• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

基于柠檬酸盐的荧光小分子与可生物降解聚合物的合成及表征

Synthesis and characterization of citrate-based fluorescent small molecules and biodegradable polymers.

作者信息

Xie Zhiwei, Kim Jimin P, Cai Qing, Zhang Yi, Guo Jinshan, Dhami Ranjodh S, Li Li, Kong Bin, Su Yixue, Schug Kevin A, Yang Jian

机构信息

Department of Biomedical Engineering, Materials Research Institutes, The Huck Institutes of Life Sciences, The Pennsylvania State University, University Park, PA 16801, United States.

Beijing Laboratory of Biomedical Materials, Beijing University of Chemical Technology, Beijing 100029, China.

出版信息

Acta Biomater. 2017 Mar 1;50:361-369. doi: 10.1016/j.actbio.2017.01.019. Epub 2017 Jan 6.

DOI:10.1016/j.actbio.2017.01.019
PMID:28069502
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5316379/
Abstract

UNLABELLED

Novel citric acid based photoluminescent dyes and biodegradable polymers are synthesized via a facile "one-pot" reaction. A comprehensive understanding of the fluorescence mechanisms of the resulting citric acid-based fluorophores is reported. Two distinct types of fluorophores are identified: a thiozolopyridine family with high quantum yield, long lifetime, and exceptional photostability, and a dioxopyridine family with relatively lower quantum yield, multiple lifetimes, and solvent-dependent band shifting behavior. Applications in molecular labeling and cell imaging were demonstrated. The above discoveries contribute to the field of fluorescence chemistry and have laid a solid foundation for further development of new fluorophores and materials that show promise in a diversity of fluorescence-based applications.

STATEMENT OF SIGNIFICANCE

Photoluminescent materials are pivotal for fluorescence based imaging, labeling and sensing applications. Understanding their fluorescence mechanism is challenging and imperative. We develop a new class of citric acid-derived fluorescent materials in forms of polymers and small molecular dyes by a one-step solvent free reaction. We discovered two different classes of citric acid-derived fluorophores. A two-ring thiozolopyridine structure demonstrates strong fluorescence and exceptional resistance to photo-bleaching. A one-ring dioxopyridine exhibits relative weak fluorescence but with intriguing excitation and solvent-dependent emission wavelength shifting. Our methodology of synthesizing citric acid-derived fluorophores and the understanding on their luminescence are instrumental to the design and production of a large number of new photoluminescent materials for biological and biomedical applications.

摘要

未标记

通过简便的“一锅法”反应合成了新型柠檬酸基光致发光染料和可生物降解聚合物。报道了对所得柠檬酸基荧光团荧光机制的全面理解。鉴定出两种不同类型的荧光团:具有高量子产率、长寿命和出色光稳定性的噻唑并吡啶家族,以及具有相对较低量子产率、多个寿命和溶剂依赖性带移行为的二氧吡啶家族。展示了其在分子标记和细胞成像中的应用。上述发现为荧光化学领域做出了贡献,并为进一步开发在多种基于荧光的应用中显示出前景的新型荧光团和材料奠定了坚实基础。

重要性声明

光致发光材料对于基于荧光的成像、标记和传感应用至关重要。理解它们的荧光机制具有挑战性且势在必行。我们通过一步无溶剂反应开发了一类新型的柠檬酸衍生荧光材料,其形式为聚合物和小分子染料。我们发现了两类不同的柠檬酸衍生荧光团。双环噻唑并吡啶结构表现出强烈的荧光和出色的抗光漂白性。单环二氧吡啶表现出相对较弱的荧光,但具有有趣的激发和溶剂依赖性发射波长移动。我们合成柠檬酸衍生荧光团的方法及其对发光的理解有助于设计和生产大量用于生物和生物医学应用的新型光致发光材料。

相似文献

1
Synthesis and characterization of citrate-based fluorescent small molecules and biodegradable polymers.基于柠檬酸盐的荧光小分子与可生物降解聚合物的合成及表征
Acta Biomater. 2017 Mar 1;50:361-369. doi: 10.1016/j.actbio.2017.01.019. Epub 2017 Jan 6.
2
Biodegradable, Elastomeric, and Intrinsically Photoluminescent Poly(Silicon-Citrates) with high Photostability and Biocompatibility for Tissue Regeneration and Bioimaging.可生物降解、弹性、本征发磷光的聚(硅柠檬酸酯),具有高稳定性和生物相容性,可用于组织再生和生物成像。
Adv Healthc Mater. 2016 Feb 4;5(3):382-92. doi: 10.1002/adhm.201500643. Epub 2015 Dec 20.
3
Synthesis of highly photoluminescent carbon dots via citric acid and Tris for iron(III) ions sensors and bioimaging.通过柠檬酸和三(羟甲基)氨基甲烷合成具有高光致发光性能的碳点用于铁(III)离子传感器和生物成像。
Talanta. 2015 Oct 1;143:107-113. doi: 10.1016/j.talanta.2015.04.015. Epub 2015 Apr 13.
4
Citrate-Based Fluorescent Biomaterials.基于柠檬酸盐的荧光生物材料。
Adv Healthc Mater. 2018 Sep;7(18):e1800532. doi: 10.1002/adhm.201800532. Epub 2018 Jul 26.
5
Development of aliphatic biodegradable photoluminescent polymers.脂肪族可生物降解光致发光聚合物的开发。
Proc Natl Acad Sci U S A. 2009 Jun 23;106(25):10086-91. doi: 10.1073/pnas.0900004106. Epub 2009 Jun 8.
6
Photoluminescent PEG based comacromers as excitation dependent fluorophores for biomedical applications.基于光致发光聚乙二醇的共聚大分子作为用于生物医学应用的激发依赖性荧光团。
Colloids Surf B Biointerfaces. 2015 Nov 1;135:243-252. doi: 10.1016/j.colsurfb.2015.07.027. Epub 2015 Jul 21.
7
Facile synthesis of fluorescent dye labeled biocompatible polymers via immortal ring-opening polymerization.通过不朽开环聚合制备荧光染料标记的生物相容性聚合物的简便方法。
Chem Commun (Camb). 2012 May 11;48(37):4483-5. doi: 10.1039/c2cc31061a. Epub 2012 Mar 30.
8
One-pot synthesis of fluorescent nitrogen-doped carbon dots with good biocompatibility for cell labeling.一锅法合成具有良好生物相容性用于细胞标记的荧光氮掺杂碳点。
Luminescence. 2017 Dec;32(8):1488-1493. doi: 10.1002/bio.3349. Epub 2017 Jun 7.
9
Facile Preparation of Bright-Fluorescent Soft Materials from Small Organic Molecules.由小分子有机化合物轻松制备高荧光软材料。
Chemistry. 2016 Jun 6;22(24):8096-104. doi: 10.1002/chem.201600448. Epub 2016 May 19.
10
Citrate-based fluorophore-modified cellulose nanocrystals as a biocompatible fluorescent probe for detecting ferric ions and intracellular imaging.基于柠檬酸盐的荧光染料修饰的纤维素纳米晶体作为一种生物相容性的荧光探针用于检测铁离子和细胞内成像。
Carbohydr Polym. 2019 Nov 15;224:115198. doi: 10.1016/j.carbpol.2019.115198. Epub 2019 Aug 13.

引用本文的文献

1
Metabotissugenic citrate biomaterials orchestrate bone regeneration via citrate-mediated signaling pathways.代谢促生源柠檬酸盐生物材料通过柠檬酸盐介导的信号通路协调骨再生。
Sci Adv. 2025 Jul 25;11(30):eady2862. doi: 10.1126/sciadv.ady2862. Epub 2025 Jul 23.
2
Dual-imaging nanoparticles based on surface-modified magnetic nanoparticles and biodegradable photoluminescent polymers.基于表面改性磁性纳米颗粒和可生物降解光致发光聚合物的双成像纳米颗粒。
Front Bioeng Biotechnol. 2025 Apr 10;13:1558817. doi: 10.3389/fbioe.2025.1558817. eCollection 2025.
3
3D Histology visualizing hypoxia-induced upregulation of N-terminal cysteine using de novo fluorophore generation.利用从头荧光团生成技术进行3D组织学可视化,观察缺氧诱导的N端半胱氨酸上调。
Redox Biol. 2025 Apr;81:103577. doi: 10.1016/j.redox.2025.103577. Epub 2025 Mar 3.
4
Citric Acid: A Nexus Between Cellular Mechanisms and Biomaterial Innovations.柠檬酸:细胞机制与生物材料创新的纽带。
Adv Mater. 2024 Aug;36(32):e2402871. doi: 10.1002/adma.202402871. Epub 2024 Jun 11.
5
Citrate-based fluorometric sensor for multi-halide sensing.用于多卤化物传感的基于柠檬酸盐的荧光传感器。
Smart Mater Med. 2022;3:374-381. doi: 10.1016/j.smaim.2022.05.001. Epub 2022 May 16.
6
Automated fabrication of a scalable heart-on-a-chip device by 3D printing of thermoplastic elastomer nanocomposite and hot embossing.通过热塑性弹性体纳米复合材料的3D打印和热压印自动制造可扩展的芯片上心脏装置。
Bioact Mater. 2023 Nov 7;33:46-60. doi: 10.1016/j.bioactmat.2023.10.019. eCollection 2024 Mar.
7
Citric Acid-Based Intrinsic Band-Shifting Photoluminescent Materials.基于柠檬酸的本征能带移动光致发光材料。
Research (Wash D C). 2023 May 29;6:0152. doi: 10.34133/research.0152. eCollection 2023.
8
Novel Injectable Fluorescent Polymeric Nanocarriers for Intervertebral Disc Application.用于椎间盘应用的新型可注射荧光聚合物纳米载体
J Funct Biomater. 2023 Jan 17;14(2):52. doi: 10.3390/jfb14020052.
9
Three-dimensional imaging and analysis of pathological tissue samples with de novo generation of citrate-based fluorophores.基于从头生成柠檬酸盐荧光团的病理组织样本的三维成像与分析
Sci Adv. 2022 Nov 18;8(46):eadd9419. doi: 10.1126/sciadv.add9419. Epub 2022 Nov 16.
10
Biodegradable and Inherently Fluorescent pH-Responsive Nanoparticles for Cancer Drug Delivery.可生物降解且具有内在荧光响应的 pH 响应型纳米粒子用于癌症药物递送。
Pharm Res. 2022 Nov;39(11):2729-2743. doi: 10.1007/s11095-022-03317-8. Epub 2022 Jun 28.

本文引用的文献

1
Nucleus-Independent Chemical Shifts:  A Simple and Efficient Aromaticity Probe.核独立化学位移:一种简单高效的芳香性探针。
J Am Chem Soc. 1996 Jul 3;118(26):6317-6318. doi: 10.1021/ja960582d.
2
Citrate-based fluorescent materials for low-cost chloride sensing in the diagnosis of Cystic Fibrosis.用于囊性纤维化诊断中低成本氯离子传感的柠檬酸盐基荧光材料。
Chem Sci. 2017 Jan 1;8(1):550-558. doi: 10.1039/C6SC02962K. Epub 2016 Aug 30.
3
Development of intrinsically photoluminescent and photostable polylactones.本征光致发光且光稳定的聚内酯的开发。
Adv Mater. 2014 Jul 9;26(26):4491-6. doi: 10.1002/adma.201306070. Epub 2014 Mar 26.
4
Origin of strong excitation wavelength dependent fluorescence of graphene oxide.氧化石墨烯强激发波长依赖荧光的起源。
ACS Nano. 2014 Jan 28;8(1):1002-13. doi: 10.1021/nn405843d. Epub 2013 Dec 26.
5
Luminescence phenomena of biodegradable photoluminescent poly(diol citrates).可生物降解的光致发光聚(二羟基柠檬酸酯)的发光现象。
Chem Commun (Camb). 2013 Jul 21;49(57):6445-7. doi: 10.1039/c3cc42661k.
6
Design Strategies for Fluorescent Biodegradable Polymeric Biomaterials.荧光可生物降解聚合物生物材料的设计策略
J Mater Chem B. 2013 Jan 14;1(2):132-148. doi: 10.1039/C2TB00071G.
7
Fluorescence imaging enabled urethane-doped citrate-based biodegradable elastomers.荧光成像是基于尿烷掺杂的柠檬酸酯的可生物降解弹性体的实现手段。
Biomaterials. 2013 May;34(16):4048-4056. doi: 10.1016/j.biomaterials.2013.02.040. Epub 2013 Mar 5.
8
Highly photoluminescent carbon dots for multicolor patterning, sensors, and bioimaging.用于多色图案化、传感器及生物成像的高光致发光碳点。
Angew Chem Int Ed Engl. 2013 Apr 2;52(14):3953-7. doi: 10.1002/anie.201300519. Epub 2013 Feb 28.
9
A unique aliphatic tertiary amine chromophore: fluorescence, polymer structure, and application in cell imaging.一种独特的脂肪族叔胺生色团:荧光、聚合物结构及在细胞成像中的应用。
J Am Chem Soc. 2012 Dec 26;134(51):20581-4. doi: 10.1021/ja310236m. Epub 2012 Dec 13.
10
Simple one-step synthesis of highly luminescent carbon dots from orange juice: application as excellent bio-imaging agents.橙汁一步法简单合成高发光碳点:作为优秀生物成像试剂的应用。
Chem Commun (Camb). 2012 Sep 11;48(70):8835-7. doi: 10.1039/c2cc33796g. Epub 2012 Jul 27.