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Synthesis, Characterization, and Biological Properties of Steroidal Ruthenium(II) and Iridium(III) Complexes Based on the Androst-16-en-3-ol Framework.
Inorg Chem 2019; 58(23):15917-15926IC

Abstract

A range of novel cyclometalated ruthenium(II) and iridium(III) complexes with a steroidal backbone based on androsterone were synthesized and characterized by NMR spectroscopy and X-ray crystallography. Their cytotoxic properties in RT112 and RT112 cP (cisplatin-resistant) cell lines as well as in MCF7 and somatic fibroblasts were compared with those of the corresponding nonsteroidal complexes and the noncyclometalated pyridyl complexes as well as with cisplatin as reference. All steroidal complexes were more active in RT112 cP cells than cisplatin, whereby the cyclometalated pyridinylphenyl complexes based on 5c showed high cytotoxicity while maintaining low resistant factors of 0.33 and 0.50.

Authors+Show Affiliations

Institute of Organic Chemistry (IOC) , Karlsruhe Institute of Technology (KIT) , Fritz-Haber-Weg 6 , 76131 Karlsruhe , Germany.Institute of Organic Chemistry (IOC) , Karlsruhe Institute of Technology (KIT) , Fritz-Haber-Weg 6 , 76131 Karlsruhe , Germany. Institute of Functional Interfaces (IFG) , Karlsruhe Institute of Technology (KIT) , Hermann von Helmholtz Platz 1 , 76344 Eggenstein-Leopoldshafen , Germany.Institute of Inorganic Chemistry, Division Molecular Chemistry , Karlsruhe Institute of Technology (KIT) , Engesserstr. 15 , 76131 Karlsruhe , Germany.Institute of Functional Interfaces (IFG) , Karlsruhe Institute of Technology (KIT) , Hermann von Helmholtz Platz 1 , 76344 Eggenstein-Leopoldshafen , Germany.Institute for Nanotechnology (INT) and Karlsruhe Nano Micro Facility (KNMF) , Karlsruhe Institute of Technology (KIT) , Hermann von Helmholtz Platz 1 , 76344 Eggenstein-Leopoldshafen , Germany.Department of Chemistry , University of Helsinki , P.O. Box 55 , 00014 Helsinki , Finland.Institute of Organic Chemistry (IOC) , Karlsruhe Institute of Technology (KIT) , Fritz-Haber-Weg 6 , 76131 Karlsruhe , Germany. Institute of Functional Interfaces (IFG) , Karlsruhe Institute of Technology (KIT) , Hermann von Helmholtz Platz 1 , 76344 Eggenstein-Leopoldshafen , Germany.Institute of Organic Chemistry (IOC) , Karlsruhe Institute of Technology (KIT) , Fritz-Haber-Weg 6 , 76131 Karlsruhe , Germany. Institute of Toxicology and Genetics , Karlsruhe Institute of Technology (KIT) , Hermann-von-Helmholtz-Platz 1 , D-76344 Eggenstein-Leopoldshafen , Germany.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31714764

Citation

Koch, Vanessa, et al. "Synthesis, Characterization, and Biological Properties of Steroidal Ruthenium(II) and Iridium(III) Complexes Based On the Androst-16-en-3-ol Framework." Inorganic Chemistry, vol. 58, no. 23, 2019, pp. 15917-15926.
Koch V, Meschkov A, Feuerstein W, et al. Synthesis, Characterization, and Biological Properties of Steroidal Ruthenium(II) and Iridium(III) Complexes Based on the Androst-16-en-3-ol Framework. Inorg Chem. 2019;58(23):15917-15926.
Koch, V., Meschkov, A., Feuerstein, W., Pfeifer, J., Fuhr, O., Nieger, M., ... Bräse, S. (2019). Synthesis, Characterization, and Biological Properties of Steroidal Ruthenium(II) and Iridium(III) Complexes Based on the Androst-16-en-3-ol Framework. Inorganic Chemistry, 58(23), pp. 15917-15926. doi:10.1021/acs.inorgchem.9b02402.
Koch V, et al. Synthesis, Characterization, and Biological Properties of Steroidal Ruthenium(II) and Iridium(III) Complexes Based On the Androst-16-en-3-ol Framework. Inorg Chem. 2019 Dec 2;58(23):15917-15926. PubMed PMID: 31714764.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis, Characterization, and Biological Properties of Steroidal Ruthenium(II) and Iridium(III) Complexes Based on the Androst-16-en-3-ol Framework. AU - Koch,Vanessa, AU - Meschkov,Anna, AU - Feuerstein,Wolfram, AU - Pfeifer,Juliana, AU - Fuhr,Olaf, AU - Nieger,Martin, AU - Schepers,Ute, AU - Bräse,Stefan, Y1 - 2019/11/12/ PY - 2019/11/13/pubmed PY - 2019/11/13/medline PY - 2019/11/13/entrez SP - 15917 EP - 15926 JF - Inorganic chemistry JO - Inorg Chem VL - 58 IS - 23 N2 - A range of novel cyclometalated ruthenium(II) and iridium(III) complexes with a steroidal backbone based on androsterone were synthesized and characterized by NMR spectroscopy and X-ray crystallography. Their cytotoxic properties in RT112 and RT112 cP (cisplatin-resistant) cell lines as well as in MCF7 and somatic fibroblasts were compared with those of the corresponding nonsteroidal complexes and the noncyclometalated pyridyl complexes as well as with cisplatin as reference. All steroidal complexes were more active in RT112 cP cells than cisplatin, whereby the cyclometalated pyridinylphenyl complexes based on 5c showed high cytotoxicity while maintaining low resistant factors of 0.33 and 0.50. SN - 1520-510X UR - https://www.unboundmedicine.com/medline/citation/31714764/Synthesis,_Characterization,_and_Biological_Properties_of_Steroidal_Ruthenium(II)_and_Iridium(III)_Complexes_Based_on_the_Androst-16-en-3-ol_Framework L2 - https://dx.doi.org/10.1021/acs.inorgchem.9b02402 DB - PRIME DP - Unbound Medicine ER -