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Synthesis, Structure, and Antiproliferative Activity of Three Gallium(III) Azole Complexes.

Zanias S, Papaefstathiou GS, Raptopoulou CP, Papazisis KT, Vala V, Zambouli D, Kortsaris AH, Kyriakidis DA, Zafiropoulos TF - Bioinorg Chem Appl (2010)

Bottom Line: As part of our interest into the bioinorganic chemistry of gallium, gallium(III) complexes of the azole ligands 2,1,3-benzothiadiazole (btd), 1,2,3-benzotriazole (btaH), and 1-methyl-4,5-diphenylimidazole (L) have been isolated.Reaction of btaH or btd with GaBr(3) or GaCl(3) resulted in the mononuclear complexes [GaBr(3)(btaH)(2)] (1) and [GaCl(3)(btd)(2)] (2), respectively, while treatment of GaCl(3) with L resulted in the anionic complex (LH)(2)[GaCl(4)] (3).All three complexes were characterized by single-crystal X-ray crystallography and IR spectroscopy, while their antiproliferative activities were investigated against a series of human and mouse cancer cell lines.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Patras, 265 04 Patras, Greece.

ABSTRACT
As part of our interest into the bioinorganic chemistry of gallium, gallium(III) complexes of the azole ligands 2,1,3-benzothiadiazole (btd), 1,2,3-benzotriazole (btaH), and 1-methyl-4,5-diphenylimidazole (L) have been isolated. Reaction of btaH or btd with GaBr(3) or GaCl(3) resulted in the mononuclear complexes [GaBr(3)(btaH)(2)] (1) and [GaCl(3)(btd)(2)] (2), respectively, while treatment of GaCl(3) with L resulted in the anionic complex (LH)(2)[GaCl(4)] (3). All three complexes were characterized by single-crystal X-ray crystallography and IR spectroscopy, while their antiproliferative activities were investigated against a series of human and mouse cancer cell lines.

No MeSH data available.


Related in: MedlinePlus

The intermixture of the weak interactions between the anions and the cations in 3. Most of the hydrogen atoms have been omitted for clarity.
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fig6: The intermixture of the weak interactions between the anions and the cations in 3. Most of the hydrogen atoms have been omitted for clarity.

Mentions: An ORTEP diagram of the asymmetric unit of 3 is shown in Figure 5. Selected bond distances and angles are listed in Table 4. The crystal of 3 consists of protonated LH+ ligand cations, tetrachlorogallate(III) anions and Cl− anions. The Ga–Cl distances in the tetrahedral [GaCl4]− ion are in the narrow range 2.152(1)–2.173(1) A° with the Cl–Ga–Cl angles varying from 107.1(1)° to 110.9(1)°. These values are similar to those observed for other complexes containing the tetrachlorogallate(-1) ion [13, 29]. The crystal structure of (LH)2[GaCl4]Cl is dominated by an intermixture of N–H⋯Cl and CMe–H⋯π hydrogen bonds, Ga–Cl⋯πazole and π-π interactions (Figure 6). The organic moieties LH+ are connected through N–H⋯Cl and C–H⋯πphenyl interactions to form a chain; data are as follows N3⋯Cl5′ (2 − x, −y, 2 − z) 3.088(3) Å, HN3⋯Cl5′ 2.24(4) Å and N3–HN3⋯Cl5′ 160(4)°; N13⋯Cl5′′ (x − 1, 1 + y, z − 1) 3.066(4) Å, HN13⋯Cl5′′ 2.19(5) Å and N13–HN13⋯Cl5′′ 177(5)°; C38⋯Centroid′ (1 − x, −y, 2 − z) 3.691(5) Å, H38A⋯Centroid′ 2.85(1) Å and C38–H38A⋯Centroid′ 147(1)°. The organic chains are bridged through Ga–Cl⋯πazole interactions to form layers [Cl1⋯Centroid′′ (−x, 1 − y, 1 − z) 3.455(2) Å and Cl4⋯Centroid′′′ (1 − x, 1 − y, 1 − z) 3.550(2) Å], which are further bridged through π-π interactions in the third dimension [centroid⋯centroid′ (1 − x, −y, 2 − z) 3.778(3) and centroid⋯centroid′′′′ (−x, 2 − y, 1 − z) 3.878(3)].


Synthesis, Structure, and Antiproliferative Activity of Three Gallium(III) Azole Complexes.

Zanias S, Papaefstathiou GS, Raptopoulou CP, Papazisis KT, Vala V, Zambouli D, Kortsaris AH, Kyriakidis DA, Zafiropoulos TF - Bioinorg Chem Appl (2010)

The intermixture of the weak interactions between the anions and the cations in 3. Most of the hydrogen atoms have been omitted for clarity.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC2913727&req=5

fig6: The intermixture of the weak interactions between the anions and the cations in 3. Most of the hydrogen atoms have been omitted for clarity.
Mentions: An ORTEP diagram of the asymmetric unit of 3 is shown in Figure 5. Selected bond distances and angles are listed in Table 4. The crystal of 3 consists of protonated LH+ ligand cations, tetrachlorogallate(III) anions and Cl− anions. The Ga–Cl distances in the tetrahedral [GaCl4]− ion are in the narrow range 2.152(1)–2.173(1) A° with the Cl–Ga–Cl angles varying from 107.1(1)° to 110.9(1)°. These values are similar to those observed for other complexes containing the tetrachlorogallate(-1) ion [13, 29]. The crystal structure of (LH)2[GaCl4]Cl is dominated by an intermixture of N–H⋯Cl and CMe–H⋯π hydrogen bonds, Ga–Cl⋯πazole and π-π interactions (Figure 6). The organic moieties LH+ are connected through N–H⋯Cl and C–H⋯πphenyl interactions to form a chain; data are as follows N3⋯Cl5′ (2 − x, −y, 2 − z) 3.088(3) Å, HN3⋯Cl5′ 2.24(4) Å and N3–HN3⋯Cl5′ 160(4)°; N13⋯Cl5′′ (x − 1, 1 + y, z − 1) 3.066(4) Å, HN13⋯Cl5′′ 2.19(5) Å and N13–HN13⋯Cl5′′ 177(5)°; C38⋯Centroid′ (1 − x, −y, 2 − z) 3.691(5) Å, H38A⋯Centroid′ 2.85(1) Å and C38–H38A⋯Centroid′ 147(1)°. The organic chains are bridged through Ga–Cl⋯πazole interactions to form layers [Cl1⋯Centroid′′ (−x, 1 − y, 1 − z) 3.455(2) Å and Cl4⋯Centroid′′′ (1 − x, 1 − y, 1 − z) 3.550(2) Å], which are further bridged through π-π interactions in the third dimension [centroid⋯centroid′ (1 − x, −y, 2 − z) 3.778(3) and centroid⋯centroid′′′′ (−x, 2 − y, 1 − z) 3.878(3)].

Bottom Line: As part of our interest into the bioinorganic chemistry of gallium, gallium(III) complexes of the azole ligands 2,1,3-benzothiadiazole (btd), 1,2,3-benzotriazole (btaH), and 1-methyl-4,5-diphenylimidazole (L) have been isolated.Reaction of btaH or btd with GaBr(3) or GaCl(3) resulted in the mononuclear complexes [GaBr(3)(btaH)(2)] (1) and [GaCl(3)(btd)(2)] (2), respectively, while treatment of GaCl(3) with L resulted in the anionic complex (LH)(2)[GaCl(4)] (3).All three complexes were characterized by single-crystal X-ray crystallography and IR spectroscopy, while their antiproliferative activities were investigated against a series of human and mouse cancer cell lines.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Patras, 265 04 Patras, Greece.

ABSTRACT
As part of our interest into the bioinorganic chemistry of gallium, gallium(III) complexes of the azole ligands 2,1,3-benzothiadiazole (btd), 1,2,3-benzotriazole (btaH), and 1-methyl-4,5-diphenylimidazole (L) have been isolated. Reaction of btaH or btd with GaBr(3) or GaCl(3) resulted in the mononuclear complexes [GaBr(3)(btaH)(2)] (1) and [GaCl(3)(btd)(2)] (2), respectively, while treatment of GaCl(3) with L resulted in the anionic complex (LH)(2)[GaCl(4)] (3). All three complexes were characterized by single-crystal X-ray crystallography and IR spectroscopy, while their antiproliferative activities were investigated against a series of human and mouse cancer cell lines.

No MeSH data available.


Related in: MedlinePlus