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新型苯并[h]吩嗪氯代物,具有磺酰胺基团,可用作液泡、内质网和质膜染色的近红外荧光探针。

Novel Benzo[]phenoxazinium Chlorides Functionalized with Sulfonamide Groups as NIR Fluorescent Probes for Vacuole, Endoplasmic Reticulum, and Plasma Membrane Staining.

机构信息

Centre of Chemistry (CQUM), Department of Chemistry, University of Minho, Campus of Gualtar, 4710-057 Braga, Portugal.

Centre of Molecular and Environmental Biology (CBMA), Department of Biology, University of Minho, Campus of Gualtar, 4710-057 Braga, Portugal.

出版信息

Int J Mol Sci. 2023 Feb 3;24(3):3006. doi: 10.3390/ijms24033006.

DOI:10.3390/ijms24033006
PMID:36769330
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9918004/
Abstract

The demand for new fluorophores for different biological target imaging is increasing. Benzo[]phenoxazine derivatives are fluorochromophores that show promising optical properties for bioimaging, namely fluorescent emission at the NIR of the visible region, where biological samples have minimal fluorescence emission. In this study, six new benzo[]phenoxazinium chlorides possessing sulfonamide groups at 5-amino-positions were synthesized and their optical and biological properties were tested. Compared with previous probes evaluated using fluorescence microscopy, using different strains, these probes, with sulfonamide groups, stained the vacuole membrane and/or the perinuclear membrane of the endoplasmic reticulum with great specificity, with some fluorochromophores capable of even staining the plasma membrane. Thus, the addition of a sulfonamide group to the benzo[]phenoxazinium core increases their specificity and attributes for the fluorescent labeling of cell applications and fractions, highlighting them as quite valid alternatives to commercially available dyes.

摘要

对用于不同生物靶标成像的新型荧光团的需求正在增加。苯并[]吩恶嗪衍生物是一类荧光团,它们在生物成像方面表现出有前途的光学性质,即在可见光区域的近红外处具有荧光发射,而生物样品在该区域的荧光发射最小。在这项研究中,合成了六个新的苯并[]吩恶嗪鎓氯化物,它们在 5-氨基位置上具有磺酰胺基团,并测试了它们的光学和生物学性质。与使用荧光显微镜评估的以前的探针相比,这些带有磺酰胺基团的探针使用不同的菌株,非常特异性地染色液泡膜和/或内质网的核周膜,一些荧光团甚至能够染色质膜。因此,在苯并[]吩恶嗪鎓核心上添加磺酰胺基团会增加它们的特异性和属性,可用于荧光标记细胞应用和细胞组分,突出了它们作为商业上可用染料的相当有效的替代品。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6856/9918004/103675699d1c/ijms-24-03006-g004a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6856/9918004/e6510e0f70f7/ijms-24-03006-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6856/9918004/db3fc7825bc8/ijms-24-03006-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6856/9918004/09932e86f65c/ijms-24-03006-g002a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6856/9918004/9530189e57fb/ijms-24-03006-g003a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6856/9918004/103675699d1c/ijms-24-03006-g004a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6856/9918004/e6510e0f70f7/ijms-24-03006-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6856/9918004/db3fc7825bc8/ijms-24-03006-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6856/9918004/09932e86f65c/ijms-24-03006-g002a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6856/9918004/9530189e57fb/ijms-24-03006-g003a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6856/9918004/103675699d1c/ijms-24-03006-g004a.jpg

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