Synthesis and evaluation of porphyrin glycoconjugates varying in linker length: preliminary effects on the photodynamic inactivation ofMycobacterium smegmatis

Abstract

Carbohydrate–porphyrin conjugates varying in the nature of the carbohydrate and the distance between the porphyrin macrocycle and the carbohydrate are reported. First studies of the impact of linker length on photodynamic inactivation are reported.

Chemical Reporters for Bacterial Glycans: Development and Applications

“…Excitingly, trehalose has also been conjugated to therapeutic payload to facilitate targeted killing of mycobacteria, published examples of which include trehalose-functionalized nanoparticles loaded with the antimycobacterial compound isoniazid 321 and trehalose-conjugated photosensitizers. 322,323 Although much work remains to be done in this regard, it is clear that early efforts to develop probes such as FITC-Tre and TreAz have ultimately opened up a wide range of basic and translational research directions. In the next two sections, we will see how foundational work on trehalose derivatives has led to the development of novel reporter probes for investigating different pathways involved in the construction and remodeling of mycolate-containing glycolipids.…”

Sonogashira cross-coupling as a key step in the synthesis of new glycoporphyrins

“…In this strategy we started with the synthesis of a porphyrin core first, followed by introduction of a glycal moiety via Sonogashira reaction. As a model porphyrin we chose (5,10,15,20)-tetrakis(4-bromophenyl)porphyrin ( 6) because it is bench-stable and smoothly available from 4-bromobenzaldehyde and pyrrole in Lindsey's conditions. 26 The glycal starting materials (Scheme 3, 7a-7c) were obtained from perbenzylated 2-iodo-D-glucal using the optimised conditions described in Table 1.…”

“…The covalent binding of porphyrins with carbohydrates are mainly achieved via C-O, 6 C-S, 7 C-N bonds, 8 amide or ester function, 9 or triazole linker. 10 The C-C conjugated porphyrins with sugars might be considered particularly interesting as nonhydrolyzable hybrids. The methodologies to obtain meso-glycosubstituted porphyrins have been well-recognized by using Lindsey's or MacDonald strategy (Scheme 1, A).…”

Click Chemistry ‐ Inspired Synthesis of Porphyrin Hybrid Glycodendrimers as Fluorescent Sensor for Cu(II) Ions

“…To study biological systems, their synthetic mimics can be designed by knitting porphyrins with a biomacromolecule conjugates, [26] and dendritic architectures. [27] Indeed, very few studies are available on porphyrin-cored glycodendrimers, [28][29][30][31][32] and hybrid glycodendrimers are still rare. Hybrid glycodendrimers have been designed to target multibacterial strains owing to their dual binding ability for particular lectins.…”