Novel complexes of ruthenium(II) with in situ formed flavanone-based ligands.

Dalton Trans., 2010,39, 9711-9718

http://pubs.rsc.org/en/content/articlelanding/2010/dt/c0dt00535e#!divAbstract


DOI: 10.1039/C0DT00535E

Justyn Ochocki,*^a   Maria Kasprzak,^a   Lilianna Chęcińska,^b  Andrea Erxleben,^c   Elżbieta Zyner,^a   Leszek Szmigiero,^d  Ariadna Garza-Ortiz^e and   Jan Reedijk^e  

Corresponding authors

^a

Department of Bioinorganic Chemistry, Medical University, Muszynskiego 1, Łódź, Poland

^b

University of Łódź, Department of Crystallography and Crystal Chemistry, Pomorska 149/153, Łódź, Poland

^c

School of Chemistry, National University of Ireland, Galway, University Road, Galway, Ireland

^d

Medical University of Łódź, Department of Nucleic Acids Biochemistry, Mazowiecka 6/8, Łódź, Poland

^e

Leiden Institute of Chemistry, Leiden University, Leiden, The Netherlands

Dalton Trans., 2010,39, 9711-9718

DOI: 10.1039/C0DT00535E





                                                                                                                   






 













Synthesis, structure and properties of two new flavanone complexes of Ru(II) are described. The new complexes form during the reaction of ruthenium(III) chloride with 3-aminoflavone (3-af) dissolved in an aliphatic alcohol. The formed products depend on the alcohol used and were found to be: cis-dichloridobis(3-imino-2-methoxyflavanone)ruthenium(II)·3H₂O (1) from a methanolic solution and cis-dichloridobis(3-imino-2-ethoxyflavanone)ruthenium(II)·2H₂O (2) from an ethanolic solution, in which the original ligand 3-af had been converted by dehydrogenative alcoholysis to an entirely new ligand. This paper presents the X-ray structure and detailed ¹H-NMR analysis of both new compounds, as well as the study of their antiproliferative activity. The coordination of Ru(II) is octahedral with [RuCl₂N₂O₂] chromophores, having trans chlorides and common Ru–L distances. Both 1 and 2 are highly cytotoxic towards the cisplatin resistant EJ and L1210 cell lines, and both complexes are as active as cisplatin in the sensitive cell lines. They display the ability to overcome cisplatin resistance in the drug resistant sub-lines EJcisR and L1210R. The present evidence suggests that the mechanism of biological activity may be different for these ruthenium compounds compared to cisplatin.

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Phosphine-based cage molecules

DOI: 10.1039/C3DT53645A (Paper) Dalton Trans., 2014, 43, 6236-6243

Julia R. Shakirova ^a, Elena V. Grachova ^a, Antti J. Karttunen ^b, Vladislav V. Gurzhiy ^a, Sergey P. Tunik *^a and Igor O. Koshevoy *^c
aSt.-Petersburg State University, Department of Chemistry, St.-Petersburg, Russia. E-mail: stunik@inbox.ru; Fax: +7 812 4286939; Tel: +7 812 4284028
^bUniversity of Jyväskylä, Department of Chemistry, PO Box 35, FI-40014 Jyväskylä, Finland
^cUniversity of Eastern Finland, Department of Chemistry, Joensuu 80101, Finland. E-mail: igor.koshevoy@uef.fi; Fax: +358 13 2513390; Tel: +358 50 4422694

Received 28th December 2013 , Accepted 4th February 2014

First published on the web 5th March 2014

http://pubs.rsc.org/en/content/articlehtml/2014/dt/c3dt53645a


 
Scheme 1 Metallophilicity-assisted assembly of the gold–phosphine cages (A – ref. 15, B and C – the current work).







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508 Da MAA

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A predicted structure for the 508-Da MAA with an absorption maximum at 334 nm and a molecular formula of C₂₀H₃₂N₂O₁₃. Hexose is bound to porphyra-334 at C7 position. Red arrows and blue dashed lines represent the apparent HMBC and COSY correlations, respectively. The red dashed arrow represents probable HMBC correlation. - See more at: http://www.mdpi.com/1660-3397/11/9/3124/htm#sthash.skOGZCsp.dpuf

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A predicted structure for the 508-Da MAA with an absorption maximum at 334 nm and a molecular formula of C₂₀H₃₂N₂O₁₃. Hexose is bound to porphyra-334 at C7 position. Red arrows and blue dashed lines represent the apparent HMBC and COSY correlations, respectively. The red dashed arrow represents probable HMBC correlation. - See more at: http://www.mdpi.com/1660-3397/11/9/3124/htm#sthash.skOGZCsp.dpuf

A predicted structure for the 508-Da MAA with an absorption maximum at 334 nm and a molecular formula of C₂₀H₃₂N₂O₁₃. Hexose is bound to porphyra-334 at C7 position. Red arrows and blue dashed lines represent the apparent HMBC and COSY correlations, respectively. The red dashed arrow represents probable HMBC correlation. - See more at: http://www.mdpi.com/1660-3397/11/9/3124/htm#sthash.skOGZCsp.dpuf

Smenamides A and B

Smenamides A and B


http://www.mdpi.com/1660-3397/11/11/4451/htm

3.3. Smenamide A (1)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2326 ([M + Na]⁺, C₂₈H₃₇ClN₂O₄Na⁺, calcd. 532.2334), m/z 501.2509 ([M + Na]⁺, C₂₈H₃₈ClN₂O₄⁺, calcd. 501.2515); MS isotope pattern: M (100%), M + 1 (32%, calcd. 31.5%), M + 2 (37%, calcd. 36.0%), M + 3 (10%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.2557 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2092 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1384 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1618 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0836 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0472 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; UV (MeOH): λ_max(ε) 287 nm (8200), 246 nm (46000), 225 nm (92000); CD (MeOH): λ_max(Δε) 238 (+33), 219 (−30).

3.4. Smenamide B (2)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2320 ([M + Na]⁺, calcd. for C₂₈H₃₇ClN₂O₄Na⁺ 532.2334), m/z 501.2505 ([M + Na]⁺, calcd. for C₂₈H₃₈ClN₂O₄⁺ 501.2515); MS isotope pattern: M (100%), M + 1 (31%, calcd. 31.5%), M + 2 (36%, calcd. 36.0%), M + 3 (11%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.25567 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2091 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1383 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1617 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0835 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0471 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; ¹H and ¹³C NMR: Supplementary Table S1; UV (MeOH): λ_max(ε) 287 nm (15000), 248 nm (42000), 225 nm (84000); CD (MeOH): λ_max(Δε) 237 (+7.3).

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Mar. Drugs 2013, 11(11), 4451-4463; doi:10.3390/md11114451 - See more at: http://www.mdpi.com/1660-3397/11/11/4451/htm#sthash.TkQbBhDy.dpuf

Mar. Drugs 2013, 11(11), 4451-4463; doi:10.3390/md11114451 - See more at: http://www.mdpi.com/1660-3397/11/11/4451/htm#sthash.TkQbBhDy.dpuf

 

3.3. Smenamide A (1)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2326 ([M + Na]⁺, C₂₈H₃₇ClN₂O₄Na⁺, calcd. 532.2334), m/z 501.2509 ([M + Na]⁺, C₂₈H₃₈ClN₂O₄⁺, calcd. 501.2515); MS isotope pattern: M (100%), M + 1 (32%, calcd. 31.5%), M + 2 (37%, calcd. 36.0%), M + 3 (10%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.2557 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2092 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1384 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1618 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0836 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0472 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; UV (MeOH): λ_max(ε) 287 nm (8200), 246 nm (46000), 225 nm (92000); CD (MeOH): λ_max(Δε) 238 (+33), 219 (−30).

3.4. Smenamide B (2)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2320 ([M + Na]⁺, calcd. for C₂₈H₃₇ClN₂O₄Na⁺ 532.2334), m/z 501.2505 ([M + Na]⁺, calcd. for C₂₈H₃₈ClN₂O₄⁺ 501.2515); MS isotope pattern: M (100%), M + 1 (31%, calcd. 31.5%), M + 2 (36%, calcd. 36.0%), M + 3 (11%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.25567 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2091 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1383 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1617 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0835 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0471 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; ¹H and ¹³C NMR: Supplementary Table S1; UV (MeOH): λ_max(ε) 287 nm (15000), 248 nm (42000), 225 nm (84000); CD (MeOH): λ_max(Δε) 237 (+7.3).

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3.3. Smenamide A (1)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2326 ([M + Na]⁺, C₂₈H₃₇ClN₂O₄Na⁺, calcd. 532.2334), m/z 501.2509 ([M + Na]⁺, C₂₈H₃₈ClN₂O₄⁺, calcd. 501.2515); MS isotope pattern: M (100%), M + 1 (32%, calcd. 31.5%), M + 2 (37%, calcd. 36.0%), M + 3 (10%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.2557 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2092 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1384 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1618 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0836 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0472 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; UV (MeOH): λ_max(ε) 287 nm (8200), 246 nm (46000), 225 nm (92000); CD (MeOH): λ_max(Δε) 238 (+33), 219 (−30).

3.4. Smenamide B (2)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2320 ([M + Na]⁺, calcd. for C₂₈H₃₇ClN₂O₄Na⁺ 532.2334), m/z 501.2505 ([M + Na]⁺, calcd. for C₂₈H₃₈ClN₂O₄⁺ 501.2515); MS isotope pattern: M (100%), M + 1 (31%, calcd. 31.5%), M + 2 (36%, calcd. 36.0%), M + 3 (11%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.25567 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2091 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1383 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1617 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0835 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0471 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; ¹H and ¹³C NMR: Supplementary Table S1; UV (MeOH): λ_max(ε) 287 nm (15000), 248 nm (42000), 225 nm (84000); CD (MeOH): λ_max(Δε) 237 (+7.3).

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Mar. Drugs 2013, 11(11), 4451-4463; doi:10.3390/md11114451 - See more at: http://www.mdpi.com/1660-3397/11/11/4451/htm#sthash.TkQbBhDy.dpuf

3.3. Smenamide A (1)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2326 ([M + Na]⁺, C₂₈H₃₇ClN₂O₄Na⁺, calcd. 532.2334), m/z 501.2509 ([M + Na]⁺, C₂₈H₃₈ClN₂O₄⁺, calcd. 501.2515); MS isotope pattern: M (100%), M + 1 (32%, calcd. 31.5%), M + 2 (37%, calcd. 36.0%), M + 3 (10%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.2557 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2092 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1384 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1618 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0836 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0472 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; UV (MeOH): λ_max(ε) 287 nm (8200), 246 nm (46000), 225 nm (92000); CD (MeOH): λ_max(Δε) 238 (+33), 219 (−30).

3.4. Smenamide B (2)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2320 ([M + Na]⁺, calcd. for C₂₈H₃₇ClN₂O₄Na⁺ 532.2334), m/z 501.2505 ([M + Na]⁺, calcd. for C₂₈H₃₈ClN₂O₄⁺ 501.2515); MS isotope pattern: M (100%), M + 1 (31%, calcd. 31.5%), M + 2 (36%, calcd. 36.0%), M + 3 (11%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.25567 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2091 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1383 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1617 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0835 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0471 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; ¹H and ¹³C NMR: Supplementary Table S1; UV (MeOH): λ_max(ε) 287 nm (15000), 248 nm (42000), 225 nm (84000); CD (MeOH): λ_max(Δε) 237 (+7.3).

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Mar. Drugs 2013, 11(11), 4451-4463; doi:10.3390/md11114451 - See more at: http://www.mdpi.com/1660-3397/11/11/4451/htm#sthash.TkQbBhDy.dpuf

3.3. Smenamide A (1)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2326 ([M + Na]⁺, C₂₈H₃₇ClN₂O₄Na⁺, calcd. 532.2334), m/z 501.2509 ([M + Na]⁺, C₂₈H₃₈ClN₂O₄⁺, calcd. 501.2515); MS isotope pattern: M (100%), M + 1 (32%, calcd. 31.5%), M + 2 (37%, calcd. 36.0%), M + 3 (10%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.2557 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2092 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1384 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1618 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0836 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0472 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; UV (MeOH): λ_max(ε) 287 nm (8200), 246 nm (46000), 225 nm (92000); CD (MeOH): λ_max(Δε) 238 (+33), 219 (−30).

3.4. Smenamide B (2)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2320 ([M + Na]⁺, calcd. for C₂₈H₃₇ClN₂O₄Na⁺ 532.2334), m/z 501.2505 ([M + Na]⁺, calcd. for C₂₈H₃₈ClN₂O₄⁺ 501.2515); MS isotope pattern: M (100%), M + 1 (31%, calcd. 31.5%), M + 2 (36%, calcd. 36.0%), M + 3 (11%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.25567 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2091 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1383 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1617 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0835 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0471 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; ¹H and ¹³C NMR: Supplementary Table S1; UV (MeOH): λ_max(ε) 287 nm (15000), 248 nm (42000), 225 nm (84000); CD (MeOH): λ_max(Δε) 237 (+7.3).

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Smenamides A and B

Smenamides A and B

Structures of smenamide A (1) and B (2).

Structures of smenamide A (1) and B (2).

Structures of smenamide A (1) and B (2).

Structures of smenamide A (1) and B (2).

Structures of smenamide A (1) and B (2).

Structures of smenamide A (1) and B (2).