High photodynamic activities of water-soluble inclusion complexes of 5,15-diazaporphyrins in cyclodextrin

Abstract

Inclusion complexes of 5,15-diazaporphyrin derivatives in trimethyl-β-cyclodextrin exhibited high photodynamic activity under visible-light irradiation at wavelengths greater than 620 nm.

Improved Stability and Photodynamic Activity of Water‐Soluble 5,15‐Diazaporphyrins Incorporated in β‐(1,3‐1,6)‐d‐Glucan with On‐Off Switch

“…In contrast, the absorbance at 384 nm of an aqueous solution of b-1,3-glucan-complexed 3 with ac oncentrationo f 0.1 mm was constant for one week (Figure 3c and 3d), showing that the aqueous solution of b-1,3-glucan-complexed 3 was stable. [8] Generally,C Dx-complexed guest molecules are unstable because intermolecular complexation-decomplexation exchange takes place between free and complexed CDxs. [8] Generally,C Dx-complexed guest molecules are unstable because intermolecular complexation-decomplexation exchange takes place between free and complexed CDxs.…”

“…HeLa cells were exposed to each complex for 24 hw ith or without light irradiation for 30 min in the wavelength range of 610-740-nm. 0.047, 0.15, and 0.022 mm,r espectively), [8] indicatingt hat these photodynamic activities were mainly dependent on the characteristics of 1-3 themselves. In contrast, b-1,3-glucan-complexed 1-3 showed toxicityt hat increased in ad ose-dependent manner upon photoirradiation (> 610 nm).…”

“…[8] Preparation of b-1,3-glucan-complexed diazaporphyrin derivatives 1, 2,o r3 (2.00 10 À6 mol) and b-1,3-glucan (10.0 mg) were placed in an agate capsule with two agate-mixing balls and mixed vigorously at 30 Hz for 20 min using ah igh-speed vibration mill (MM 200;R etsch Co.,L td.,H aan, Germany). 9,10-Anthracenediyl-bis(methylene)dimalonic acid (ABDA) was purchased from Sigma-Aldrich (St Louis, MO, USA).…”

“…Porphyrind erivatives and analogues,s uch as phthalocyanines and chlorines, that are sensitive to long-wavelengthl ight (> 600 nm), are ex-pectedt ob ee ffective PSs because deeper tissue penetration is achieved in that wavelength region. [7,8] However, aqueous solutionso fd iazaporphyrin (1 and 2)-TMe-b-CDx complexes are unstable and show decreased absorbance for seven days (Figure 1). [4][5][6] Diazaporphyrins show a large absorption at wavelengths over 600 nm andh ave am ore compacts tructure than phthalocyanines.…”

“…Therefore, diazaporphyrins can form the complexes with two trimethyl-b-cyclodextrins( TMe-b-CDxs) that show higherp hotodynamic activity. [7,8] However, aqueous solutionso fd iazaporphyrin (1 and 2)-TMe-b-CDx complexes are unstable and show decreased absorbance for seven days (Figure 1). To solve these problems, in this study, b-(1,3-1,6)-d-glucan (b-1,3-glucan), which has a sugar chain similart ot hose of cyclodextrins, was applieda s the water-solubilizing agent.…”