Free base porphyrin–cyanine dye conjugate: synthesis and optical properties

Tanaka, T., & Osuka, A. (2015). Conjugated porphyrin arrays: Synthesis, properties and applications for functional materials. Chemical Society Reviews, 44, 943–969.

Article  CAS  PubMed  Google Scholar 

Senge, M. O., Sergeeva, N. N., & Hale, K. J. (2021). Classic highlights in porphyrin and porphyrinoid total synthesis and biosynthesis. Chemical Society Reviews, 50, 4730–4789.

Article  CAS  PubMed  Google Scholar 

Shindy, H. A. (2017). Fundamentals in the chemistry of cyanine dyes: A review. Dyes and Pigments, 145, 505–513.

Article  CAS  Google Scholar 

Nödling, A. R., Mills, E. M., Li, X., et al. (2020). Cyanine dye mediated mitochondrial targeting enhances the anti-cancer activity of small-molecule cargoes. Chemical Communications, 56, 4672–4675.

Article  PubMed  Google Scholar 

Abd El-Aal, R. M., & Younis, M. (2004). Synthesis and antimicrobial activity of certain novel monomethine cyanine dyes. Dyes and Pigments, 60, 205–214.

Article  CAS  Google Scholar 

Eissa, F. (2009). Preparation, antibacterial activity and absorption spectra of pyrazolo–oxadiazine cyanine Dyes. Journal of the Chinese Chemical Society, 56, 843–849.

Article  CAS  Google Scholar 

Delaey, E., van Laar, F., De Vos, D., et al. (2000). Comparative study of the photosensitizing characteristics of some cyanine dyes. Journal of Photochemistry and Photobiology B: Biology, 55, 27–36.

Article  CAS  PubMed  Google Scholar 

Li, Y., Zhou, Y., Yue, X., et al. (2021). Cyanine conjugates in cancer theranostics. Bioactive Materials, 6, 794–809.

Article  CAS  PubMed  Google Scholar 

Shi, C., Wu, J. B., & Pan, D. (2016). Review on near-infrared heptamethine cyanine dyes as theranostic agents for tumor imaging, targeting, and photodynamic therapy. Journal of Biomedial Optics, 21, 050901.

Article  Google Scholar 

Feng, L., Chen, W., Ma, X., et al. (2020). Near-infrared heptamethine cyanines (Cy7): From structure, property to application. Organic & Biomolecular Chemistry, 18, 9385–9397.

Article  CAS  Google Scholar 

Giovannetti, R. (2012). The use of spectrophotometry UV-Vis for the study of porphyrins [Internet]. Macro to Nano Spectroscopy. https://doi.org/10.5772/38797

Article  Google Scholar 

Jeong, H.-G., & Choi, M.-S. (2016). Design and properties of porphyrin-based singlet oxygen generator. Israel Journal of Chemistry, 56, 110–118.

Article  CAS  Google Scholar 

Habermeyer, B., & Guilard, R. (2018). Some activities of PorphyChem illustrated by the applications of porphyrinoids in PDT, PIT and PDI. Photochemical & Photobiological Sciences, 17, 1675–1690.

Article  CAS  Google Scholar 

Melissari, Z., Williams, R. M., & Senge, M. (2021). Porphyrinoids for photodynamic therapy. In H. Lang & T. Rueffer (Eds.), Applications of porphyrinoids as functional materials (pp. 252–291). Croydon: Royal Society of Chemistry.

Chapter  Google Scholar 

James, N. S., Cheruku, R. R., Missert, J. R., et al. (2018). Measurement of cyanine dye photobleaching in photosensitizer cyanine dye conjugates could help in optimizing light dosimetry for improved photodynamic therapy of cancer. Molecules, 23, 1842–1853.

Article  PubMed  PubMed Central  Google Scholar 

Ogawa, K., Nagatsuka, Y., & Kobuke, Y. (2011). Synthesis and photophysical properties of doubly porphyrin-substituted cyanine dye. Journal of Porphyrins and Phthalocyanines, 15, 678–685.

Article  CAS  Google Scholar 

Zhdanova, K. A., Ezhov, A. V., Bragina, N. A., et al. (2018). Synthesis of new binary porphyrin–cyanine conjugates and their self-aggregation in organic-aqueous media. Mendeleev Communications, 28, 626–628.

Article  CAS  Google Scholar 

Adler, A. D., Longo, F. R., Finarelli, J. D., et al. (1967). A simplified synthesis for meso-tetraphenylporphine. Journal of Organic Chemistry, 32, 476.

Article  CAS  Google Scholar 

Yang, G., Zhang, Y., Zou, J., et al. (2019). Synthesis and biological evaluation of genistein-IR783 conjugate: cancer cell targeted delivery in MCF-7 for superior anti-cancer therapy. Molecules, 24, 4120–4136.

Article  Google Scholar 

Taniguchi, M., Lindsey, J. S., Bocian, D. F., et al. (2021). Comprehensive review of photophysical parameters (ε, Φf, τs) of tetraphenylporphyrin (H2TPP) and zinc tetraphenylporphyrin (ZnTPP)—Critical benchmark molecules in photochemistry and photosynthesis. Journal of Photochemistry and Photobiology, 46, 100401.

Article  CAS  Google Scholar 

Patel, N. J., Chen, Y., Joshi, P., et al. (2016). Effect of metalation on porphyrin-based bifunctional agents in tumor imaging and photodynamic therapy. Bioconjugate Chemistry, 27, 667–680.

Article  CAS  PubMed  PubMed Central  Google Scholar 

Bricks, J. L., Slominskii, Y. L., Panas, I. D., et al. (2017). Fluorescent J-aggregates of cyanine dyes: Basic research and applications review. Methods and Applications in Fluorescence, 6, 012001.

Article  PubMed  Google Scholar 

Subuddhi, U., Haldar, S., Sankararaman, S., et al. (2006). Photophysical behaviour of 1-(4-N, N-Dimethylaminophenylethynl)Pyrene (DMAPEPy) in homogeneous media. Photochemical & Photobiological Sciences, 5, 459–466.

Article  CAS  Google Scholar 

Wang, Y., Gu, Y., Zuo, Z., et al. (2011). Choosing optimal wavelength for photodynamic therapy of port wine stains by mathematic simulation. Journal of Biomedical Optics, 16, 098001.

Article  PubMed  Google Scholar 

Nielsen, K. P., Juzeniene, A., Juzenas, P., et al. (2005). Choice of optimal wavelength for PDT: The significance of oxygen depletion. Photochemistry and Photobiology, 81, 1190–1194.

Article  CAS  PubMed  Google Scholar 

Seybold, P. G., & Gouterman, M. (1969). Porphyrins. XIII: Fluorescence spectra and quantum yields. Journal of Molecular Spectroscopy, 31, 1–13.

Article  CAS  Google Scholar 

Panigrahi, S. K., & Mishra, A. K. (2019). Inner filter effect in fluorescence spectroscopy: As a problem and as a solution. Journal of Photochemistry and Photobiology, 41, 100318.

Article  Google Scholar 

Brancato, G., Signore, G., Neyroz, P., et al. (2015). Dual fluorescence through Kasha’s rule breaking: An unconventional photomechanism for intracellular probe design. The Journal of Physical Chemistry B, 119, 6144–6154.

Article  CAS  PubMed  Google Scholar 

Hananya, N., Green, O., Blau, R., et al. (2017). Highly efficient chemiluminescence probe for the detection of singlet oxygen in living cells. Angewandte Chemie International Edition, 56, 11793–11796.

Article  CAS  PubMed  Google Scholar 

Gibbons, D. J., Boh, A., Habermeyer, B., Villandier, N., Leroy-Lhez, S., & Williams, R. M. (2022). Photo-activated thin films of porphyrins for reactive oxygen species generation. Journal of Porphyrins and Phthalocyanines, 26, 550–562.

Article  CAS  Google Scholar 

James, N. S., Chen, Y., Joshi, P., et al. (2013). Evaluation of polymethine dyes as potential probes for near infrared fluorescence imaging of tumors: Part – 1. Theranostics, 3, 692–702.

Article  PubMed  PubMed Central  Google Scholar 

Mazur, L. M., Roland, T., Leroy-Lhez, S., et al. (2019). Efficient singlet oxygen photogeneration by zinc porphyrin dimers upon one- and two-photon excitation. The Journal of Physical Chemistry B, 123, 4271–4277.

Article  CAS  PubMed  Google Scholar 

Schmidt, R., Tanielian, C., Dunsbach, R., et al. (1994). Phenalenone, a universal reference compound for the determination of quantum yields of singlet oxygen O2(1Δg) sensitization. Journal of Photochemistry and Photobiology A: Chemistry, 79, 11–17.

Article  CAS  Google Scholar 

Wilkinson, F., Helman, W. P., & Ross, A. B. (1995). Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. Journal of Physical and Chemical Reference Data, 24, 663–677. https://doi.org/10.1063/1.5559655

Article  CAS  Google Scholar 

Gibbons, D. J., Farawar, A., Mazzella, P., et al. (2020). Making triplets from photo-generated charges: Observations, mechanisms and theory. Photochemical & Photobiological Sciences, 19, 136–158.

Article  CAS  Google Scholar 

Filatov, M. A., Karuthedath, S., Polestshuk, P. M., et al. (2018). Control of triplet state generation in heavy atom-free BODIPY–anthracene dyads by media polarity and structural factors. Physical Chemistry Chemical Physics: PCCP, 20, 8016–8031.

Article  CAS  PubMed  Google Scholar 

Colvin, M. T., Ricks, A. B., Scott, A. M., et al. (2012). Intersystem crossing involving strongly spin exchange-coupled radical ion pairs in donor–bridge–acceptor molecules. Journal of Physical Chemistry A, 116, 1923–1930.

Article  CAS  PubMed  Google Scholar 

Vân Anh, N., Schlosser, F., Groeneveld, M. M., Van Stokkum, I. H. M., Würthner, F., & Williams, R. M. (2009). Photoinduced interactions in a pyrene-calix[4]arene-perylene bisimide dye system: Probing ground-state conformations with excited-state dynamics of charge separation and recombination. Journal of Physical Chemistry C, 113, 18358–18368.

Article  Google Scholar 

Demas, J. N., & Crosby, G. A. (1971). The measurement of photoluminescence quantum yields a review. Journal of Physics Chemistry, 75, 991–1024.

Article  Google Scholar 

Origin, Version (2018b). OriginLab Corporation. Northampton.

Kumpulainen, T., Bakker, B. H., Hilbers, M., et al. (2015). Synthesis and spectroscopic characterization of 1,8-naphthalimide derived “super” photoacids. The Journal of Physical Chemistry B, 119, 2515–2524.

Article  CAS  PubMed  Google Scholar 

留言 (0)

沒有登入
gif