Abstract
The reaction of cobalt(ɪɪ) chloride with p-Br-benzoyl-β-(piperidin-1-yl)propioamid-oxime (Linit) in methanol leads to the hydrolysis of the ligand at the -OCO- ester bond and the formation of the mixed-valence hexanuclear ionic complex [CoII2CoIII4(HL)4(L)2(O)-(Cl)4]Cl2•4CH3OH (1) (L is β-(piperidin-l-yl)propioamidoxime). According to the X-ray diffraction data, the ligand (L) in 1 is coordinated to the complexing agent in different modes: the μ3-bridging-chelating mode (involving deprotonated amino groups) and the μ2- and μ3-bridging-chelating modes in the case of a coordinated amino group. Two cobalt atoms of the hexanuclear metal core have a tetrahedral coordination geometry (CoIIN2Cl2; CNCoII = 4), whereas the other four cobalt atoms are in an octahedral coordination environment of nitrogen and oxygen atoms forming the polyhedra of composition CoIIIO3N3 and CoIIIO4N2 (CNCoIII = 6). The evaluation of the in vitro biological activity of 1 against the non-pathogenic (virulent H37Rv model) mycobacterial strain of Mycolicibacterium smegmatis showed an increase in the efficiency of complex 1 by more than 4–12 times compared to the previously studied CoII,III complexes.
Similar content being viewed by others
References
M. M. Rashad, O. A. Fouad, Mater. Chem. Phys., 2005, 94, 365; DOI: https://doi.org/10.1016/j.matchemphys.2005.05.028.
M. K. Karunananda, F. X. Vázquez, E. E. Alp, W. Bi, S. Chattopadhyay, T. Shibatad, N. P. Mankad, Dalton Trans., 2014, 43, 13661; DOI: https://doi.org/10.1039/C4DT01841A.
M. Veith, M. Haas, V. Huch, Chem. Mater., 2005, 17, 95; DOI: https://doi.org/10.1021/cm0401802.
R. V. Godbole, P. Rao, P. S. Alegaonkar, S. Bhagwat, Mater. Chem. Phys., 2015, 161, 135; DOI: https://doi.org/10.1016/j.matchemphys.2015.05.028.
L. W. Yeary, J. W. Moon, C. J. Rawn, L. J. Love, A. J. Rondinone, J. R. Thompson, B. C. Chakoumakos, T. J. Phelps, J. Magn. Magn. Mater., 2011, 323, 3043; DOI: https://doi.org/10.1016/j.jmmm.2011.06.049.
K. D. Mjos, C. Orvig, Chem. Rev., 2014, 114, 4540; DOI: https://doi.org/10.1021/cr400460s.
M. J. Cleare, J. D. Hoeschele, Bioinorg. Chem., 1973, 2, 187; DOI: https://doi.org/10.1016/S0006-3061(00)80249-5.
M. J. Cleare, J. D. Hoeschele, Platinum Met. Rev., 1973, 17, 2.
S. Gibaud, G. Jaouen, Med. Organometall. Chem., 2010, 32, 1; DOI: https://doi.org/10.1007/978-3-642-13185-1_1.
M. Patra, G. Gasser, N. Metzler-Nolte, Dalton Trans., 2012, 41, 6350; DOI: https://doi.org/10.1039/C2DT12460B.
E. S. Honsa, M. D. L. Johnson, J. W. Rosch, Front. Cell. Infect. Microbiol., 2013, 3, 92; DOI: https://doi.org/10.3389/fcimb.2013.00092.
P. Nagababu, J. Naveena, L. Latha, P. Pallavi, S. Harish, S. Satyanarayana, Canad. J. Microbiol., 2006, 52, 1247; DOI: https://doi.org/10.1139/w06-087.
K. Phopin, N. Sinthupoom, L. Treeratanapiboon, S. Kunwittaya, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, EXCLI J., 2016, 15, 144; DOI: https://doi.org/10.17179/excli2016-101.
B. Rosenberg, L. Vancamp, T. Krigas, Nature, 1965, 205, 698; DOI: https://doi.org/10.1038/205698A0.
O. Krasnovskaya, A. Naumov, D. Guk, P. Gorelkin, A. Erofeev, E. Beloglazkina, A. Majouga, Int. J. Mol. Sci., 2020, 21, 3965; DOI: https://doi.org/10.3390/ijms21113965.
A. H. Ngwane, R. D. Petersen, B. Baker, I. Wiid, H. Wong, R. K. Haynes, IUBMB Life, 2019, 71, 532; DOI: https://doi.org/10.1002/iub.2002.
I. A. Lutsenko, D. E. Baravikov, M. A. Kiskin, Yu. V. Nelyubina, P. V. Primakov, O. B. Bekker, A. V. Khoroshilov, A. A. Sidorov, I. L. Eremenko, Russ. J. Coord. Chem., 2020, 46, 411; DOI: https://doi.org/10.1134/S1070328420060056.
I. A. Lutsenko, D. S. Yambulatov, M. A. Kiskin, Yu. V. Nelyubina, P. V. Primakov, O. B. Bekker, A. A. Sidorov, I. L. Eremenko, Russ. J. Coord. Chem., 2020, 46, 787; DOI: https://doi.org/10.1134/S1070328420120040.
I. A. Lutsenko, D. S. Yambulatov, M. A. Kiskin, Yu. V. Nelyubina, P. V. Primakov, O. B. Bekker, O. A. Levitskiy, T. V. Magdesieva, V. K. Imshennik, Yu. V. Maksimov, A. A. Sidorov, V. N. Danilenko, I. L. Eremenko, Chem. Select., 2020, 5, 11837; DOI: https://doi.org/10.1002/slct.202003101.
I. A. Lutsenko, M. A. Kiskin, K. A. Koshenskova, P. V. Primakov, A. V. Khoroshilov, O. B. Bekker, I. L. Eremenko, Russ. Chem. Bull., 2021, 70, 463; DOI: https://doi.org/10.1007/s11172-021-3109-3.
M. A. Uvarova, I. A. Lutsenko, M. A. Kiskin, Yu. V. Nelyubina, P. V. Primakov, K. A. Babeshkin, N. N. Efimov, A. S. Goloveshkin, M. A. Shmelev, A. V. Khoroshilov, E. M. Zueva, M. M. Petrova, O. B. Bekker, I. L. Eremenko, Polyhedron, 2021, 203, 115241; DOI: https://doi.org/10.1016/j.poly.2021.115241.
I. A. Lutsenko, M. E. Nikiforova, K. A. Koshenskova, M. A. Kiskin, Yu. V. Nelyubina, P. V. Primakov, M. V. Fedin, O. B. Becker, V. O. Shender, I. K. Malyants, I. L. Eremenko, Russ. J. Coord. Chem., 2021, 47, 879; DOI: 101134/S1070328421350013.
I. A. Lutsenko, D. E. Baravikov, K. A. Koshenskova, M. A. Kiskin, Yu. V. Nelyubina, P. V. Primakov, Y. K. Voronina, V. V. Garaeva, D. A. Aleshin, T. M. Aliev, V. N. Danilenko, O. B. Bekker, I. L. Eremenko, RSC Advances, 2022, 12, 5173; DOI: https://doi.org/10.1039/d1ra08555g.
Pat. 2592 (Kazakhstan); Byul. Izobret. [Inventor Bull.], 2018, 4 (in Russian).
Pat. 102219 (Kazakhstan); Byul. Izobret. [Inventor Bull.], 2018, 18 (in Russian).
Pat. 1983 (Kazakhstan); Byul. Izobret. [Inventor Bull.], 2017, 2 (in Russian).
Pat. 12701 (Kazakhstan); Byul. Izobret. [Inventor Bull.], 2006, 7 (in Russian).
V. N. Serezhkin, A. V. Vologzhanina, L. B. Serezhkina, E. S. Smirnova, E. V. Grachova, P. V. Ostrova, M. Y. Antipin, Acta Cryst., 2009, B65, 45; DOI: https://doi.org/10.1107/S0108768108038846.
C. R. Groom, I. J. Bruno, M. P. Lightfoot, S. C. Ward, Acta Cryst., 2016, 72, 171; DOI: https://doi.org/10.1107/S2052520616003954.
G. Y. An, Hong-Bo Wang, Ai-Li Cui, Hui-Zhong Kou, New J. Chem., 2014, 38, 5037; DOI: https://doi.org/10.1039/C4NJ01055H.
H.-Z. Kou, G.-Y. An, C.-M. Ji, B.-W. Wang, A.-L. Cui, Dalton Trans., 2010, 39, 9604; DOI: https://doi.org/10.1039/C0DT00528B.
C.-M. Ji, H.-J. Yang, C.-C. Zhao, V. Tangoulis, A.-L. Cui, H.-Z. Kou, Cryst. Growth Des., 2009, 9, 4607; DOI: https://doi.org/10.1021/cg900975y.
X. Jiang, G.-Y. An, C.-M. Liu, H.-Z. Kou, Eur. J. Inorg. Chem., 2015, 32, 5314; DOI: https://doi.org/10.1002/ejic.201500930.
C. G. Efthymiou, L. Cunha-Silva, S. P. Perlepes, E. K. Brechin, R. Inglis, M. Evangelisti, C. Papatriantafyllopoulou, Dalton Trans., 2016, 45, 17409; DOI: https://doi.org/10.1039/C6DT03511F.
S. Ramon-García, C. Ng, H. Anderson, J. D. Chao, X. Zheng, T. Pfeifer, Y. Av-Gay, M. Roberge, C. J. Thompson, Antimikrob. Agen. Chemother., 2011, 8, 3861; DOI: https://doi.org/10.1128/AAC.00474-11.
O. B. Bekker, D. N. Sokolov, O. A. Luzina, N. I. Komarova, Yu. V. Gatilov, S. N. Andreevskaya, T. G. Smirnova, D. A. Maslov, L. N. Chernousova, N. F. Salakhutdinov, V. N. Danilenko, Med. Chem. Res., 2015, 24, 2926; DOI: https://doi.org/10.1007/s00044-015-1348-2.
L. A. Kayukova, I. S. Zhumadildaeva, K. D. Praliyev, Russ. Chem. Bull., 2002, 51, 2100; DOI: https://doi.org/10.1023/A:1021628430346.
T. G. G. Battye, L. Kontogiannis, O. Johnson, H. R. Powell, A. G. W. Leslie, Acta Cryst., 2011, D67, 271; DOI: https://doi.org/10.1107/s0907444910048675.
P. Evans, Acta Cryst., 2006, D62, 72; DOI: https://doi.org/10.1107/S0907444905036693.
G. M. Sheldrick, Acta Cryst., 2015, A71, 3; DOI: https://doi.org/10.1107/S2053273314026370.
G. M. Sheldrick, Acta Cryst., 2015, C71, 3; DOI: https://doi.org/10.1107/S2053229614024218.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst., 2009, 42, 339; DOI: https://doi.org/10.1107/S0021889808042726.
Funding
The study was funded by the Science Committee of the Ministry of Education and Science of the Republic of Kazakhstan (grant for IRN Project No. AP08856440 and IRN Program No. BR10965255). Elemental analysis and IR spectroscopy were performed using the equipment of the Joint Research Center of Physical Investigation Methods for Substances and Materials of the N. S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences (JRC PMR IGIC RAS). The X-ray diff raction study of compound 1 was carried out at the National Research Center “Kurchatov Institute”. A. V. Vologzhanina is grateful to the Ministry of Science and Higher Education of the Russian Federation for the financial support (state assignment No. AAAAA18-118012590337-6).
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2172–2178, October, 2022.
No human or animal subjects were used in this research.
The authors declare no competing interests.
Rights and permissions
About this article
Cite this article
Lutsenko, I.A., Vologzhanina, A.V., Kayukova, L.A. et al. Mixed-valence hexanuclear CoII,III complex with amidoxime: synthesis, structure, and in vitro biological activity against the non-pathogenic strain of Mycolicibacterium smegmatis. Russ Chem Bull 71, 2172–2178 (2022). https://doi.org/10.1007/s11172-022-3643-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-022-3643-7