Julolidinyl Aza-BODIPYs As NIR-II Fluorophores for the Bioimaging of Nanocarriers

Overview

Journal Acta Pharm Sin B

Publisher Elsevier

Specialty Pharmacology

Date 2024 Jul 19

PMID 39027233

Authors

Chang Liu

Yifan Cai

Zichen Zhang

Yi Lu

Quangang Zhu

Haisheng He

Zhongjian Chen

Weili Zhao

Wei Wu

Affiliations

Soon will be listed here.

Abstract

The aggregation-caused quenching (ACQ) rationale has been employed to improve the fluorescence imaging accuracy of nanocarriers by precluding free probe-derived interferences. However, its usefulness is undermined by limited penetration and low spatiotemporal resolution of NIR-I (700-900 nm) bioimaging owing to absorption and diffraction by biological tissues and tissue-derived autofluorescence. This study aimed to develop ACQ-based NIR-II (1000-1700 nm) probes to further improve the imaging resolution and accuracy. The strategy employed is to install highly planar and electron-rich julolidine into the 3,5-position of aza-BODIPY based on the larger substituent effects. The newly developed probes displayed remarkable photophysical properties, with intense absorption centered at approximately 850 nm and bright emission in the 950-1300 nm region. Compared with the NIR-I counterpart P2, the NIR-II probes demonstrated superior water sensitivity and quenching stability. ACQ1 and ACQ6 exhibited more promising ACQ effects with absolute fluorescence quenching at water fractions above 40% and higher quenching stability with less than 2.0% fluorescence reillumination in plasma after 24 h of incubation. Theoretical calculations verified that molecular planarity is more important than hydrophobicity for ACQ properties. Additionally, and reillumination studies revealed less than 2.5% signal interference from prequenched ACQ1, in contrast to 15% for P2.

References

Liu S, Li Y, Kwok R, Lam J, Tang B . Structural and process controls of AIEgens for NIR-II theranostics. Chem Sci. 2021; 12(10):3427-3436. PMC: 8179408. DOI: 10.1039/d0sc02911d. View

Tian R, Zeng Q, Zhu S, Lau J, Chandra S, Ertsey R . Albumin-chaperoned cyanine dye yields superbright NIR-II fluorophore with enhanced pharmacokinetics. Sci Adv. 2019; 5(9):eaaw0672. PMC: 6744268. DOI: 10.1126/sciadv.aaw0672. View

Shi J, Kantoff P, Wooster R, Farokhzad O . Cancer nanomedicine: progress, challenges and opportunities. Nat Rev Cancer. 2016; 17(1):20-37. PMC: 5575742. DOI: 10.1038/nrc.2016.108. View

Ding B, Xiao Y, Zhou H, Zhang X, Qu C, Xu F . Polymethine Thiopyrylium Fluorophores with Absorption beyond 1000 nm for Biological Imaging in the Second Near-Infrared Subwindow. J Med Chem. 2018; 62(4):2049-2059. DOI: 10.1021/acs.jmedchem.8b01682. View

Yao C, Chen Y, Zhao M, Wang S, Wu B, Yang Y . A Bright, Renal-Clearable NIR-II Brush Macromolecular Probe with Long Blood Circulation Time for Kidney Disease Bioimaging. Angew Chem Int Ed Engl. 2021; 61(5):e202114273. DOI: 10.1002/anie.202114273. View

Li C, Chen G, Zhang Y, Wu F, Wang Q . Advanced Fluorescence Imaging Technology in the Near-Infrared-II Window for Biomedical Applications. J Am Chem Soc. 2020; 142(35):14789-14804. DOI: 10.1021/jacs.0c07022. View

Bjornmalm M, Thurecht K, Michael M, Scott A, Caruso F . Bridging Bio-Nano Science and Cancer Nanomedicine. ACS Nano. 2017; 11(10):9594-9613. DOI: 10.1021/acsnano.7b04855. View

Wang S, Fan Y, Li D, Sun C, Lei Z, Lu L . Anti-quenching NIR-II molecular fluorophores for in vivo high-contrast imaging and pH sensing. Nat Commun. 2019; 10(1):1058. PMC: 6401027. DOI: 10.1038/s41467-019-09043-x. View

Liu C, Jin Y, Ji X, Zhao W, Dong X . Access to Pyridinyl or Pyridinium Aza-BODIPYs with Tunable Near-Infrared Fluorescence through ICT from 4-Pyridinyl Pyrroles. Chemistry. 2022; 28(56):e202201503. DOI: 10.1002/chem.202201503. View

10.

Gorman A, Killoran J, OShea C, Kenna T, Gallagher W, OShea D . In vitro demonstration of the heavy-atom effect for photodynamic therapy. J Am Chem Soc. 2004; 126(34):10619-31. DOI: 10.1021/ja047649e. View

11.

McDonnell S, OShea D . Near-infrared sensing properties of dimethlyamino-substituted BF2-azadipyrromethenes. Org Lett. 2006; 8(16):3493-6. DOI: 10.1021/ol061171x. View

12.

Zhao W, Carreira E . Conformationally restricted aza-BODIPY: highly fluorescent, stable near-infrared absorbing dyes. Chemistry. 2006; 12(27):7254-63. DOI: 10.1002/chem.200600527. View

13.

Yuan H, Zhao W, Wu W . How can aggregation-caused quenching based bioimaging of drug nanocarriers be improved?. Ther Deliv. 2019; 11(1):809-812. DOI: 10.4155/tde-2019-0082. View

14.

Adarsh N, Krishnan M, Ramaiah D . Sensitive naked eye detection of hydrogen sulfide and nitric oxide by aza-BODIPY dyes in aqueous medium. Anal Chem. 2014; 86(18):9335-42. DOI: 10.1021/ac502849d. View

15.

Jiao L, Wu Y, Ding Y, Wang S, Zhang P, Yu C . Conformationally restricted aza-dipyrromethene boron difluorides (aza-BODIPYs) with high fluorescent quantum yields. Chem Asian J. 2014; 9(3):805-10. DOI: 10.1002/asia.201301362. View

16.

Wang C, Qian Y . A water soluble carbazolyl-BODIPY photosensitizer with an orthogonal D-A structure for photodynamic therapy in living cells and zebrafish. Biomater Sci. 2019; 8(3):830-836. DOI: 10.1039/c9bm01709g. View

17.

Hu X, Dong X, Lu Y, Qi J, Zhao W, Wu W . Bioimaging of nanoparticles: the crucial role of discriminating nanoparticles from free probes. Drug Discov Today. 2016; 22(2):382-387. DOI: 10.1016/j.drudis.2016.10.002. View

18.

Griffiths G, Nystrom B, Sable S, Khuller G . Nanobead-based interventions for the treatment and prevention of tuberculosis. Nat Rev Microbiol. 2010; 8(11):827-34. PMC: 8826847. DOI: 10.1038/nrmicro2437. View

19.

Patra J, Das G, Fraceto L, Campos E, Del Pilar Rodriguez-Torres M, Acosta-Torres L . Nano based drug delivery systems: recent developments and future prospects. J Nanobiotechnology. 2018; 16(1):71. PMC: 6145203. DOI: 10.1186/s12951-018-0392-8. View

20.

Cabral H, Miyata K, Osada K, Kataoka K . Block Copolymer Micelles in Nanomedicine Applications. Chem Rev. 2018; 118(14):6844-6892. DOI: 10.1021/acs.chemrev.8b00199. View