| 466 | 1 | 5 |
| 下载次数 | 被引频次 | 阅读次数 |
为了解决氟硼荧类染料(BODIPY)在肿瘤诊断中吸收波长短、水溶性和生物相容性差的问题,设计开发了2种吸收波长达到近红外区的BODIPY分子,并通过与DSPE-PEG2000-MAL-RGD(PC-RGD)自组装形成具有良好水溶性和生物相容性的纳米粒子。研究了纳米粒子的荧光成像能力,结果表明:单取代分子3a和双取代分子3b的荧光发射波长分别达到了650和775 nm,且双取代分子3b表现出更大的斯托克斯位移,这是由于其具有更高的共轭程度。另外包裹后的纳米粒子表现出良好水溶性和生物相容性,为其作为肿瘤诊断的荧光探针提供了基础。
Abstract：In order to solve the problem of short absorption wavelength, poor water solubility and poor biocompatibility of Fluoroboron-fluorescent dyes(BODIPY) in tumor diagnosis, two BODIPY molecules with absorption wavelengths reaching the near-infrared region have been designed and synthesized, and they have been combined with DSPE-PEG2000-MAL-RGD(PC-RGD) to form nanoparticles with good water solubility and biocompatibility. Then the fluorescence imaging ability of nanoparticles was studied. The results showed that the fluorescence emission wavelengths of the mono-substituted molecule 3 a and the di-substituted molecule 3 b reached 650 and 775 nm, respectively. And di-substituted molecule 3 b shows greater Stokes shift than 3 a due to its higher degree of conjugation. Moreover, the encapsulated nanoparticles show good water solubility and biocompatibility, which provides a possibility as fluorescent probes for tumor diagnosis.
[1] LIU Y,BHATTARAI P,DAI Z,et al.Photothermal therapy and photoacoustic imaging via nanotheranostics in fighting cancer[J].Chemical Society Reviews,2019,48(7):2053-2108
[2] RAJORA M A,LOU J W H,ZHENG G.Advancing porphyrin’s biomedical utility via supramolecular chemistry[J].Chemical Society Reviews,2017,46(21):6433-6469
[3] PENG J,ZHAO L,ZHU X,et al.Hollow silica nanoparticles loaded with hydrophobic phthalocyanine for near-infrared photodynamic and photothermal combination therapy[J].Biomaterials,2013,34(32):7905-7912
[4] NGUYEN V N,YIM Y,KIM S,et al.Molecular design of highly efficient heavy-atom-free triplet BODIPY derivatives for photodynamic therapy and bioimaging[J].Angewandte Chemie International Edition,2020,59(23):8957-8962
[5] WANG C,CHENG L,LIU Y,et al.Imaging-guided pH-sensitive photodynamic therapy using charge reversible upconversion nanoparticles under near-infrared light[J].Advanced Functional Materials,2013,23(24):3077-3086
[6] SWEDIN R,ZATSIKHA Y V,HEALY A T,et al.Rapid excited-state deactivation of BODIPY derivatives by a boron-bound catechol[J].The Journal of Physical Chemistry Letters,2019,10(8):1828-1832
[7] CUI A,PENG X,FAN J,et al.Synthesis,spectral properties and photostability of novel boron-dipyrromethene dyes[J].Journal of Photochemistry and Photobiology A:Chemistry,2007,186(1):85-92
[8] LIU N,ZHU M,NIU N,et al.Aza-BODIPY probe-decorated mesoporous black TiO2 nanoplatform for the highly efficient synergistic phototherapy[J].ACS Applied Materials & Interfaces,2020,12(37):41071-41078
[9] LOUDET A,BURGESS K.BODIPY dyes and their derivatives:Syntheses and spectroscopic properties[J].Chemical Reviews,2007,107(11):4891-4932
[10] ZHANG J,BAO X,ZHOU J,et al.A mitochondria-targeted turn-on fluorescent probe for the detection of glutathione in living cells[J].Biosensors and Bioelectronics,2016,85:164-170
[11] YUAN P,RUAN Z,JIANG W,et al.Oxygen self-sufficient fluorinated polypeptide nanoparticles for NIR imaging-guided enhanced photodynamic therapy[J].Journal of Materials Chemistry B,2018,6(15):2323-2331
[12] 王红萍，崔爱军，田茂忠，等.氟硼荧(BODIPY)染料的研究进展[J].当代化工，2007,36(2):198-201WANG Hongping,CUI Aijun,TIAN Maozhong,et al.Development of boron dipyrromethene(BODIPY) fluorophores[J].Contemporary Chemical Industry,2007,36(2):198-201(in Chinese)
[13] BOENS N,LEEN V,DEHAEN W.Fluorescent indicators based on BODIPY[J].Chemical Society Reviews,2012,41(3):1130-1172
[14] 卢博为，孟舒献，冯亚青.氟硼荧类亲水性生物荧光探针的研究进展[J].有机化学，2018,38(2):350-362LU Bowei,MENG Shuxian,FENG Yaqing.Progress of fluorescent bio-probe based on water-soluble boron-dipyrromethene[J].Chinese Journal of Organic Chemistry,2018,38(2):350-362(in Chinese)
[15] NIU S,ULRICH G,ZIESSEL R,et al.Water-soluble BODIPY derivatives[J].Organic Letters,2009,11(10):2049-2052
[16] GUO Z,ZOU Y,HE H,et al.Bifunctional platinated nanoparticles for photoinduced tumor ablation[J].Advanced Materials,2016,28(46):10155-10164
[17] WANG Z,IVANOV M,GAO Y,et al.Spin-orbit charge-transfer intersystem crossing (ISC) in compact electron donor-acceptor dyads:ISC mechanism and application as novel and potent photodynamic therapy reagents[J].Chemistry-A European Journal,2020,26(5):1091-1102
[18] QIN Y,LIU X,JIA P,et al.BODIPY-based macrocycles[J].Chemical Society Reviews,2020,49(16):5678-5703
[19] RUAN Z,MIAO W,YUAN P,et al.High singlet oxygen yield photosensitizer based polypeptide nanoparticles for low-power near-infrared light imaging-guided photodynamic therapy[J].Bioconjugate Chemistry,2018,29(10):3441-3451
[20] SUN F,YANG G,ZHANG Q,et al.The self-assembly of monosubstituted BODIPY and HFBI-RGD[J].RSC Advances,2018,8(38):21472-21479
[21] VANKAYALA R,HWANG K C.Near-infrared-light-activatable nanomaterial-mediated phototheranostic nanomedicines:An emerging paradigm for cancer treatment[J].Advanced Materials,2018,30(23):1706320-1706347
[22] 钮文杰.含氮稠杂环有机小分子荧光化合物的合成及其性能研究[D].杭州：浙江工业大学，2020NIU Wenjie.Synthesis and properties of nitrogencontaining condensed heterocyclic organic small molecule fluorescent compounds[D].Hangzhou:Zhejiang University of Technology,2020 (in Chinese)
基本信息:
DOI：10.13353/j.issn.1004.9533.20210123
中图分类号:O657.3;TB383.1;R730.4
引用信息:
[1]尹娟娟,冯彤,薛中博,等.新型氟硼二吡咯纳米粒子荧光探针的合成与性能[J].化学工业与工程,2022,39(01):19-26.DOI:10.13353/j.issn.1004.9533.20210123.
基金信息:
国家自然科学基金资助项目(21676187)