Arginine‐Substituted Phthalocyanine with Concentration‐Driven Self‐Disaggregation Performance: Synthesis, Properties and Mechanistic Study

Wang, Ao; Zhou, Ruoyu; Zhou, Lin; Sun, Kang; Zhou, Jiahong; Wei, Shaohua; Jiang, Jianchun

doi:10.1002/asia.201601133

Cited by 4 publications

(4 citation statements)

References 42 publications

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“…The breaking of such cluster formations is expected due to the introduction of steric hindrance through the aliphatic chain. 33,34 The absorption and emission spectra of product obtained by hydrothermal reaction of citric acid and butyl amine are shown in Figure 2, parts E and F, respectively. A very sharp absorption peak in water is observed at 333 nm.…”

Section: Resultsmentioning

confidence: 99%

“…To provide direct experimental evidence to the involvement of the pyrido group of citrazinic acid in H-bonded clusters, we have chosen butyl amine as one of the precursor in synthesis along with citric acid. The breaking of such cluster formations is expected due to the introduction of steric hindrance through the aliphatic chain. , The absorption and emission spectra of product obtained by hydrothermal reaction of citric acid and butyl amine are shown in Figure , parts E and F, respectively. A very sharp absorption peak in water is observed at 333 nm.…”

Section: Resultsmentioning

confidence: 99%

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Connecting the Dots of Carbon Nanodots: Excitation (In)dependency and White-Light Emission in One-Step

et al. 2019

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The synthetic origin of nanocarbon and its role on the luminescence properties of carbon nanodots, in particular, citric acid derived ones, remain an enigma to date. We report here, for the very first time, that citrazinic acid alone builds a nanocarbon structure upon incubation in dimethylformamide at room temperature. The emission properties of incubated fluorophore resemble that of a nanodot. The dispersion of the H-bonded cluster’s size originated from citrazinic acid only is the cause of excitation-dependent emission. We have shown that the steric hindrance caused by the presence of alkyl chain of butyl amine restricts such dispersions, resulting in excitation-independent emission, a molecular behavior. On the other hand, for achieving white-light emission through a one-step method, the solvothermal reaction of citric acid with ammonium thiocyanate has been performed. The ground-state heterogeneity and luminescence properties are strongly influenced by the solvent polarity. We identify the existence of blue-, green-, and red-emissive fluorophores in a product obtained from solvothermal reaction. The computed vertical excitations of the molecular fluorophore predicted by the reaction mechanism are in good agreement with the experimental observations. Unprecedently, a product-embedded PVA/PVP film exhibits white light emission under irradiation of UV light, 365 nm. The mechanism of white light emission is attributed to effective energy transfer among fluorophores.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Connecting the Dots of Carbon Nanodots: Excitation (In)dependency and White-Light Emission in One-Step

et al. 2019

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“…4-(3,4-Dicyanophenoxy) benzoic acid was synthesized according to our previous report . Then, the abovementioned product (586.3 mg, 2.22 mmol) and Zn(OAc) 2 (241.7 mg, 1.32 mmol) were dissolved in 1-pentanol (8 mL).…”

Section: Methodsmentioning

confidence: 99%

“…4-(3,4-Dicyanophenoxy) benzoic acid was synthesized according to our previous report. 33 Then, the abovementioned product (586.3 mg, 2.22 mmol) and Zn(OAc) 2 (241.7 mg, 1.32 mmol) were dissolved in 1pentanol (8 mL). Under the protection of N 2 , the reaction temperature was increased to 90 °C for 1 h. Later, 1,8diazabicyclo [5,4,0]undec-7-ene (DBU, 300 μL) was added and continued heating to 140 °C for reacting for 12 h. Later, when cooled down to room temperature, residual 1-pentanol was dislodged via vacuum distillation.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Multiple Functions Integrated inside a Single Molecule for Amplification of Photodynamic Therapy Activity

Shi

Zhan

et al. 2019

Mol. Pharmaceutics

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Nitric oxide (NO) can play both prosurvival and prodeath roles in photodynamic therapy (PDT). The generation efficiency of peroxynitrite anions (ONOO–), by NO and superoxide anions (O2 •–), significantly influenced the outcome. Reports indicated that such efficiency is closely related to the distance between NO and O2 •–. Thus, in this manuscript, l-arginine (Arg) ethyl ester-modified zinc phthalocyanine (Arg-ZnPc) was designed and synthesized as a photosensitizer (PS) and NO donor. Post light irradiation, the guanido of Arg-ZnPc can be effectively oxidized by the generated reactive oxygen species (ROS) in the PDT process to release NO. Such a strategy could ensure O2 •– and NO generation in the same place at the same time to guarantee effective ONOO– formation. In addition, NO has other multiple synergistic cancer treatment functions, including tumor tissue vasodilatation for drug extravasation promotion, P-glycoprotein (P-gp) downregulation for drug efflux inhibition, and glutathione depletion for cancer cell endogenous antioxidant defense destruction. In vitro and in vivo results indicated that the effective ONOO– formation and multiple functions of Arg-ZnPc could synergistically enhance its PDT activity and ensure satisfactory cancer treatment outcome.

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Positively charged phthalocyanine-arginine conjugates as efficient photosensitizer for photodynamic therapy

Wang

Zhou

et al. 2017

Bioorganic & Medicinal Chemistry

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Arginine‐Substituted Phthalocyanine with Concentration‐Driven Self‐Disaggregation Performance: Synthesis, Properties and Mechanistic Study

Cited by 4 publications

References 42 publications

Connecting the Dots of Carbon Nanodots: Excitation (In)dependency and White-Light Emission in One-Step

Connecting the Dots of Carbon Nanodots: Excitation (In)dependency and White-Light Emission in One-Step

Multiple Functions Integrated inside a Single Molecule for Amplification of Photodynamic Therapy Activity

Positively charged phthalocyanine-arginine conjugates as efficient photosensitizer for photodynamic therapy

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