Synthesis and antiproliferative activity of new chlorin e6 glycoconjugates

Kuzmina, Natalia S.; Otvagin, Vasilii F.; Krylova, Lubov V.; Nyuchev, Alexander V.; Romanenko, Yu. V.; Койфман, О. И.; Balalaeva, Irina V.; Fedorov, Alexey Yu.

doi:10.1016/j.mencom.2020.03.009

Cited by 12 publications

(8 citation statements)

References 28 publications

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“…Infrared spectra were measured in KBr tablets on the "IR Prestige 21" device (Shimadzu). 1 H (working frequency 300 MHz) and 13 C (working frequency 75 MHz) NMR spectra of the synthesized compounds were recorded on Bruker AVANCE-II-300 (standard impulse Bruker software for one and two-dimensional experiments). UV-vis spectra were recorded on a spectrometer UV-1700 "Shimadzu" (wavelength range of 200-1100 nm).…”

Section: Generalmentioning

confidence: 99%

“…[9,22] Chlorophyll a derivatives are a good basis for obtaining new antitumor and PS. [2] For the introduction of carbohydrate fragments to the periphery of the chlorophyll a derivatives macrocycle, click chemistry, [2,13] metathesis reactions, [2] the formation of ester [23,24] and amide bonds, [2] as well as alkylation of amino groups. [25] In the case of alkylation of amino groups, a stable C-N-C bond is formed between the fragments of chlorin e 6 and galactose.…”

Section: Introductionmentioning

confidence: 99%

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Novel Hydrophilic Conjugates of Chlorin e6 with Fructose: Synthesis and Estimation of Photodynamic Activity

Mal’shakova,

Pylina,

Belykh

2023

MHC

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The conjugates of natural and synthetic porphyrins with carbohydrates are known to be promising antitumor photosensitizers (PS). The presence of monosaccharide fragments at the periphery of the porphyrin macrocycle leads to an increase in bioavailability and increases their uptake by cancer cells. We synthesized new hydrophilic conjugates of chlorin e 6 with fructose by alkylation of the amino groups of chlorin e 6 amides with one and two ethylenediamine or hexamethylenediamine fragments on the macrocycle periphery with triflate of 2,3:4,5-di-O-isopropylidene-β-Dfructopyranose, followed by removal of diisopropylidene protection by 70% aqueous trifluoroacetic acid. In all cases, monoalkylation occurs, which allows the chemoselective insertion of one fructose fragment for each amino group present in the initial chlorin. For most of the studied compounds, it is possible to obtain a solution containing at least 0.2 mg/mL without the use of auxiliary substances, which indicates the possibility of obtaining water-soluble forms. The synthesized conjugates were shown to exhibit pronounced photodynamic activity at concentrations at which dark cytotoxic effect is not observed (HeLa, A549, HT-29 cancer cell cultures were used as test objects).

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Section: Generalmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Novel Hydrophilic Conjugates of Chlorin e6 with Fructose: Synthesis and Estimation of Photodynamic Activity

Mal’shakova,

Pylina,

Belykh

2023

MHC

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“…154 Eventually, we expected to see a pronounced synergism for the new conjugate 108 under both dark and light activation. In addition, tetraalkyl ammonium groups were swapped for a carbohydrate, imparting additional hydrophilicity 155 and affinity to carbohydrate receptors often expressed by tumors. 60 The selectivity of the obtained conjugate 108 was investigated in two cell lines: the A431 cell line (EGFR-positive) and the CHO cell line (EGFR-negative) (Figure 25).…”

Section: Cytotoxic Drugsmentioning

confidence: 99%

Conjugates of Porphyrinoid-Based Photosensitizers with Cytotoxic Drugs: Current Progress and Future Directions toward Selective Photodynamic Therapy

et al. 2022

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Photodynamic therapy (PDT) is a treatment modality where light-mediated activation of photosensitizers in a patient’s body leads to the generation of cytotoxic reactive oxygen species (ROS), eliminating cancer cells. One direction that has been firmly established over past years is the conjugation of photosensitizers with various molecules that demonstrate their own cytotoxic activity. As a result, improved selectivity and treatment outcomes are observed compared to those of unconjugated drugs. The attractiveness of such an approach is due to the variability of cytotoxic warheads and specific linkers available for the construction of conjugates. In this review, we summarize and analyze data concerning these inventions with the ultimate goal to find a promising conjugation partner for a porphyrinoid-based photosensitizer. The current challenges toward successful conjugation are also outlined and discussed. We hope that this review will motivate researchers to pay closer attention to conjugates and possibilities hidden in these molecules for the PDT of cancer.

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“…This is achieved by conjugating or encapsulating second-generation photosensitizers with compounds that have an affinity for tumor cells or their expressed receptors [ 8 , 19 , 28 ]. Biomarkers such as peptides [ 29 ], carbohydrates [ 30 ], vitamins [ 31 ], growth factor receptors [ 32 ], antibodies [ 33 ], and others serve this purpose. This approach enhances the pharmacokinetics, pharmacodynamics, and bioavailability of the photosensitive drug, improves water solubility, and stabilizes the conjugate during use [ 24 ].…”

Section: Introductionmentioning

confidence: 99%

Enhancing Precision in Photodynamic Therapy: Innovations in Light-Driven and Bioorthogonal Activation

Kuzmina,

Fedotova,

Jankovic

et al. 2024

Pharmaceutics

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Over the past few decades, photodynamic therapy (PDT) has evolved as a minimally invasive treatment modality offering precise control over cancer and various other diseases. To address inherent challenges associated with PDT, researchers have been exploring two promising avenues: the development of intelligent photosensitizers activated through light-induced energy transfers, charges, or electron transfers, and the disruption of photosensitive bonds. Moreover, there is a growing emphasis on the bioorthogonal delivery or activation of photosensitizers within tumors, enabling targeted deployment and activation of these intelligent photosensitive systems in specific tissues, thus achieving highly precise PDT. This concise review highlights advancements made over the last decade in the realm of light-activated or bioorthogonal photosensitizers, comparing their efficacy and shaping future directions in the advancement of photodynamic therapy.

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Synthesis and antiproliferative activity of new chlorin e6 glycoconjugates

Cited by 12 publications

References 28 publications

Novel Hydrophilic Conjugates of Chlorin e6 with Fructose: Synthesis and Estimation of Photodynamic Activity

Novel Hydrophilic Conjugates of Chlorin e6 with Fructose: Synthesis and Estimation of Photodynamic Activity

Conjugates of Porphyrinoid-Based Photosensitizers with Cytotoxic Drugs: Current Progress and Future Directions toward Selective Photodynamic Therapy

Enhancing Precision in Photodynamic Therapy: Innovations in Light-Driven and Bioorthogonal Activation

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