Photo-induced anticancer activity and singlet oxygen production of prodigiosenes

Abstract

The photo-induced cytotoxicity of prodigiosenes is reported. One prodigiosene represents a synthetic analogue of the natural product prodigiosin, and two are conjugated to molecules that target the estrogen receptor (ER). A comparison of incubation and irradiation frameworks for the three prodigiosenes is reported, with activity against ER- and ER+ lines explored. Furthermore, the ability of the three prodigiosenes to photosensitise the production of singlet oxygen is demonstrated, shedding mechanistic light onto possible photodynamic therapeutic effects of this class of tripyrroles.

Investigating Alkylated Prodigiosenes and Their Cu(II)‐Dependent Biological Activity: Interactions with DNA, Antimicrobial and Photoinduced Anticancer Activity

“…S‐9 for full overview). In similar fashion to the prodigiosenes previously studied in the literature, [76–78] the irradiation of C6 , C11 , and C16 with light probably induces the formation of singlet oxygen via the generation of a π‐radical cation of the prodigiosene, which in turn also favors the ROS formation in the case of the redox‐active Cu(II) complexes. Although no clear trend between different lengths of the alkyl substituent is observed in the dark or after irradiation, the inferior cytotoxicity of C0 and its complex CuC0 compared to the alkylated analogues shows an undeniable effect of the hydrophobic substituent on the cytotoxic properties of this family of compounds.…”

“…Thompson et al . further studied the light‐induced cytotoxic activity of prodigiosenes with and without estrogen receptor targeting moieties [78] . They used 9,10‐dimethylantracene (DMA) as a singlet oxygen scavenger, therefore confirming a type II photooxidation mechanism that involves the formation of singlet oxygen.…”

“…Thompson et al further studied the light-induced cytotoxic activity of prodigiosenes with and without estrogen receptor targeting moieties. [78] They used 9,10-dimethylantracene (DMA) as a singlet oxygen scavenger, therefore confirming a type II photooxidation mechanism that involves the formation of singlet oxygen. Photoinduced toxicity of the Cu(II) complexes has not been studied before, probably in large part because of the expected high dark cytotoxicity of these compounds.…”

Lysosomes Targeting pH Activable Imaging‐Guided Photodynamic Agents

“…[73] The capability of PS 1-3 to generate 1 O 2 was thus investigated using a protocol adapted from the literature (Table 1). [74] A solution of the PS, without and upon protonation with HCl vapours, and the 1,3-diphenylisobenzofuran (DPBF), as 1 O 2 scavenger, in EtOH was irradiated at specific time intervals with a monochromator centred at 505 nm (see SI). The production of 1 O 2 was calculated following the decrease of the maximum absorbance of the DBPF at 410 nm.…”

Modelling approaches to predict light absorption in gas-liquid flow photosensitized oxidations

“…[34] DMA absorbs light between 230-400 nm (Figure 3), while the resulting endoperoxide does not absorb light in the same region. [35] The photooxidation of DMA was studied in the presence of commonly used photosensitizers such as tetraphenylporphyrin (TPP) [36], RB [35], Methylene Blue (MB) [37] and eosine [37] and was used to evaluate the efficiency of singlet oxygen generation of new photosensitizers [38][39][40][41][42]. RB was chosen as photosensitizer because its absorption spectrum overlaps, as shown in Figure 3, with the emission at 525 nm of our green LEDs and produces singlet oxygen in high yields [1].…”