Аннотация (русский):
The review deals with literature and own experimental data for synthesis, structural features, spectral, acid-basic and coordinating properties of aromatic macroheterocycles – corroles. Perspectives of practical application of these compounds are considered briefly. Relationship between corrole properties and its geometrical and π-electronic structure is demonstrated. It is shown that corroles have number of features and unique characteristics in despite of insignificant change of structure compared to the most studied class of macroheterocyclic compounds – porphyrins.

Ключевые слова:
tetrapyrrolic macroheterocyclic compounds; porphyrins; corroles; synthesis; spectral characteristics; acid-basic and coordinating properties; metallocomplexes; catalysis; photodynamic therapy

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122. Berezin D.B., Shukhto O.V., Thao Vu Thi, Karimov D.R., Berezin B.D. Kinetic stability of corrol complexes with manganese, copper, and zinc in media based on acetic and sulfuric acids. J. Inorg. Chem. 2014. V. 59. No. 12. P. 1769-1776 (in Russian).

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124. Nardis S., Pomarico G., Stefanelli M., Lentini S., Cicero D.O., Fronczek F.R., Smith K.M., Paolesse R. The scope of the β-halogenation of triarylcorroles. J. Porph. Phthaloc. 2016. V. 20. P. 465-474.

125. Stefanelli M., Naitana M.L., Chiarini M., Nardis S., Ricci A., Fronczek F.R., Lo Sterzo C., Smith K.M., Paolesse R. Efficient synthesis of β-alkynylcorroles. Eur. J. Org. Chem. 2015. V. 2015. N 31. P. 6811-6816.

126. Vestfrid J., Botoshansky M., Palmer J.H., Durrell A.C., Gray H.B., Gross Z. Iodinated aluminium(III) corroles with long-lived triplet excited states. J. Am. Chem. Soc. 2011. V. 133. P. 12899–12901.

127. Vestfrid J., Goldberg I., Gross Z. Tuning the photophysical and redox properties of metallocorroles by iodination. Inorg. Chem. 2014. V. 53. P. 10536–10542.

128. Mahammed A., Botoshansky M., Gross Z. Chlorinated corroles. Dalton Trans. 2012. V. 41. P. 10938 – 10940.

129. Ngo T.H., Puntoriero F., Nastasi F., Robeyns K., Van Meervelt N., Campagna S., Dehaen W., Maes W. Synthetic, structural and photophysical exploration of meso-pyrimidinylsubstituted AB2-corroles. Chem.- Eur. J. 2010. V. 16. P. 5691–5705.

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133. Schmidlehner M., Faschinger F., Reith L.M., Ertl M., Schoefberger W. Water-soluble metalated and non-metalated A2B- and A3-corrole/aminoacid conjugates: syntheses, characterization and properties. Appl. Organometal. Chem. 2013. V. 27. N. 7. P. 395–405.

134. Stefanelli M., Mandoj F., Mastroianni M., Nardis S., Mohite P., Fronczek F.R., Smith K.M., Kadish K.M., Xiao X., Ou Z., Chen P., Paolesse R. Amination reaction on copper and germanium β-nitrocorrolates. Inorg. Chem. 2011. V. 50. P. 8281–8292.

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136. Scrivanti A., Beghetto V., Matteoli U., Antonaroli S., Marini A., Mandoj F., Paolesse R., Crociani B. Iminophosphine-palladium(0) complexes as highly active catalysts in the Suzuki reaction. Synthesis of undecaaryl substituted corroles. Tetrahedron Lett. 2004. V. 45. N. 30. P. 5861–5864.

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138. Gao D., Andeme Edzang J., Diallo A.K., Dutrong T., Balaban T.S., Videlot-Ackermann, Terazzi E., Canard G. Light absorption and hole-transport properties of copper corroles: from aggregates to a liquid crystal mesophase. New J. Chem. 2015. V. 39. P. 7140-7146.

139. Gao D., Canard G., Giorgi M., Vanloot P., Balaban T.S. Electronic and steric effects of the peripheral substitution in deca- and undecaaryl metallocorroles. Eur. J. Inorg. Chem. 2014. N. 2. V. 2014. – P. 279–287.

140. Berezin D.B., Krestyaninov M.A. Structure of H-associates of porphyrins, inverted porphyrinoids, and corroles with N.N-dimethylformamide. J. Struct. Chem. 2014. V. 55. No. 5. P. 868−876 (in Russian).

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142. Ou Z., Sun H., Zhu W., Da Z., Kadish K.M. Solvent and acidity effects on the UV-visible spectra and protonation-deprotonation of free-base octaethylcorrole. J. Porph. Phthaloc. 2008. V. 12. P. 1–10.

143. Shen J., Shao J., Ou Z., E W., Koszarna B., Gryko D.T., Kadish K.M. Electrochemistry and spectroelectrochemistry of meso-substituted free-base corroles in nonaqueous media: reactions of (Cor)H3, [(Cor)H4]+ and [(Cor)H2]-. Inorg. Chem. 2006. V.45. N.5. P. 2251–2265.

144. Ventura B., Degli Esposti A., Koszarna B., Gryko D.T., Flamigni L. Photophysical characterization of free-base corroles, promising chromophores for light energy conversion and singlet oxygen generation. New J. Chem. 2005. V. 29. P. 1559–1566.

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146. Karimov D.R., Barannikov V.P., Maltseva O.V., Kumeev R.S., Berezin D.B. Unfinished acid-base interactions of corroles with electron-donor solvents. Izvestiya VUZov. Chemistry and Chemical Technology 2011. No. 4. P. 26–33 (in Russian).

147. Berezin D.B., Karimov D.R. Porphyrins and porphyrin analogs interactions to coordinating organic solvents. Macroheterocycles. 2009. N. 2. P. 42–51.

148. Ou Z., Shen J., Shao J., E W., Galezowski M., Gryko D.T., Kadish K.M. Protonated free-base corroles: acidity, electrochemistry and spectroelectrochemistry of [(Cor)H4]+, [(Cor)H5]2+ and [(Cor)H6]3+. Inorg. Chem. 2007. V.46. N.7. P. 2775–2786.

149. Likhonina A.E., Krestyaninov M.A., Morshnev F.K., Cretan E.L., Kudayarova T.V., Berezin D.B. Interaction of meso-phenyl-substituted porphyrinoids with carbon acids and thermal analysis of their cationic salts. J. Phys. Chem. 2020. V. 94. No. 1. P. 110–118 (in Russian).

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154. Stefanelli M., Nardis S., Tortora L., Fronczek F.R., Smith K.M., Licoccia S., Paolesse R. Nitration of iron corrolates: further evidence for non-innocence of the corrole ligand. Chem. Commun. 2011. V. 47. P. 4255–4257.

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156. Gross Z., Simkhovich L., Galili N. First catalysis by corrole metal complexes: epoxidation, hydroxylation and cyclopropanation. Chem. Commun. 1999. P. 599–600.

157. Gross Z., Golubkov G., Simkhovich L. Epoxidation catalysis by a manganese corrole and isolation of an oxomanganese(V) corrole. Angew. Chem., Int. Ed. 2000. V. 39. P. 4045–4047.

158. Liu H.-Y., Lai T.-S., Yeung L.-L., Chang C.K. First synthesis of perfluorinated corrole and its Mn=O complex. Org. Lett. 2003. V. 5. P. 617–620.

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160. Luobeznova I., Raizman M., Goldberg I., Gross Z. Synthesis and full characterization of molybdenum and antimony corroles and utilization of the latter complexes as very efficient catalysts for highly selective aerobic oxygenation reactions. Inorg. Chem. 2006. V.45. P. 386–394.

161. Wagnert L., Berg A., Stavitski E., Berthold T., Kothe G., Goldberg I., Mahammed A., Simkhovich L., Gross Z., Levanon H. Exploring the photoexcited triplet states of aluminum and tin corroles by time-resolved Q-band EPR. Appl. Magn. Reson. 2006. V. 30. P. 591–604.

162. Collman J.P., Zeng L., Decreau R.A. Multiple active oxidants in competitive epoxidations catalyzed by porphyrins and corroles. Chem. Commun. 2003. P. 2974–2975.

163. Wang S.H., Mandimutsira B.S., Todd R., Ramdhanie B., Fox J.P., Goldberg D.P. Catalytic sulfoxidation and epoxidation with a Mn(III) triazacorrole: evidence for a “third oxidant” in high-valent porphyrinoid oxidations. J. Am. Chem. Soc. 2004. V. 126. P. 18–19.

164. Bose S., Pariyar A., Biswas A.N., Das P., Bandyopadhyay P. Manganese(III) corrole catalyzed selective oxidation of alcohols to carbonyl compounds by tert-butyl peroxide under mild condition. Catal. Commun. 2011. V. 12. P. 446–449.

165. Meier-Callahan A.E., Di Bilio A.J., Simkhovich L., Mahammed A., Goldberg I., Gray H.B., Gross Z. Chromium corroles in four oxidation states. Inorg. Chem. 2001. V.40. P. 6788–6793.

166. Mahammed A., Gray H.B., Meier-Callahan A.E., Gross Z. Aerobic oxidations catalysed by chromium corroles. J. Am. Chem. Soc. 2003. V. 125. P. 1162–1163.

167. Collman J.P., Kaplum M., Decreau R.A. Metal corroles as electrocatalysts for oxygen reduction. Dalton Trans. 2006. P. 554–559.

168. Mahammed A., Gross Z. Albumin-conjugated corrole metal complexes: extremely simple yet very efficient biomimetic oxidation systems. J. Am. Chem. Soc. 2005. V. 127. P. 2883–2887.

169. Mahammed A., Gross Z. Highly efficient catalase activity of metallocorroles. Chem. Commun. 2010. V. 46. P. 7040–7042.

170. Bazanov M.I., Berezina N.M., Karimov D.R., Berezin D.B. Electrochemical and electrocatalytic properties of meso-triphenylcorrole and its complexes with Mn (III), Co(III), Cu (III) and Zn (II). Electrochemistry. 2012. V. 48. No. 9. P. 992–997 (in Russian).

171. Berezina N.M., Karimov D.R., Bazanov M.I., Berezin D.B. Influence of functional substitution on electrochemical characteristics and electrocatalytic activity of meso-triphenylcorrole and its complexes with Cu(III) and Mn(III). Izvestiya VUZov. Chemistry and Chemical Technology 2013. V. 56. Issue 6. P. 37–41 (in Russian).

172. Berezina N.M., Thao Vu Thi, Karimov D.R., Kumeev R.S., Kustov A.V., Bazanov M.I., Berezin D.B. Synthesis and properties of products of β-bromination of metal complexes of meso-triphenylcorrole. J. General Chem. 2014 V. 84. No. 4. P. 661–669 (in Russian).

173. Berezina N.M., Thao Vu Thi, Berezin D.B., Bazanov M.I. Synthesis and redox characteristics of iron complexes with triphenyl-substituted corroles when exposed to argon and oxygen. J. Inorg. Chem. 2017. V. 62. No. 12. P. 1614-1619 (in Russian).

174. Simkhovich L., Mahammed A., Goldberg I., Gross Z. Synthesis and characterization of germanium, tin, phosphorus, iron, and rhodium complexes of tris(pentafluorophenyl)corrole, and the utilization of the iron and rhodium corroles as cyclopropanation catalysts. Chem. Eur. J. 2001. V. 7. P. 1041–1055.

175. Aviv I., Gross Z. Iron corroles and porphyrins as very efficient and highly selective catalysts for the reactions of α-diazo esters with amines. Synlett. 2006. V. 6. P. 951–953.

176. Aviv I., Gross Z. Iron porphyrins catalyse the synthesis of non-protected amino acid esters from ammonia and diazoacetates. Chem. Commun. 2006. P. 4477–4479.

177. Simkhovich L., Gross Z. Iron(IV) corroles are potent catalysts for aziridination of olefins by chloramine-T. Tetrahedron Lett. 2001. V. 42. P. 8089–8092.

178. Mairena M.A., Diaz-Requejo M.M., Belderrain T.R., Nicasio M.C., Trofimenko S., Perez P.J. Copper-homoscorpionate complexes as very active catalysts for the olefin aziridination reaction. Organometallics. 2004. V. 23. P. 253–256.

179. Jain S.L., Sain B. Metallophthalocyanines as potent catalysts for aziridination of olefins. J. Mol. Catal. A. Chem. 2003. V. 195. P. 283–287.

180. Nakano K., Kobayashi K., Ohkawara T., Imoto H., Nozaki K. Copolymerization of epoxides with carbon dioxide catalyzed by iron-corrole complexes: synthesis of a crystalline copolymer. J. Am. Chem. Soc. 2013. V. 135. P. 8456-8459.

181. Barbe J.-M., Canard G., Brandes S., Jerome F., Dubois G., Guilard R. Metallocorroles as sensing components for gas sensors: remarkable affinity and selectivity of cobalt(III) corroles for CO vs. O2 and N2. Dalton Trans. 2004. P. 1208–1214.

182. Barbe J.-M., Canard G., Brandes S., Guilard R. Selective chemisorption of carbon monoxide by organic-inorganic hybrid materials incorporating cobalt(III) corroles as sensing components. Chem. Eur. J. 2007. V. 13. P. 2118-2129.

183. Kim K., Kim I., Maiti N., Kwon S.J., Bucella D., Egorova O.A., Lee Y.S., Kwak J., Churchill D.G. A study of nerve agent model organophosphonate binding with manganese-A2B-corrole and -A2B2-porphyrin systems. Polyhedron. 2009. V. 28. P. 2418-2430.

184. Mahammed A., Weaver J.J., Gray H.B., Abdelas M., Gross Z. How acidic are corroles and why? Tetrahedron Lett. 2003. V. 44. P. 2077-2079.

185. Li C.-Y., Zhang X.-B., Han Z.-X., Akermark B., Sun L., Shen G.-L., Yu R.-Q. A wide pH range optical sensing system based on a sol-gel encapsulated amino-functionalized corrole. Analyst. 2006. V. 133. P. 388-393.

186. Zhang X.-B., Han Z.-X., Fang Z.-H., Shen G.-L., Yu R.-Q. 5,10,15-Tris(pentafluorophenyl)corrole as highly selective neutral carrier for a silver ion-sensitive electrode. Anal. Chim. Acta. 2006. V. 562. P. 210-215.

187. He C.-L., Ren F.-L., Zhang X.-B., Han Z.-X. A fluorescent chemical sensor for Hg(II) based on a corrole derivative in a PVC matrix. Talanta. 2006. V. 70. P. 364-369.

188. Radecki J., Stenka I., Dolusic E., Dehaen W., Plavec J. Potentiometric discrimination of neutral forms of nitrophenol isomers by liquid membrane electrodes incorporated with corroles. Comb. Chem. High Throughput Screening. 2004. V. 7. P. 375–381.

189. Radecki J., Dehaen W. Nitrogen-containing macrocycles as host molecules for the recognition of undissociated phenol derivatives: mechanism of potenciometric signal generation. Comb. Chem. High Throughput Screening. 2006. V. 9. P. 399-406.

190. Radecki J., Stenka I., Dolusic E., Dehaen W. Corroles as receptors in liquid membrane electrodes and their potentiometric response towards salicylic acid. Electrochim. Acta. 2006. V. 51. P. 2282-2288.

191. Walker D., Chappel S., Mahammed A., Weaver J.J., Brunschwig B.S., Winkler J.R., Gray H.B., Zaban A., Gross Z. Corrole-sensitized TiO2 solar cells. J. Porph. Phthaloc. 2006. V. 10. P. 1259-1262.

192. Wiedau-Pazos M., Goto J.J., Rabizadeh S., Gralla E.B., Roe J.A., Lee M.K., Valentine J.S., Bredsen D.E. Altered reactivity of superoxide dismutase in familial amyotrophic lateral sclerosis. Science. 1996. V. 271. P. 515-518.

193. Yondim M.B.H., Mandel S., Amit T., Bar-Am O., Kupershmidt L., Gross Z., Mahammed A., Saltsman I., Okun Z. Corroles for neuroprotection and neurorescue. US. Pat. 20110098262, 28.04.2011.

194. Teo R.D., Hwang J.Y., Termini J., Gross Z., Gray H.B. Fighting cancer with corroles. Chem. Rev. 2016. V. 117 (4). P. 2711-2729.

195. Hwang J.Y., Lubow J., Chu D. A mechanistic study of tumor-targeted corrole toxicity. Mol. Pharm. 2011. V. 8. P. 2233-2243.

196. Agostinis P., Berg K., Cengel K.A. Photodynamic therapy of cancer: an update. Cancer J. Clin. 2011. V. 61. P. 250-281.

197. Lim P., Mahammed A., Okun Z., Saltsman I., Gross Z., Gray H.B., Termini J. Differential cytostatic and cytotoxic action of metallocorroles against human cancer cells: potential platforms for anticancer drug development. Chem. Res. Toxicol. 2012. V. 25. P. 400−409.

198. Vakrat-Haglili Y., Weiner L., Brumfeld V. The microenvironment effect on the generation of reactive oxygen species by Pd−bacteriopheophorbide. J. Am. Chem. Soc. 2005. V. 127. P. 6487–6497.

199. Aviezer D., Cotton S., David M., Segev A., Khaselev N., Galili N., Gross Z., Yayon A. Porphyrin analogues as novel antagonists of fibroblast growth factor and vascular endothelial growth factor receptor binding that inhibit endothelial cell proliferation, tumor progression, and metastasis. Cancer Res. 2000. V. 60. P. 2973–2980.

200. Sims J. D., Hwang J.Y., Wagner Sh. A corrole nanobiologic elicits tissue-activated MRI contrast enhancementand tumor-targeted toxicity. J. Contr. Release. 2015. V. 217. P. 92-101.

201. Tsyb A.F., Kaplan M.A., Romanko Yu.S., Popuchiev V.V. Clinical aspects of photodynamic therapy. N.F. Bochkareva Scientific Literature Publishing House. Kaluga. 2009. 204 p. (in Russian).

202. Huang L., Dai T., Hamblin M.R. Antimicrobial photodynamic inactivation and photodynamic therapy for infections. In: Photodynamic therapy. Methods and Protocols. Charles J. Gomer Ed. Humana Press. 2010. P. 155-175.

203. Preuss A., Saltsman I., Mahammed A. Photodynamic inactivation of moldi fungi spores by newly developed charged corroles. J. Photochem. Photobiol. B: Biology. 2014. V. 133. P. 39-46.

204. Pohl J., Saltsman I., Mahammed A., Gross Z., Röder B. Inhibition of green algae growth by corrole-based photosensitizers. J. Appl. Microbiol. 2014. V. 118. P. 305-312.

205. Hwang J.Y., Wachsmann-Hogiu S., Ramanujan V.K. Multimodal wide-field two-photon excitation imaging: characterization of the technique for in vivo applications. Biomed. Opt. Express. 2011. V. 2. N. 2. P. 356- 364.