Tetrahedron Letters最新文献_第2页

Dual-type photodynamic therapy enabled by fluorinated BODIPY-liposome hybrids for enhanced antibacterial efficacy 双型光动力疗法启用氟化bodipy -脂质体混合物，以增强抗菌功效

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-09-18 DOI: 10.1016/j.tetlet.2025.155830

Zhihua Chen , Jincheng Zhu , Mengxing Wang , Qinglin Wu , Yichun Xu , Lei Cui , Kewen Zheng

{"title":"Dual-type photodynamic therapy enabled by fluorinated BODIPY-liposome hybrids for enhanced antibacterial efficacy","authors":"Zhihua Chen , Jincheng Zhu , Mengxing Wang , Qinglin Wu , Yichun Xu , Lei Cui , Kewen Zheng","doi":"10.1016/j.tetlet.2025.155830","DOIUrl":"10.1016/j.tetlet.2025.155830","url":null,"abstract":"<div><div>The widespread misuse of antibiotics has accelerated bacterial evolution, precipitating a global antimicrobial resistance (AMR) crisis. Photodynamic therapy (PDT) has recently emerged as a promising alternative due to its non-invasiveness, cost-effectiveness and broad-spectrum antimicrobial activity. Boron-dipyrromethene (BODIPY) derivatives constitute a promising class of organic photosensitizers with experimentally verified photodynamic activity. However, conventional BODIPY-based photosensitizers face significant limitations: their inherent hydrophobicity reduces reactive oxygen species (ROS) generation efficiency, diminishes antimicrobial coverage, and may paradoxically promote resistance development. Furthermore, their exclusive production of Type I PDT, without complementary Type II mechanisms, substantially restricts their therapeutic potential. ‌Herein, a series of photosensitizers (PSs) with antibacterial properties was developed by leveraging electron push-pull systems coupled with heavy-atom effects. In addition to enhance the aqueous solubility of photosensitizers, three types were encapsulated into liposomes via the thin film hydration method. Benefiting from sufficient molecular rotors and high electronegativity of fluorine, the developed BDP-F Lips exhibit superior ROS generation capacity under laser irradiation, concurrently producing both Type I and Type II PDT, thereby demonstrating excellent antibacterial efficacy.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155830"},"PeriodicalIF":1.5,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145128257","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Ru(II)-catalyzed regioselective [3+2] spiroannulation of 4-arylquinazolin-2(1H)-ones with ynones Ru（II）催化4-芳基喹唑啉-2(1H)- 1与炔酮的区域选择性[3+2]旋环反应

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-09-18 DOI: 10.1016/j.tetlet.2025.155824

T. Ravi Teja , Ch. Ajay , S. Karthik , B. Sridhar , B.V. Subba Reddy

引用次数: 0

Isosulochrin xanthone and isosulochrin depsidone heterodimers from the endophytic fungus Colletotrichum sp. NF02092 内生真菌Colletotrichum sp. NF02092的异桃金酮山酮和异桃金酮异二聚体

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-09-18 DOI: 10.1016/j.tetlet.2025.155832

Xing Guo , Yang Zhao , Yan Wang, Huiming Ge, Bo Zhang

引用次数: 0

Efficient and improved synthesis of kukoamine D and N1,N5,N14-tris(dihydrocaffeoyl)spermine kukoamine D和N1，N5， n14 -三（二氢咖啡因基）精胺的高效改进合成

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-09-17 DOI: 10.1016/j.tetlet.2025.155831

Lijuan Zhai, Lili He, Jingwen Ji, Yuanyu Gao, Jian Sun

{"title":"Efficient and improved synthesis of kukoamine D and N1,N5,N14-tris(dihydrocaffeoyl)spermine","authors":"Lijuan Zhai, Lili He, Jingwen Ji, Yuanyu Gao, Jian Sun","doi":"10.1016/j.tetlet.2025.155831","DOIUrl":"10.1016/j.tetlet.2025.155831","url":null,"abstract":"<div><div>Natural products kukoamine D and <em>N</em><sup><em>1</em></sup>,<em>N</em><sup><em>5</em></sup>,<em>N</em><sup><em>14</em></sup>-tris(dihydrocaffeoyl)spermine, two hydrocaffeoylspermine alkaloids predominantly isolated from <em>Solanaceae</em> plants, exhibit diverse pharmacological activities. However, low natural contents and inefficient synthesis methods limit their applications. Commencing with tert-butyloxycarbonyl (Boc)-protected 1,4-butanediamine, we synthesized kukoamine D and <em>N</em><sup><em>1</em></sup>,<em>N</em><sup><em>5</em></sup>,<em>N</em><sup><em>14</em></sup>-tris(dihydrocaffeoyl)spermine via an eight-step sequence, achieving overall yields of 29 % and 20 %, respectively. We used a one-pot two-step, nitrile reductive amination method using a nickel chloride (NiCl<sub>2</sub>·6H<sub>2</sub>O)/sodium borohydride (NaBH<sub>4</sub>) system, followed by active esters amidation. The synthesis is simple, cost effective, and scalable. This approach provides a practical route for the industrial production of structurally similar natural products, facilitating pharmacological studies and analog development.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155831"},"PeriodicalIF":1.5,"publicationDate":"2025-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145109542","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Diastereoselective, photocatalytic [2 + 2] dimerizations of alkenylboronic acids promoted by sugar alcohols 糖醇促进烯基硼酸的非对映选择性光催化[2 + 2]二聚化反应

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-09-15 DOI: 10.1016/j.tetlet.2025.155827

Anastasia Charlery, Shrey P. Desai, Matthew T. Zambri, Mark S. Taylor

引用次数: 0

Structure–selectivity correlation in asymmetric baeyer–villiger oxidation of 3-arylcyclobutanones by a flavinium ion-pair catalyst 黄离子对催化3-芳基环丁酮不对称baeyer-villiger氧化的结构-选择性关系

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-09-13 DOI: 10.1016/j.tetlet.2025.155826

Junya Fujimoto , Eika Suruga , Natsuhiko Sugimura , Kana Yamamoto

引用次数: 0

C3-selective CH borylation of indoles by supported gold catalysts 负载金催化剂催化吲哚的c3选择性CH硼化反应

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-09-13 DOI: 10.1016/j.tetlet.2025.155758

Hiroki Miura , Miyu Chida , Tetsuya Shishido

引用次数: 0

Photoinduced regioselective CH thiocyanation and selenocyanation of arylamines 光诱导芳胺的区域选择性硫氰化和硒氰化

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-09-12 DOI: 10.1016/j.tetlet.2025.155819

Chang Liu, Qiping He, Haiyue Yang, Hao Jin, Siyu Wang, Mingquan Yuan, Yi Jin

引用次数: 0

Effect of additives on the asymmetric reduction of fluorinated ketones using cyanobacterium Synechocystis sp. PCC 6803 添加剂对聚胞蓝藻不对称还原氟酮的影响

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-09-11 DOI: 10.1016/j.tetlet.2025.155822

Satsuki Fukui , Itsuku Makigawa , Yuya Machi , Hideo Kojima , Satomi Takeda , Rio Yamanaka

{"title":"Effect of additives on the asymmetric reduction of fluorinated ketones using cyanobacterium Synechocystis sp. PCC 6803","authors":"Satsuki Fukui , Itsuku Makigawa , Yuya Machi , Hideo Kojima , Satomi Takeda , Rio Yamanaka","doi":"10.1016/j.tetlet.2025.155822","DOIUrl":"10.1016/j.tetlet.2025.155822","url":null,"abstract":"<div><div>The asymmetric reduction of fluorinated ketones (<strong>1a–c</strong>) was investigated using the wild-type cyanobacterium Synechocystis sp. PCC 6803 at 25 °C for 24 h. Under red LED illumination (660 nm, 10 μmol m<sup>−2</sup> s<sup>−1</sup>), the photosynthetic system promoted cofactor regeneration, enhancing the formation of optically active alcohols (<strong>2a–c</strong>). The effect of substrate concentration was found to significantly influence stereoselectivity: at low concentrations, L-alcohols were predominantly formed, whereas at higher concentrations, a shift toward D-selectivity was observed, especially for substrate <strong>1c</strong> (41 % ee (L) at 0.05 mM; 87 % ee (D) at 5 mM). Furthermore, <strong>1a</strong> acted as a competitive inhibitor in the reduction of <strong>1c</strong>, effectively altering the enantioselectivity. Additionally, hyperosmotic conditions induced by 0.5 M sorbitol or 0.25 M NaCl increased the yield of L-alcohols, likely by upregulating the expression of the fabG gene, which encodes an NADPH-dependent ketoreductase. These findings provide new insights into the control of stereoselectivity and reaction efficiency in photobiocatalytic reductions using whole-cell cyanobacteria.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155822"},"PeriodicalIF":1.5,"publicationDate":"2025-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145105228","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Copper iron oxide promoted cascade annulation between 2′-nitrochalcones and NH pyrazoles 铜氧化铁促进了2′-硝基查尔酮和NH吡唑之间的级联环

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-09-11 DOI: 10.1016/j.tetlet.2025.155825

Phuong T. Dinh , Quan Q.T. Pham , Dat T. Huynh , Tung T. Nguyen , Ngoc D.Q. Chau

引用次数: 0