Organotin Schiff bases as halofluorochromic dyes: green synthesis, chemio-photophysical characterization, DFT, and their fluorescent bioimaging <i>in vitro</i>

López-Espejel, Margarita; Gómez-Treviño, J. Alberto; Muñoz‐Flores, Blanca M.; Treto‐Suárez, Manuel A.; Schott, Eduardo; Páez‐Hernández, Dayán; Zárate, Ximena; Jiménez-Pérez, Vı́ctor M.

doi:10.1039/d1tb01405f

Cited by 20 publications

(21 citation statements)

References 61 publications

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“…The representative 119 Sn NMR spectra of 1−3 are shown in Figure S4, which is the characteristic of a pentacoordinated tin atom with diphenyl substituent. [37][38][39]42,45 This is also in accordance with the solved XRD structures of 2−5 where it is observed that the tin atoms are present in trigonal bipyramidal geometry.…”

Section: General Methods Of Multicomponent Reactions For the Synthesi...supporting

confidence: 82%

“…Intracellular pH is a factor that is helpful in distinguishing between cancerous and normal cells. ,, Therefore, it is highly essential to design and synthesize fluorescent compounds which are responsive to pH for bioimaging purposes in living cells. Here, we checked the halofluorochromic effect of 1–5 in the pH range of 4–8 (Figures and S18).…”

Section: Results and Discussionmentioning

confidence: 99%

“…These values are very similar to the previously reported mononuclear organotin(IV) complexes. 38,39,42,45 Also, there is an intermolecular hydrogen bond present in complex 2 (Figure S1) between the phenolic oxygen atom (O1) and the Br(2) atom of salicylaldehyde moiety with a bond distance of 3.063 Å.…”

Section: General Methods Of Multicomponent Reactions For the Synthesi...mentioning

confidence: 99%

“…On the other hand, luminescent organotin compounds have been proven to have significant potential in the fields of photonics, biomedical, and optoelectronics. − Organotin compounds exhibit a variety of biological properties, including antibacterial, antiproliferative, antimicrobial, and DNA-binding activities. − Another alluring property of organotin complexes is that they can act as fluorescence bioimaging agents for the localization of specific organelles in live cells by using confocal microscopy. While recently several organotin(IV) complexes have been synthesized with significant luminescent properties for use in organic light-emitting diodes(OLEDs), , and biological studies, still it is important to note that bioimaging studies of organotin(IV) complexes are scarcely reported. − ,, …”

Section: Introductionmentioning

confidence: 99%

“…To the best of our knowledge, no organotin complexes have yet been examined for mitochondrial imaging experiments, despite a few organotin complexes being used for bio-imaging as a cytoplasmic marker. ,,,, Therefore, we present an array of new organotin complexes that possess superior photostability, as well as the first tin(IV) system that is specifically localized within living mitochondria.…”

Section: Introductionmentioning

confidence: 99%

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Mitochondria-Targeted Luminescent Organotin(IV) Complexes: Synthesis, Photophysical Characterization, and Live Cell Imaging

et al. 2022

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Five fluorescent ONO donor-based organotin(IV) complexes, [Sn IV (L 1−5 )Ph 2 ] (1−5), were synthesized by the onepot reaction method and fully characterized spectroscopically including the single-crystal X-ray diffraction studies of 2−4. Detailed photophysical characterization of all compounds was performed. All the compounds exhibited high luminescent properties with a quantum yield of 17−53%. Additionally, the results of cellular permeability analysis suggest that they are lipophilic and easily absorbed by cells. Confocal microscopy was used to examine the live cell imaging capability of 1−5, and the results show that the compounds are mostly internalized in mitochondria and exhibit negligible cytotoxicity at imaging concentration. Also, 1−5 exhibited high photostability as compared to the commercial dye and can be used in long-term real-time tracking of cell organelles. Also, it is found that the probes (1−5) are highly tolerable during the changes in mitochondrial morphology. Thus, this kind of low-toxic organotin-based fluorescent probe can assist in imaging of mitochondria within living cells and tracking changes in their morphology.

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Section: General Methods Of Multicomponent Reactions For the Synthesi...supporting

confidence: 82%

Section: Results and Discussionmentioning

confidence: 99%

Section: General Methods Of Multicomponent Reactions For the Synthesi...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Mitochondria-Targeted Luminescent Organotin(IV) Complexes: Synthesis, Photophysical Characterization, and Live Cell Imaging

et al. 2022

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Creation of Excitation‐Driven Hypervalent Tin(IV) Compounds For Aggregation‐Induced Emission and Application to Thermoresponsive Luminescent Films Below Freezing Point

Gon,

Shibahara,

Tanimura

et al. 2024

Chemistry An Asian Journal

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Although many researchers have devoted their much effort to establish the strategy for developing a stimuli‐responsive molecule and tuning of their properties according to the preprogrammed design, it is still challenging to create desired molecules from the scratch. We recently demonstrated that the molecules with a large structural difference between the theoretically optimized structures in the ground and excited states have a potential to exhibit stimuli‐responsive luminescent properties. We defined these molecules as an excitation‐driven molecule and have shown that they are a versatile platform for designing stimuli‐responsive luminescent molecules. Herein, based on the concept of excitation‐driven molecules, we show that the hypervalent tin‐fused azomethine (TAm) compounds possessing aggregation‐induced emission (AIE) properties can be obtained by simple chemical modification with a methyl group although conventional TAm derivatives are well known to be highly luminescent compounds in solution. Furthermore, by combining the solid‐state luminescence property of AIE and the coordination number shifts of the hypervalent tin atom, the thermoresponsive films operating below the freezing point are fabricated with the polymer. In this study, we apply the concept of excitation‐driven molecules to the hypervalent compounds and demonstrate to obtain the novel functional materials.

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Quantum-mechanical study of a MO2(cyclam)+ complexes series with M = Mn, Tc, Re

Schott,

Treto-Suárez,

Zarate

et al. 2024

Computational and Theoretical Chemistry

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Organotin Schiff bases as halofluorochromic dyes: green synthesis, chemio-photophysical characterization, DFT, and their fluorescent bioimaging in vitro

Abstract: Fluorescent bioimaging is an excellent tool in cellular biology and it will be a powerful technic in modern medicine as noninvasive imaging technologies where tumoral and normal cells must be...

Cited by 20 publications

References 61 publications

Mitochondria-Targeted Luminescent Organotin(IV) Complexes: Synthesis, Photophysical Characterization, and Live Cell Imaging

Mitochondria-Targeted Luminescent Organotin(IV) Complexes: Synthesis, Photophysical Characterization, and Live Cell Imaging

Creation of Excitation‐Driven Hypervalent Tin(IV) Compounds For Aggregation‐Induced Emission and Application to Thermoresponsive Luminescent Films Below Freezing Point

Quantum-mechanical study of a MO2(cyclam)+ complexes series with M = Mn, Tc, Re

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