Synthesis of novel long wavelength cationic chlorins via stereoselective aldol-like condensation

Li, Jia Zhu; Wang, Jin Jun; Yoon, Il; Cui, Bing Cun; Shim, Young Key

doi:10.1016/j.bmcl.2012.01.088

Cited by 39 publications

(35 citation statements)

References 27 publications

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“…3 2 -Quinolinium substituted cationic chlorins 53-55 (λ max = 727-763 nm) ( Figure 13) were also prepared via a similar method by the same authors. 173,174 The obvious red shift of these cationic chlorins compared to their corresponding precursors was due to the strong electron-withdrawing effect of the cationic substituents located at the 3 2 -position. 173 Preliminary in vitro photodynamic effects proved that these novel long wavelength cationic chlorins showed drug-and concentration-dependent phototoxicity against HeLa cell lines.…”

Section: Chlorophyll A-based Long Wavelength Cationic Chlorinsmentioning

confidence: 99%

“…173 Preliminary in vitro photodynamic effects proved that these novel long wavelength cationic chlorins showed drug-and concentration-dependent phototoxicity against HeLa cell lines. 174 In order to compare the PDT efficacy of 3 2 -cationic chlorins and 13-cationic chlorins, in the same study 13 1 -pyridinium substituted purpurinimide 57 and chlorin e 6 59 were also prepared stepwise from MPa 1 as shown in Scheme 14. It was found by the authors that …”

Section: Chlorophyll A-based Long Wavelength Cationic Chlorinsmentioning

confidence: 99%

“…Evaluation of these long wavelength cationic chlorins as DNA intercalation agents is also in progress. 174 Absorption properties of selected chlorin derivatives are shown in Table 5. 26,30,126,169,173,174 IC 50 values for the selected chlorins and the GNPs are shown in Tables 6 173 and 7.…”

Section: Surface Plasmon Resonance (Spr) and Gnpsmentioning

confidence: 99%

“…174 Absorption properties of selected chlorin derivatives are shown in Table 5. 26,30,126,169,173,174 IC 50 values for the selected chlorins and the GNPs are shown in Tables 6 173 and 7. 26,30 frequency is formed which matches the electron oscillation frequencies within the NPs.…”

Section: Surface Plasmon Resonance (Spr) and Gnpsmentioning

confidence: 99%

See 3 more Smart Citations

Ionic Liquid-Based Chlorins and Type III Mechanism of Photodynamic Therapy (PDT)

Yoon¹,

Demberelnyamba²,

Li³

et al. 2014

Handbook of Porphyrin Science

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Section: Chlorophyll A-based Long Wavelength Cationic Chlorinsmentioning

confidence: 99%

Section: Chlorophyll A-based Long Wavelength Cationic Chlorinsmentioning

confidence: 99%

Section: Surface Plasmon Resonance (Spr) and Gnpsmentioning

confidence: 99%

Section: Surface Plasmon Resonance (Spr) and Gnpsmentioning

confidence: 99%

See 2 more Smart Citations

Ionic Liquid-Based Chlorins and Type III Mechanism of Photodynamic Therapy (PDT)

Yoon¹,

Demberelnyamba²,

Li³

et al. 2014

Handbook of Porphyrin Science

Self Cite

View full text Add to dashboard Cite

“…PSs with long wavelength absorption should exhibit deeper tissue penetration, which is very useful to treat large and deeply seated tumors [10–12]. Therefore, the synthesis of novel purpurinimides has become the focus in PDT studies.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Novel Purpurinimides as Photosensitizers for Photodynamic Therapy

Cui

Yoon

et al. 2014

IJMS

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A series of novel purpurinimides with long wavelength absorption were designed and synthesized to develop novel and potential photosensitizers. These compounds were investigated through reduction, oxidation, rearrangement reaction and amidation reactions of methyl pheophorbide a. They demonstrated a considerable bathochromic shift of the major absorption band in the red region of the optical spectrum (695–704 nm). Newly synthesized purpurinimides were screened for their antitumor activities, and showed higher photodynamic efficiency against A549 cell lines as compared to purpurin-18 methyl ester. The results revealed the novel purpurinimides could be potential photosensitizers.

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Efficient Synthesis of Long‐wavelength Absorbing Cyanochlorophyll a Derivatives via Stereoselective Horner–Wadsworth–Emmons Reaction

Wang

Liu

et al. 2020

Bulletin Korean Chem Soc

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In this article, we report the stereoselective Horner-Wadsworth-Emmons reaction of reactive carbonyl-substituted chlorophyll a derivatives with diethyl cyanomethylphosphonate. We found that the formyl or keto group at the chlorin periphery can react stereoselectively with phosphonate carbanions to produce a series of cyanomethylenesubstituted chlorins with predominantly E geometry. Considering that no consistent records are available in the literature on the results of the allomerization of methyl pyropheophorbide a, we propose a reliable process for the transformation of this chlorophyll derivative. Our methodology represents a simple and efficient way for the preparation of novel, differently functionalized long-wavelength absorbing chlorins, those can be applied for photodynamic therapy, solar cells, and other relevant purposes.

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Synthesis of novel long wavelength cationic chlorins via stereoselective aldol-like condensation

Cited by 39 publications

References 27 publications

Ionic Liquid-Based Chlorins and Type III Mechanism of Photodynamic Therapy (PDT)

Ionic Liquid-Based Chlorins and Type III Mechanism of Photodynamic Therapy (PDT)

Synthesis and Characterization of Novel Purpurinimides as Photosensitizers for Photodynamic Therapy

Efficient Synthesis of Long‐wavelength Absorbing Cyanochlorophyll a Derivatives via Stereoselective Horner–Wadsworth–Emmons Reaction

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