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tzme-caged 7-hydroxycoumarin dye ( 4b′ , fig. s2 )  (Bioarray Inc)

 
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    Bioarray Inc tzme-caged 7-hydroxycoumarin dye ( 4b′ , fig. s2 )
    Isonitrile-mediated uncaging of amines and phenols from Tzmoc and <t>TzMe</t> derivatives. (a) Structures of tetrazylmethyloxycarbonyl (Tzmoc) and tetrazylmethyl (TzMe) groups used to cage amines and phenols, respectively. (b) Synthesis of Tzmoc or TzMe-caged probes (conditions and yields described in the ESI ). (c) Structures of reporter probes and isonitrile triggers used in this study. (d) Kinetics of pNA release from 4a triggered by different isonitriles (c( 4a ) = 0.2 mM, c(R–NC) = 2 mM, DMSO : PBS pH 7.4 (4 : 1, v/v), T = 37 °C, λ = 435 nm, n = 3). (e) Kinetics of pNA release from 4a triggered by n -BuNC catalysed by serum albumin (c( 4a ) = 8 μM, c( n -BuNC) = 6 mM, c(HSA) = 2 mg mL –1 , DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ = 385 nm, n = 3). (f) Kinetics of O -carboxymethyl fluorescein release <t>from</t> <t>4b</t> triggered by TMS-MeNC or n -BuNC (c( 4b ) = 8 μM, c(R–NC) = 6 mM, DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ ex = 488 nm, λ em = 520 nm, n = 3).
    Tzme Caged 7 Hydroxycoumarin Dye ( 4b′ , Fig. S2 ), supplied by Bioarray Inc, used in various techniques. Bioz Stars score: 90/100, based on 1 PubMed citations. ZERO BIAS - scores, article reviews, protocol conditions and more
    https://www.bioz.com/product/tzme-caged+7-hydroxycoumarin+dye+(+4b%E2%80%B2+%2C+fig%2E+s2++)/tzme+caged+7+hydroxycoumarin+dye+++4b++++fig++s2+++/pmc07012038-57-4-21
    Average 90 stars, based on 1 article reviews
    tzme-caged 7-hydroxycoumarin dye ( 4b′ , fig. s2 ) - by Bioz Stars, 2026-10
    90/100 stars

    Images

    1) Product Images from "Isonitrile-responsive and bioorthogonally removable tetrazine protecting groups † †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc04649f "

    Article Title: Isonitrile-responsive and bioorthogonally removable tetrazine protecting groups † †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc04649f

    Journal: Chemical Science

    doi: 10.1039/c9sc04649f

    Isonitrile-mediated uncaging of amines and phenols from Tzmoc and TzMe derivatives. (a) Structures of tetrazylmethyloxycarbonyl (Tzmoc) and tetrazylmethyl (TzMe) groups used to cage amines and phenols, respectively. (b) Synthesis of Tzmoc or TzMe-caged probes (conditions and yields described in the ESI ). (c) Structures of reporter probes and isonitrile triggers used in this study. (d) Kinetics of pNA release from 4a triggered by different isonitriles (c( 4a ) = 0.2 mM, c(R–NC) = 2 mM, DMSO : PBS pH 7.4 (4 : 1, v/v), T = 37 °C, λ = 435 nm, n = 3). (e) Kinetics of pNA release from 4a triggered by n -BuNC catalysed by serum albumin (c( 4a ) = 8 μM, c( n -BuNC) = 6 mM, c(HSA) = 2 mg mL –1 , DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ = 385 nm, n = 3). (f) Kinetics of O -carboxymethyl fluorescein release from 4b triggered by TMS-MeNC or n -BuNC (c( 4b ) = 8 μM, c(R–NC) = 6 mM, DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ ex = 488 nm, λ em = 520 nm, n = 3).
    Figure Legend Snippet: Isonitrile-mediated uncaging of amines and phenols from Tzmoc and TzMe derivatives. (a) Structures of tetrazylmethyloxycarbonyl (Tzmoc) and tetrazylmethyl (TzMe) groups used to cage amines and phenols, respectively. (b) Synthesis of Tzmoc or TzMe-caged probes (conditions and yields described in the ESI ). (c) Structures of reporter probes and isonitrile triggers used in this study. (d) Kinetics of pNA release from 4a triggered by different isonitriles (c( 4a ) = 0.2 mM, c(R–NC) = 2 mM, DMSO : PBS pH 7.4 (4 : 1, v/v), T = 37 °C, λ = 435 nm, n = 3). (e) Kinetics of pNA release from 4a triggered by n -BuNC catalysed by serum albumin (c( 4a ) = 8 μM, c( n -BuNC) = 6 mM, c(HSA) = 2 mg mL –1 , DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ = 385 nm, n = 3). (f) Kinetics of O -carboxymethyl fluorescein release from 4b triggered by TMS-MeNC or n -BuNC (c( 4b ) = 8 μM, c(R–NC) = 6 mM, DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ ex = 488 nm, λ em = 520 nm, n = 3).

    Techniques Used:

    TMS-MeNC mediated removal of TzMe-modified molecules on proteins, in the presence of cells, and in zebrafish embryos. (a) In-gel analysis of the fluorescent turn-on signal on SNAP protein labelled with 4b-BG (10 μM) and subsequent deprotection of the TzMe group with TMS-MeNC (100 μM); lanes 1 and 6 contain the protein ladder (for an expanded view of the fluorescence and Coomassie-stained gel and mass spectroscopy verification, see Fig. S34–S37 in the ESI ). (b) Structure of Tzmoc-caged doxorubicin prodrug (5) and dose–response curves for cytotoxicity studies with A549 cells after 72 h. (c) Cartoon representation of experiment to demonstrate the release of O -carboxymethyl fluorescein and fluorescence turn-on upon incubation with TMS-MeNC. (d) Visualization of the fluorescence signal in live zebrafish (scale bar = 200 μm) after a 2 h incubation with either 20 μM TMS-MeNC or DMSO.
    Figure Legend Snippet: TMS-MeNC mediated removal of TzMe-modified molecules on proteins, in the presence of cells, and in zebrafish embryos. (a) In-gel analysis of the fluorescent turn-on signal on SNAP protein labelled with 4b-BG (10 μM) and subsequent deprotection of the TzMe group with TMS-MeNC (100 μM); lanes 1 and 6 contain the protein ladder (for an expanded view of the fluorescence and Coomassie-stained gel and mass spectroscopy verification, see Fig. S34–S37 in the ESI ). (b) Structure of Tzmoc-caged doxorubicin prodrug (5) and dose–response curves for cytotoxicity studies with A549 cells after 72 h. (c) Cartoon representation of experiment to demonstrate the release of O -carboxymethyl fluorescein and fluorescence turn-on upon incubation with TMS-MeNC. (d) Visualization of the fluorescence signal in live zebrafish (scale bar = 200 μm) after a 2 h incubation with either 20 μM TMS-MeNC or DMSO.

    Techniques Used: Modification, Fluorescence, Staining, Mass Spectrometry, Incubation

    Dual release of two orthogonal fluorophores from ICPr- and TzMe-caged dyes in live zebrafish. (a) Cartoon representation of experiment demonstrating the dual release and fluorescence turn-on of O -carboxymethyl fluorescein and resorufin upon reaction of 4b and ICPr-rsf , and the corresponding control experiment with non-injected fish. (b) Visualization of fluorescein and resorufin fluorescence signal in live zebrafish (scale bar = 200 μm) injected with 4b after a 2 h incubation with 10 μM ICPr-rsf . (c) Visualization of fluorescein and resorufin fluorescence signal in non- 4b injected control live zebrafish (scale bar = 200 μm) after a 2 h incubation with 10 μM ICPr-rsf .
    Figure Legend Snippet: Dual release of two orthogonal fluorophores from ICPr- and TzMe-caged dyes in live zebrafish. (a) Cartoon representation of experiment demonstrating the dual release and fluorescence turn-on of O -carboxymethyl fluorescein and resorufin upon reaction of 4b and ICPr-rsf , and the corresponding control experiment with non-injected fish. (b) Visualization of fluorescein and resorufin fluorescence signal in live zebrafish (scale bar = 200 μm) injected with 4b after a 2 h incubation with 10 μM ICPr-rsf . (c) Visualization of fluorescein and resorufin fluorescence signal in non- 4b injected control live zebrafish (scale bar = 200 μm) after a 2 h incubation with 10 μM ICPr-rsf .

    Techniques Used: Fluorescence, Injection, Incubation



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    tzme-caged 7-hydroxycoumarin dye ( 4b′ , fig. s2 )  (Bioarray Inc)
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    Bioarray Inc tzme-caged 7-hydroxycoumarin dye ( 4b′ , fig. s2 )
    Isonitrile-mediated uncaging of amines and phenols from Tzmoc and <t>TzMe</t> derivatives. (a) Structures of tetrazylmethyloxycarbonyl (Tzmoc) and tetrazylmethyl (TzMe) groups used to cage amines and phenols, respectively. (b) Synthesis of Tzmoc or TzMe-caged probes (conditions and yields described in the ESI ). (c) Structures of reporter probes and isonitrile triggers used in this study. (d) Kinetics of pNA release from 4a triggered by different isonitriles (c( 4a ) = 0.2 mM, c(R–NC) = 2 mM, DMSO : PBS pH 7.4 (4 : 1, v/v), T = 37 °C, λ = 435 nm, n = 3). (e) Kinetics of pNA release from 4a triggered by n -BuNC catalysed by serum albumin (c( 4a ) = 8 μM, c( n -BuNC) = 6 mM, c(HSA) = 2 mg mL –1 , DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ = 385 nm, n = 3). (f) Kinetics of O -carboxymethyl fluorescein release <t>from</t> <t>4b</t> triggered by TMS-MeNC or n -BuNC (c( 4b ) = 8 μM, c(R–NC) = 6 mM, DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ ex = 488 nm, λ em = 520 nm, n = 3).
    Tzme Caged 7 Hydroxycoumarin Dye ( 4b′ , Fig. S2 ), supplied by Bioarray Inc, used in various techniques. Bioz Stars score: 90/100, based on 1 PubMed citations. ZERO BIAS - scores, article reviews, protocol conditions and more
    https://www.bioz.com/product/tzme-caged+7-hydroxycoumarin+dye+(+4b%E2%80%B2+%2C+fig%2E+s2++)/tzme+caged+7+hydroxycoumarin+dye+++4b++++fig++s2+++/pmc07012038-57-4-21
    Average 90 stars, based on 1 article reviews
    tzme-caged 7-hydroxycoumarin dye ( 4b′ , fig. s2 ) - by Bioz Stars, 2026-10
    90/100 stars
    		  Buy from Supplier

    Image Search Results


    Isonitrile-mediated uncaging of amines and phenols from Tzmoc and TzMe derivatives. (a) Structures of tetrazylmethyloxycarbonyl (Tzmoc) and tetrazylmethyl (TzMe) groups used to cage amines and phenols, respectively. (b) Synthesis of Tzmoc or TzMe-caged probes (conditions and yields described in the ESI ). (c) Structures of reporter probes and isonitrile triggers used in this study. (d) Kinetics of pNA release from 4a triggered by different isonitriles (c( 4a ) = 0.2 mM, c(R–NC) = 2 mM, DMSO : PBS pH 7.4 (4 : 1, v/v), T = 37 °C, λ = 435 nm, n = 3). (e) Kinetics of pNA release from 4a triggered by n -BuNC catalysed by serum albumin (c( 4a ) = 8 μM, c( n -BuNC) = 6 mM, c(HSA) = 2 mg mL –1 , DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ = 385 nm, n = 3). (f) Kinetics of O -carboxymethyl fluorescein release from 4b triggered by TMS-MeNC or n -BuNC (c( 4b ) = 8 μM, c(R–NC) = 6 mM, DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ ex = 488 nm, λ em = 520 nm, n = 3).

    Journal: Chemical Science

    Article Title: Isonitrile-responsive and bioorthogonally removable tetrazine protecting groups † †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc04649f

    doi: 10.1039/c9sc04649f

    Figure Lengend Snippet: Isonitrile-mediated uncaging of amines and phenols from Tzmoc and TzMe derivatives. (a) Structures of tetrazylmethyloxycarbonyl (Tzmoc) and tetrazylmethyl (TzMe) groups used to cage amines and phenols, respectively. (b) Synthesis of Tzmoc or TzMe-caged probes (conditions and yields described in the ESI ). (c) Structures of reporter probes and isonitrile triggers used in this study. (d) Kinetics of pNA release from 4a triggered by different isonitriles (c( 4a ) = 0.2 mM, c(R–NC) = 2 mM, DMSO : PBS pH 7.4 (4 : 1, v/v), T = 37 °C, λ = 435 nm, n = 3). (e) Kinetics of pNA release from 4a triggered by n -BuNC catalysed by serum albumin (c( 4a ) = 8 μM, c( n -BuNC) = 6 mM, c(HSA) = 2 mg mL –1 , DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ = 385 nm, n = 3). (f) Kinetics of O -carboxymethyl fluorescein release from 4b triggered by TMS-MeNC or n -BuNC (c( 4b ) = 8 μM, c(R–NC) = 6 mM, DMSO : PBS pH 7.4 (1 : 4, v/v), T = 37 °C, λ ex = 488 nm, λ em = 520 nm, n = 3).

    Article Snippet: First, we assessed a TzMe-caged 7-hydroxycoumarin dye ( 4b′ , Fig. S2 ) in a human liver microsome stability assay (Creative Bioarray, USA) and the probe exhibited good stability ( t 1/2 = 52.11 min; Cl int = 33.36 mL min –1 kg –1 ; Fig. S6 ) even under these harsh conditions.

    Techniques:

    TMS-MeNC mediated removal of TzMe-modified molecules on proteins, in the presence of cells, and in zebrafish embryos. (a) In-gel analysis of the fluorescent turn-on signal on SNAP protein labelled with 4b-BG (10 μM) and subsequent deprotection of the TzMe group with TMS-MeNC (100 μM); lanes 1 and 6 contain the protein ladder (for an expanded view of the fluorescence and Coomassie-stained gel and mass spectroscopy verification, see Fig. S34–S37 in the ESI ). (b) Structure of Tzmoc-caged doxorubicin prodrug (5) and dose–response curves for cytotoxicity studies with A549 cells after 72 h. (c) Cartoon representation of experiment to demonstrate the release of O -carboxymethyl fluorescein and fluorescence turn-on upon incubation with TMS-MeNC. (d) Visualization of the fluorescence signal in live zebrafish (scale bar = 200 μm) after a 2 h incubation with either 20 μM TMS-MeNC or DMSO.

    Journal: Chemical Science

    Article Title: Isonitrile-responsive and bioorthogonally removable tetrazine protecting groups † †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc04649f

    doi: 10.1039/c9sc04649f

    Figure Lengend Snippet: TMS-MeNC mediated removal of TzMe-modified molecules on proteins, in the presence of cells, and in zebrafish embryos. (a) In-gel analysis of the fluorescent turn-on signal on SNAP protein labelled with 4b-BG (10 μM) and subsequent deprotection of the TzMe group with TMS-MeNC (100 μM); lanes 1 and 6 contain the protein ladder (for an expanded view of the fluorescence and Coomassie-stained gel and mass spectroscopy verification, see Fig. S34–S37 in the ESI ). (b) Structure of Tzmoc-caged doxorubicin prodrug (5) and dose–response curves for cytotoxicity studies with A549 cells after 72 h. (c) Cartoon representation of experiment to demonstrate the release of O -carboxymethyl fluorescein and fluorescence turn-on upon incubation with TMS-MeNC. (d) Visualization of the fluorescence signal in live zebrafish (scale bar = 200 μm) after a 2 h incubation with either 20 μM TMS-MeNC or DMSO.

    Article Snippet: First, we assessed a TzMe-caged 7-hydroxycoumarin dye ( 4b′ , Fig. S2 ) in a human liver microsome stability assay (Creative Bioarray, USA) and the probe exhibited good stability ( t 1/2 = 52.11 min; Cl int = 33.36 mL min –1 kg –1 ; Fig. S6 ) even under these harsh conditions.

    Techniques: Modification, Fluorescence, Staining, Mass Spectrometry, Incubation

    Dual release of two orthogonal fluorophores from ICPr- and TzMe-caged dyes in live zebrafish. (a) Cartoon representation of experiment demonstrating the dual release and fluorescence turn-on of O -carboxymethyl fluorescein and resorufin upon reaction of 4b and ICPr-rsf , and the corresponding control experiment with non-injected fish. (b) Visualization of fluorescein and resorufin fluorescence signal in live zebrafish (scale bar = 200 μm) injected with 4b after a 2 h incubation with 10 μM ICPr-rsf . (c) Visualization of fluorescein and resorufin fluorescence signal in non- 4b injected control live zebrafish (scale bar = 200 μm) after a 2 h incubation with 10 μM ICPr-rsf .

    Journal: Chemical Science

    Article Title: Isonitrile-responsive and bioorthogonally removable tetrazine protecting groups † †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc04649f

    doi: 10.1039/c9sc04649f

    Figure Lengend Snippet: Dual release of two orthogonal fluorophores from ICPr- and TzMe-caged dyes in live zebrafish. (a) Cartoon representation of experiment demonstrating the dual release and fluorescence turn-on of O -carboxymethyl fluorescein and resorufin upon reaction of 4b and ICPr-rsf , and the corresponding control experiment with non-injected fish. (b) Visualization of fluorescein and resorufin fluorescence signal in live zebrafish (scale bar = 200 μm) injected with 4b after a 2 h incubation with 10 μM ICPr-rsf . (c) Visualization of fluorescein and resorufin fluorescence signal in non- 4b injected control live zebrafish (scale bar = 200 μm) after a 2 h incubation with 10 μM ICPr-rsf .

    Article Snippet: First, we assessed a TzMe-caged 7-hydroxycoumarin dye ( 4b′ , Fig. S2 ) in a human liver microsome stability assay (Creative Bioarray, USA) and the probe exhibited good stability ( t 1/2 = 52.11 min; Cl int = 33.36 mL min –1 kg –1 ; Fig. S6 ) even under these harsh conditions.

    Techniques: Fluorescence, Injection, Incubation