d-Mannose-appended 5,15-diazaporphyrin for photodynamic therapy

Abstract

5,15-Diazaporphyrin appended with D-mannose moieties has been prepared through Suzuki–Miyaura cross-couplig and SN2 alkylation. The resultant diazaporphyrin was enough hydrophilic to exhibit sufficient solubilty to aqueous media. Because of the...

Recent advances in the synthesis of diazaporphyrins and their chalcogen derivatives

“…To improve the solubility of the DAP-based photosensitizer in aqueous media and enhance its penetration in cancer cells for PDT applications, Shinokubo et al introduced d -mannose units on the meso -mesityl groups of 10,20-dimesityl-DAP free base, through the S N 2 reaction of 37 (Ar = 4-HOC 6 H 4 ) with a protected mannose-appended alkyl bromide (Scheme 35). 51 The acetyl groups on the mannose moieties of coupling product 63 were cleaved cleanly upon treatment with NaOMe in THF at room temperature. The mannose-appended DAP 64 , which was highly soluble in water containing DMSO (5%), showed low dark cytotoxicity and strong in vitro photodynamic activity not only at the nanomolar level but also at short light irradiation times under photoexcitation at 650 nm.…”

Self-assembled porphyrin–peptide cages for photodynamic therapy

“…15,16 The conjugation to biomolecules such as peptides or carbohydrates can therefore be of interest to improve solubility, but also to position functional groups that improve cell internalization 17,18 and may promote targeted delivery. [19][20][21][22][23][24][25] PDT has indeed a local effect due to the limited diffusion of ROS/ 1 O 2 (10 nm-2 µm) [26][27][28] which potency depends on the precise subcellular localization of the photosensitizer. Peptides are water-soluble and biocompatible building blocks which are interesting in this regard due to (i) their ability to engage in β-sheets formation and thus direct the precise self-assembly of porphyrinbased photosensitizers, (ii) the sensitivity of their assemblies to pH or enzymes, and (iii) their cell-penetrating and targeting features.…”

Morpholinyl silicon phthalocyanine nanoparticles with lysosome cell death and two-photon imaging functions for in vitro photodynamic therapy of cancer cells

“…Photodynamic therapy (PDT) is a non-invasive treatment that involves photosensitizers (PSs), specific wavelength light, and oxygen to generate highly toxic reactive oxygen species (ROS), leading to cancer cell death (Ali et al, 2022;Biyiklioglu et al, 2022). Some traditional methods, such as chemotherapy, radiotherapy, and surgical treatment, are applied in cancer treatment.…”