Novel Application of NIR-I-Absorbing Quinoidal Conjugated Polymer as a Photothermal Therapeutic Agent

Choi, Yeonsu; Min, Kiyoon; Han, Nara; Tae, Giyoong; Kim, Dong‐Yu

doi:10.1021/acsami.3c06807

Cited by 9 publications

(4 citation statements)

References 60 publications

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“…GPC chromatograms of P(Fl-Phos(Et)-EDOT) ( m : 0.98) and P(Fl-Phos(Et)-DMeOTh) ( m : 0.67) are shown in Figure S31. Although GPC profiles for the polymers were broad, this characteristic is acceptable for the application , and postfunctionalization. , The phosphonylated polymers were found to exhibit lower GPC molecular weights than their precursor polymers, likely because the polymers were aggregated as a result of the introduction of polar diethyl phosphonate, , and their apparent molecular weights decreased. In addition, the contact angle for a water droplet on the phosphonylated polymer films was smaller than that for the precursor polymer films (Figure S32), which is the same tendency observed in the case of P(Fl-Th-Phos(Et)).…”

Section: Resultsmentioning

confidence: 99%

“…P(Fl-Th) was prepared by Suzuki–Miyaura coupling polymerization of 9,9-dioctylfluorene-2,7-diboronic acid ester with 2,5-dibromothiophene. , The gel permeation chromatography (GPC) profile of P(Fl-Th) was M n = 9.6 kDa, M w = 22.5 kDa, and PDI = 2.4, where M n , M w , and PDI are the number-average molecular weight, weight-average molecular weight, and the polydispersity index, respectively. Although the GPC profile had a broad peak, the precursor polymers are useful for application , and postfunctionalization. , A drop of P(Fl-Th) solution (5 mg/mL CHCl 3 ) was cast onto a Pt plate (2 × 2 cm), which was used as an anode. First, the anodic phosphonylation of P(Fl-Th) was conducted under constant-current conditions in an acetonitrile (MeCN) solution containing triethyl phosphite (P(OEt) 3 ) as the phosphonate source and tetrabutylammonium hexafluorophosphate ( n Bu 4 NPF 6 ) as the supporting electrolyte.…”

Section: Resultsmentioning

confidence: 99%

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Electrochemical Postfunctionalization of Thiophene–Fluorene Alternating Copolymers via Anodic C–H Phosphonylation

Taniguchi,

Kurioka,

Sato

et al. 2024

Macromolecules

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Phosphonylated polymers are attractive materials due to their applications in chemical sensors and their unique electronic properties. Because of its mild reaction conditions and simple protocol, anodic phosphonylation is a favorable strategy for introducing phosphonate into the main chains of π-conjugated polymers. However, the precursor polymer for the reaction remains limited to poly(3-hexylthiophene), and in addition, the degree of substitution is still low. Here, we demonstrated the anodic phosphonylation of thiophene−fluorene alternating copolymers (P(Fl-Th)) using triethyl phosphite as a phosphonate source. The reaction proceeded efficiently in the presence of 2,6-lutidine, and the phosphonate was selectively introduced into the electron-rich thiophene moiety. The optoelectronic properties of the phosphonylated polymer were gradually varied by tuning the degree of substitution. Interestingly, various trialkyl phosphites, such as P(O n Bu) 3 , P(O i Pr) 3 , and P(OC 2 H 4 Cl) 3 , were suitable for the anodic phosphonylation. We also found that the phosphonate groups could be introduced into the fluorene moieties through the design of appropriate precursor polymers. Furthermore, constantpotential anodic phosphonylation instead of the constant-current method led to quantitative functionalization.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Electrochemical Postfunctionalization of Thiophene–Fluorene Alternating Copolymers via Anodic C–H Phosphonylation

Taniguchi,

Kurioka,

Sato

et al. 2024

Macromolecules

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“…The development of photothermal therapy has been accelerated by significant research on NIR‐sensitive photothermal agents, including organic small molecule dyes, conjugated polymers, and metallic plasmonic nanoparticles (e.g., gold nanorods and quantum dots). [ 6–14 ] These photosensitive materials are able to undergo photoexcitation, resulting in the production of thermal energy via the photothermal effect. [ 15,16 ] Among those NIR‐sensitive reagents, small molecule organic dyes have attracted significant interest because of their low toxicity, excellent biocompatibility, and tunable spectral properties through structural modifications.…”

Section: Introductionmentioning

confidence: 99%

Indocyanine Green‐Glycogen Conjugates for Near‐Infrared‐Triggered Photothermal Cancer Therapy

Shirinichi,

Karkera,

Ibrahim

et al. 2023

Macro Chemistry & Physics

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Photothermal reagents sensitive to near‐infrared (NIR) light are promising imaging agents and therapeutics for anticancer applications because of the deep tissue penetration of NIR light, allowing for spatiotemporal control over the therapeutic activity, with minimal damage to normal tissues. Herein, a new class of NIR‐sensitive biopolymer‐based nanoparticles is presented by covalently conjugating indocyanine green (ICG) onto the surface of naturally occurring glycogen nanoparticles. The resulting ICG‐glycogen conjugates exhibit a markedly enhanced aqueous stability in comparison to free ICG molecules. Furthermore, an efficient light‐to‐heat conversion is enabled by ICG‐glycogen conjugates, as evidenced by the elevated temperatures of their aqueous solutions upon exposure to NIR light. Critically, ICG‐glycogen conjugates are capable of cell internalization, and under NIR irradiation the effective eradication of breast cancer cells, demonstrating their potential in photothermal therapy for cancer.

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“…However, the potential cytotoxicity of inorganic materials largely restricts their further application [ 13 ]. Compared with inorganic materials, organic molecules have more unique advantages in the practice of anti-tumor therapy, such as better biocompatibility, more finely adjusted optical properties and chemical structure [ 14 ]. Therefore, organic materials are the best candidates for large-scale clinical application in the future, which has attracted more and more researchers’ attention.…”

Section: Introductionmentioning

confidence: 99%

A novel polymer enabled by polymerized small molecule strategy for tumor photothermal and photodynamic therapy

Xie,

Wang,

Zeng

et al. 2023

J Nanobiotechnol

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Photothermal therapy (PTT) and photodynamic therapy (PDT) are effective method for tumor treatment. However, the limited variety and quantity of photothermal agents (PTAs) and photosensitizer (PSs) are still major challenges. Moreover, the cell apoptosis mechanism induced by PDT and PTT is still elusive. A fused-ring small molecule acceptor–donor acceptor′ donor–acceptor (A-DA′D-A) type of Y5 (Scheme 1) has a narrow band-gap and strong light absorption. Herein, we used Y5 to polymerize with thiophene unit to obtain polymer PYT based on polymerized small molecule strategy, and PYT nanoparticles (PYT NPs) was prepared via one-step nanoprecipitation strategy with DSPE-PEG2000. PYT NPs had excellent biocompatibility, good photostability, high photothermal conversion efficiency (67%) and reactive oxygen species (ROS) production capacity under 808 nm laser irradiation (PYT NPs + NIR). In vitro and in vivo experiments revealed that PYT NPs + NIR had the ability to completely ablate tumor cells. It was demonstrated that cell apoptosis induced by PYT NPs + NIR was closely related to mitochondrial damage. This study provides valuable guidance for constructing high-performance organic PTAs and PSs for tumor treatment.

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Novel Application of NIR-I-Absorbing Quinoidal Conjugated Polymer as a Photothermal Therapeutic Agent

Cited by 9 publications

References 60 publications

Electrochemical Postfunctionalization of Thiophene–Fluorene Alternating Copolymers via Anodic C–H Phosphonylation

Electrochemical Postfunctionalization of Thiophene–Fluorene Alternating Copolymers via Anodic C–H Phosphonylation

Indocyanine Green‐Glycogen Conjugates for Near‐Infrared‐Triggered Photothermal Cancer Therapy

A novel polymer enabled by polymerized small molecule strategy for tumor photothermal and photodynamic therapy

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