Bisindolylmaleimides with Large Stokes Shift and Long-Lasting Chemiluminescence Properties

Nakazono, Manabu; Nanbu, Shinkoh; Uesaki, Akihiro; Kuwano, Ryoichi; Kashiwabara, Manabu; Zaitsu, Kiyoshi

doi:10.1021/ol701431g

Cited by 45 publications

(37 citation statements)

References 14 publications

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“…The expansion of the π-conjugation, the π-bond electronic structure and the oxidation of the CC bond at the 2,3-position of the maleimide moiety are crucial for producing these fluorescence properties. 20 As shown in the present study, the two tested PKC inhibitors, Ro-81-3220 and bisindolylmaleimide II, cause negligible fluorescence when used at their IC 50 (with respect to PKC) but cause strong fluorescence when applied at low micromolar concentrations (Figure 1). This intrinsic property of the two PKC inhibitors caused the previously reported apparent differences in the CD63 and CD203c fluorescence 16 The rejected role of supraoptimal concentrations of PKC inhibitors in decoupling CD63 and CD203c externalization has indirect applications beyond the scope of the present study.…”

Section: Discussionsupporting

confidence: 69%

“…Various bisindolylmaleimides have fluorescence emission maxima wavelengths longer than 500 nm, with large Stokes shifts longer than 200 nm, and different fluorescence emission wavelengths at an excitation wavelength of 365 nm. The expansion of the π‐conjugation, the π‐bond electronic structure and the oxidation of the CC bond at the 2,3‐position of the maleimide moiety are crucial for producing these fluorescence properties . As shown in the present study, the two tested PKC inhibitors, Ro‐81‐3220 and bisindolylmaleimide II, cause negligible fluorescence when used at their IC 50 (with respect to PKC) but cause strong fluorescence when applied at low micromolar concentrations (Figure ).…”

Section: Discussionsupporting

confidence: 63%

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Updates on the surface antigens of basophils: CD16 on basophils of patients with respiratory or insect venom allergy and the rejection of CD203c and CD63 externalization decoupling by bisindolylmaleimides

Heneberg

Riegerová

Říhová

et al. 2018

Clin Experimental Allergy

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Summary Background CD16 was previously suggested to be a new marker of basophils that is subject to downregulation by FcεRI crosslinking. Certain compounds, including supraoptimal concentrations of the PKC inhibitors, bisindolylmaleimides, decouple the release of granules containing CD203c, CD63 and histamine, and may thus help to identify the mechanisms related to the CD16 externalization. Objective We hypothesized that CD16 is differentially expressed on the surface of basophils in patients with birch pollen or insect venom allergy and is subject to a regulation in response to allergens. We also employed CD203c and CD63 externalization decoupling by bisindolylmaleimides. Methods We performed a basophil activation test coupled with CD16 and histamine detection using cells isolated from patients with allergy to birch pollen or insect venom and negative controls. We employed two PKC inhibitors, bisindolylmaleimide II and Ro 31‐8220 at their supraoptimal concentrations and, after difficulties reproducing previously published data, we analyzed the fluorescence of these inhibitors alone. We identified the CD16 isoforms by sequencing nested RT‐PCR amplicons from flow cytometry sorted basophils and by cleaving the CD16b GPI anchor using a phospholipase C. Results We provide the first evidence that CD16a is expressed as a surface antigen on a small subpopulation of human basophils in patients with respiratory and insect venom allergy, and this antigen shows increased surface expression following allergen challenge or FcεRI crosslinking. We rejected the apparent decoupling of the surface expression of basophil activation markers following the administration of bisindolylmaleimides. Conclusions & Clinical Relevance The inclusion of αCD16 in negative selection cocktails selects against a subset of basophils that are CD16+ or CD16dim. Using CD16dim basophils and unstained leucocytes, we show that previous studies with supraoptimal concentrations of bisindolylmaleimides are likely flawed and are not associated with the differential expression of CD203c and CD63.

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Section: Discussionsupporting

confidence: 69%

Section: Discussionsupporting

confidence: 63%

Updates on the surface antigens of basophils: CD16 on basophils of patients with respiratory or insect venom allergy and the rejection of CD203c and CD63 externalization decoupling by bisindolylmaleimides

Heneberg

Riegerová

Říhová

et al. 2018

Clin Experimental Allergy

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“…5 Additionally, recent studies have shown possible application of these natural products as selective and sensitive chemical sensors based on their unique chemiluminescence properties. 6 …”

Section: Introductionmentioning

confidence: 99%

Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines

et al. 2013

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A full account of our concise and enantioselective total syntheses of all known (−)-trigonoliimine alkaloids is described. Our retrobiosynthetic analysis of these natural products enabled identification of a single bistryptamine precursor as a precursor to all known trigonoliimines through a sequence of transformations involving asymmetric oxidation and reorganization. Our enantioselective syntheses of these alkaloids enabled the revision of the absolute stereochemistry of (−)-trigonoliimines A, B, and C. We report that trigonoliimines A, B, C, and structurally related compounds showed weak anticancer activities against HeLa and U-937 cells.

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“…Various representative chemiluminescent compounds such as luminol, [1][2][3][4] indole, [5,6] acridinium ester [7][8][9][10] and lophine derivatives [11,12] were developed and the chemiluminescence (CL) properties of each were studied. However, these representative chemiluminescent compounds require strongly alkaline conditions to obtain strong CL intensity.…”

Section: Introductionmentioning

confidence: 99%

Enhancement effect on the chemiluminescence of acridinium esters under neutral conditions

Nakazono

Nanbu

2017

Luminescence

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Enhancement effect on the chemiluminescence of acridinium ester derivatives under neutral conditions was investigated. Additions of phenols did not enhance the chemiluminescence intensities of acridinium ester derivatives in the presence of horseradish peroxidase and hydrogen peroxide. Additions of cetyltrimethylammonium bromide apparently enhanced the chemiluminescence intensities of phenyl 10-methyl-10λ -acridine-9-carboxylate derivatives with electron-withdrawing groups at the 4-position of the phenyl group. In particular, the chemiluminescence intensity of 4-(trifluoromethyl)phenyl 10-methyl-10λ -acridine-9-carboxylate trifluoromethanesulfonate salt was 5.5 times stronger in the presence of cetyltrimethylammonium bromide than in its absence at pH 7. The chemiluminescence intensity of 3,4-dicyano-phenyl 10-methyl-10λ -acridine-9-carboxylate trifluoromethanesulfonate salt was 46 times stronger in the presence of cetyltrimethylammonium bromide at pH 7 than in its absence at pH 10.

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Bisindolylmaleimides with Large Stokes Shift and Long-Lasting Chemiluminescence Properties

Cited by 45 publications

References 14 publications

Updates on the surface antigens of basophils: CD16 on basophils of patients with respiratory or insect venom allergy and the rejection of CD203c and CD63 externalization decoupling by bisindolylmaleimides

Updates on the surface antigens of basophils: CD16 on basophils of patients with respiratory or insect venom allergy and the rejection of CD203c and CD63 externalization decoupling by bisindolylmaleimides

Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines

Enhancement effect on the chemiluminescence of acridinium esters under neutral conditions

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