Highly positive-charged zinc(II) phthalocyanine as non-aggregated and efficient antifungal photosensitizer

Li, Xingshu; Guo, Jun; Zhuang, Jingjing; Zheng, Biyuan; Ke, Mei‐Rong; Huang, Jian‐Dong

doi:10.1016/j.bmcl.2015.04.004

Cited by 52 publications

(19 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Methylene blue (MB), phthalonitrile, 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU), zinc acetate and BSA monomer were purchased from Sigma-Aldrich. ZnPcS 8 , ZnPcS 4 and ZnPcN 12 were prepared using our previously described procedure 35-37. The synthetic details of ZnPcS 2 and ZnPcN 4 are shown in the supplementary materials.…”

Section: Methodsmentioning

confidence: 99%

Water-Soluble Phthalocyanines Selectively Bind to Albumin Dimers: A Green Approach Toward Enhancing Tumor-Targeted Photodynamic Therapy

Jeong

Lee

et al. 2019

Theranostics

Self Cite

View full text Add to dashboard Cite

Targeted delivery of therapeutic agents is of particular interest in the field of cancer treatment. However, there is an urgent need for developing clinically promising targeting approaches that can be readily administered in a green manner.Methods: Five phthalocyanine derivatives bearing different anionic and cationic groups were designed and synthesized. Then, their binding affinity with albumin were studied using gel assays, optical spectra and computational simulation. Finally, in vitro and in vivo fluorescence imaging and photodynamic therapy (PDT) evaluations were carried out.Results: The two positively charged compounds could selectively bind to albumin dimer over albumin monomer, while the three negatively charged phthalocyanines could bind to both albumin monomer and dimer. Following systemic administration, the phthalocyanines show improved tumor accumulation via transport by natural albumin. PDT evaluations indicate that one of the positively charged compounds, ZnPcN4, shows outstanding phototherapeutic efficacy against tumors in preclinical models.Conclusion: Our findings demonstrate that the use of water-soluble phthalocyanines as photosensitizers and in vivo albumin as a natural carrier may provide a green and efficient approach for tumor-targeted imaging and therapy.

show abstract

Section: Methodsmentioning

confidence: 99%

Water-Soluble Phthalocyanines Selectively Bind to Albumin Dimers: A Green Approach Toward Enhancing Tumor-Targeted Photodynamic Therapy

Jeong

Lee

et al. 2019

Theranostics

Self Cite

View full text Add to dashboard Cite

show abstract

“… 12 – 17 Introduction of quaternary ammonium groups on phthalocyanines is an attractive approach to improve hydrophilicity and the affinity for the outer membrane of bacteria. 18 , 19 In addition, recent studies have suggested that boronic acid groups are very useful for bacterial targeting because of their ability to form a pair of covalent bonds with glycans on the surface of bacteria. 20 – 22 Therefore, the 3-{ N -(4-boronobenzyl)- N , N -dimethylammonium}phenoxy-substituted zinc( ii ) phthalocyanine PcN4-BA ( Fig.…”

Section: Introductionmentioning

confidence: 99%

A boronic acid-functionalized phthalocyanine with an aggregation-enhanced photodynamic effect for combating antibiotic-resistant bacteria

Lee

et al. 2020

Chem. Sci.

View full text Add to dashboard Cite

show abstract

“…Peripherally charged substituents prevent aggregation, greatly improve compatibility of metallophthalocyanines (Me-Pcs) with aqueous media and increase singlet oxygen yield generation up to 0.60–0.65 values for octa-substituted compounds [16]. Cationic substituted Me-Pcs with long triplet lifetimes, high photostability, and high yields of singlet oxygen are potent antimicrobial photosensitizers against both gram-positive and gram-negative bacteria, pathogenic fungi, and viruses [17,18,19].…”

Section: Introductionmentioning

confidence: 99%

Ultrastructural Aspects of Photodynamic Inactivation of Highly Pathogenic Avian H5N8 Influenza Virus

Korneev

Kurskaya

Sharshov

et al. 2019

Viruses

View full text Add to dashboard Cite

Ultrastructural studies revealing morphological differences between intact and photodynamically inactivated virions can point to inactivation mechanisms and molecular targets. Using influenza as a model system, we show that photodynamic virus inactivation is possible without total virion destruction. Indeed, irradiation with a relatively low concentration of the photosensitizer (octacationic octakis(cholinyl) zinc phthalocyanine) inactivated viral particles (the virus titer was determined in Madin Darby Canine Kidney (MDCK) cells) but did not destroy them. Transmission electron microscopy (TEM) revealed that virion membranes kept structural integrity but lost their surface glycoproteins. Such structures are known as “bald” virions, which were first described as a result of protease treatment. At a higher photosensitizer concentration, the lipid membranes were also destroyed. Therefore, photodynamic inactivation of influenza virus initially results from surface protein removal, followed by complete virion destruction. This study suggests that photodynamic treatment can be used to manufacture “bald” virions for experimental purposes. Photodynamic inactivation is based on the production of reactive oxygen species which attack and destroy biomolecules. Thus, the results of this study can potentially apply to other enveloped viruses and sources of singlet oxygen.

show abstract

Highly positive-charged zinc(II) phthalocyanine as non-aggregated and efficient antifungal photosensitizer

Cited by 52 publications

References 41 publications

Water-Soluble Phthalocyanines Selectively Bind to Albumin Dimers: A Green Approach Toward Enhancing Tumor-Targeted Photodynamic Therapy

Water-Soluble Phthalocyanines Selectively Bind to Albumin Dimers: A Green Approach Toward Enhancing Tumor-Targeted Photodynamic Therapy

A boronic acid-functionalized phthalocyanine with an aggregation-enhanced photodynamic effect for combating antibiotic-resistant bacteria

Ultrastructural Aspects of Photodynamic Inactivation of Highly Pathogenic Avian H5N8 Influenza Virus

Contact Info

Product

Resources

About