PEG-modified aziridines for stereoselective synthesis of water-soluble fulleropyrrolidines

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PEG-modified aziridines for stereoselective synthesis of water-soluble fulleropyrrolidines. / Kazakova, Angelina V. ; Konev, Alexander S. ; Zorin, Ivan M. ; Poshekhonov, Igor S. ; Korzhikov-Vlakh, Viktor A. ; Khlebnikov, Alexander F. .

In: Organic and Biomolecular Chemistry, Vol. 17, No. 46, 14.12.2019, p. 9864-9873.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{0a8e9e5ddf094e4a9344ca5dc9a9ee81,

title = "PEG-modified aziridines for stereoselective synthesis of water-soluble fulleropyrrolidines",

abstract = "Diastereoselective synthesis of water-soluble fullerene compound bearing pharmacophore fulleropyrrolidine-2{\textquoteright},5{\textquoteright}-dicarboxalate unit is reported. The stereocontrol of the product configuration is achieved through stereospecificity of two consequtive concerted reactions: electrocyclic aziridine ring...Diastereoselective synthesis of water-soluble fullerene compound bearing pharmacophore fulleropyrrolidine-2{\textquoteright},5{\textquoteright}-dicarboxalate unit is reported. The stereocontrol of the product configuration is achieved through stereospecificity of two consequtive concerted reactions: electrocyclic aziridine ring opening followed by 1,3-dipolar cycloaddition of the resulting azomethyne ylide. The solubility in water (up to 20 μM through direct dissolution) is secured by introducing polyethylene glycol (PEG) hydrophilic pendant. The structure and molecular-mass distribution of the resulitng PEGylated fulleropyrrolidine are exhaustively characterized by 1H, 13C NMR and HRMS. According to absorbance spectroscopy, AFM and DLS studies, synthesized compound tends to aggregate in aqueous media forming associates of ca. 4–9 nm radius surrounded by a solvation shell resulting in effective hydrodynamic diameter of ca. 90 nm. In view of notable solubility in water, well-defined chemical structure and resemblence to the compounds with known anti-HIV activity, the synthesized PEGylated diethyl trans-fulleropyrrolidine-2{\textquoteright},5{\textquoteright}-dicarboxalate might be an attractive candidate for biological evaluation.",

keywords = "AGGREGATION BEHAVIOR, CYCLOADDITION, FULLERENE DERIVATIVES, HIV-1 PROTEASE, INHIBITION, PHOTODYNAMIC THERAPY, TARGET-SELECTIVE PHOTODEGRADATION, YLIDES",

author = "Kazakova, {Angelina V.} and Konev, {Alexander S.} and Zorin, {Ivan M.} and Poshekhonov, {Igor S.} and Korzhikov-Vlakh, {Viktor A.} and Khlebnikov, {Alexander F.}",

note = "Funding Information: This work was financially supported by the Russian Science Foundation (19–13–00039). This research was performed using resources of the Centre for Magnetic Resonance, the Centre for Chemical Analysis and Materials, and the Educational Resource Centre of Chemistry of Research park of St. Petersburg State University, and the assistance of the specialists of the research park is gratefully acknowledged.",

year = "2019",

month = dec,

day = "14",

doi = "10.1039/C9OB01949A",

language = "English",

volume = "17",

pages = "9864--9873",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "46",

}

RIS

TY - JOUR

T1 - PEG-modified aziridines for stereoselective synthesis of water-soluble fulleropyrrolidines

AU - Kazakova, Angelina V.

AU - Konev, Alexander S.

AU - Zorin, Ivan M.

AU - Poshekhonov, Igor S.

AU - Korzhikov-Vlakh, Viktor A.

AU - Khlebnikov, Alexander F.

N1 - Funding Information: This work was financially supported by the Russian Science Foundation (19–13–00039). This research was performed using resources of the Centre for Magnetic Resonance, the Centre for Chemical Analysis and Materials, and the Educational Resource Centre of Chemistry of Research park of St. Petersburg State University, and the assistance of the specialists of the research park is gratefully acknowledged.

PY - 2019/12/14

Y1 - 2019/12/14

N2 - Diastereoselective synthesis of water-soluble fullerene compound bearing pharmacophore fulleropyrrolidine-2’,5’-dicarboxalate unit is reported. The stereocontrol of the product configuration is achieved through stereospecificity of two consequtive concerted reactions: electrocyclic aziridine ring...Diastereoselective synthesis of water-soluble fullerene compound bearing pharmacophore fulleropyrrolidine-2’,5’-dicarboxalate unit is reported. The stereocontrol of the product configuration is achieved through stereospecificity of two consequtive concerted reactions: electrocyclic aziridine ring opening followed by 1,3-dipolar cycloaddition of the resulting azomethyne ylide. The solubility in water (up to 20 μM through direct dissolution) is secured by introducing polyethylene glycol (PEG) hydrophilic pendant. The structure and molecular-mass distribution of the resulitng PEGylated fulleropyrrolidine are exhaustively characterized by 1H, 13C NMR and HRMS. According to absorbance spectroscopy, AFM and DLS studies, synthesized compound tends to aggregate in aqueous media forming associates of ca. 4–9 nm radius surrounded by a solvation shell resulting in effective hydrodynamic diameter of ca. 90 nm. In view of notable solubility in water, well-defined chemical structure and resemblence to the compounds with known anti-HIV activity, the synthesized PEGylated diethyl trans-fulleropyrrolidine-2’,5’-dicarboxalate might be an attractive candidate for biological evaluation.

AB - Diastereoselective synthesis of water-soluble fullerene compound bearing pharmacophore fulleropyrrolidine-2’,5’-dicarboxalate unit is reported. The stereocontrol of the product configuration is achieved through stereospecificity of two consequtive concerted reactions: electrocyclic aziridine ring...Diastereoselective synthesis of water-soluble fullerene compound bearing pharmacophore fulleropyrrolidine-2’,5’-dicarboxalate unit is reported. The stereocontrol of the product configuration is achieved through stereospecificity of two consequtive concerted reactions: electrocyclic aziridine ring opening followed by 1,3-dipolar cycloaddition of the resulting azomethyne ylide. The solubility in water (up to 20 μM through direct dissolution) is secured by introducing polyethylene glycol (PEG) hydrophilic pendant. The structure and molecular-mass distribution of the resulitng PEGylated fulleropyrrolidine are exhaustively characterized by 1H, 13C NMR and HRMS. According to absorbance spectroscopy, AFM and DLS studies, synthesized compound tends to aggregate in aqueous media forming associates of ca. 4–9 nm radius surrounded by a solvation shell resulting in effective hydrodynamic diameter of ca. 90 nm. In view of notable solubility in water, well-defined chemical structure and resemblence to the compounds with known anti-HIV activity, the synthesized PEGylated diethyl trans-fulleropyrrolidine-2’,5’-dicarboxalate might be an attractive candidate for biological evaluation.

KW - AGGREGATION BEHAVIOR

KW - CYCLOADDITION

KW - FULLERENE DERIVATIVES

KW - HIV-1 PROTEASE

KW - INHIBITION

KW - PHOTODYNAMIC THERAPY

KW - TARGET-SELECTIVE PHOTODEGRADATION

KW - YLIDES

UR - http://www.scopus.com/inward/record.url?scp=85075812810&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/pegmodified-aziridines-stereoselective-synthesis-watersoluble-pyrrolofullerenes

U2 - 10.1039/C9OB01949A

DO - 10.1039/C9OB01949A

M3 - Article

VL - 17

SP - 9864

EP - 9873

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 46

ER -

ID: 49173158