Metal-(Acyclic Diaminocarbene) Complexes Demonstrate Nanomolar Antiproliferative Activity against Triple-Negative Breast Cancer

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Metal-(Acyclic Diaminocarbene) Complexes Demonstrate Nanomolar Antiproliferative Activity against Triple-Negative Breast Cancer. / Каткова, Светлана Александровна ; Бунев, Александр Сиясатович; Гасанов, Ровшан Эльбрус оглы; Кульша, Андрей Вячеславович; Хоченков, Дмитрий Александрович; Ивашкевич , Олег Анатольевич; Серебрянская, Татьяна Владимировна; Кинжалов, Михаил Андреевич.

In: Chemistry - A European Journal, 16.02.2024.

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

Author

Каткова, Светлана Александровна ; Бунев, Александр Сиясатович ; Гасанов, Ровшан Эльбрус оглы ; Кульша, Андрей Вячеславович ; Хоченков, Дмитрий Александрович ; Ивашкевич , Олег Анатольевич ; Серебрянская, Татьяна Владимировна ; Кинжалов, Михаил Андреевич. / Metal-(Acyclic Diaminocarbene) Complexes Demonstrate Nanomolar Antiproliferative Activity against Triple-Negative Breast Cancer. In: Chemistry - A European Journal. 2024.

BibTeX

@article{88ec09ee9c8f472d8d49c28d8d54dad6,

title = "Metal-(Acyclic Diaminocarbene) Complexes Demonstrate Nanomolar Antiproliferative Activity against Triple-Negative Breast Cancer",

abstract = "Hydrolytically stable PdII and PtII complexes supported by acyclic diaminocarbene ligands represent a novel class of structural organometallic anticancer agents exhibiting nanomolar antiproliferative activity in a panel of cancer cell lines (IC50 0.07–0.81 μM) and up to 300-fold selectivity for cancer cells over normal primary fibroblasts. The lead drug candidate was 300 times more potent than cisplatin in vitro and showed higher efficacy in reducing the growth of aggressive MDA-MB-231 xenograft tumors in mice. {\textcopyright} 2024 Wiley-VCH GmbH.",

keywords = "antitumor agents, diaminocarbenes, drug discovery, palladium, platinum, Cancer cells, Cells, Diseases, Drug products, Mammals, Organometallics, Palladium compounds, Platinum compounds, Acyclic diaminocarbenes, Anti-cancer agents, Antiproliferative activities, Antitumour agents, Cancer cell lines, Diaminocarbenes, Drug discovery, Nanomolar, Triple-negative breast cancers, Cell culture",

author = "Каткова, {Светлана Александровна} and Бунев, {Александр Сиясатович} and Гасанов, {Ровшан Эльбрус оглы} and Кульша, {Андрей Вячеславович} and Хоченков, {Дмитрий Александрович} and Ивашкевич, {Олег Анатольевич} and Серебрянская, {Татьяна Владимировна} and Кинжалов, {Михаил Андреевич}",

note = "Export Date: 11 March 2024 CODEN: CEUJE Адрес для корреспонденции: Kinzhalov, M.A.; Saint Petersburg State University, 7/9 Universitetskaya Nab., Russian Federation; эл. почта: m.kinzhalov@spbu.ru Сведения о финансировании: Russian Science Foundation, RSF, 24‐23‐00367 Текст о финансировании 1: This work was supported by the Russian Science Foundation (project 24‐23‐00367; synthesis and physicochemical study). The DFT calculations were performed by A.V.K. and O.A.I. in the framework of the State Program for Scientific Research of the Republic of Belarus “Chemical processes, reagents and technologies, bioregulators and bioorganic chemistry” (project 2.2.01.06, st. reg. N 20210516). The authors wish to thank Dr. Alena Gnedina (Institute of Cytology RAS) and Palina Nepachalovich (TU Dresden) for fruitful discussions. Measurements were performed at the Center for Magnetic Resonance, the Center for X‐ray Diffraction Studies, the Center for Chemical Analysis and Materials Research, the Center for Diagnostics of Functional Materials for Medicine, Pharmacology and Nanoelectronics, the Thermogravimetric and Calorimetric Research Centre, and the Cryogenic Department (all belonging to St. Petersburg State University). The JC‐1 dye was provided by the company Lumiprobe RUS Ltd. o Пристатейные ссылки: Sung, H., Ferlay, J., Siegel, R.L., Laversanne, M., Soerjomataram, I., Jemal, A., Bray, F., (2021) Ca-Cancer J. Clin., 71, pp. 209-249; Liao, G., Yang, Y., Xie, A., Jiang, Z., Liao, J., Yan, M., Zhou, Y., Li, X., (2022) Front. Cell Dev. Biol., 10; Li, Y., Zhang, H., Merkher, Y., Chen, L., Liu, N., Leonov, S., Chen, Y., (2022) J. Hematol. Oncol., 15, p. 121; Bianchini, G., Balko, J.M., Mayer, I.A., Sanders, M.E., Gianni, L., (2016) Nat. Rev. Clin. Oncol., 13, pp. 674-690; Lee, J.S., Yost, S.E., Yuan, Y., (2020) Cancers, 12, p. 1404; Nayeem, N., Contel, M., (2021) Chem. Eur. J., 27, pp. 8891-8917; Zhang, J.-J., Xu, Q.-J., Schmidt, C., Maaty, M.A.A.E., Song, J., Yu, C., Zhou, J., W{\"o}lfl, S., (2023) J. Med. Chem., 66, pp. 3995-4008; Dilruba, S., Kalayda, G.V., (2016) Cancer Chemother. Pharmacol., 77, pp. 1103-1124; Siddik, Z.H., (2003) Oncogene, 22, pp. 7265-7279; McWhinney, S.R., Goldberg, R.M., McLeod, H.L., (2009) Mol. Cancer Ther., 8, pp. 10-16; Scattolin, T., Voloshkin, V.A., Visentin, F., Nolan, S.P., (2021) Cell Rep. Phys. Sci., 2; Wang, C.H., Shih, W.C., Chang, H.C., Kuo, Y.Y., Hung, W.C., Ong, T.G., Li, W.S., (2011) J. Med. Chem., 54, pp. 5245-5249; Ibrahim, N., Touj, N., Koko, W., Khan, T., Ozdemir, I., Yasar, S., Hamdi, N., (2020) Catalysts, 10; Fong, T.T.H., Lok, C.N., Chung, C.Y.S., Fung, Y.M.E., Chow, P.K., Wan, P.K., Che, C.M., (2016) Angew. Chem. Int. Ed., 55, pp. 11935-11939; Serebryanskaya, T.V., Kinzhalov, M.A., Bakulev, V., Alekseev, G., Andreeva, A., Gushchin, P.V., Protas, A., Kasyanenko, N.A., (2020) New J. Chem., 44, pp. 5762-5773; Kathuria, D., Raul, A.D., Wanjari, P., Bharatam, P.V., (2021) Eur. J. Med. Chem., 219; Rusanov, D.A., Zou, J., Babak, M.V., (2022) Pharmaceuticals, 15, p. 453; Gopalakrishnan, D., Ganeshpandian, M., Loganathan, R., Bhuvanesh, N.S.P., Sabina, X.J., Karthikeyan, J., (2017) RSC Adv., 7, pp. 37706-37719; Babak, M.V., Chong, K.R., Rapta, P., Zannikou, M., Tang, H.M., Reichert, L., Chang, M.R., Ang, W.H., (2021) Angew. Chem. Int. Ed., 60, pp. 13405-13413; O′Neil, N.J., Bailey, M.L., Hieter, P., (2017) Nat. Rev. Genet., 18, pp. 613-623; Menendez, J.A., Oliveras-Ferraros, C., Cuf{\'i}, S., Corominas-Faja, B., Joven, J., Martin-Castillo, B., Vazquez-Martin, A., (2012) Cell Cycle, 11, pp. 2782-2792; Feng, J., Lu, H., Ma, W., Tian, W., Lu, Z., Yang, H., Cai, Y., Jia, W., (2022) Protein Cell, 13, pp. 825-841; Benjamin, D., Robay, D., Hindupur, S.K., Pohlmann, J., Colombi, M., El-Shemerly, M.Y., Maira, S.M., Hall, M.N., (2018) Cell Rep., 25, pp. 3047-3058. , e3044; Kocemba-Pilarczyk, K.A., Trojan, S., Ostrowska, B., Lasota, M., Dudzik, P., Kusior, D., Kot, M., (2020) Pharmacol. Rep., 72, pp. 1407-1417; Karami, K., Parsianrad, F., Alinaghi, M., Amirghofran, Z., (2017) Inorg. Chim. Acta, 467, pp. 46-55; Katkova, S.A., Kinzhalov, M.A., Tolstoy, P.M., Novikov, A.S., Boyarskiy, V.P., Ananyan, A.Y., Gushchin, P.V., Kukushkin, V.Y., (2017) Organometallics, 36, pp. 4145-4159; Farrell, N.P., (2015) Chem. Soc. Rev., 44, pp. 8773-8785; Theodossiou, T.A., Ali, M., Grigalavicius, M., Grallert, B., Dillard, P., Schink, K.O., Olsen, C.E., Berg, K., (2019) npj Breast Cancer, 5, p. 13; Lunetti, P., Di Giacomo, M., Vergara, D., De Domenico, S., Maffia, M., Zara, V., Capobianco, L., Ferramosca, A., (2019) FEBS J., 286, pp. 688-709; Miripour, Z.S., Abbasvandi, F., Aghaee, P., NajafiKhoshnoo, S., Faramarzpour, M., Mohaghegh, P., Hoseinpour, P., Abdolahad, M., (2022) Bioeng. Transl. Med., 7; Semenza, G.L., (2019) Annu. Rev. Pharmacol. Toxicol., 59, pp. 379-403; Wang, Y., Hu, J., Cai, Y., Xu, S., Weng, B., Peng, K., Wei, X., Liang, G., (2013) J. Med. Chem., 56, pp. 9601-9611; Isaacs, J.S., Jung, Y.J., Mole, D.R., Lee, S., Torres-Cabala, C., Chung, Y.-L., Merino, M., Neckers, L., (2005) Cancer Cell, 8, pp. 143-153; Jeney, A., Hujber, Z., Szoboszlai, N., Full{\'a}r, A., Ol{\'a}h, J., Pap, {\'E}., M{\'a}rk, {\'A}., Sebesty{\'e}n, A., (2016) Cancer Cell Int., 16, p. 4; Elmore, S., (2007) Toxicol. Pathol., 35, pp. 495-516; Ga{\l}czy{\'n}ska, K., Drulis-Kawa, Z., Arabski, M., (2020) Molecules, 25, p. 3492; Yang, T., Zhu, M., Jiang, M., Yang, F., Zhang, Z., (2022) Front. Pharmacol., 13; Endale, H.T., Tesfaye, W., Mengstie, T.A., (2023) Front. Cell Dev. Biol., 11; Zhao, Y., Li, Y., Zhang, R., Wang, F., Wang, T., Jiao, Y., (2020) OncoTargets Ther., 13, pp. 5429-5441; Li, J., He, D., Li, S., Xiao, J., Zhu, Z., (2023) Front. Immunol., 14; Yang, F., Xiao, Y., Ding, J.H., Jin, X., Ma, D., Li, D.Q., Shi, J.X., Shao, Z.M., (2023) Cell Metab., 35, pp. 84-100. , e108; Yin, H., Zhu, M., (2012) Free Radical Res., 46, pp. 959-974; Kondo, A., Maeta, M., Oka, A., Tsujitani, S., Ikeguchi, M., Kaibara, N., (1996) Br. J. Cancer., 73, pp. 1166-1170; Vojtek, M., Gon{\c c}alves-Monteiro, S., {\v S}eminsk{\'a}, P., Valov{\'a}, K., Bell{\'o}n, L., Dias-Pereira, P., Marques, F., Diniz, C., (2022) Biomedicine, 10, p. 210; Chow, K.H.M., Sun, R.W.Y., Lam, J.B.B., Li, C.K.L., Xu, A., Ma, D.-L., Abagyan, R., Che, C.-M., (2010) Cancer Res., 70, pp. 329-337; Frik, M., Mart{\'i}nez, A., Elie, B.T., Gonzalo, O., Ram{\'i}rez de Mingo, D., Sana{\'u}, M., S{\'a}nchez-Delgado, R., Contel, M., (2014) J. Med. Chem., 57, pp. 9995-10012; Boros, E., Dyson, P.J., Gasser, G., (2020) Chem, 6, pp. 41-60; D{\"o}rr, M., Meggers, E., (2014) Curr. Opin. Chem. Biol., 19, pp. 76-81",

year = "2024",

month = feb,

day = "16",

doi = "10.1002/chem.202400101",

language = "Английский",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-Blackwell",

}

RIS

TY - JOUR

T1 - Metal-(Acyclic Diaminocarbene) Complexes Demonstrate Nanomolar Antiproliferative Activity against Triple-Negative Breast Cancer

AU - Каткова, Светлана Александровна

AU - Бунев, Александр Сиясатович

AU - Гасанов, Ровшан Эльбрус оглы

AU - Кульша, Андрей Вячеславович

AU - Хоченков, Дмитрий Александрович

AU - Ивашкевич , Олег Анатольевич

AU - Серебрянская, Татьяна Владимировна

AU - Кинжалов, Михаил Андреевич

N1 - Export Date: 11 March 2024 CODEN: CEUJE Адрес для корреспонденции: Kinzhalov, M.A.; Saint Petersburg State University, 7/9 Universitetskaya Nab., Russian Federation; эл. почта: m.kinzhalov@spbu.ru Сведения о финансировании: Russian Science Foundation, RSF, 24‐23‐00367 Текст о финансировании 1: This work was supported by the Russian Science Foundation (project 24‐23‐00367; synthesis and physicochemical study). The DFT calculations were performed by A.V.K. and O.A.I. in the framework of the State Program for Scientific Research of the Republic of Belarus “Chemical processes, reagents and technologies, bioregulators and bioorganic chemistry” (project 2.2.01.06, st. reg. N 20210516). The authors wish to thank Dr. Alena Gnedina (Institute of Cytology RAS) and Palina Nepachalovich (TU Dresden) for fruitful discussions. Measurements were performed at the Center for Magnetic Resonance, the Center for X‐ray Diffraction Studies, the Center for Chemical Analysis and Materials Research, the Center for Diagnostics of Functional Materials for Medicine, Pharmacology and Nanoelectronics, the Thermogravimetric and Calorimetric Research Centre, and the Cryogenic Department (all belonging to St. Petersburg State University). The JC‐1 dye was provided by the company Lumiprobe RUS Ltd. o Пристатейные ссылки: Sung, H., Ferlay, J., Siegel, R.L., Laversanne, M., Soerjomataram, I., Jemal, A., Bray, F., (2021) Ca-Cancer J. Clin., 71, pp. 209-249; Liao, G., Yang, Y., Xie, A., Jiang, Z., Liao, J., Yan, M., Zhou, Y., Li, X., (2022) Front. Cell Dev. Biol., 10; Li, Y., Zhang, H., Merkher, Y., Chen, L., Liu, N., Leonov, S., Chen, Y., (2022) J. Hematol. Oncol., 15, p. 121; Bianchini, G., Balko, J.M., Mayer, I.A., Sanders, M.E., Gianni, L., (2016) Nat. Rev. Clin. Oncol., 13, pp. 674-690; Lee, J.S., Yost, S.E., Yuan, Y., (2020) Cancers, 12, p. 1404; Nayeem, N., Contel, M., (2021) Chem. Eur. J., 27, pp. 8891-8917; Zhang, J.-J., Xu, Q.-J., Schmidt, C., Maaty, M.A.A.E., Song, J., Yu, C., Zhou, J., Wölfl, S., (2023) J. Med. Chem., 66, pp. 3995-4008; Dilruba, S., Kalayda, G.V., (2016) Cancer Chemother. Pharmacol., 77, pp. 1103-1124; Siddik, Z.H., (2003) Oncogene, 22, pp. 7265-7279; McWhinney, S.R., Goldberg, R.M., McLeod, H.L., (2009) Mol. Cancer Ther., 8, pp. 10-16; Scattolin, T., Voloshkin, V.A., Visentin, F., Nolan, S.P., (2021) Cell Rep. Phys. Sci., 2; Wang, C.H., Shih, W.C., Chang, H.C., Kuo, Y.Y., Hung, W.C., Ong, T.G., Li, W.S., (2011) J. Med. Chem., 54, pp. 5245-5249; Ibrahim, N., Touj, N., Koko, W., Khan, T., Ozdemir, I., Yasar, S., Hamdi, N., (2020) Catalysts, 10; Fong, T.T.H., Lok, C.N., Chung, C.Y.S., Fung, Y.M.E., Chow, P.K., Wan, P.K., Che, C.M., (2016) Angew. Chem. Int. Ed., 55, pp. 11935-11939; Serebryanskaya, T.V., Kinzhalov, M.A., Bakulev, V., Alekseev, G., Andreeva, A., Gushchin, P.V., Protas, A., Kasyanenko, N.A., (2020) New J. Chem., 44, pp. 5762-5773; Kathuria, D., Raul, A.D., Wanjari, P., Bharatam, P.V., (2021) Eur. J. Med. Chem., 219; Rusanov, D.A., Zou, J., Babak, M.V., (2022) Pharmaceuticals, 15, p. 453; Gopalakrishnan, D., Ganeshpandian, M., Loganathan, R., Bhuvanesh, N.S.P., Sabina, X.J., Karthikeyan, J., (2017) RSC Adv., 7, pp. 37706-37719; Babak, M.V., Chong, K.R., Rapta, P., Zannikou, M., Tang, H.M., Reichert, L., Chang, M.R., Ang, W.H., (2021) Angew. Chem. Int. Ed., 60, pp. 13405-13413; O′Neil, N.J., Bailey, M.L., Hieter, P., (2017) Nat. Rev. Genet., 18, pp. 613-623; Menendez, J.A., Oliveras-Ferraros, C., Cufí, S., Corominas-Faja, B., Joven, J., Martin-Castillo, B., Vazquez-Martin, A., (2012) Cell Cycle, 11, pp. 2782-2792; Feng, J., Lu, H., Ma, W., Tian, W., Lu, Z., Yang, H., Cai, Y., Jia, W., (2022) Protein Cell, 13, pp. 825-841; Benjamin, D., Robay, D., Hindupur, S.K., Pohlmann, J., Colombi, M., El-Shemerly, M.Y., Maira, S.M., Hall, M.N., (2018) Cell Rep., 25, pp. 3047-3058. , e3044; Kocemba-Pilarczyk, K.A., Trojan, S., Ostrowska, B., Lasota, M., Dudzik, P., Kusior, D., Kot, M., (2020) Pharmacol. Rep., 72, pp. 1407-1417; Karami, K., Parsianrad, F., Alinaghi, M., Amirghofran, Z., (2017) Inorg. Chim. Acta, 467, pp. 46-55; Katkova, S.A., Kinzhalov, M.A., Tolstoy, P.M., Novikov, A.S., Boyarskiy, V.P., Ananyan, A.Y., Gushchin, P.V., Kukushkin, V.Y., (2017) Organometallics, 36, pp. 4145-4159; Farrell, N.P., (2015) Chem. Soc. Rev., 44, pp. 8773-8785; Theodossiou, T.A., Ali, M., Grigalavicius, M., Grallert, B., Dillard, P., Schink, K.O., Olsen, C.E., Berg, K., (2019) npj Breast Cancer, 5, p. 13; Lunetti, P., Di Giacomo, M., Vergara, D., De Domenico, S., Maffia, M., Zara, V., Capobianco, L., Ferramosca, A., (2019) FEBS J., 286, pp. 688-709; Miripour, Z.S., Abbasvandi, F., Aghaee, P., NajafiKhoshnoo, S., Faramarzpour, M., Mohaghegh, P., Hoseinpour, P., Abdolahad, M., (2022) Bioeng. Transl. Med., 7; Semenza, G.L., (2019) Annu. Rev. Pharmacol. Toxicol., 59, pp. 379-403; Wang, Y., Hu, J., Cai, Y., Xu, S., Weng, B., Peng, K., Wei, X., Liang, G., (2013) J. Med. Chem., 56, pp. 9601-9611; Isaacs, J.S., Jung, Y.J., Mole, D.R., Lee, S., Torres-Cabala, C., Chung, Y.-L., Merino, M., Neckers, L., (2005) Cancer Cell, 8, pp. 143-153; Jeney, A., Hujber, Z., Szoboszlai, N., Fullár, A., Oláh, J., Pap, É., Márk, Á., Sebestyén, A., (2016) Cancer Cell Int., 16, p. 4; Elmore, S., (2007) Toxicol. Pathol., 35, pp. 495-516; Gałczyńska, K., Drulis-Kawa, Z., Arabski, M., (2020) Molecules, 25, p. 3492; Yang, T., Zhu, M., Jiang, M., Yang, F., Zhang, Z., (2022) Front. Pharmacol., 13; Endale, H.T., Tesfaye, W., Mengstie, T.A., (2023) Front. Cell Dev. Biol., 11; Zhao, Y., Li, Y., Zhang, R., Wang, F., Wang, T., Jiao, Y., (2020) OncoTargets Ther., 13, pp. 5429-5441; Li, J., He, D., Li, S., Xiao, J., Zhu, Z., (2023) Front. Immunol., 14; Yang, F., Xiao, Y., Ding, J.H., Jin, X., Ma, D., Li, D.Q., Shi, J.X., Shao, Z.M., (2023) Cell Metab., 35, pp. 84-100. , e108; Yin, H., Zhu, M., (2012) Free Radical Res., 46, pp. 959-974; Kondo, A., Maeta, M., Oka, A., Tsujitani, S., Ikeguchi, M., Kaibara, N., (1996) Br. J. Cancer., 73, pp. 1166-1170; Vojtek, M., Gonçalves-Monteiro, S., Šeminská, P., Valová, K., Bellón, L., Dias-Pereira, P., Marques, F., Diniz, C., (2022) Biomedicine, 10, p. 210; Chow, K.H.M., Sun, R.W.Y., Lam, J.B.B., Li, C.K.L., Xu, A., Ma, D.-L., Abagyan, R., Che, C.-M., (2010) Cancer Res., 70, pp. 329-337; Frik, M., Martínez, A., Elie, B.T., Gonzalo, O., Ramírez de Mingo, D., Sanaú, M., Sánchez-Delgado, R., Contel, M., (2014) J. Med. Chem., 57, pp. 9995-10012; Boros, E., Dyson, P.J., Gasser, G., (2020) Chem, 6, pp. 41-60; Dörr, M., Meggers, E., (2014) Curr. Opin. Chem. Biol., 19, pp. 76-81

PY - 2024/2/16

Y1 - 2024/2/16

N2 - Hydrolytically stable PdII and PtII complexes supported by acyclic diaminocarbene ligands represent a novel class of structural organometallic anticancer agents exhibiting nanomolar antiproliferative activity in a panel of cancer cell lines (IC50 0.07–0.81 μM) and up to 300-fold selectivity for cancer cells over normal primary fibroblasts. The lead drug candidate was 300 times more potent than cisplatin in vitro and showed higher efficacy in reducing the growth of aggressive MDA-MB-231 xenograft tumors in mice. © 2024 Wiley-VCH GmbH.

AB - Hydrolytically stable PdII and PtII complexes supported by acyclic diaminocarbene ligands represent a novel class of structural organometallic anticancer agents exhibiting nanomolar antiproliferative activity in a panel of cancer cell lines (IC50 0.07–0.81 μM) and up to 300-fold selectivity for cancer cells over normal primary fibroblasts. The lead drug candidate was 300 times more potent than cisplatin in vitro and showed higher efficacy in reducing the growth of aggressive MDA-MB-231 xenograft tumors in mice. © 2024 Wiley-VCH GmbH.

KW - antitumor agents

KW - diaminocarbenes

KW - drug discovery

KW - palladium

KW - platinum

KW - Cancer cells

KW - Cells

KW - Diseases

KW - Drug products

KW - Mammals

KW - Organometallics

KW - Palladium compounds

KW - Platinum compounds

KW - Acyclic diaminocarbenes

KW - Anti-cancer agents

KW - Antiproliferative activities

KW - Antitumour agents

KW - Cancer cell lines

KW - Diaminocarbenes

KW - Drug discovery

KW - Nanomolar

KW - Triple-negative breast cancers

KW - Cell culture

UR - https://www.mendeley.com/catalogue/82b39c87-320f-3558-81f5-db9a7674c36d/

U2 - 10.1002/chem.202400101

DO - 10.1002/chem.202400101

M3 - статья

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

M1 - e202400101

ER -

ID: 117120693