Design features for optimization of tetrapyrrole macrocycles as antimicrobial and anticancer photosensitizers

Alejandra Martinez De Pinillos Bayona, Pawel Mroz, Connor Thunshelle, Michael R. Hamblin

Research output: Contribution to journalEditorial

26 Citations (Scopus)

Abstract

Photodynamic therapy (PDT) uses non-toxic dyes called photosensitizers (PS) and harmless visible light that combine to form highly toxic reactive oxygen species that kill cells. Originally, a cancer therapy, PDT, now includes applications for infections. The most widely studied PS are tetrapyrrole macrocycles including porphyrins, chlorins, bacteriochlorins, and phthalocyanines. The present review covers the design features in PS that can work together to maximize the PDT activity for various disease targets. Photophysical and photochemical properties include the wavelength and size of the long-wavelength absorption peak (for good light penetration into tissue), the triplet quantum yield and lifetime, and the propensity to undergo type I (electron transfer) or type II (energy transfer) photochemical mechanisms. The central metal in the tetrapyrrole macrocycle has a strong influence on the PDT activity. Hydrophobicity and charge are important factors that govern interactions with various types of cells (cancer and microbial) in vitro and the pharmacokinetics and biodistribution in vivo. Hydrophobic structures tend to be water insoluble and require a drug delivery vehicle for maximal activity. Molecular asymmetry and amphiphilicity are also important for high activity. In vivo some structures possess the ability to selectively accumulate in tumors and to localize in the tumor microvasculature producing vascular shutdown after illumination.

Original languageEnglish (US)
Pages (from-to)192-206
Number of pages15
JournalChemical Biology and Drug Design
Volume89
Issue number2
DOIs
StatePublished - Feb 1 2017

Fingerprint

Tetrapyrroles
Photodynamic therapy
Photosensitizing Agents
Photochemotherapy
Tumors
Neoplasms
Light
Wavelength
Pharmacokinetics
Poisons
Energy Transfer
Porphyrins
Quantum yield
Hydrophobicity
Microvessels
Lighting
Drug delivery
Hydrophobic and Hydrophilic Interactions
Energy transfer
Blood Vessels

Keywords

  • bacteriochlorin
  • biodistribution
  • chlorin
  • pharmacodynamics
  • photodynamic therapy
  • photosensitizer
  • phthalocyanine
  • porphyrin

Cite this

Design features for optimization of tetrapyrrole macrocycles as antimicrobial and anticancer photosensitizers. / Martinez De Pinillos Bayona, Alejandra; Mroz, Pawel; Thunshelle, Connor; Hamblin, Michael R.

In: Chemical Biology and Drug Design, Vol. 89, No. 2, 01.02.2017, p. 192-206.

Research output: Contribution to journalEditorial

Martinez De Pinillos Bayona, Alejandra ; Mroz, Pawel ; Thunshelle, Connor ; Hamblin, Michael R. / Design features for optimization of tetrapyrrole macrocycles as antimicrobial and anticancer photosensitizers. In: Chemical Biology and Drug Design. 2017 ; Vol. 89, No. 2. pp. 192-206.
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