Abstract

Diastereoselective synthesis of water-soluble fullerene compounds bearing a pharmacophore pyrrolofullerene-2′,5′-dicarboxylate unit is reported. The stereocontrol of the product configuration is achieved through stereospecificity of two consecutive 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 a polyethylene glycol (PEG) hydrophilic pendant. The structure and molecular-mass distribution of the resulting PEGylated fulleropyrrolidines are exhaustively characterized by 1H, 13C NMR and HRMS. According to absorbance spectroscopy, AFM and DLS studies, the synthesized compound tends to aggregate in aqueous media forming associates of ca. 4–9 nm radius surrounded by a solvation shell resulting in an effective hydrodynamic diameter of ca. 90 nm. In view of notable solubility in water, well-defined chemical structure and resemblance to the compounds with known anti-HIV activity, the synthesized PEGylated diethyl trans-pyrrolofullerene-2′,5′-dicarboxylate might be an attractive candidate for biological evaluation.
Original languageEnglish
Pages (from-to)9864-9873
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number46
Early online date21 Oct 2019
DOIs
Publication statusPublished - 27 Nov 2019

Fingerprint

Aziridines
Solubility
glycols
polyethylenes
Bearings (structural)
Water Wells
Water wells
Fullerenes
Cycloaddition
Water
Solvation
Cycloaddition Reaction
Molecular mass
Hydrodynamics
synthesis
solubility
Molecular Structure
water
Spectrum Analysis
Dissolution

Cite this

@article{0a8e9e5ddf094e4a9344ca5dc9a9ee81,
title = "PEG-modified aziridines for stereoselective synthesis of water-soluble fulleropyrrolidines",
abstract = "Diastereoselective synthesis of water-soluble fullerene compounds bearing a pharmacophore pyrrolofullerene-2′,5′-dicarboxylate unit is reported. The stereocontrol of the product configuration is achieved through stereospecificity of two consecutive 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 a polyethylene glycol (PEG) hydrophilic pendant. The structure and molecular-mass distribution of the resulting PEGylated fulleropyrrolidines are exhaustively characterized by 1H, 13C NMR and HRMS. According to absorbance spectroscopy, AFM and DLS studies, the synthesized compound tends to aggregate in aqueous media forming associates of ca. 4–9 nm radius surrounded by a solvation shell resulting in an effective hydrodynamic diameter of ca. 90 nm. In view of notable solubility in water, well-defined chemical structure and resemblance to the compounds with known anti-HIV activity, the synthesized PEGylated diethyl trans-pyrrolofullerene-2′,5′-dicarboxylate might be an attractive candidate for biological evaluation.",
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.}",
year = "2019",
month = "11",
day = "27",
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",

}

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.

PY - 2019/11/27

Y1 - 2019/11/27

N2 - Diastereoselective synthesis of water-soluble fullerene compounds bearing a pharmacophore pyrrolofullerene-2′,5′-dicarboxylate unit is reported. The stereocontrol of the product configuration is achieved through stereospecificity of two consecutive 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 a polyethylene glycol (PEG) hydrophilic pendant. The structure and molecular-mass distribution of the resulting PEGylated fulleropyrrolidines are exhaustively characterized by 1H, 13C NMR and HRMS. According to absorbance spectroscopy, AFM and DLS studies, the synthesized compound tends to aggregate in aqueous media forming associates of ca. 4–9 nm radius surrounded by a solvation shell resulting in an effective hydrodynamic diameter of ca. 90 nm. In view of notable solubility in water, well-defined chemical structure and resemblance to the compounds with known anti-HIV activity, the synthesized PEGylated diethyl trans-pyrrolofullerene-2′,5′-dicarboxylate might be an attractive candidate for biological evaluation.

AB - Diastereoselective synthesis of water-soluble fullerene compounds bearing a pharmacophore pyrrolofullerene-2′,5′-dicarboxylate unit is reported. The stereocontrol of the product configuration is achieved through stereospecificity of two consecutive 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 a polyethylene glycol (PEG) hydrophilic pendant. The structure and molecular-mass distribution of the resulting PEGylated fulleropyrrolidines are exhaustively characterized by 1H, 13C NMR and HRMS. According to absorbance spectroscopy, AFM and DLS studies, the synthesized compound tends to aggregate in aqueous media forming associates of ca. 4–9 nm radius surrounded by a solvation shell resulting in an effective hydrodynamic diameter of ca. 90 nm. In view of notable solubility in water, well-defined chemical structure and resemblance to the compounds with known anti-HIV activity, the synthesized PEGylated diethyl trans-pyrrolofullerene-2′,5′-dicarboxylate might be an attractive candidate for biological evaluation.

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 -