Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2011 Dec 23;17(1):98-144.
doi: 10.3390/molecules17010098.

Like a bolt from the blue: phthalocyanines in biomedical optics

Nawal Sekkat  1 , Hubert van den Bergh, Tebello Nyokong, Norbert Lange
Affiliations
Review

Like a bolt from the blue: phthalocyanines in biomedical optics

Nawal Sekkat et al. Molecules. .

Abstract

The purpose of this review is to compile preclinical and clinical results on phthalocyanines (Pcs) as photosensitizers (PS) for Photodynamic Therapy (PDT) and contrast agents for fluorescence imaging. Indeed, Pcs are excellent candidates in these fields due to their strong absorbance in the NIR region and high chemical and photo-stability. In particular, this is mostly relevant for their in vivo activation in deeper tissular regions. However, most Pcs present two major limitations, i.e., a strong tendency to aggregate and a low water-solubility. In order to overcome these issues, both chemical tuning and pharmaceutical formulation combined with tumor targeting strategies were applied. These aspects will be developed in this review for the most extensively studied Pcs during the last 25 years, i.e., aluminium-, zinc- and silicon-based Pcs.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Chemical structures of clinically relevant “non-phthalocyanine” photosensitizers.
Figure 2
Figure 2
(a) General chemical structure of metallated phthalocyanines; (b) Typical absorption and emission spectra of metallated Pc (e.g., zinc based phthalocyanine in DMSO).
Figure 3
Figure 3
A homologous series of AlPc alkylsulfonamides.
Figure 4
Figure 4
Chemical structure of the bombesin-AlPcS4 conjugate 5 for the targeting of GRPR.
Figure 5
Figure 5
Chemical structure of AlPc 6–10 [106,107].
Figure 6
Figure 6
Structures of compounds 11, 12 and 13 [122].
Figure 7
Figure 7
Chemical structure of phthalocyanine 14i.e., ZnPcS2P2.
Figure 8
Figure 8
Chemical structure of hydroxylated phthalocyanines 15–21.
Figure 9
Figure 9
Structure of the fluorinated ZnPc 22, 23 and 24.
Figure 10
Figure 10
Structure of the zinc hexadecafluorinated Pc 25 and its monosulfonated analogue 26.
Figure 11
Figure 11
Chemical structure of octapentyl and octadecyl ZnPcs 27 and 28.
Figure 12
Figure 12
Chemical structure of phthalocyanines 29 and 30.
Figure 13
Figure 13
Structure of compounds 31–34.
Figure 14
Figure 14
Structure of compounds 35, 36 and 37.
Figure 15
Figure 15
Chemical structure of phthalocyanines 38–43.
Figure 16
Figure 16
Chemical structure of compounds 44–48.
Figure 17
Figure 17
Chemical structure of Pc 4 (49) and derivatives 50–58 [187,188,189,190,191,192,193,194].
See this image and copyright information in PMC

References

    1. McKeown N.B. The synthesis of symmetrical phthalocyanines. In: Kadish K.M., Smith K.M., Guilard R., editors. The Porphyrin Handbook. Academic Press; San Diego, CA, USA: 2003. pp. 61–124.
    1. Thomas A.L. Phthalocyanine Research and Applications. CRC Press; Baton Rouge, FL, USA: 1990. p. 2.
    1. McKeown N.B. An introduction to the phthalocyanines. In: McKeown N.B., editor. Phthalocyanine Materials: Synthesis, Structure and Function. Cambridge University Press; Cambridge, UK: 1998. pp. 1–10.
    1. Geng Y.Y., Gu D.H., Wu Y.Q., Gan F.X. High speed recording property of phthalocyanine thin film for compact disc recordable. Proc. SPIE Int. Soc. Opt. Eng. 2003;63:63–66.
    1. Petritsch K., Friend R.H., Lux A., Rozenberg G., Moratti S.C., Holmes A.B. Liquid crystalline phthalocyanines in organic solar cells. Synth. Met. 1999;102:1776–1777.

Publication types

LinkOut - more resources