Porphyrin-based photosensitizers and their DNA conjugates for singlet oxygen induced nucleic acid interstrand crosslinking

2017 ◽  
Vol 15 (25) ◽  
pp. 5402-5409 ◽  
Author(s):  
Eva M. Llamas ◽  
João P. C. Tome ◽  
João M. M. Rodrigues ◽  
Tomás Torres ◽  
Annemieke Madder
Keyword(s):  
Nucleic Acid ◽  
Singlet Oxygen ◽  
Red Light ◽  
Dna Conjugates ◽  
Interstrand Crosslink ◽  
Interstrand Crosslinking

Porphyrin-based photosensitisers and their DNA conjugates have been evaluated for interstrand crosslink generation using furan containing oligonucleotides and red light.

Red light-triggered nucleic acid-templated reaction based on cyclic oligonucleotide substrates

2019 ◽  
Vol 55 (72) ◽  
pp. 10713-10716 ◽  
Author(s):  
Oleksii Zozulia ◽  
Tobias Bachmann ◽  
Nina S. Deussner-Helfmann ◽  
Frank Beierlein ◽  
Mike Heilemann ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Chemical Reaction ◽  
Red Light ◽  
Specific Detection

We developed a red light-triggered, fluorogenic chemical reaction based on cyclic oligonucleotide substrates that is accelerated over 30-fold by nucleic acid templates that allows quick and sequence specific detection of nucleic acid down to 1 nM.

scholarly journals Hydrogen Bond Acceptors and Additional Cationic Charges in Methylene Blue Derivatives: Photophysics and Antimicrobial Efficiency

2013 ◽  
Vol 2013 ◽  
pp. 1-12 ◽  
Author(s):  
Ariane Felgenträger ◽  
Tim Maisch ◽  
Daniel Dobler ◽  
Andreas Späth
Keyword(s):  
Methylene Blue ◽  
Singlet Oxygen ◽  
Direct Detection ◽  
Photophysical Properties ◽  
Red Light ◽  
Quantum Yields ◽  
Antimicrobial Efficiency ◽  
Highly Active ◽  
Light Region ◽  
Multiresistant Bacteria

Photodynamic inactivation of bacteria (PIB) by efficient singlet oxygen photosensitizers might be a beneficial alternative to antibiotics in the struggle against multiresistant bacteria. Phenothiazinium dyes belong to the most prominent classes of such sensitizers due to their intense absorption in the red-light region ( ca. 600–680 nm,  L mol−1 cm−1), their low toxicity, and their attachment/penetration abilities. Except simple substituents like alkyl or hydroxyalkyl residues, nearly no modifications of the phenothiaziniums have been pursued at the auxochromic sites. By this, the properties of methylene blue derivatives and their fields of application are limited; it remains unclear if their potential antimicrobial efficacy may be enhanced, also to compete with porphyrins. We prepared a set of six mainly novel methylene blue derivatives with the ability of additional hydrogen bonding and/or additional cationic charges to study the substituents’ effect on their activity/toxicity profiles and photophysical properties. Direct detection of singlet oxygen was performed at 1270 nm and the singlet oxygen quantum yields were determined. In suspensions with both, Gram-positive and Gram-negative bacteria, some derivatives were highly active upon illumination to inactivateS. aureusandE. coliup to 7 log10steps (99.99999%) without inherent toxicities in the nonirradiated state.

A bimodal fluorescent and photocytotoxic naphthalene diimide for theranostic applications

2016 ◽  
Vol 14 (30) ◽  
pp. 7238-7249 ◽  
Author(s):  
Erica Salvati ◽  
Filippo Doria ◽  
Francesco Manoli ◽  
Carmen D'Angelo ◽  
Annamaria Biroccio ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Cancer Cells ◽  
Fluorescence Lifetime ◽  
Red Light ◽  
Water Soluble ◽  
Fluorescence Lifetime Imaging ◽  
Lifetime Imaging ◽  
Light Emitter ◽  
Naphthalene Diimide ◽  
Theranostic Applications

We describe the bimodal activity of a water-soluble tetracationic naphthalene diimide as red light emitter for fluorescence imaging, including fluorescence-lifetime imaging, and singlet oxygen photosensitizer, inducing photocytotoxicity in cancer cells.

scholarly journals Tritolylporphyrin dimer as a new potent hydrophobic sensitizer for photodynamic therapy of melanoma.

2001 ◽  
Vol 48 (1) ◽  
pp. 277-282 ◽  
Author(s):  
A Drzewiecka ◽  
K Urbańska ◽  
Z Matuszak ◽  
M Pineiro ◽  
L G Arnaut ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Quantum Yield ◽  
Singlet Oxygen ◽  
Biological Effect ◽  
Photophysical Properties ◽  
Red Light ◽  
Human Melanoma ◽  
Oxygen Production ◽  
Absorption And Emission ◽  
Emission Properties

We report the synthesis, photochemical and photophysical properties and preliminary studies on biological effect of a new tritolylporphyrin dimer (T-D). Absorption and emission properties of T-D suggest its possible use in photodynamic therapy. T-D is capable of singlet oxygen production with 0.8 quantum yield. It also has a high photostability. The photodynamic properties of the dimer were examined following the growth of SKMEL 188 (human melanoma) cells irradiated with red light (cut off < 630 nm). The surviving fraction of the cells decreased about 3-fold (vs. non-irradiated cells) for an 81 J/cm dose. Our results suggest that tritolylporphyrine dimer T-D may be an interesting hydrophobic sensitizer for photodynamic therapy.

scholarly journals Visible-Light Triggered Templated Ligation on Surface Using Furan-Modified PNAs

2020 ◽  
Author(s):  
Alex Manicardi ◽  
Enrico Cadoni ◽  
Annemieke Madder
Keyword(s):  
Nucleic Acid ◽  
Visible Light ◽  
Singlet Oxygen ◽  
Target Detection ◽  
High Throughput ◽  
White Light ◽  
Peptide Nucleic Acids ◽  
Photo Oxidation ◽  
Reducing Conditions ◽  
Furan Moiety

Oligonucleotide-templated reactions are frequently exploited for target detection in biosensors and for the construction of DNA-based materials and probes in nanotechnology. Translation of the specifically used template chemistry from solution to surfaces, with the final aim of achieving highly selective high-throughput systems, has been difficult to reach and poorly explored. Here, we show the first example of a visible light-triggered templated ligation on a surface, employing furan-modified peptide nucleic acids (PNAs). Tailored photo-oxidation of the pro-reactive furan moiety is ensured by the simultaneous introduction of a weak photosensitizer as well as a nucleophilic moiety in the reacting PNA strand. This allows a localized production of singlet oxygen for furan activation, which is not affected by probe dilution or reducing conditions. White light irradiation in combination with recognition of a short 22mer oligo sequence that functions as a template, allows sensitive detection of nucleic acid targets in a 96 well plate format.

Saline hybrid nanoparticles with phthalocyanine and tetraphenylporphine anions showing efficient singlet-oxygen production and photocatalysis

2018 ◽  
Vol 54 (10) ◽  
pp. 1245-1248 ◽  
Author(s):  
Marieke Poß ◽  
Henriette Gröger ◽  
Claus Feldmann
Keyword(s):  
Singlet Oxygen ◽  
Red Light ◽  
Light Irradiation ◽  
Hybrid Nanoparticles ◽  
Oxygen Production ◽  
Organic Hybrid

Gd43+[AlPCS4]34− and La43+[TPPS4]34− ([AlPCS4]4−: aluminium(iii) chlorido phthalocyanine tetrasulfonate; [TPPS4]4−: tetraphenylporphine sulfonate) inorganic–organic hybrid nanoparticles show efficient 1O2 production upon daylight and red-light irradiation.

Nucleic Acid Template-Directed Assembly of Metallosalen−DNA Conjugates

2001 ◽  
Vol 123 (35) ◽  
pp. 8618-8619 ◽  
Author(s):  
Jennifer L. Czlapinski ◽  
Terry L. Sheppard
Keyword(s):  
Nucleic Acid ◽  
Directed Assembly ◽  
Dna Conjugates

scholarly journals Furan-PNA: a mildly inducible irreversible interstrand crosslinking system targeting single and double stranded DNA

2016 ◽  
Vol 52 (42) ◽  
pp. 6930-6933 ◽  
Author(s):  
A. Manicardi ◽  
E. Gyssels ◽  
R. Corradini ◽  
A. Madder
Keyword(s):  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Double Stranded Dna ◽  
Dna Strand ◽  
Interstrand Crosslinking

Furan-modified peptide nucleic acid (PNA) probes are able to crosslink to DNA strand after hybridization with complementary ssDNA or after stand displacement in dsDNA.

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