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Article: Development of a Dosage form for a Photoswitchable Local Anesthetic Ethercaine.

Noev, Alexey / Morozova, Natalia / Suvorov, Nikita / Vasil'ev, Yuriy / Pankratov, Andrei / Grin, Mikhail

2023 Volume 16, Issue 10

Abstract: The toxicity of local anesthetics is a serious problem, given their widespread use. One of the main causes of the side effects of local anesthetics is their non-selectivity of action in the body. A possible way to increase the selectivity of the action ... ...

Abstract	The toxicity of local anesthetics is a serious problem, given their widespread use. One of the main causes of the side effects of local anesthetics is their non-selectivity of action in the body. A possible way to increase the selectivity of the action of drugs is to use the photopharmacology approach. Previously, we described the light-controlled local anesthetic ethercaine, the biological effect of which can be controlled using light, thereby increasing its selectivity of action. An important limitation of ethercaine was its low solubility in water, limiting the potential of this compound. In this work, we developed a dosage form of ethercaine, which allowed us to increase its solubility from 0.6% to 2% or more. The resulting 1% solution of ethercaine hydrochloride in 4% Kolliphor ELP had high biological activity on the surface anesthesia model, while demonstrating low acute toxicity in mice with intravenous administration (4-5 times less than that of lidocaine).
Language	English
Publishing date	2023-10-02
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2193542-7
ISSN	1424-8247
ISSN	1424-8247
DOI	10.3390/ph16101398
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Thiocarbonyl Derivatives of Natural Chlorins: Synthesis Using Lawesson's Reagent and a Study of Their Properties.

Pogorilyy, Viktor / Ostroverkhov, Petr / Efimova, Valeria / Plotnikova, Ekaterina / Bezborodova, Olga / Diachkova, Ekaterina / Vasil'ev, Yuriy / Pankratov, Andrei / Grin, Mikhail

Molecules (Basel, Switzerland)

2023 Volume 28, Issue 10

Abstract: The development of sulfur-containing pharmaceutical compounds is important in the advancement of medicinal chemistry. Photosensitizers (PS) that acquire new properties upon incorporation of sulfur-containing groups or individual sulfur atoms into their ... ...

Abstract	The development of sulfur-containing pharmaceutical compounds is important in the advancement of medicinal chemistry. Photosensitizers (PS) that acquire new properties upon incorporation of sulfur-containing groups or individual sulfur atoms into their structure are not neglected, either. In this work, a synthesis of sulfur-containing derivatives of natural chlorophyll
MeSH term(s)	Chlorophyll A ; Organothiophosphorus Compounds/chemistry ; Sulfur
Chemical Substances	2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (A4125MQ8RX) ; chlorin (2683-84-3) ; Chlorophyll A (YF5Q9EJC8Y) ; Organothiophosphorus Compounds ; Sulfur (70FD1KFU70)
Language	English
Publishing date	2023-05-20
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules28104215
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Article ; Online: The First Selenoanhydride in the Series of Chlorophyll a Derivatives, Its Stability and Photoinduced Cytotoxicity.

Pogorilyy, Viktor / Plyutinskaya, Anna / Suvorov, Nikita / Diachkova, Ekaterina / Vasil'ev, Yuriy / Pankratov, Andrei / Mironov, Andrey / Grin, Mikhail

Molecules (Basel, Switzerland)

2021 Volume 26, Issue 23

Abstract: In this work, we obtained the first selenium-containing chlorin with a chalcogen atom in exlocycle E. It was shown that the spectral properties were preserved in the target compound and the stability increased at two different pH values, in comparison ... ...

Abstract	In this work, we obtained the first selenium-containing chlorin with a chalcogen atom in exlocycle E. It was shown that the spectral properties were preserved in the target compound and the stability increased at two different pH values, in comparison with the starting purpurin-18. The derivatives have sufficiently high fluorescence and singlet oxygen quantum yields. The photoinduced cytotoxicity of sulfur- and selenium-anhydrides of chlorin p
MeSH term(s)	Animals ; Cell Line, Tumor ; Chlorophyll A/analogs & derivatives ; Chlorophyll A/pharmacology ; Mice ; Organoselenium Compounds/chemistry ; Organoselenium Compounds/pharmacology ; Photosensitizing Agents/chemistry ; Photosensitizing Agents/pharmacology ; Porphyrins/chemistry ; Porphyrins/pharmacology ; Sarcoma/drug therapy
Chemical Substances	Organoselenium Compounds ; Photosensitizing Agents ; Porphyrins ; chlorin (2683-84-3) ; Chlorophyll A (YF5Q9EJC8Y)
Language	English
Publishing date	2021-12-01
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules26237298
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Article ; Online: A Novel Photoswitchable Azobenzene-Containing Local Anesthetic Ethercaine with Light-Controlled Biological Activity In Vivo.

Noev, Alexey / Kuznetsov, Nikita / Korenev, Georgiy / Morozova, Natalia / Vasil'ev, Yuriy / Suvorov, Nikita / Diachkova, Ekaterina / Usachev, Maksim / Pankratov, Andrei / Grin, Mikhail

International journal of molecular sciences

2022 Volume 23, Issue 10

Abstract: Pain is a common symptom that impairs the quality of life for people around the world. Local anesthetics widely used for pain relief have a number of side effects, which makes the development of both new drugs and new ways to control their activity ... ...

Abstract	Pain is a common symptom that impairs the quality of life for people around the world. Local anesthetics widely used for pain relief have a number of side effects, which makes the development of both new drugs and new ways to control their activity particularly important. Photopharmacology makes it possible to reduce the side effects of an anesthetic and control its biological activity in the body. The purpose of this work was to create a new light-controlled local anesthetic and study its biological activity in animals. A compound with a simple scheme of synthesis was chosen to shift the UV-Vis absorption band towards the visible range of the spectrum and was synthesized for the first time. Some computer calculations were performed to make sure that the aforementioned changes would not lead to loss of biological activity. The micellar form of the new compound was prepared, and in vivo biological studies were carried out in rabbits. The existence of a local anesthetic effect, which disappeared almost completely on irradiation with light (λ = 395 nm), was shown using the surface anesthesia model. Moreover, the possibility of multiple reversible changes in the biological activity of ethercaine under the action of light was demonstrated. The latter compound manifests no local irritating effect, either. The data obtained indicate the prospects for the development of new compounds based on azobenzene for light-controlled local anesthesia.
MeSH term(s)	Anesthesia, Local ; Anesthetics, Local/pharmacology ; Animals ; Azo Compounds ; Humans ; Pain ; Quality of Life ; Rabbits
Chemical Substances	Anesthetics, Local ; Azo Compounds ; azobenzene (F0U1H6UG5C)
Language	English
Publishing date	2022-05-11
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2019364-6
ISSN	1422-0067 ; 1422-0067 ; 1661-6596
ISSN (online)	1422-0067
ISSN	1422-0067 ; 1661-6596
DOI	10.3390/ijms23105352
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Article ; Online: Tin Carboxylate Complexes of Natural Bacteriochlorin for Combined Photodynamic and Chemotherapy of Cancer è.

Tikhonov, Sergey / Ostroverkhov, Petr / Suvorov, Nikita / Mironov, Andrey / Efimova, Yulia / Plutinskaya, Anna / Pankratov, Andrei / Ignatova, Anastasia / Feofanov, Alexey / Diachkova, Ekaterina / Vasil'ev, Yuriy / Grin, Mikhail

International journal of molecular sciences

2021 Volume 22, Issue 24

Abstract: Photodynamic therapy (PDT) is currently one of the most promising methods of cancer treatment. However, this method has some limitations, including a small depth of penetration into biological tissues, the low selectivity of accumulation, and hypoxia of ... ...

Abstract	Photodynamic therapy (PDT) is currently one of the most promising methods of cancer treatment. However, this method has some limitations, including a small depth of penetration into biological tissues, the low selectivity of accumulation, and hypoxia of the tumor tissues. These disadvantages can be overcome by combining PDT with other methods of treatment, such as radiation therapy, neutron capture therapy, chemotherapy, etc. In this work, potential drugs were obtained for the first time, the molecules of which contain both photodynamic and chemotherapeutic pharmacophores. A derivative of natural bacteriochlorophyll a with a tin IV complex, which has chemotherapeutic activity, acts as an agent for PDT. This work presents an original method for obtaining agents of combined action, the structure of which is confirmed by various physicochemical methods of analysis. The method of molecular modeling was used to investigate the binding of the proposed drugs to DNA. In vitro biological tests were carried out on several lines of tumor cells: Hela, A549, S37, MCF7, and PC-3. It was shown that the proposed conjugates of binary action for some cell lines had a dark cytotoxicity that was significantly higher (8-10 times) than the corresponding metal complexes of amino acids, which was explained by the targeted chemotherapeutic action of the tin (IV) complex due to chlorin. The greatest increase in efficiency relative to the initial dipropoxy-BPI was found for the conjugate with lysine as a chelator of the tin cation relative to cell lines, with the following results: S-37 increased 3-fold, MCF-7 3-fold, and Hela 2.4-fold. The intracellular distribution of the obtained agents was also studied by confocal microscopy and showed a diffuse granular distribution with predominant accumulation in the near nuclear region.
MeSH term(s)	A549 Cells ; Coordination Complexes/chemistry ; Coordination Complexes/pharmacology ; HeLa Cells ; Humans ; MCF-7 Cells ; Neoplasms/drug therapy ; Photochemotherapy ; Photosensitizing Agents/chemistry ; Photosensitizing Agents/pharmacology ; Porphyrins/chemistry ; Porphyrins/pharmacology ; Tin/chemistry ; Tin/pharmacology
Chemical Substances	Coordination Complexes ; Photosensitizing Agents ; Porphyrins ; bacteriochlorin ; Tin (7440-31-5)
Language	English
Publishing date	2021-12-17
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2019364-6
ISSN	1422-0067 ; 1422-0067 ; 1661-6596
ISSN (online)	1422-0067
ISSN	1422-0067 ; 1661-6596
DOI	10.3390/ijms222413563
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Article ; Online: Preclinical Study of Biofunctional Polymer-Coated Upconversion Nanoparticles.

Guryev, Evgenii L / Shilyagina, Natalia Y / Kostyuk, Alexey B / Sencha, Ludmila M / Balalaeva, Irina V / Vodeneev, Vladimir A / Kutova, Olga M / Lyubeshkin, Alexander V / Yakubovskaya, Raisa I / Pankratov, Andrei A / Ingel, Faina I / Novik, Tamara S / Deyev, Sergey M / Ermilov, Sergey A / Zvyagin, Andrei V

Toxicological sciences : an official journal of the Society of Toxicology

2019 Volume 170, Issue 1, Page(s) 123–132

Abstract: Upconversion nanoparticles (UCNPs) are new-generation photoluminescent nanomaterials gaining considerable recognition in the life sciences due to their unique optical properties that allow high-contrast imaging in cells and tissues. Upconversion ... ...

Abstract	Upconversion nanoparticles (UCNPs) are new-generation photoluminescent nanomaterials gaining considerable recognition in the life sciences due to their unique optical properties that allow high-contrast imaging in cells and tissues. Upconversion nanoparticle applications in optical diagnosis, bioassays, therapeutics, photodynamic therapy, drug delivery, and light-controlled release of drugs are promising, demanding a comprehensive systematic study of their pharmacological properties. We report on production of biofunctional UCNP-based nanocomplexes suitable for optical microscopy and imaging of HER2-positive cells and tumors, as well as on the comprehensive evaluation of their pharmacokinetics, pharmacodynamics, and toxicological properties using cells and laboratory animals. The nanocomplexes represent a UCNP core/shell structure of the NaYF4:Yb, Er, Tm/NaYF4 composition coated with an amphiphilic alternating copolymer of maleic anhydride with 1-octadecene (PMAO) and conjugated to the Designed Ankyrin Repeat Protein (DARPin 9_29) with high affinity to the HER2 receptor. We demonstrated the specific binding of UCNP-PMAO-DARPin to HER2-positive cancer cells in cultures and xenograft animal models allowing the tumor visualization for at least 24 h. An exhaustive study of the general and specific toxicity of UCNP-PMAO-DARPin including the evaluation of their allergenic, immunotoxic, and reprotoxic properties was carried out. The obtained experimental body of evidence leads to a conclusion that UCNP-PMAO and UCNP-PMAO-DARPin are functional, noncytotoxic, biocompatible, and safe for imaging applications in cells, small animals, and prospective clinical applications of image-guided surgery.
MeSH term(s)	Animals ; CHO Cells ; Cell Line, Tumor ; Cricetulus ; Drug Evaluation, Preclinical ; Erbium/chemistry ; Escherichia coli/genetics ; Fluorides/chemistry ; Humans ; Luminescent Measurements ; Mammary Neoplasms, Experimental/diagnostic imaging ; Nanoparticles/chemistry ; Nanoparticles/metabolism ; Nanoparticles/toxicity ; Polymers/chemistry ; Polymers/pharmacokinetics ; Polymers/toxicity ; Receptor, ErbB-2/genetics ; Surface Properties ; Thulium/chemistry ; Tissue Distribution ; Whole Body Imaging/methods ; Yttrium/chemistry
Chemical Substances	Polymers ; sodium yttriumtetrafluoride ; Yttrium (58784XQC3Y) ; Erbium (77B218D3YE) ; Thulium (8RKC5ATI4P) ; ERBB2 protein, human (EC 2.7.10.1) ; Receptor, ErbB-2 (EC 2.7.10.1) ; Fluorides (Q80VPU408O)
Language	English
Publishing date	2019-04-12
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1420885-4
ISSN	1096-0929 ; 1096-6080
ISSN (online)	1096-0929
ISSN	1096-6080
DOI	10.1093/toxsci/kfz086
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Article: Preclinical Study of Biofunctional Polymer-Coated Upconversion Nanoparticles

Toxicological sciences. 2019 July 01, v. 170, no. 1

2019

Abstract	Upconversion nanoparticles (UCNPs) are new-generation photoluminescent nanomaterials gaining considerable recognition in the life sciences due to their unique optical properties that allow high-contrast imaging in cells and tissues. Upconversion nanoparticle applications in optical diagnosis, bioassays, therapeutics, photodynamic therapy, drug delivery, and light-controlled release of drugs are promising, demanding a comprehensive systematic study of their pharmacological properties. We report on production of biofunctional UCNP-based nanocomplexes suitable for optical microscopy and imaging of HER2-positive cells and tumors, as well as on the comprehensive evaluation of their pharmacokinetics, pharmacodynamics, and toxicological properties using cells and laboratory animals. The nanocomplexes represent a UCNP core/shell structure of the NaYF4:Yb, Er, Tm/NaYF4 composition coated with an amphiphilic alternating copolymer of maleic anhydride with 1-octadecene (PMAO) and conjugated to the Designed Ankyrin Repeat Protein (DARPin 9_29) with high affinity to the HER2 receptor. We demonstrated the specific binding of UCNP-PMAO-DARPin to HER2-positive cancer cells in cultures and xenograft animal models allowing the tumor visualization for at least 24 h. An exhaustive study of the general and specific toxicity of UCNP-PMAO-DARPin including the evaluation of their allergenic, immunotoxic, and reprotoxic properties was carried out. The obtained experimental body of evidence leads to a conclusion that UCNP-PMAO and UCNP-PMAO-DARPin are functional, noncytotoxic, biocompatible, and safe for imaging applications in cells, small animals, and prospective clinical applications of image-guided surgery.
Keywords	allergenicity ; animal models ; bioassays ; composite polymers ; image analysis ; immunotoxicity ; light microscopy ; maleic anhydrides ; medicinal properties ; nanoparticles ; neoplasm cells ; neoplasms ; optical properties ; pharmacodynamics ; pharmacokinetics ; photochemotherapy ; photoluminescence ; surgery ; tissues ; toxicology
Language	English
Dates of publication	2019-0701
Size	p. 123-132.
Publishing place	Oxford University Press
Document type	Article
ZDB-ID	1420885-4
ISSN	1096-0929 ; 1096-6080
ISSN (online)	1096-0929
ISSN	1096-6080
DOI	10.1093/toxsci/kfz086
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Synthesis, Characterization, and Preclinical Evaluation of a Small-Molecule Prostate-Specific Membrane Antigen-Targeted Monomethyl Auristatin E Conjugate.

Machulkin, Aleksei E / Uspenskaya, Anastasia A / Zyk, Nikolay U / Nimenko, Ekaterina A / Ber, Anton P / Petrov, Stanislav A / Polshakov, Vladimir I / Shafikov, Radik R / Skvortsov, Dmitry A / Plotnikova, Ekaterina A / Pankratov, Andrei A / Smirnova, Galina B / Borisova, Yulia A / Pokrovsky, Vadim S / Kolmogorov, Vasilii S / Vaneev, Alexander N / Khudyakov, Alexander D / Chepikova, Olga E / Kovalev, Sergey /

Zamyatnin, Andrey A / Erofeev, Alexander / Gorelkin, Petr / Beloglazkina, Elena K / Zyk, Nikolay V / Khazanova, Elena S / Majouga, Alexander G

Journal of medicinal chemistry

2021 Volume 64, Issue 23, Page(s) 17123–17145

Abstract: Prostate cancer is the second most common type of cancer among men. Its main method of treatment is chemotherapy, which has a wide range of side effects. One of the solutions to this challenge is targeted delivery to prostate cancer cells. Here we ... ...

Abstract	Prostate cancer is the second most common type of cancer among men. Its main method of treatment is chemotherapy, which has a wide range of side effects. One of the solutions to this challenge is targeted delivery to prostate cancer cells. Here we synthesized a novel small-molecule PSMA-targeted conjugate based on the monomethyl auristatin E. Its structure and conformational properties were investigated by NMR spectroscopy. Cytotoxicity, intracellular reactive oxygen species induction, and stability under liver microsomes and P450-cytochrome species were investigated for this conjugate. The conjugate demonstrated 77-85% tumor growth inhibition levels on 22Rv1 (PSMA (+)) xenografts, compared with a 37% inhibition level on PC-3 (PSMA (-)) xenografts, in a single dose of 0.3 mg/kg and a sufficiently high therapeutic index of 21. Acute, chronic, and subchronic toxicities and pharmacokinetics have shown that the synthesized conjugate is a promising potential agent for the chemotherapy of prostate cancer.
MeSH term(s)	Antigens, Surface/chemistry ; Cell Line, Tumor ; Coordination Complexes/chemical synthesis ; Coordination Complexes/chemistry ; Coordination Complexes/pharmacology ; Glutamate Carboxypeptidase II/chemistry ; Humans ; Male ; Microsomes, Liver/enzymology ; Microsomes, Liver/metabolism ; Oligopeptides/chemistry ; Prostatic Neoplasms/pathology ; Reactive Oxygen Species/metabolism ; Xenograft Model Antitumor Assays
Chemical Substances	Antigens, Surface ; Coordination Complexes ; Oligopeptides ; Reactive Oxygen Species ; FOLH1 protein, human (EC 3.4.17.21) ; Glutamate Carboxypeptidase II (EC 3.4.17.21) ; monomethyl auristatin E (V7I58RC5EJ)
Language	English
Publishing date	2021-11-19
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.1c01157
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Article: Tissue distribution and in vivo photosensitizing activity of 13,15-[N-(3-hydroxypropyl)]cycloimide chlorin p6 and 13,15-(N-methoxy)cycloimide chlorin p6 methyl ester.

Karmakova, Tatyana / Feofanov, Alexei / Pankratov, Andrei / Kazachkina, Natalia / Nazarova, Anna / Yakubovskaya, Raisa / Lebedeva, Victoria / Ruziyev, Ramzes / Mironov, Andrey / Maurizot, Jean-Claude / Vigny, Paul

Journal of photochemistry and photobiology. B, Biology

2006 Volume 82, Issue 1, Page(s) 28–36

Abstract: Photosensitizers 13,15-[N-(3-hydroxypropyl)]cycloimide chlorin p6 (HPC) and 13,15-(N-methoxy)cycloimide chlorin p6 methyl ester (MMC) absorb at 711 nm and possess high photoinduced cytotoxicity in vitro. Here we report, that photodynamic therapy with HPC ...

Abstract	Photosensitizers 13,15-[N-(3-hydroxypropyl)]cycloimide chlorin p6 (HPC) and 13,15-(N-methoxy)cycloimide chlorin p6 methyl ester (MMC) absorb at 711 nm and possess high photoinduced cytotoxicity in vitro. Here we report, that photodynamic therapy with HPC and MMC provide considerable antitumor effect in mice bearing subcutaneous P338 lymphoma. The highest antitumor effect was achieved at a dose of 4 micromol/kg when 1.5 h delay between dye injection and light irradiation (drug-light interval) was used. According to the confocal spectral imaging studies of tissue sections this drug-light interval corresponds to a maximum of tumor accumulation of MMC and HPC (tumor to skin accumulation ratio is 8-10). Short (15 min) drug-light interval can be used for efficient vasculature-targeted photodynamic therapy with HPC at a dose of 1 micromol/kg, whereas MMC is ineffective at the short drug-light interval. Relationships between the features of tissue distribution and efficacy of photodynamic therapy at different drug-light intervals are discussed for HPC and MMC.
MeSH term(s)	Animals ; Cell Line, Tumor ; Dose-Response Relationship, Drug ; Dose-Response Relationship, Radiation ; Female ; Mice ; Microscopy, Confocal ; Photochemotherapy ; Photosensitizing Agents/chemistry ; Photosensitizing Agents/pharmacokinetics ; Porphyrins/chemistry ; Porphyrins/pharmacokinetics ; Structure-Activity Relationship ; Time Factors ; Tissue Distribution/drug effects ; Tissue Distribution/physiology ; Tissue Distribution/radiation effects
Chemical Substances	13,15-(N-methoxy)cycloimide chlorin p6 methyl ester ; 13,15-N-(3'-hydroxypropyl)cycloimide chlorin p6 ; Photosensitizing Agents ; Porphyrins
Language	English
Publishing date	2006-01-02
Publishing country	Switzerland
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	623022-2
ISSN	1873-2682 ; 1011-1344
ISSN (online)	1873-2682
ISSN	1011-1344
DOI	10.1016/j.jphotobiol.2005.08.006
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