Fluorescent kapakahines serve as non-toxic probes for live cell Golgi imaging

Rocha, Danilo D.; Espejo, Vinson R.; Rainier, Jon D.; Clair, James J. La; Costa-Lotufo, Letı́cia V.

doi:10.1016/j.lfs.2015.06.014

Cited by 12 publications

(9 citation statements)

References 39 publications

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“…On this basis, the rapid uptake and subcellular localization of fluorescently‐labeled analogues of the cyclic depsipeptide kapakahine E was reported. [ 82 ] Specific localisation within the Golgi apparatus was confirmed by colocalization experiments with other commercially‐available markers. Nucleic acids are another example of widely targeted macromolecules inside cells.…”

Section: Biological Applications Of Fluorescent Cyclic Peptide Probesmentioning

confidence: 89%

Fluorescent cyclic peptides for cell imaging

2020

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Fluorescent cyclic peptides are excellent chemical scaffolds to build optical agents for molecular imaging. In addition to their favorable physicochemical properties, they can be modified with multiple organic fluorophores and generate useful probes for biological assays targeting specific proteins, namely receptors or enzymes. In this article, we review recent advances in the synthetic approaches for the preparation of fluorescent cyclic peptides as well as some of their applications in biological imaging, from in vitro live‐cell imaging studies to in vivo characterization of preclinical models.

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Section: Biological Applications Of Fluorescent Cyclic Peptide Probesmentioning

confidence: 89%

Fluorescent cyclic peptides for cell imaging

2020

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“…Microscopic images treated with 5a and 6a without "Lipofectamine system" did not show clear localization images, suggesting the efficacy of this system (Figure 3; Lipofectamine 2000 (−)). [20] were compared. In this experiment, the treatment of the permeabilization buffer, containing Triton X-100 damaged the fluorescent staining by 5a.…”

Section: Of 11mentioning

confidence: 99%

“…In spite of their unique structures, their detailed biological functions or modes of action are still unknown. In 2015, Rocha et al prepared fluorescent probe of kapakahine E, an analogue of 1, by derivatization at the free amino group of the synthetically prepared kapakahine E with the fluorescent coumarin, and visualized its localization in Golgi apparatus in cells [20]. Although total synthesis of smaller sized kapakahines B, E, and F has been achieved [21][22][23][24][25], the most potent and largest kapakahine A has not yet been synthesized.…”

Section: Introductionmentioning

confidence: 99%

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Small-Scale Preparation of Fluorescently Labeled Chemical Probes from Marine Cyclic Peptides, Kapakahines A and F

Kamihira

Nakao

2021

Marine Drugs

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A number of bioactive marine natural products have been isolated so far, but it is still difficult to disclose their modes of action. In this study, we prepared fluorescently labeled chemical probes from the cytotoxic marine cyclic peptides kapakahines A (1) and F (2) to visualize their localization as the first step of the study of their modes of action. We used fluorescent dyes 3a or 3a/b (a 1:1 mixture of 3a and 3b) whose terminal N-hydroxysuccinimide (NHS) group can react with the free amino groups of kapakahines. The fluorescently labeled kapakahine A (Kap A-5-FL, 5a) stained P388 murine leukemia cells and HeLa human cervical cancer cells, while cells treated with fluorescently labeled kapakahine F (Kap F-5-FL, 6a) only weakly stained them. Further analysis of the confocal images of the stained cells with higher magnification (×100) indicated the localization of Kap A-5-FL (5a) in the cells. In this paper, we report the small-scale preparation and a new delivery method of fluorescent probes, as well as the application of these procedures to cell staining.

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“…Rocha et al synthesized a fluorescent probe comprising kapakahine E conjugated with coumarin and found that the fluorescent probe localized to the Golgi apparatus in PC-3M prostate carcinoma cells [ 9 ]. In a previous study, we prepared a fluorescent probe of kapakahine A [Kap A-5FL ( 2 )] by direct coupling with an FITC derivative with an active ester linker [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Application of a Chemical Probe for Identifying the Targets of the Marine Cyclic Peptide Kapakahine A

Kamihira

Nakao

2022

Molecules

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Marine organisms are a rich source of bioactive secondary metabolites. Although many marine natural products with bioactivities have been isolated, successful elucidation of their mechanisms of action remains limited. In this study, we prepared a probe molecule based on the marine cyclic peptide kapakahine A (1) by introducing a linker with an azide terminal group, which enables the introduction of fluorescent groups for the effective monitoring of subcellular localization, or coupling to affinity beads for the pull-down of target proteins. The results of LC/MS/MS measurements, ProteinPilot analysis, and Western blotting suggest that kapakahine A interacts with the mitochondrial inner membrane proteins PHB1, PHB2, and ANT2, which is consistent with the results of the subcellular localization analysis using a fluorescent probe.

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Fluorescent kapakahines serve as non-toxic probes for live cell Golgi imaging

Cited by 12 publications

References 39 publications

Fluorescent cyclic peptides for cell imaging

Fluorescent cyclic peptides for cell imaging

Small-Scale Preparation of Fluorescently Labeled Chemical Probes from Marine Cyclic Peptides, Kapakahines A and F

Preparation and Application of a Chemical Probe for Identifying the Targets of the Marine Cyclic Peptide Kapakahine A

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