细菌叶绿素二聚体作为溶剂极性依赖性近红外荧光团和活性氧物种光敏剂。
Bacteriochlorin Dyads as Solvent Polarity Dependent Near-Infrared Fluorophores and Reactive Oxygen Species Photosensitizers.
机构信息
Department of Chemistry and Biochemistry, University of Maryland, Baltimore County , 1000 Hilltop Circle, Baltimore, Maryland 21250, United States.
Biotechnology Career Academy, Applications and Research Laboratory, Howard County Public School System , Ellicott City, Maryland 21042, United States.
出版信息
Org Lett. 2016 Sep 16;18(18):4590-3. doi: 10.1021/acs.orglett.6b02237. Epub 2016 Sep 7.
Abstract
Symmetrical, near-infrared absorbing bacteriochlorin dyads exhibit gradual reduction of their fluorescence (intensity and lifetime) and reactive oxygen species photosensitization efficiency (ROS) with increasing solvent dielectric constant ε. For the directly linked dyad, significant reduction is observed even in solvents of moderate ε, while for the dyad containing a 1,4-phenylene linker, reduction is more parallel to an increase in solvent ε. Bacteriochlorin dyads are promising candidates for development of environmentally responsive fluorophores and ROS sensitizers.
摘要
具有对称结构、近红外吸收的细菌叶绿素二聚体，随着溶剂介电常数 ε 的增加，其荧光（强度和寿命）和活性氧物种光敏化效率（ROS）逐渐降低。对于直接连接的二聚体，即使在中等 ε 的溶剂中，也观察到显著的降低，而对于含有 1,4-亚苯基连接体的二聚体，降低更与溶剂 ε 的增加平行。细菌叶绿素二聚体是开发环境响应荧光团和 ROS 敏化剂的有前途的候选物。
相似文献
1
Bacteriochlorin Dyads as Solvent Polarity Dependent Near-Infrared Fluorophores and Reactive Oxygen Species Photosensitizers.
Org Lett. 2016 Sep 16;18(18):4590-3. doi: 10.1021/acs.orglett.6b02237. Epub 2016 Sep 7.
2
Near-IR emissive chlorin-bacteriochlorin energy-transfer dyads with a common donor and acceptors with tunable emission wavelength.
J Org Chem. 2013 Nov 1;78(21):10678-91. doi: 10.1021/jo4016858. Epub 2013 Oct 14.
3
BODIPY-Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands.
J Org Chem. 2017 Dec 15;82(24):13068-13075. doi: 10.1021/acs.joc.7b02031. Epub 2017 Nov 22.
4
Examination of chlorin-bacteriochlorin energy-transfer dyads as prototypes for near-infrared molecular imaging probes.
Photochem Photobiol. 2008 Sep-Oct;84(5):1061-72. doi: 10.1111/j.1751-1097.2008.00409.x. Epub 2008 Jul 25.
5
Chlorin-bacteriochlorin energy-transfer dyads as prototypes for near-infrared molecular imaging probes: controlling charge-transfer and fluorescence properties in polar media.
Photochem Photobiol. 2009 Jul-Aug;85(4):909-20. doi: 10.1111/j.1751-1097.2008.00532.x. Epub 2009 Feb 13.
6
Symmetrical and Nonsymmetrical Meso-Meso Directly Linked Hydroporphyrin Dyads: Synthesis and Photochemical Properties.
Inorg Chem. 2018 Mar 19;57(6):2977-2988. doi: 10.1021/acs.inorgchem.7b02200. Epub 2017 Nov 15.
7
In vitro photodynamic therapy and quantitative structure-activity relationship studies with stable synthetic near-infrared-absorbing bacteriochlorin photosensitizers.
J Med Chem. 2010 May 27;53(10):4018-27. doi: 10.1021/jm901908s.
8
Enhanced Cellular Uptake and Photodynamic Effect with Amphiphilic Fluorinated Porphyrins: The Role of Sulfoester Groups and the Nature of Reactive Oxygen Species.
Int J Mol Sci. 2020 Apr 16;21(8):2786. doi: 10.3390/ijms21082786.
9
Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer.
Bioconjug Chem. 2019 Jan 16;30(1):169-183. doi: 10.1021/acs.bioconjchem.8b00820. Epub 2018 Dec 14.
10
[New photosensitizers of bacteriochlorin series for photodynamic cancer therapy].
Bioorg Khim. 2003 Mar-Apr;29(2):214-21. doi: 10.1023/a:1023272718636.
引用本文的文献
1
Exciton delocalization in a fully synthetic DNA-templated bacteriochlorin dimer.
Phys Chem Chem Phys. 2023 Oct 25;25(41):28437-28451. doi: 10.1039/d3cp01634j.
2
Picolyl Porphyrin Nanostructures as a Functional Drug Entrant for Photodynamic Therapy in Human Breast Cancers.
ACS Omega. 2019 Jul 29;4(7):12808-12816. doi: 10.1021/acsomega.9b01380. eCollection 2019 Jul 31.
3
Molecular Structure of the Photo-Oxidation Product of Ellagic Acid in Solution.
ACS Omega. 2018 Sep 14;3(9):11179-11183. doi: 10.1021/acsomega.8b01716. eCollection 2018 Sep 30.
4
PyrrolylBODIPYs: Syntheses, Properties, and Application as Environment-Sensitive Fluorescence Probes.
ACS Omega. 2017 Jul 13;2(7):3551-3561. doi: 10.1021/acsomega.7b00444. eCollection 2017 Jul 31.
5
Water-soluble chiral tetrazine derivatives: towards the application of circularly polarized luminescence from upper-excited states to photodynamic therapy.
Chem Sci. 2019 Mar 8;10(15):4163-4168. doi: 10.1039/c9sc00264b. eCollection 2019 Apr 21.
6
Excitonic Interactions in Bacteriochlorin Homo-Dyads Enable Charge Transfer: A New Approach to the Artificial Photosynthetic Special Pair.
J Phys Chem B. 2018 Apr 12;122(14):4131-4140. doi: 10.1021/acs.jpcb.8b02123. Epub 2018 Mar 27.
7
Symmetrical and Nonsymmetrical Meso-Meso Directly Linked Hydroporphyrin Dyads: Synthesis and Photochemical Properties.
Inorg Chem. 2018 Mar 19;57(6):2977-2988. doi: 10.1021/acs.inorgchem.7b02200. Epub 2017 Nov 15.
8
Synthesis and Spectral Properties of meso-Arylbacteriochlorins, Including Insights into Essential Motifs of their Hydrodipyrrin Precursors.
Molecules. 2017 Apr 14;22(4):634. doi: 10.3390/molecules22040634.
本文引用的文献
1
An ultrasensitive near-infrared ratiometric fluorescent probe for imaging mitochondrial polarity in live cells and .
Chem Sci. 2016 Feb 1;7(2):1588-1593. doi: 10.1039/c5sc04099j. Epub 2015 Nov 23.
2
Directly linked hydroporphyrin dimers.
Chem Commun (Camb). 2016 Jul 12;52(58):9056-8. doi: 10.1039/c6cc00516k.
3
Effects of Strong Electronic Coupling in Chlorin and Bacteriochlorin Dyads.
J Phys Chem A. 2016 Jan 28;120(3):379-95. doi: 10.1021/acs.jpca.5b10686. Epub 2016 Jan 14.
4
Two-Photon Absorbing Dyes with Minimal Autofluorescence in Tissue Imaging: Application to in Vivo Imaging of Amyloid-β Plaques with a Negligible Background Signal.
J Am Chem Soc. 2015 Jun 3;137(21):6781-9. doi: 10.1021/jacs.5b03548. Epub 2015 May 21.
5
Ratiometric fluorescence imaging of cellular polarity: decrease in mitochondrial polarity in cancer cells.
Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2510-4. doi: 10.1002/anie.201410645. Epub 2015 Jan 8.
6
Fluorogenic squaraine dimers with polarity-sensitive folding as bright far-red probes for background-free bioimaging.
J Am Chem Soc. 2015 Jan 14;137(1):405-12. doi: 10.1021/ja5111267. Epub 2014 Dec 29.
7
Chemical modification of a tetrapyrrole-type photosensitizer: tuning application and photochemical action beyond the singlet oxygen channel.
J Phys Chem B. 2014 Oct 9;118(40):11646-58. doi: 10.1021/jp507270k. Epub 2014 Sep 26.
8
Direct measurement of the dielectric polarization properties of DNA.
Proc Natl Acad Sci U S A. 2014 Sep 2;111(35):E3624-30. doi: 10.1073/pnas.1405702111. Epub 2014 Aug 18.
9
Strongly conjugated hydroporphyrin dyads: extensive modification of hydroporphyrins' properties by expanding the conjugated system.
J Org Chem. 2014 Sep 5;79(17):7910-25. doi: 10.1021/jo501041b. Epub 2014 Aug 8.
10
Physicochemical properties of cells and their effects on intrinsically disordered proteins (IDPs).
Chem Rev. 2014 Jul 9;114(13):6661-714. doi: 10.1021/cr400695p. Epub 2014 Jun 5.
Zotero 插件