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Literature DB >> 21966031

Synthesis and photophysics of an octathioglycosylated zinc(II) phthalocyanine.

Amit Aggarwal¹, Sunaina Singh, Yazhou Zhang, Mariah Anthes, Diana Samaroo, Ruomei Gao, Charles Michael Drain.

Abstract

A water soluble zinc(II) phthalocyanine symmetrically appended with eight thioglucose units was synthesized from commercially available hexadecafluorophthalocyaninatozinc(II) by controlled nucleophilic substitution of the peripheral fluoro groups. The photophysical properties and cancer cell uptake studies of this nonhydrolyzable thioglycosylated phthalocyanine are reported. The new compound has amphiphilic character, is chemically stable, and can potentially be used as a photosensitizer in photodynamic therapy.

Entities: CellLine Chemical Disease

Year: 2011 PMID： 21966031 PMCID： PMC3182128 DOI： 10.1016/j.tetlet.2011.08.028

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

31 in total

1. On the origin of cancer cells.

Authors: O WARBURG
Journal: Science Date: 1956-02-24 Impact factor: 47.728

2. Glycerol and galactose substituted zinc phthalocyanines. Synthesis and photodynamic activity.

Authors: Yunus Zorlu; Mahmut Ali Ermeydan; Fabienne Dumoulin; Vefa Ahsen; Huguette Savoie; Ross W Boyle
Journal: Photochem Photobiol Sci Date: 2009-01-14 Impact factor: 3.982

3. A new glycosidation method through nitrite displacement on substituted nitrobenzenes.

Authors: Xavier Alvarez-Micó; Mario J F Calvete; Michael Hanack; Thomas Ziegler
Journal: Carbohydr Res Date: 2006-11-21 Impact factor: 2.104

4. pH-responsive, TiO2-attached porphyrin for singlet oxygen production in an aqueous solution.

Authors: Wenbing Li; Naveen Gandra; Erick D Ellis; Shavelle Courtney; Shufang Li; Ebonie Butler; Ruomei Gao
Journal: ACS Appl Mater Interfaces Date: 2009-08 Impact factor: 9.229

5. Direct observation and quantitative characterization of singlet oxygen in aqueous solution upon UVA excitation of 6-thioguanines.

Authors: Yazhou Zhang; Xianchun Zhu; Joshua Smith; Makeisha T Haygood; Ruomei Gao
Journal: J Phys Chem B Date: 2011-02-04 Impact factor: 2.991

6. Synthesis and photophysical properties of thioglycosylated chlorins, isobacteriochlorins, and bacteriochlorins for bioimaging and diagnostics.

Authors: Sunaina Singh; Amit Aggarwal; Sebastian Thompson; João P C Tomé; Xianchun Zhu; Diana Samaroo; Mikki Vinodu; Ruomei Gao; Charles Michael Drain
Journal: Bioconjug Chem Date: 2010-10-21 Impact factor: 4.774

7. Synthesis, photophysical and photochemical properties of poly(oxyethylene)-substituted zinc phthalocyanines.

Authors: Devrim Atilla; Mahmut Durmuş; Ayşe Gül Gürek; Vefa Ahsen; Tebello Nyokong
Journal: Dalton Trans Date: 2007-02-16 Impact factor: 4.390

8. Glycosylated zinc(II) phthalocyanines as efficient photosensitisers for photodynamic therapy. Synthesis, photophysical properties and in vitro photodynamic activity.

Authors: Chi-Fung Choi; Jian-Dong Huang; Pui-Chi Lo; Wing-Ping Fong; Dennis K P Ng
Journal: Org Biomol Chem Date: 2008-04-18 Impact factor: 3.876

9. Polysubstituted phthalocyanines by nucleophilic substitution reactions on hexadecafluorophthalocyanines.

Authors: Clifford C Leznoff; José L Sosa-Sanchez
Journal: Chem Commun (Camb) Date: 2004-01-13 Impact factor: 6.222

10. Biological activities of phthalocyanines--XVI. Tetrahydroxy- and tetraalkylhydroxy zinc phthalocyanines. Effect of alkyl chain length on in vitro and in vivo photodynamic activities.

Authors: R W Boyle; C C Leznoff; J E van Lier
Journal: Br J Cancer Date: 1993-06 Impact factor: 7.640

5 in total

Synthesis and photophysics of an octathioglycosylated zinc(II) phthalocyanine.

1. On the origin of cancer cells.

2. Glycerol and galactose substituted zinc phthalocyanines. Synthesis and photodynamic activity.

3. A new glycosidation method through nitrite displacement on substituted nitrobenzenes.

4. pH-responsive, TiO2-attached porphyrin for singlet oxygen production in an aqueous solution.

5. Direct observation and quantitative characterization of singlet oxygen in aqueous solution upon UVA excitation of 6-thioguanines.

6. Synthesis and photophysical properties of thioglycosylated chlorins, isobacteriochlorins, and bacteriochlorins for bioimaging and diagnostics.

7. Synthesis, photophysical and photochemical properties of poly(oxyethylene)-substituted zinc phthalocyanines.

8. Glycosylated zinc(II) phthalocyanines as efficient photosensitisers for photodynamic therapy. Synthesis, photophysical properties and in vitro photodynamic activity.

9. Polysubstituted phthalocyanines by nucleophilic substitution reactions on hexadecafluorophthalocyanines.

10. Biological activities of phthalocyanines--XVI. Tetrahydroxy- and tetraalkylhydroxy zinc phthalocyanines. Effect of alkyl chain length on in vitro and in vivo photodynamic activities.

1. Synthesis and cell phototoxicity of a triply bridged fused diporphyrin appended with six thioglucose units.

Review 2. Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics.

Review 3. Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics.

4. Characterization and photodynamic activity of a new phthalocyanine nanoparticles.

5. Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives.