A new GSH-responsive prodrug of 5-aminolevulinic acid for photodiagnosis and photodynamic therapy of tumors

Li, Ké; Dong, Wenyi; Qiu, Ling; Liu, Qingzhu; Lv, Gaochao; Peng, Ying; Xie, Minhao; Lin, Jianguo

doi:10.1016/j.ejmech.2019.111582

Cited by 22 publications

(7 citation statements)

References 27 publications

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“…So GSH has emerged as a popular biodegradable polymer and GSH-sensitive linkage (disulfide) has been extensively evaluated in GSH-sensitive drug delivery systems for cancer therapy (Jabir et al, 2020 ). Cystamine (SS) is a GSH-sensitive linker that could offer response on the reduction environment such as tumor site, examples include the SS was used to prepare a GSH-responsive prodrug for photodiagnosis and photodynamic therapy of tumors (Li et al, 2019 ).…”

Section: Introductionmentioning

confidence: 99%

Prostate-specific membrane antigen targeted, glutathione-sensitive nanoparticles loaded with docetaxel and enzalutamide for the delivery to prostate cancer

Chen

et al. 2022

Drug Delivery

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Prostate cancer (PCa) is the most common malignant tumor in men. Chemotherapy with docetaxel (DTX) and novel hormonal agents such as enzalutamide (EZL) and abiraterone are the preferred first-line therapeutic regimens. Prostate-specific membrane antigen (PSMA) is overexpressed on the surface of PCa cells. This study aimed to prepare a PSMA targeted (Glutamate-Urea-Lysine, GUL ligand modified), glutathione (GSH)-sensitive (Cystamine, SS), DTX and EZL co-loaded nanoparticles (GUL-SS DTX/EZL-NPs) to treat PCa. Polyethylene glycol (PEG) was conjugated with oleic acid (OA) using a GSH-sensitive ligand: cystamine (PEG-SS-OA). GUL was covalently coupled to PEG-SS-OA to achieve GUL-PEG-SS-OA. GUL-PEG-SS-OA was used to prepare GUL-SS DTX/EZL-NPs. To evaluate the in vitro and in vivo efficiency of the system, human prostate cancer cell lines and PCa cells bearing mice were applied. Single drug-loaded nanoparticle and free drugs systems were utilized for the comparison of the anticancer ability. GUL-SS DTX/EZL-NPs showed a size of 143.7 ± 4.1 nm, with a PDI of 0.162 ± 0.037 and a zeta potential of +29.1 ± 2.4 mV. GUL-SS DTX/EZL-NPs showed high cancer cell uptake of about 70%, as well as higher cell growth inhibition efficiency (a maximum 79% of cells were inhibited after treatment) than single drug-loaded NPs and free drugs. GUL-SS DTX/EZL-NPs showed the most prominent tumor inhibition ability and less systemic toxicity. The novel GUL-SS DTX/EZL-NPs could be used as a promising system for PCa therapy.

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Section: Introductionmentioning

confidence: 99%

Prostate-specific membrane antigen targeted, glutathione-sensitive nanoparticles loaded with docetaxel and enzalutamide for the delivery to prostate cancer

Chen

et al. 2022

Drug Delivery

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“…A GSH and GSSG assay kit (Beyotime Institute of Biotechnology, Shanghai, People’s Republic of China) was utilized to determine the intracellular reduced (GSH) and oxidized (GSSG) glutathione. Briefly, A549/DDP cells were treated with 0, 10, 15, or 20 μM compound 12 for 24 h; then, the GSH/GSSG ratio was measured following the instructions that were with the kit …”

Section: Methodsmentioning

confidence: 99%

Naphtho-γ-pyrone Dimers from an Endozoic Aspergillus niger and the Effects of Coisolated Monomers in Combination with Cisplatin on a Cisplatin-Resistant A549 Cell Line

Liu

Guo

et al. 2021

J. Nat. Prod.

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Chemotherapy resistance is one of the main causes of lung cancer treatment failure, and a combination regimen may be an effective way to overcome this. Here we report 5 new (1–3, 7, and 9) and 15 known polyketides, isolated from an endozoic Aspergillus niger. The structures of the new compounds were determined by the interpretation of IR, HRESIMS, NMR, and ECD spectra. The ESI-MS/MS fragmentation of the isolated naphtho-γ-pyrone isomers in positive mode is discussed. The effects of isolated compounds in combination with cisplatin (DDP) on a DDP-resistant A549 cell line (A459/DDP) are investigated. The most active compound, 12, could reduce the ratio of GSH/GSSG, promote the generation of intracellular ROS, and cooperate with DDP to down-regulated levels of Nrf2, Akt, HO-1, and NQO1, suggesting that inhibition of Nrf2 and Akt pathways might be involved in the combined effect of 12 and DDP in A549/DDP cells.

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“…Recent studies on ALA prodrugs have focused on the design of small molecule prodrugs or smart nanosystems that release ALA effectively within targeted cells through a range of specific stimuli. This includes exploiting the elevated levels of phosphatase or β-glucuronidase activity in certain tumour cells [20,21], or changes in intracellular glutathione concentration [22], as well as the development of pH-responsive systems from which ALA is released upon delivery to the lowered pH environment of endosomes/lysosomes [23,24]. We have previously described the synthesis and evaluation in vitro and in vivo of a range of simple dipeptide prodrugs of ALA that both show enhanced cellular uptake relative to ALA itself and are cleaved by cell-line specific protease activities to produce PpIX [25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Peptide-targeted dendrimeric prodrugs of 5-aminolevulinic acid: A novel approach towards enhanced accumulation of protoporphyrin IX for photodynamic therapy

Tewari

Dondi

Yaghini

et al. 2021

Bioorganic Chemistry

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A new GSH-responsive prodrug of 5-aminolevulinic acid for photodiagnosis and photodynamic therapy of tumors

Cited by 22 publications

References 27 publications

Prostate-specific membrane antigen targeted, glutathione-sensitive nanoparticles loaded with docetaxel and enzalutamide for the delivery to prostate cancer

Prostate-specific membrane antigen targeted, glutathione-sensitive nanoparticles loaded with docetaxel and enzalutamide for the delivery to prostate cancer

Naphtho-γ-pyrone Dimers from an Endozoic Aspergillus niger and the Effects of Coisolated Monomers in Combination with Cisplatin on a Cisplatin-Resistant A549 Cell Line

Peptide-targeted dendrimeric prodrugs of 5-aminolevulinic acid: A novel approach towards enhanced accumulation of protoporphyrin IX for photodynamic therapy

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