Bis-Dithiocarbamates derived from 1,10-diaza-18-crown-6 as ligand tectons for 1D, 2D and 3D supramolecular structure arrangements

Arenaza‐Corona, Antonino; Villamil‐Ramos, Raúl; Guerrero‐Álvarez, Jorge; Höpfl, Herbert; Barba, Víctor

doi:10.1039/c9ce01755k

Cited by 4 publications

(11 citation statements)

References 41 publications

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“…The bands at approximately 1430 cm –1 are typical for metal-coordinated triphenylphospine ligands [ν(P–C)]. These results agree with the proposed structures. , …”

Section: Resultssupporting

confidence: 85%

“…Potassium N , N ′-bis(dithiocarbamate)-1,10-diaza-18-crown-6 ( K 2 L ) was prepared from the reaction of 1,10-diaza-18-crown-6, CS 2 , and KOH in methanol, employing slight modifications of the methods described in the literature. , K 2 L was not isolated but used in situ for the preparation of the group 10 metal complexes . Compounds 1 and 2 were obtained from the reaction of K 2 L with 2 equiv of [M(PPh 3 ) 2 Cl 2 ] (M = Pd, Pt) in the conditions described in the Experimental Section (see Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…All reagents and solvents were purchased from Sigma-Aldrich, Chemical Co., and Merck and used without further purification. Potassium N , N ′-bis(dithiocarbamate)-1,10-diaza-18-crown-6 ( K 2 L ) was synthesized as previously described …”

Section: Methodsmentioning

confidence: 99%

“…Potassium N,N′-bis(dithiocarbamate)-1,10-diaza-18crown-6 (K 2 L) was synthesized as previously described. 37 Physical Methods. Melting points were measured on a Buchi B-540 apparatus.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…In the potassium salt K 2 L, the S−C−S angle has a value of 121.39(9)°. 37 55 Concerning the aza crown ether-dtc ligand conformation, the X-ray diffraction analysis shows that in all compounds the two pendants are oriented in an anti-disposition (Figure 5); however, the aza crown ether moiety adopts different conformations and crystallographic symmetry. Compounds 4 and 5 exhibit a quasi-chair conformation 56 with crystallographic Cytotoxicity and Resistant Profiles.…”

Section: Synthesis and Characterization Of The Complexesmentioning

confidence: 99%

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Further Approaches in the Design of Antitumor Agents with Response to Cell Resistance: Looking toward Aza Crown Ether-dtc Complexes

et al. 2020

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The dianionic aza crown ether-dtc N,N′-bis-(dithiocarbamate)-1,10-diaza-18-crown-6 (L 2− ) is a versatile ligand capable of yielding binuclear complexes with group 10 elements, also known as Ni-triade, [μ-(κ 2 -S,-S′-L)M 2 (PPh 3 ) 4 ]Cl 2 (M = Pd (1), Pt (2)), [μ-(κ 2 -S,-S′-L)M 2 (PPh 3 ) 4 ](BPh 4 ) 2 (M = Pd (3), Pt (4)), and μ-(κ-S,-S′-L)Ni 2 (PPh 3 ) 2 Cl 2 ( 5), and has proven to be an excellent option to the design of metal-based drugs able to provide multiple response to cell resistance. Palladium and platinum complexes, 1 and 2, were tested for cytotoxicity in the human cervix carcinoma cell line HeLa-229, the human ovarian carcinoma cell line A2780, and the cisplatin-resistant mutant A2780cis, finding significant activity toward all three cancer cell lines, with low micromolar IC 50 values, comparable to cisplatin. Markedly, against the cisplatin resistant cell line A2780cis, compound 2 exhibits better cytotoxic activity than the clinical drug (IC 50 = 2.3 ± 0.2 μM for 2 versus 3.6 ± 0.5 μM for cisplatin). Moreover, an enhancement of the antitumor response is achieved when adding an equimolar amount of alkali metal chloride (NaCl or KCl) to the medium, for instance, testing compound 1 against the cisplatin-resistant A2780cis cells, the IC 50 decreases from 9.3 ± 0.4 to 7.4 ± 0.3 and 5.4 ± 0.1 μM, respectively, after addition of the salt solution. For the platinum derivative 2, the IC 50 improves by ca. 40% reaching 1.3 ± 0.1 μM when potassium chloride is added. Likewise, the resistant factor found for 2 (RF = 1) confirms that this complex circumvents cisplatin-resistance in A2780cis and is improved with the addition of potassium chloride (RF = 0.65). The presence of the aza crown ether moiety as linker in the systems studied herein is a key point since, in addition to allowing and facilitating interaction with alkali metal ions, this unit is flexible enough to adapt to a variety of environments, as confirmed by the Xray crystal structures described, where different conformations and ways to fold in are found. In order to gain insight into the electronic and structural facts involved in the interaction of complex 2 with the alkali metal ions, a DFT study was performed, and the description of the molecular electrostatic potentials (MEPs) is also presented.

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“…The bands at approximately 1430 cm –1 are typical for metal-coordinated triphenylphospine ligands [ν(P–C)]. These results agree with the proposed structures. , …”

Section: Resultssupporting

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…Potassium N,N′-bis(dithiocarbamate)-1,10-diaza-18crown-6 (K 2 L) was synthesized as previously described. 37 Physical Methods. Melting points were measured on a Buchi B-540 apparatus.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Synthesis and Characterization Of The Complexesmentioning

confidence: 99%

See 3 more Smart Citations