Drug delivery function of carboxymethyl-β-cyclodextrin modified upconversion nanoparticles for adamantine phthalocyanine and their NIR-triggered cancer treatment

Abstract

Near-infrared (NIR) light triggered photodynamic therapy (PDT), based on upconversion nanoparticles (UCNPs), has attracted great attention because of its high tissue penetration and low photodamage to living organisms. However, most UCNPs cannot be stably dispersed in aqueous solution and cannot carry photosensitive drugs directly. Besides, UCNP mediated PDT is a fluorescence resonance energy transfer (FRET) process from the UCNPs to the attached photosensitive drugs. So the drug and UCNPs must be stably connected and close enough. In this manuscript, carboxymethyl-β-cyclodextrin (COOH-β-CD) was used to connect UCNPs and adamantine modified phthalocyanine (Ad-ZnPc) through a self-assembly process followed by a host-guest interaction. COOH-β-CD can provide good water solubility of the system and short-distance linking between the UCNPs and Ad-ZnPc. Most importantly, the system has a strong NIR light triggered PDT activity toward cancer cells.

Resveratrol Functionalized Carboxymethyl-β-Cyclodextrin: Synthesis, Characterization, and Photostability

“…One of the modified derivatives is carboxymethyl-β-cyclodextrin (CM-β-CD), which has the carboxylmethyl groups on the sides of β-CD. Nowadays, CM-β-CD is widely used in many fields [27][28][29][30]. For instance, Furusaki groups successfully synthesized the conjugate of CM-β-CD with chitosan, which demonstrated the better inclusion ability with 6-(ptoluidino)-2-naphthalene-6-sulfonate [27].…”

Use of Cyclodextrins in Anticancer Photodynamic Therapy Treatment

“…Conjugating the CD to the UCNPs aims to confine the PSs, prevent their release, and maintain their accessibility to the UCNPs to ensure the activation of the PS through the pre-mentioned FRET process. Thus, to avoid the liberation of ZnPc and strengthen the interactions between ZnPc and CD/UCNPs, Wang et al [ 192 ] functionalized ZnPc with adamantane (Ada-ZnPc) and synthetized a stable Ada-ZnPc@β-CD-COOH/UCNP complex ( Figure 55 ). The prepared Ada-ZnPc@β-CD-COOH/UCNPs had the advantageous properties of β-CD-COOH, especially its good water solubility.…”

Fluorescence Resonance Energy Transfer Systems in Supramolecular Macrocyclic Chemistry

“…This requires the emergence of the host-guest complexes must bring the FRET pairs to the suitable and rigid relative position so as to guarantee the energy transfer efficiency. Apart from the above two types of exploitation of the host-guest components, supramolecular macrocycles, especially CDs, were also introduced into FRET systems to form host-guest pairs, mainly for the purposes of improving the water-solubility and biocompatibility or reducing the toxicity [ 54 , 55 ]. Although these studies comprise both host-guest units and FRET elements, the unique advantages of host-guest chemistry were not demonstrated to the fullest, so we will not include them in the main discussion.…”