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Synthesis and properties of photo-activable phthalocyanines: a brief overview

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Abstract

Phthalocyanines (Pcs) can very well satisfy the different demands of photosensitizer in photodynamic therapy (PDT) such as absorption, amphiphilicity and most importantly, high photochemical reactivity, depending on the subtle interplay of structure–function relationships. They have been shown to be phototoxic against a number of tumor cells. Certain criteria of ideal photosensitizers for PDT were described. A brief summary of the synthesis and some properties of photo-activable Pcs have been presented and an outlook for future photocytotoxic Pcs given. These Pcs are classified into three groups: (1) Pcs with different peripheral and/or non-peripheral substitution; (2) Pcs with different axial substitution; (3) Pcs with different metal center.

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Notes

  1. Heavy atom effect enhances the rate of a spin-forbidden process by the presence of an atom of high atomic number, which is either pert of, or external to, the excited molecular entity. Mechanistically, it responds to a spin–orbit coupling enhancement produced by a heavy atom [14].

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Acknowledgments

This work was supported in part by the National Natural Science Foundation of China for the Distinguished Young Scholar Fund to C. Zhang (50925207), the Ministry of Science and Technology of China for the International Science Linkages Program (2009DFA50620) and in part through the Special Fund for International Collaboration & Exchange of Jiangsu Province (BZ2008049).

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Authors and Affiliations

  1. Molecular Materials Research Center, School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, People’s Republic of China

    Aijian Wang & Chi Zhang

  2. China-Australia Joint Research Center for Functional Molecular Materials, Scientific Research Academy, School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, People’s Republic of China

    Lingliang Long

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  1. Aijian Wang
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Correspondence to Chi Zhang.

Glossary

Pc

Phthalocyanine

Nc

Naphthalocyanine

PDT

Photodynamic therapy is a binary therapy involving the combination of light and a chemical substance (a photosensitizer), which results in cell damage or death [14]

ΦF

Fluorescence quantum yields are the ratio of photons absorbed to photons emitted through fluorescence. They could be determined by the comparative method (Eq. 1): ΦF = ΦF (Std) · FA Std η 2/F Std Aη 2Std , where F and F Std are the areas under the fluorescence emission curves of the samples and the reference, respectively; A and A Std are the respective absorbance of the sample and standard at the excitation wavelengths, respectively; η and η Std are the refractive indices of solvents used for the sample and standard, respectively [63]. The sample and the standard should be excited at the same relevant wavelength

τF

Fluorescence lifetimes refer to the average time that a molecule remains in its excited state before returning to its ground state. They were evaluated using Eq. 2: ΦF = τF/τ0, where τF is the fluorescence lifetime. The τ0 is the natural radiative life time which can be determined using PhotochemCAD program using the Strickler–Berg equation [57]

ΦT

Triplet quantum yields usually were determined using the comparative method based on the triplet decay, using Eq. 3: Φ SampleT  = Φ StdT  · ΔA SampleT  · ε Std/ΔA StdT  · ε Sample, where ΔA SampleT and ΔA StdT are the changes in the triplet state absorbance of metal Pcs and the standard, respectively. ε Sample and ε Std are the triplet state extinction coefficients for the metal Pcs and the standard, respectively. Φ StdT is the triplet state quantum yield for the standard [16]. Triplet lifetimes (τT) were determined by exponential fitting of the kinetic curves using OriginPro 7.5 software [53]

ΦΔ

Singlet oxygen quantum yield is a key property of a photosensitizer. It was defined as the number of molecules of 1O2 molecules generated for each photon absorbed by a photosensitizer. Equation 4 was used for the calculations of the singlet oxygen yield: ΦΔ = Φ StdΔ  · R · I Stdabs /R Std · I abs, where Φ StdΔ is the singlet oxygen quantum yield for the standard. R and R Std are the trap photobleaching rates in the presence of studied samples and references, respectively. I abs and I Stdabs are the intensities of light absorption by the studied samples and the standards, respectively [58]

DBU

1,8-Diazabicyclo-[5,4,0]undec-7-ene

IC50

Half maximal inhibitory concentration, which is defined as the dye concentration required to kill 50% of the cells

DMSO

Dimethylsulfoxide

THF

Tetrahydrofuran

DMF

Dimethylformamide

DPBF

1,3-Diphenylisobenzofuran

HOMO, LUMO

Highest occupied molecular orbital and the lowest unoccupied molecular orbital, respectively. The energy difference between the HOMO and LUMO is termed as the band gap

LD90

Lethal dose 90%. The estimated dose at which 90% of the cells is expected to die

SNO

Human oesophageal carcinoma cells

BSA

Bovine serum albumin

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Wang, A., Long, L. & Zhang, C. Synthesis and properties of photo-activable phthalocyanines: a brief overview. J Incl Phenom Macrocycl Chem 71, 1–24 (2011). https://doi.org/10.1007/s10847-010-9918-x

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