2-, 3-, and 4-(1-Oxo-1H-2,3-dihydroisoindol-2-yl)benzoic acids and their corresponding organotin carboxylates: Synthesis, characterization, fluorescent, and biological activities

Cai, Shaojun; Chen, Yong; Sun, Wenxia; Li, Hui; Chen, Yun; Yuan, Shishan

doi:10.1016/j.bmcl.2010.08.034

Cited by 24 publications

(5 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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%

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

et al. 2022

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

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

et al. 2022

View full text Add to dashboard Cite

show abstract

“…However, these platinum-based complexes have encountered much resistance and exhibited severe side effects, e.g., nephrotoxicity and neurotoxicity. , Consequently, to overcome these limitations, a significant number of alternative metal- and organometal-based − anticancer drugs were developed. In this respect, among the main-group metal compounds, organotin(IV) compounds have attracted more consideration due to their pharma value and biological activity. − In some cases, they are more effective than cisplatin in vitro tests and exhibit the most effective antitumor activities. , To date, a substantial number of organotin(IV) compounds have been tested as antitumor agents. ,,, Also, it is documented that their cytotoxicity is employed by the apoptosis mode via different pathways, e.g., interaction with DNA, change in the Ca 2+ homeostasis, caspase modulation, and so on. Furthermore, as compared to the mononuclear organotin complexes, di- or polynuclear organotin complexes have several advantages.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Diorganotin(IV) Complexes as Anticancer Agents: Study of Cytotoxicity, Cellular Localization, and Mechanism of Cell Death

et al. 2023

View full text Add to dashboard Cite

Three luminescent mixed ligand diorganotin(IV) complexes [Sn2Ph4(L)1–3(DPA)(MeOH)Cl] (where L1 = (Z)-N-((E)-3-ethoxy-2-hydroxybenzylidene)isonicotinohydrazonic acid, L2 = (Z)-N-((E)-5-bromo-2-hydroxybenzylidene)isonicotinohydrazonic acid, L3 = (Z)-N-((E)-2-hydroxy-3-methoxybenzylidene)isonicotinohydrazonic acid, and DPA = dipicolinic acid) (1–3) were synthesized and characterized physiochemically along with the single-crystal X-ray diffraction analysis of 1 and 3. Aqueous phase stabilities of the complexes were performed with UV–vis and 1H nuclear magnetic resonance, suggesting that they are stable in aqueous/biological media. The interaction of 1–3 with DNA was evaluated through analytical methods, which supported the intercalation mode of binding. Also, the interaction of complexes with bovine serum albumin was evaluated with fluorescence quenching experiments showing static quenching. In addition, the results of partition coefficients and cellular uptake suggest that the complexes are hydrophobic and can easily enter the cells. Cytotoxic potential of 1–3 was evaluated against HeLa, HT-29 (cancerous), and NIH-3T3 (normal) cell lines. Complex 2 is the most cytotoxic of the series having IC50 4.2 ± 0.7 μM against HeLa cells. Furthermore, all the complexes showed an apoptotic cell death confirmed by acridine orange/ethidium bromide, cell cycle analysis, and Annexin V-FITC/PI double staining assays. Finally, by using live cell confocal microscopy, it was found that the compounds target the mitochondria of cancer cells and raise the reactive oxygen species level.

show abstract

“…4). In addition, some isoindolinone derivatives show a large variety of biological activities [21–23], such as COX-2 inhibition [24], glucokinase activation [25], sodium channel blocking [26], antimycobacterial [27], antiproliferative [28] or carbonic anhydrase inhibition [29], as well as antifungal and antibacterial properties [30].…”

Section: Introductionmentioning

confidence: 99%

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

Marigorta

Santos

Retana

et al. 2019

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Benzo-fused γ-lactam rings such as isoindolin-2-ones and 2-oxindoles are part of the structure of many pharmaceutically active molecules. They can be often synthesized by means of multicomponent approaches and recent contributions in this field are summarized in this review. Clear advantages of these methods include the efficiency in saving raw materials and working time. However, there is still a need of new catalytic systems to allow the enantioselective preparation of these heterocycles by multicomponent reactions.

show abstract

2-, 3-, and 4-(1-Oxo-1H-2,3-dihydroisoindol-2-yl)benzoic acids and their corresponding organotin carboxylates: Synthesis, characterization, fluorescent, and biological activities

Cited by 24 publications

References 39 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

Fluorescent Diorganotin(IV) Complexes as Anticancer Agents: Study of Cytotoxicity, Cellular Localization, and Mechanism of Cell Death

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

Contact Info

Product

Resources

About