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PHOTOCHEMISTRY AND PHOTOBIOLOGY · 2023 ·Vol. 99 ·期 5 ·1310-1317 · IF 3.3

Photocontrolled Release of Carbendazim from Photocaged Molecule

Xiaoyi Dai,Zhong Li,Xusheng Shao

Carbendazim (MBC) is a high-efficient and broad-spectrum fungicide, but excessive residues caused by its improper use have caused health toxicity and environmental pollution. It is an irresistible trend to find green, safe, accurate and controllable release technology of MBC. To achieve the purpose of safe and efficient use of MBC, photolabile protecting group was used to realize the controllable release. This study aimed to covalently link MBC and 6-nitropiperonyl alcohol (NP) to synthesize photocaged molecule NP-MBC. The photodegradation test showed that NP-MBC could effectively release MBC under ultraviolet light. The antifungal activity of NP-MBC showed significant difference against Rhizoctonia solani , Sclerotinia sclerotiorum and Fusarium graminearum before and after irradiation, and the effects on mycelial morphology are different. The hyphae morphology of R. solani and F. graminearum changed significantly, and mycelia were severely damaged. The hyphae surface of former was swollen and broken, and the latter was collapsed and shriveled after NP-MBC light treatment. NP-MBC could realize the light-controlled release of MBC, and the antifungal activity before and after irradiation was significantly different, which provides an effective way to release MBC.

研究领域: 植物保护 · 环境科学
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CARBOHYDRATE POLYMERS · 2016 · IF 4.219

Novel moisture-preserving derivatives of hyaluronan resistant to hyaluronidase and protective to UV light

Feifei Sun,Hong Niu,Dongdong Wang,Yuanyuan Wu,Haibo Mu,Lili Ma,Jinyou Duan

Current studies have revealed the excellent moisture absorption-retention capacity of hyaluronan (HA); however, HA is easily degraded by hyaluronidase on the surface of skin. So, it is very necessary to develop an alternative derivative with low cytotoxicity and resistance to hyaluronidase. Herein, a HA decorated with photocaged groups was synthesized. The moisture absorption-retention capacity and hyaluronidase resistance of photocaged HA (HA-DMNB) and products of HA-DMNB irradiated by ultraviolet for different time (IHA-DMNB), were investigated. Results show that HA-DMNB is more resistant to hyaluronidase than HA, and HA-DMNB could release free carboxyl groups of HA upon ultraviolet to bond with H 2 O. More importantly, HA-DMNB was protective against UV light. In addition, HA-DMNB and IHA-DMNB were observed to be nontoxic to HaCat cells. This study indicates that HA-DMNB may be effectively used as a moisture-preserving reagent.

研究领域: 生物化学 · 皮肤科学 · 材料科学
✓ 已验证 DOI PubMed 高影响因子
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CARBOHYDRATE POLYMERS · 2017 · IF 4.811

A novel photocleavable heparin derivative with light controllable anticoagulant activity

Feifei Sun,Yinyin Liu,Dongdong Wang,Zhaojie Wang,Haibo Mu,Feng Wang,Kan Ding,Jinyou Duan

Heparin (HP) has enormous potential for clinical medication applications owing to its anticoagulant activity. However, the strong anticoagulant capacity of HP also leads to some side effects. Herein, a photocaged derivative (HP-DMNB) of HP was synthesized for light control of its anticoagulant activity. The synthesized HP-DMNB was characterized by NMR and FTIR analysis, which confirmed the successful modification of HP with the photocleavable 4,5-dimethoxyl-2-nitrobenzyl (DMNB) groups. After the modification, the molecular weight of HP-DMNB (DS = 0.34%) changed from 61 to 71 kDa. Anticoagulant activity analysis showed that HP-DMNB had a reduced anticoagulant capacity compared with commercial HP, while its anticoagulant activity will regain after releasing the free carboxyl groups of HP under UV light. In addition, HP-DMNB and its UV irradiated products were observed to possess good biocompatibility through the MTT assays and live-dead assays with HaCaT cells, which may have impacts on the clinical medication applications of HP.

研究领域: 药理学 · 生物化学 · 医学材料科学
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PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES · 2016 ·Vol. 15 ·期 11 ·1442-1447 · IF 2.235

Benzoylformamides as versatile photocaged bases for redox free radical photopolymerization

Xu Ruixin,He Minghui,Yang Jianwen

Benzoylformamides (BFAs) are proposed as photocaged bases for redox free radical photopolymerization (FRP). Initially the dissolving capacity of BFAs was evaluated. Besides our previously reported photo-latent anion polymerization, BFAs, as versatile photocaged bases, can not only initiate the FRP of acrylates unassisted, but also perform redox FRP in combination with a benzoyl peroxide initiator. We detail a model photopolymerization in the presence of BFA-dBA ( N , N -dibenzyl-2-oxo-2-phenylacetamide) as the photocaged base. In combination with a benzoyl peroxide initiator, BFAs are able to initiate the amine-mediated redox photopolymerization of acrylates, and enhance the photopolymerization rate. Finally, we investigated the mechanism of the radical formation to initiate the redox FRP, as exemplified by BFA-dBA.

CAS / MDL: 94-36-0
研究领域: 材料科学 · 化学
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CHINESE CHEMICAL LETTERS · 2014 · IF 1.178

Benzoylformamides as new photocaged bases for photo-latent anion polymerization

Ming-Hui He,Mei-Lin Su,Zhao-Hui Yu,Guang-Xue Chen,Zhao-Hua Zeng,Jian-Wen Yang

Benzoylformamide (BFA) derivatives are proposed as new photocaged bases with good solubility in epoxy resin. Initially their structures were confirmed by 1 H NMR, 13 C NMR, and elemental analysis. Next, we detail their thermal stability, solubility behavior, and photolysis products. Furthermore, the model photo-latent anion polymerization (AP) of epoxide system in the presence of BFA-dBA ( N , N -dibenzyl-2-oxo-2-phenylacetamide) as a photocaged base has been investigated, and excellent photopolymerization profile is obtained.

研究领域: 材料科学 · 化学
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Cells · 2023 ·Vol. 12 ·期 19 ·2351 · IF 6

Red-Light-Activatable AND-Gated Antitumor Immunosuppressant

Ziqi Zhou,Yan Zhang,Simin Xia,Xi Chen

Immunosuppressants are emerging as promising candidates for cancer therapy with lower cytotoxicity compared to traditional chemotherapy drugs; yet, the intrinsic side effects such as immunosuppression remain a critical concern. Herein, we introduce a photoactivatable antitumor immunosuppressant called dmBODIPY-FTY720 (BF) that shows no cytotoxicity but can be temporally and locally activated by deep-red light illumination to induce tumor cell apoptosis. To further reduce potential side effects, we integrate BF with another classic photosensitizer called methylene blue (MB) that is activated under the same wavelength of deep-red light (>650 nm) and successfully establish a red-light-activatable AND Boolean logic gate through a mechanism that we found to be synergetic apoptotic induction. At further decreased dosages, deep-red light illumination does not induce cell death in the presence of either BF or MB, but significant cancer cell death is triggered in the presence of both drugs. Therefore, the dosage of BF is further reduced, which will be highly beneficial to minimize any potential side effects of BF. This AND-gated strategy has been successfully applied in vivo for effective suppression of hepatocarcinoma tumors in living mice.Keywords:antitumor immunosuppressant;FTY720;logic gate;BODIPY photocage;red light;photodynamic therapy

CAS / MDL: 162359-56-0
研究领域: 癌症治疗 · 药理学 · 光化学
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RSC Advances · 2016 ·Vol. 7 ·期 2 ·914-918 · IF 3.289

Phototriggered base proliferation: a powerful 365 nm LED photoclick tool for nucleophile-initiated thiol-Michael addition reaction

Ruixin Xu,Xiaoyuan Guan,Minghui He,Jianwen Yang

Photocaged amines (PCAs) can allow a spatiotemporal control of the highly versatile and widely implemented nucleophile-catalyzed thiol-Michael addition reaction. However, a major challenge with most PCAs is that their relatively low quantum yields easily lead to low photosensitivity, especially under the radiation of light-emitting diodes (LEDs). In this paper, the phototriggered base proliferation (PBP) reaction as a powerful 365 nm LED photoclick tool is presented for the nucleophile-initiated thiol-Michael addition reaction. Compared to the PCA system, the advantages of this approach lie in its enhanced photosensitivity, increased reaction rate and elevated conversion. Finally, due to the persistent interactions of the produced longeval amine, remarkable post conversion was thus initially achieved after irradiation.

研究领域: 有机化学 · 光化学 · 生物化学
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Polymer Chemistry · 2013 ·Vol. 5 ·期 8 ·2951-2960 · IF 5.231

N-Phthaloyltranexamic acid ammonium salt derivatives as photocaged superbase for redox free radical photopolymerization

Minghui He,Guangxue Chen,Xun Huang,Ruixin Xu,Zhaohua Zeng,Jianwen Yang

N-Phthaloyltranexamic acid ammonium salt derivatives integrating with peroxides can invoke redox photopolymerization and propagating polymerization. A series of N-phthaloyltranexamic acid ammonium salt derivatives based on benzophenone, thioxanthen, and naphtha chromophores as novel photocaged bases were synthesized and characterized. In combination with a benzoyl peroxide initiator, these structures were able to initiate the amine-mediated redox photopolymerization of acrylates. In particular, the covalent binding of N-phthalimidoamino acid and type II chromophores (thioxanthone, benzophenone) improved remarkably the photoreactivity of photocaged bases (thioxanthen-DBU and benzophenone-DBU) compared to the parent compound. Furthermore, naphthal-DBU matches well the emission spectra of the mercury lamp with a dominant emission wavelength at 365 nm. More importantly, phthal-DBU & BPO as a new photocaged redox combination can invoke controlled redox polymerization within an irradiation time of 3 min. Finally, due to the persistent interaction of the produced longeval amine with peroxides, remarkable post conversion after irradiation, which is significant for preparation of photo-screened materials, was thus initially achieved in the redox photopolymerization.

研究领域: 材料化学 · 高分子科学 · 有机化学
✓ 已验证 DOI 高影响因子
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DYES AND PIGMENTS · 2022 · IF 5.122

A naphthalimide-based fluorescent probe for quantitative sensing of UV light

Maolin Wang,Tingwen Wei,Long Jiang,Jing Wang,Yajing Li,Wenyan Wu,Xiaojian Huang,Fang Wang,Sheng Lu,Xiaoqiang Chen

Developing ultraviolet (UV) sensors that can visualize UV light in the environment for productive life has been widely practiced. A challenging problem that arises in this domain is the quantitative analysis of UV light . In this study, we identified a novel naphthalimide derivative, NDGF , which can undergo decomposition to various degrees when irradiated by UV light with different intensities, so as to produce corresponding fluorescence intensities . Moreover, NDGF was prepared as a UV-responsive film NDGF-PEO which also has outstanding competence in the quantification of UV intensity. The surprising thing is that this novel UV-responsive decomposition mechanism of NDGF has been demonstrated and has great potential to open new doors for the development of naphthalimide-based photocages and novel UV quantitative sensors.

CAS / MDL: 97-02-9 68441-17-8
研究领域: 材料科学 · 光化学 · 分析化学 · 传感器
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ACS Sensors · 2018 · IF 5.711

Photocaged Nanoparticle Sensor for Sensitive MicroRNA Imaging in Living Cancer Cells with Temporal Control

Yi Shen,Zhi Li,Ganglin Wang,Nan Ma

Sensitive imaging of microRNA in living cells is of great value for disease diagnostics and prognostics. While signal amplification-based strategies have been developed for imaging low-abundance disease-relevant microRNA molecules, precise temporal control over sensor activity in living cells still remains a challenge, and limits their applications for sensing microRNA concentration dynamics. Herein, we report a class of photocaged nanoparticle sensors for highly sensitive imaging of microRNA in living cells with temporal control. The sensor features a DNA-templated gold nanoparticle-quantum dot satellite nanostructure which is temporarily inactivated by a photocaged DNA mask. Upon UV light irradiation, the sensor restores its activity for catalytic sensing of microRNA in living cells via entropy-driven two-step toehold-mediated strand displacement reactions. We show that the sensor exhibits quick response to UV light, robust intracellular stability, and high specificity and sensitivity for the microRNA target. On the basis of this strategy, precise control over sensor activity is achieved using an external light trigger, where on-demand sensing could be potentially performed with spatiotemporal control.

研究领域: 生物医学工程 · 纳米技术 · 分子生物学 · 癌症诊断
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF MEDICINAL CHEMISTRY · 2024 · IF 6.8

Light-Activable Inhibitor Overcomes Antimicrobial Resistance and Regulates Antibacterial Activity

Zhuang Ma,Boxuan Hou,Anhui Liao,Ying Tan,Chunyan Tan,Yuyang Jiang

Overuse of antibiotics and the widespread environmental accumulation of antibiotics drive the evolution and spread of antimicrobial resistance, posing a significant global health threat by reducing the effectiveness of available treatments and increasing the risk of untreatable infections. We designed and synthesized PhoPS, a novel photocaged β-lactamase inhibitor, which incorporates the pharmacophore of sulbactam caged with a photoresponsive moiety of o-nitrobiphenyl derivative. Experimental results demonstrate its rapid photoactivation, good stability in solution, and light-activated β-lactamase inhibition in vitro. PhoPS displays synergy with a cephalosporin antibiotic cefoperazone against both susceptible and resistant strains of Escherichia coli and biofilm formation. Additionally, PhoPS treatment demonstrates the potential to suppress the development of resistance in E. coli. These findings suggest that PhoPS offers a promising approach for restoring the efficacy of existing antibiotics and mitigating the emergence of AMR.

研究领域: 微生物学 · 药学 · 生物技术
✓ 已验证 DOI PubMed 高影响因子
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Matter · 2022 · IF 19.967

Constructing ultra-stable photothermal plastics assisted by carbon dots with photocaged reactivity

Jianyong Wan,Jiaxiu Wang,Hongda Guo,Keliang Wan,Xinpeng Zhao,Jian Li,Shujun Li,Zhijun Chen,Shouxin Liu,Kai Zhang

Summary Photothermal materials, especially photothermal plastics, are crucial building blocks for functional devices. Covalently immobilizing the photothermal carbon dots in plastic matrix is a promising method for producing efficient photothermal plastics. However, the reactive moieties of photothermal carbon dots are often destroyed because of harsh preparation conditions, preventing their covalent interaction with plastic matrix. Here, we conceptualized carbon dots with photocaged reactivity (P-CDs) for producing ultra-stable photothermal plastics. During the formation of P-CDs, hydroxyl moieties were maintained in the preparation environment. Upon UV irradiation, hydroxyl moieties of P-CDs were in situ converted into aldehyde groups and reacted with amino groups in the polysaccharide matrix, producing P-CD plastics. As-obtained P-CD plastics showed strong stability against solution immersion and UV aging. In particular, the P-CD plastics showed a high photothermal conversion efficiency of 46.6%. Such efficient and robust photothermal P-CD plastics were further applied to prepare a solar-driven thermoelectric generator (TEG) for energy generation.

研究领域: 材料科学 · 纳米技术 · 能源材料 · 光热转换
✓ 已验证 DOI 高影响因子
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