAIDs in mitochondria towards cancer therapy.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":null,"pages":null},"PeriodicalIF":3.5,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102562","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
High performance deep-blue emitters with a Commission International de l'Eclairage (CIE) coordinate of CIEy ≤ 0.08 are highly desired in ultrahigh-definition displays. Herein, we designed and synthesized an efficient D‒π‒A deep-blue emitter, 2-(6-([1,1':3',1''-terphenyl]-5'-yl)pyridin-3-yl)-1-phenyl-1H-phenanthro[9,10-d] imidazole (mPTPH), using the synergistic effect of intramolecular hydrogen bond (H-bond) and hybridized excited state. Single-crystal structure analysis confirmed that there exist intra- and intermolecular H-bond interactions which could inhibit the structure vibration and increase photoluminescence efficiency. The photophysical and theoretical results show that mPTPH exhibited hybridized local and charge-transfer (HLCT) feature with strong deep-blue emission. Ultimately, the non-doped device based on mPTPH exhibited high maximum luminance of 20610 cd m-2. The doped device achieved high maximum external quantum efficiency of 5.4% and small efficiency roll-off with deep-blue emission peak of 413 nm and CIE coordinate of (0.16, 0.08).
{"title":"Efficient deep-blue fluorescent OLEDs based on a D‒π‒A emitter profiting from intramolecular hydrogen bonds and a hybridized excited state.","authors":"Ying Ji, Chenglin Ma, Xu Qiu, Xinyong Liu, Jingwei Li, Jiadong Zhou, Shanfeng Xue","doi":"10.1002/asia.202400957","DOIUrl":"https://doi.org/10.1002/asia.202400957","url":null,"abstract":"<p><p>High performance deep-blue emitters with a Commission International de l'Eclairage (CIE) coordinate of CIEy ≤ 0.08 are highly desired in ultrahigh-definition displays. Herein, we designed and synthesized an efficient D‒π‒A deep-blue emitter, 2-(6-([1,1':3',1''-terphenyl]-5'-yl)pyridin-3-yl)-1-phenyl-1H-phenanthro[9,10-d] imidazole (mPTPH), using the synergistic effect of intramolecular hydrogen bond (H-bond) and hybridized excited state. Single-crystal structure analysis confirmed that there exist intra- and intermolecular H-bond interactions which could inhibit the structure vibration and increase photoluminescence efficiency. The photophysical and theoretical results show that mPTPH exhibited hybridized local and charge-transfer (HLCT) feature with strong deep-blue emission. Ultimately, the non-doped device based on mPTPH exhibited high maximum luminance of 20610 cd m-2. The doped device achieved high maximum external quantum efficiency of 5.4% and small efficiency roll-off with deep-blue emission peak of 413 nm and CIE coordinate of (0.16, 0.08).</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":null,"pages":null},"PeriodicalIF":3.5,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102564","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
B V Subba Reddy, Chidrawar Ajay, Sridhar Balasubramanian
An efficient Rh(III)-catalyzed C-H functionalization of 3-aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides with diaryl and dialkyl alkynes has been developed for the first time to the synthesis of 1-aminoisoquinoline derivatives in a single step. This method involves through the formation of two C-C bonds and one C-N bond followed by desulfonylation to generate a novel series of isoquinolines in good to excellent yields. This is a direct method to produce pharmaceutically more relevant scaffolds with a high functional diversity.
{"title":"Rh(III)-Catalyzed Sequential ortho-C-H Bond Annulation and Desulfonylation of 3-Aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides: Access to 1-Aminoisoquinolines.","authors":"B V Subba Reddy, Chidrawar Ajay, Sridhar Balasubramanian","doi":"10.1002/asia.202400723","DOIUrl":"https://doi.org/10.1002/asia.202400723","url":null,"abstract":"<p><p>An efficient Rh(III)-catalyzed C-H functionalization of 3-aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides with diaryl and dialkyl alkynes has been developed for the first time to the synthesis of 1-aminoisoquinoline derivatives in a single step. This method involves through the formation of two C-C bonds and one C-N bond followed by desulfonylation to generate a novel series of isoquinolines in good to excellent yields. This is a direct method to produce pharmaceutically more relevant scaffolds with a high functional diversity.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":null,"pages":null},"PeriodicalIF":3.5,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102570","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kaempferia subglobosa is a perennial medicinal plant in the Zingiberaceae family, identified as a new species in January 2024. To uncover the biological benefits of K. subglobosa and its compounds, investigation of the metabolites of the roots and rhizomes, yielded three new monoterpene-chalcone conjugates, the globosones A-C, representing a rare metabolite group within the Zingiberaceae, along with six known compounds. The biogenetic pathway for the globosones involves an oxidative [3+2] cycloaddition between α-phellandrene and 4'-methoxy-4,2',6'-trihydroxychalcone. Biological testing revealed potent xanthine oxidase (XO) inhibition by globosones A and B, with IC50 values of 7.0 ± 1.0 and 3.0 ± 0.2 μM, respectively, surpassing the positive control drug allopurinol (IC50 7.2 ± 0.1 µM). Globosones A-C also showed good aromatase inhibition (IC50 3.0-3.5 μM). Molecular docking studies indicated that globosones A and B may inhibit xanthine oxidase through binding at the FAD domain site. The physicochemical properties of these isolates suggest that they possess characteristics suitable for additional biological assessment in more advanced test systems. This study enhances an understanding of monoterpene-chalcone conjugate inhibitors of XO, and offers preliminary insights into the metabolites and bioactivities of K. subglobosa, uncovering potent biological activities associated with this newly discovered plant species.
亚球花山柰(Kaempferia subglobosa)是一种姜科多年生药用植物,于 2024 年 1 月被鉴定为新物种。为了揭示亚球山柰(K. subglobosa)及其化合物的生物功效,研究人员对其根部和根茎的代谢物进行了研究,发现了三种新的单萜查尔酮共轭物--球果酮 A-C(globosones A-C),以及六种已知化合物,它们代表了姜科植物中一个罕见的代谢物群。钩藤酮的生物发生途径包括α-黄柏烯和(4'-甲氧基-4,2',6'-三羟基查尔酮)之间的氧化[3+2]环加成反应。生物测试表明,球松 A 和球松 B 对黄嘌呤氧化酶(XO)具有强效抑制作用,其 IC50 值分别为 7.0 ± 1.0 和 3.0 ± 0.2 μM,超过了阳性对照药物别嘌醇(IC50 值为 7.2 ± 0.1 µM)。球酮 A-C 也显示出良好的芳香化酶抑制作用(IC50 3.0-3.5 μM)。分子对接研究表明,球酮 A 和 B 可通过与 FAD 结构域位点结合来抑制黄嘌呤氧化酶。这些分离物的理化性质表明,它们具有适合在更先进的测试系统中进行更多生物学评估的特性。这项研究加深了人们对单萜查尔酮共轭物 XO 抑制剂的了解,并初步揭示了 K. subglobosa 的代谢物和生物活性,发现了与这一新发现植物物种相关的强大生物活性。
{"title":"Xanthine Oxidase Inhibition by Monoterpene-Chalcone Conjugates from Kaempferia subglobosaand Molecular Docking Insights.","authors":"Jutatip Boonsombat, Orawan Jongsomjainuk, Sanit Thongnest, Jitnapa Sirirak, Paratchata Batsomboon, Saroj Ruchisansakun, Surasak Prachya, Chulabhorn Mahidol, Somsak Ruchirawat","doi":"10.1002/asia.202400677","DOIUrl":"https://doi.org/10.1002/asia.202400677","url":null,"abstract":"<p><p>Kaempferia subglobosa is a perennial medicinal plant in the Zingiberaceae family, identified as a new species in January 2024. To uncover the biological benefits of K. subglobosa and its compounds, investigation of the metabolites of the roots and rhizomes, yielded three new monoterpene-chalcone conjugates, the globosones A-C, representing a rare metabolite group within the Zingiberaceae, along with six known compounds. The biogenetic pathway for the globosones involves an oxidative [3+2] cycloaddition between α-phellandrene and 4'-methoxy-4,2',6'-trihydroxychalcone. Biological testing revealed potent xanthine oxidase (XO) inhibition by globosones A and B, with IC50 values of 7.0 ± 1.0 and 3.0 ± 0.2 μM, respectively, surpassing the positive control drug allopurinol (IC50 7.2 ± 0.1 µM). Globosones A-C also showed good aromatase inhibition (IC50 3.0-3.5 μM). Molecular docking studies indicated that globosones A and B may inhibit xanthine oxidase through binding at the FAD domain site. The physicochemical properties of these isolates suggest that they possess characteristics suitable for additional biological assessment in more advanced test systems. This study enhances an understanding of monoterpene-chalcone conjugate inhibitors of XO, and offers preliminary insights into the metabolites and bioactivities of K. subglobosa, uncovering potent biological activities associated with this newly discovered plant species.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":null,"pages":null},"PeriodicalIF":3.5,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102573","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}