2022
DOI: 10.1021/acs.jmedchem.1c00750
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One- and Two-Photon Uncaging of Carbon Monoxide (CO) with Real-Time Monitoring: On-Demand Carbazole-Based Dual CO-Releasing Platform to Test over Single and Combinatorial Approaches for the Efficient Regression of Orthotopic Murine Melanoma In Vivo

Abstract: Herein, we report three new metal-free, photochemically active single, dual, and combinatorial CORMs (photoCORMs) based on a carbazole-fused 1,3-dioxol-2-one moiety which released one equivalent of CO, two equivalent of CO, and a combination of one equivalent of each CO and anticancer drug upon one- and two-photon excitation, respectively. The photoCORMs exhibited good cellular uptake and real-time monitoring ability of CO uncaging by a color change approach in cancerous B16F10 cells. Interestingly, the cytoto… Show more

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Cited by 18 publications
(14 citation statements)
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“…[21][22][23][24] More recently, the CO-releasing ability of a number of organic compounds (α-diketones, flavones, quinolone, oxalates, boron carboxylates, and carbazoles) have also been explored, some of which showed controlled CO release to specific targets upon visible light irradiation. [25][26][27][28][29][30][31] The anticancer activity of few manganese(I) tricarbonyl complexes containing nitrogen-based ligands are reported in the literature. [32,33] The complexes a and b show antiproliferative activity against breast cancer cell lines under UV irradiation whereas c, d, and e show a dose-dependent toxicity towards breast and colon cancer cells when exposed to low power visible light (Figure 1).…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…[21][22][23][24] More recently, the CO-releasing ability of a number of organic compounds (α-diketones, flavones, quinolone, oxalates, boron carboxylates, and carbazoles) have also been explored, some of which showed controlled CO release to specific targets upon visible light irradiation. [25][26][27][28][29][30][31] The anticancer activity of few manganese(I) tricarbonyl complexes containing nitrogen-based ligands are reported in the literature. [32,33] The complexes a and b show antiproliferative activity against breast cancer cell lines under UV irradiation whereas c, d, and e show a dose-dependent toxicity towards breast and colon cancer cells when exposed to low power visible light (Figure 1).…”
Section: Introductionmentioning
confidence: 99%
“…[ 21–24 ] More recently, the CO‐releasing ability of a number of organic compounds (α‐diketones, flavones, quinolone, oxalates, boron carboxylates, and carbazoles) have also been explored, some of which showed controlled CO release to specific targets upon visible light irradiation. [ 25–31 ]…”
Section: Introductionmentioning
confidence: 99%
“…Since the 1970s, a considerable effort has been dedicated both to the development of novel photoactivatable chemical probes and their applications in various experimental studies. Regarding the scope of PPG applications, the caged substrate could be as Encyclopedia 2022, 2 1227 simple as a proton or an inorganic species or ion (e.g., Ca 2+ [15], Zn 2+ [16], CO [17], NO [18], H 2 S [19]), it could be a small molecule (e.g., second messenger (such as inositol-1,4,5-triphosphate (IP 3 ) [20]), neurotransmitter (notably GABA and glutamate [21,22]), nucleotide [23], peptide [24], drug molecule [25] (such as antibiotics [26], analgesics [27] or anticancer agents [28]) or a more complex biomolecule (e.g., enzymes [29], RNA [30] or DNA [31]) (Figure 3).…”
Section: The Substrate Scope Of Ppgsmentioning
confidence: 99%
“…Since the 1970s, a considerable effort has been dedicated both to the development of novel photoactivatable chemical probes and their applications in various experimental studies. Regarding the scope of PPG applications, the caged substrate could be as simple as a proton or an inorganic species or ion (e.g., Ca 2+ [15], Zn 2+ [16], CO [17], NO [18], H2S [19]), it could be a small molecule (e.g., second messenger (such as inositol-1,4,5-triphosphate (IP3) [20]), neurotransmitter (notably GABA and glutamate [21,22]), nucleotide [23], peptide [24], drug molecule [25] (such as antibiotics [26], analgesics [27] or anticancer agents [28]) or a more complex biomolecule (e.g., enzymes [29], RNA [30] or DNA [31]) (Figure 3). Examples of PPG applications for small molecules/inorganic species: (A) calcium caging with photoactivatable EGTA [32], (B) neurotransmitter glutamate caging with MNI [21], (C) caging the anticancer agent vemurafenib with a nitrobenzyl PPG [33], (D) a coumarin PPG-caged antibiotic agent [34], (E) a coumarin PPG-caged analgesic [27].…”
Section: The Substrate Scope Of Ppgsmentioning
confidence: 99%
“…Among them, sulfur dioxide (SO 2 ) is an important species for maintaining the redox balance in organisms and plays an important role in many bioactivities, including regulating vascular function [ 4 ] and protecting against acute lung injury [ 5 ]. It is also considered to be the fourth possible gas messenger molecule after nitric oxide [ 6 ], hydrogen sulfide [ 7 , 8 ] and carbon monoxide [ 9 , 10 ]. SO 2 can be inhaled from the environment and can be synthesized endogenously through an enzymatic reaction in vivo.…”
Section: Introductionmentioning
confidence: 99%