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菲啶 - 芘共轭物作为DNA/RNA的荧光探针和二肽基肽酶的无活性突变体。

Phenanthridine-pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme.

作者信息

Matić Josipa, Tandarić Tana, Radić Stojković Marijana, Šupljika Filip, Karačić Zrinka, Tomašić Paić Ana, Horvat Lucija, Vianello Robert, Tumir Lidija-Marija

机构信息

Laboratory for Biomolecular Interactions and Spectroscopy, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia.

Laboratory for the Computational Design and Synthesis of Functional Materials, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia.

出版信息

Beilstein J Org Chem. 2023 Apr 26;19:550-565. doi: 10.3762/bjoc.19.40. eCollection 2023.

DOI:10.3762/bjoc.19.40
PMID:37153642
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10155618/
Abstract

Two novel conjugate molecules were designed: pyrene and phenanthridine-amino acid units with a different linker length between the aromatic fragments. Molecular modelling combined with spectrophotometric experiments revealed that in neutral and acidic buffered water solutions conjugates predominantly exist in intramolecularly stacked conformations because of the π-π stacking interaction between pyrene and phenanthridine moieties. The investigated systems exhibited a pH-dependent excimer formation that is significantly red-shifted relative to the pyrene and phenanthridine fluorescence. While the conjugate with a short linker showed negligible spectrophotometric changes due to the polynucleotide addition, the conjugate with a longer and more flexible linker exhibited a micromolar and submicromolar binding affinity for ds-polynucleotides and inactivated a mutant of dipeptidyl peptidase enzyme E451A. Confocal microscopy revealed that the conjugate with the longer linker entered the HeLa cell membranes and blue fluorescence was visualized as the dye accumulated in the cell membrane.

摘要

设计了两种新型共轭分子

芘和菲啶 - 氨基酸单元，其芳香片段之间的连接子长度不同。分子建模与分光光度实验相结合表明，在中性和酸性缓冲水溶液中，由于芘和菲啶部分之间的π - π堆积相互作用，共轭物主要以分子内堆积构象存在。所研究的体系表现出pH依赖性的准分子形成，相对于芘和菲啶荧光有明显的红移。虽然短连接子的共轭物由于添加多核苷酸而显示出可忽略不计的分光光度变化，但具有更长且更灵活连接子的共轭物对双链多核苷酸表现出微摩尔和亚微摩尔的结合亲和力，并使二肽基肽酶E451A突变体失活。共聚焦显微镜显示，具有较长连接子的共轭物进入了HeLa细胞膜，并且随着染料在细胞膜中积累，可见蓝色荧光。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/02a0bd33fb1a/Beilstein_J_Org_Chem-19-550-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/1c44c8daf212/Beilstein_J_Org_Chem-19-550-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/be3fdb2cf050/Beilstein_J_Org_Chem-19-550-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/e59018bc3c49/Beilstein_J_Org_Chem-19-550-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/9ee2c6e25493/Beilstein_J_Org_Chem-19-550-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/7dd8b5097dd0/Beilstein_J_Org_Chem-19-550-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/693835702cdf/Beilstein_J_Org_Chem-19-550-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/08998e2db46c/Beilstein_J_Org_Chem-19-550-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/b3e62c1f7dd2/Beilstein_J_Org_Chem-19-550-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/02a0bd33fb1a/Beilstein_J_Org_Chem-19-550-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/1c44c8daf212/Beilstein_J_Org_Chem-19-550-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/be3fdb2cf050/Beilstein_J_Org_Chem-19-550-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/e59018bc3c49/Beilstein_J_Org_Chem-19-550-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/9ee2c6e25493/Beilstein_J_Org_Chem-19-550-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/7dd8b5097dd0/Beilstein_J_Org_Chem-19-550-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/693835702cdf/Beilstein_J_Org_Chem-19-550-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/08998e2db46c/Beilstein_J_Org_Chem-19-550-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/b3e62c1f7dd2/Beilstein_J_Org_Chem-19-550-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fc9/10155618/02a0bd33fb1a/Beilstein_J_Org_Chem-19-550-g008.jpg

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