Hydrazide–Hydrazone Small Molecules as AIEgens: Illuminating Mitochondria in Cancer Cells

Patil, Sohan; Pandey, Shalini; Singh, Amit Kumar; Radhakrishna, Mithun; Basu, Sudipta

doi:10.1002/chem.201901074

Cited by 28 publications

(31 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Triphenylphosphonium (TPP) always acts like a mitochondrial targeting ligand and can be taken by the mitochondrial membrane. It is a small molecule which can be used primarily for mitochondrial targeting ( Patil et al, 2019 ). Although TPP is the most used mitochondrion tropic ligand and is able to deliver cargos to the mitochondria, the targeted drug delivery of TPP derivatives is limited due to its rapid clearance in circulation ( Mo et al, 2012 ; Marrache et al, 2014 ; Yue et al, 2016 ).…”

Section: Mitochondria and Mitochondria-targeted Nanocarriersmentioning

confidence: 99%

Mitochondria-Targeted Nanocarriers Promote Highly Efficient Cancer Therapy: A Review

Zeng

Fang

Zhang

et al. 2021

Front. Bioeng. Biotechnol.

View full text Add to dashboard Cite

Mitochondria are the primary organelles which can produce adenosine triphosphate (ATP). They play vital roles in maintaining normal functions. They also regulated apoptotic pathways of cancer cells. Given that, designing therapeutic agents that precisely target mitochondria is of great importance for cancer treatment. Nanocarriers can combine the mitochondria with other therapeutic modalities in cancer treatment, thus showing great potential to cancer therapy in the past few years. Herein, we summarized lipophilic cation- and peptide-based nanosystems for mitochondria targeting. This review described how mitochondria-targeted nanocarriers promoted highly efficient cancer treatment in photodynamic therapy (PDT), chemotherapy, combined immunotherapy, and sonodynamic therapy (SDT). We further discussed mitochondria-targeted nanocarriers’ major challenges and future prospects in clinical cancer treatment.

show abstract

Section: Mitochondria and Mitochondria-targeted Nanocarriersmentioning

confidence: 99%

Mitochondria-Targeted Nanocarriers Promote Highly Efficient Cancer Therapy: A Review

Zeng

Fang

Zhang

et al. 2021

Front. Bioeng. Biotechnol.

View full text Add to dashboard Cite

show abstract

“…A new family of fluorescent materials based on hydrazones, which can emit various colors of white, yellow, or green fluorescence in solution, solid and hydrogel states, is very promising in the fields of, for example, chemosensors, photochromism, and photopharmacology, due to their diverse functions and facile synthesis. Hydrazone‐based AIE materials have been reported to respond to various environments and stimulation, including H + ‐induced aggregate emission . However, it is still challenging to design easily synthesized, stable, and tunable AIE materials.…”

Section: Figurementioning

confidence: 99%

“…The fluorescence quantum yield of compound 3 and 4 were found to be 5.3 and 5.1 %, respectively,m oreover,t he quantum yield of 3c is 22.6 %, these numbers are comparable or higher than those of structurally similar hydrazones. [18,19] On the other hand, 3a and 3b exhibit lower quantum yields (0.75 and 0.06 %), which means that the anion-exchange reaction of 3 may be ap otential method for fluorescencep robing of halide ions. .…”

mentioning

confidence: 99%

Tunable Aggregation‐Induced Emission of Imidazole Hydrazones by pH and Anions

Tian

Zheng

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

Aggregation-induced emission (AIE) materials have drawn great attention for applicationsa so rganic light-emitting diodes (OLED) and probes. The applications are, however,r estricted by the complexs yntheses and hydrophobic properties. Herein, ao ne-step synthesis of an AIE materialb ased on imidazole hydrazone is assessed. Protonation of the imidazole-H leads to emission color changef rom yellow to green in the solid state. The emission color is recovered upon imidazole-H + deprotonation. Moreover,t he emission wavelength shifts from 532 to 572 nm by anion exchange. In addition, an enhanced emission (F F up to 22.6 %) was obtained with the Br À anion compared with NTf 2 À ,S bCl 5 À ,P F 6 À ,a nd OTf À anions.X -ray crystallography studies togetherw ith theoretical calculations show that the enhanced emissiono f hydrazone salts arises from strong hydrogen bondingb etween the hydrazone proton andt he halide ion (Cl À or Br À ).

show abstract

“…They undergo easy dehydration to 1,3,4-oxadiazoles that present a variety of biological activities [33,34]. Hydrazide-hydrazones provide interesting properties in the field of supramolecular architecture [35][36][37][38][39], organic synthesis [33,40], chemo-and physical imaging [41][42][43][44], coordination [45][46][47][48][49], and in inorganic chemistry [50][51][52][53]. The numerous biologically active hydrazide-hydrazones are particularly worth paying attention to [54].…”

Section: Introductionmentioning

confidence: 99%

Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies

Maniak

Talma

Giurg

2021

IJMS

View full text Add to dashboard Cite

Laccase from pathogenic fungi participates in both the delignification and neutralization of phytoantibiotics. Furthermore, it interferes with the hormone signaling in plants and catalyzes melanization. Infections of these pathogens contribute to loss in forestry, agriculture, and horticulture. As there is still a need to expand knowledge on efficient defense strategies against phytopathogenic fungi, the present study aimed to reveal more information on the molecular mechanisms of laccase inhibition with natural and natural-like carboxylic acid semi-synthetic derivatives. A set of hydrazide-hydrazones derived from carboxylic acids, generally including electron-rich arene units that serve as a decoy substrate, was synthesized and tested with laccase from Trametes versicolor. The classic synthesis of the title inhibitors proceeded with good to almost quantitative yield. Ninety percent of the tested molecules were active in the range of KI = 8–233 µM and showed different types of action. Such magnitude of inhibition constants qualified the hydrazide-hydrazones as strong laccase inhibitors. Molecular docking studies supporting the experimental data explained the selected derivatives’ interactions with the enzyme. The results are promising in developing new potential antifungal agents mitigating the damage scale in the plant cultivation, gardening, and horticulture sectors.

show abstract

Hydrazide–Hydrazone Small Molecules as AIEgens: Illuminating Mitochondria in Cancer Cells

Abstract: AIEgens = Aggregation-induced-emission luminogens.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.

Cited by 28 publications

References 48 publications

Mitochondria-Targeted Nanocarriers Promote Highly Efficient Cancer Therapy: A Review

Mitochondria-Targeted Nanocarriers Promote Highly Efficient Cancer Therapy: A Review

Tunable Aggregation‐Induced Emission of Imidazole Hydrazones by pH and Anions

Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies

Contact Info

Product

Resources

About