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

(2017) ORGANIC & BIOMOLECULAR CHEMISTRY. 15(25). p.5402-5409
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Abstract
The development of methods for the generation of site-selective interstrand crosslinks (ICLs) in synthetic oligonucleotides provides a platform for the study of ICL repair mechanisms and the stabilisation of DNA-based materials. Our group has previously reported on the use of a furan moiety as a masked reactive functionality for ICL generation and recently introduced the use of O-1(2) as an efficient light-induced oxidant. Here, the use of porphyrin-based photosensitizers (PSs) has been explored for ICL generation. The efficiency of the ICL reaction has been investigated using PSs added into solution as well as attached to oligonucleotide probes. Interestingly, even a highly hydrophobic phthalocyanine was able to produce ICLs. Either in solution or conjugated to an ON, chlorin e6 was the most efficient ICL generator for the current purpose.
Keywords
PHOTODYNAMIC THERAPY, REDUCTIVE AMINATION, VISIBLE-LIGHT, OLIGONUCLEOTIDE, CANCER, OLIGODEOXYNUCLEOTIDES, PHOTOINACTIVATION, LYSINE, FURAN, WATER

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Citation

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Chicago
Llamas Garcinuño, Eva Marina, João Tomé, João MM Rodrigues, Tomas Torres, and Annemieke Madder. 2017. “Porphyrin-based Photosensitizers and Their DNA Conjugates for Singlet Oxygen Induced Nucleic Acid Interstrand Crosslinking.” Organic & Biomolecular Chemistry 15 (25): 5402–5409.
APA
Llamas Garcinuño, E. M., Tomé, J., Rodrigues, J. M., Torres, T., & Madder, A. (2017). Porphyrin-based photosensitizers and their DNA conjugates for singlet oxygen induced nucleic acid interstrand crosslinking. ORGANIC & BIOMOLECULAR CHEMISTRY, 15(25), 5402–5409.
Vancouver
1.
Llamas Garcinuño EM, Tomé J, Rodrigues JM, Torres T, Madder A. Porphyrin-based photosensitizers and their DNA conjugates for singlet oxygen induced nucleic acid interstrand crosslinking. ORGANIC & BIOMOLECULAR CHEMISTRY. 2017;15(25):5402–9.
MLA
Llamas Garcinuño, Eva Marina, João Tomé, João MM Rodrigues, et al. “Porphyrin-based Photosensitizers and Their DNA Conjugates for Singlet Oxygen Induced Nucleic Acid Interstrand Crosslinking.” ORGANIC & BIOMOLECULAR CHEMISTRY 15.25 (2017): 5402–5409. Print.
@article{8534816,
  abstract     = {The development of methods for the generation of site-selective interstrand crosslinks (ICLs) in synthetic oligonucleotides provides a platform for the study of ICL repair mechanisms and the stabilisation of DNA-based materials. Our group has previously reported on the use of a furan moiety as a masked reactive functionality for ICL generation and recently introduced the use of O-1(2) as an efficient light-induced oxidant. Here, the use of porphyrin-based photosensitizers (PSs) has been explored for ICL generation. The efficiency of the ICL reaction has been investigated using PSs added into solution as well as attached to oligonucleotide probes. Interestingly, even a highly hydrophobic phthalocyanine was able to produce ICLs. Either in solution or conjugated to an ON, chlorin e6 was the most efficient ICL generator for the current purpose.},
  author       = {Llamas Garcinu{\~n}o, Eva Marina and Tom{\'e}, Jo{\~a}o and Rodrigues, Jo{\~a}o MM and Torres, Tomas and Madder, Annemieke},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY},
  keyword      = {PHOTODYNAMIC THERAPY,REDUCTIVE AMINATION,VISIBLE-LIGHT,OLIGONUCLEOTIDE,CANCER,OLIGODEOXYNUCLEOTIDES,PHOTOINACTIVATION,LYSINE,FURAN,WATER},
  language     = {eng},
  number       = {25},
  pages        = {5402--5409},
  title        = {Porphyrin-based photosensitizers and their DNA conjugates for singlet oxygen induced nucleic acid interstrand crosslinking},
  url          = {http://dx.doi.org/10.1039/c7ob01269a},
  volume       = {15},
  year         = {2017},
}

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