Photophysical Properties of Neutral and Cationic Tetrapyridinoporphyrazines

Martí, Cristina; Nonell, Santi; Nicolau, Mónica; Torres, Tomás

doi:10.1562/0031-8655(2000)0710053pponac2.0.co2

Cited by 55 publications

(15 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Taking in account the energy of the 0-0 electronic transitions, the energy levels of the singlet excited stated (E s ) were calculated ( Table 2). These results are in agreement with those previously reported for similar phthalocyanines in different media [14].…”

Section: Spectroscopic Studiessupporting

confidence: 94%

Synthesis of A3B-phthalocyanine Derivatives Bearing N-heterocycles as Potential Cationic Photodynamic Agents

Durantini

Tempesti

2007

Proceedings of the 11th International Electronic Conference on Synthetic Organic Chemistry

View full text Add to dashboard Cite

Unsymmetrically substituted A 3 B-phthalocyanine derivatives bearing annulated 6membered N-heterocycles, pyridine and pyrazine rings, have been synthesized by ring expansion reaction of subphthalocyanines. The geometrically constrained subphthalocyanines (A 3 ) were reacted with 1,2-phthalonitrile derivatives (B), in presence of 8-diazabicyclo[5.4.0]undec-7-ene (DBU), to form the A 3 B-phthalocyanine. The reactions were carried out in DMSO/1chloronaphthalene at 130-140 °C for 15 h. This approach produces selectively A 3 B-phthalocyanineswith high yields (75-90%) and it requires simple purification procedure since there are not byproducts. The spectroscopic properties of the A 3 B-phthalocyanines were compared with its homologous non-substituted Zn(II)phthalocyanine. In these compounds, annulated 6-membered Nheterocycles are precursors of cationic groups by methylation and therefore they represent interesting agents with potential applications in photodynamic inactivation of microorganisms.

show abstract

Section: Spectroscopic Studiessupporting

confidence: 94%

Synthesis of A3B-phthalocyanine Derivatives Bearing N-heterocycles as Potential Cationic Photodynamic Agents

Durantini

Tempesti

2007

Proceedings of the 11th International Electronic Conference on Synthetic Organic Chemistry

View full text Add to dashboard Cite

show abstract

“…Although ZnTMPyPz is a potent 1 O 2 photosensitizer in solution [20], irradiation of ZnTMPyPz-loaded E. coli cells suspended in D-PBS did not produce any clear time-resolved 1 O 2 phosphorescence signal at 1,270 nm (see Supplementary Information). Neither a higher contact time of ZnTMPyPz (3 h), nor a higher acquisition time of the 1 O 2 phosphorescence signal (12 million laser pulses) produced any detectable signal.…”

Section: Resultsmentioning

confidence: 99%

Singlet Oxygen in Antimicrobial Photodynamic Therapy: Photosensitizer-Dependent Production and Decay in E. coli

Ragàs

Agut

et al. 2013

Molecules

Self Cite

View full text Add to dashboard Cite

Several families of photosensitizers are currently being scrutinized for antimicrobial photodynamic therapy applications. Differences in physical and photochemical properties can lead to different localization patterns as well as differences in singlet oxygen production and decay when the photosensitizers are taken up by bacterial cells. We have examined the production and fate of singlet oxygen in Escherichia coli upon photosensitization with three structurally-different cationic photosensitizers, namely New Methylene Blue N (NMB), a member of the phenothiazine family, ACS268, a hydrophobic porphyrin with a single cationic alkyl chain, and zinc(II)-tetramethyltetrapyridinoporphyrazinium salt, a phthalocyanine-like photosensitizer with four positive charges on the macrocycle core. The kinetics of singlet oxygen production and decay indicate different localization for the three photosensitizers, whereby NMB appears to localize in an aqueous-like microenvironment, whereas ACS268 localizes in an oxygen-shielded site, highly reactive towards singlet oxygen. The tetracationic zinc(II) tetrapyridinoporphyrazine is extensively aggregated in the bacteria and fails to produce any detectable singlet oxygen.

show abstract

“…These values can be recorded as a function of laser energy and of the solution absorbance for the sample and reference photosensitizers. Linear plots of the energy at each absorbance can be plotted (with the absorption factor) to produce slopes equivalent to the quantum yield (Marti et al , 2000). …”

Section: Experimental Methods To Determine the Rate Parametersmentioning

confidence: 99%

On thein vivophotochemical rate parameters for PDT reactive oxygen species modeling

Kim¹,

Ghogare²,

Greer³

et al. 2017

Phys. Med. Biol.

View full text Add to dashboard Cite

Photosensitizer photochemical parameters are crucial data in accurate dosimetry for photodynamic therapy (PDT) based on photochemical modeling. Progress has been made in the last few decades in determining the photochemical properties of commonly used photosensitizers (PS), but mostly in solution or in-vitro. Recent developments allow for the estimation of some of these photochemical parameters in-vivo. This review will cover the currently available in-vivo photochemical properties of photosensitizers as well as the techniques for measuring those parameters. Furthermore, photochemical parameters that are independent of environmental factors or are universal for different photosensitizers will be examined. Most photosensitizers discussed in this review are of the type II (singlet oxygen) photooxidation category, although type I photosensitizers that involve other reactive oxygen species (ROS) will be discussed as well. The compilation of these parameters will be essential for ROS modeling of PDT.

show abstract

Photophysical Properties of Neutral and Cationic Tetrapyridinoporphyrazines

Cited by 55 publications

References 32 publications

Synthesis of A3B-phthalocyanine Derivatives Bearing N-heterocycles as Potential Cationic Photodynamic Agents

Synthesis of A3B-phthalocyanine Derivatives Bearing N-heterocycles as Potential Cationic Photodynamic Agents

Singlet Oxygen in Antimicrobial Photodynamic Therapy: Photosensitizer-Dependent Production and Decay in E. coli

On thein vivophotochemical rate parameters for PDT reactive oxygen species modeling

Contact Info

Product

Resources

About