Biologically Active Fullerene Derivatives
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Biologically Active Fullerene Derivatives Z. M. Sarkisyana,* a St.
Petersburg State Pediatric Medical University, St. Petersburg, 194100 Russia *e-mail: [email protected] Received May 6, 2020; revised May 14, 2020; accepted May 18, 2020
Abstract—The review summarizes the data on the synthesis of fullerene C60 and C70 derivatives with various biological activities. Keywords: fullerene, fullerene derivatives, anti-HIV activity, antiviral activity, antiamyloid properties
DOI: 10.1134/S1070363220100072 Leading organic synthesis laboratories across the world are increasingly focused on the preparation of compounds based on C60 and C70 fullerenes. One promising line of research in this field involves the synthesis of new fullerene derivatives that will be readily soluble not only in chemical solvents but also in water and will possess various biological activities. Multiple reactivity displayed by fullerenes via [2+1], [2+3] cycloaddition, as well as electrophilic and radical addition reactions, makes it possible to model and subsequently synthesize polyfunctional biologically active compounds [1, 2]. Mutations in the human immunodeficiency virus HIV1 have motivated the ongoing search for medications effective in fighting HIV proper. There exist a number of licensed drugs able to inhibit the activity of HIV-1 reverse transcriptase, which is the key component of the virus, providing fragmentation and cleavage of proteins into constituents of the capsids of new virions [3]. Studies on anti-HIV activity of fullerene derivatives [4, 5] demonstrated the effectiveness of N,N-dimethyl[70] fulleropyrrolidinium iodide 1 (Scheme 1) in inhibiting the production and maturation of Gag and Gag-Pol, which are key polyproteins of HIV-1 retrovirus. In 2018, Castro et al. [6] synthesized new C60 fullerene derivatives including curcumin and curcuminoids with a variety of end groups through the addition-elimination process (Bingel reaction) using carbon tetrabromide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in o-dichlorobenzene at room temperature (Scheme 2). Fullerocurcuminoid C60 derivatives 2a–2k were obtained in 23–55% yields. Among them, curcumin
derivative 2a proved to possess not only anti-HIV but also anticancer, antioxidant, and neuroprotective activities. Kornev et al. [7] reported on the preparation of watersoluble poly(carboxyalkylphenyl) derivatives of C70 fullerene C70[p-C6H4(CH2)nCOOH]8 (n = 2, 3) 3. To this end, polychlorinated derivatives were first obtained, and this was followed by arylation of the resultant C70Cl8 and C70Cl10 compounds and by the acidic hydrolysis procedure [7] (Scheme 3). One of the polycarboxylic derivatives was found to display activity toward the key HIV glycoprotein GP120 which is a trigger for virus attachment to the host cell, unrecognizable by antibodies. Low cytotoxicity of the polycarboxyfullerenes was examined by in vivo treatment of mice. In parallel, antiviral activity of the proposed fullerene C70 derivatives in the form of their potassium salts (potassium carboxylate, n = 3) agai
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