The effect of specific modifications of the amine ligands on the solubility, stability, CO release to myoglobin and whole blood, cell toxicity and haemolytic index of [Mo(CO)4(NR3)2] complexes

Lukas Kromer; Ana Catarina Coelho; Isabel Bento; Ana Rita Marques; Carlos Jose Romao

doi:10.1016/j.jorganchem.2013.12.009

The effect of specific modifications of the amine ligands on the solubility, stability, CO release to myoglobin and whole blood, cell toxicity and haemolytic index of [Mo(CO)₄(NR₃)₂] complexes

Lukas Kromer, Ana Catarina Coelho, Isabel Bento, Ana Rita Marques, Carlos Jose Romao

Instituto de Tecnologia Química e Biológica António Xavier (ITQB)

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

6 Citations (Scopus)

Abstract

A series of cis-[Mo(CO)₄(amine)₂] complexes (NR ₃ = morpholine 1; 4-Me-piperazine, 2; H₂NCH ₂CH₂NH₂, 3; H₂NCH₂CH ₂-morpholine (4) R₂NCH₂CH₂- piperazine-4-Me (R = H, 5); R = Me, 6); Me₂NCH₂CH ₂NMe₂, 7) was prepared in good yields, in a one-step microwave-assisted synthesis. The X-ray diffraction structures of the complexes 4, 5 and 6 are reported. The stability of the complexes 1-7 in aqueous, aerobic media was studied by UV-Vis spectrophotometry, RP-HPLC and gas chromatography at several pH values. Stability beyond 1 h requires bidentate ligands with at least one tertiary amine ligand and increases in the order 4 <5 <6. Stability is approximately the same at pH 7.5 and pH 3.9 for 5 and 6 in solutions acidified with HCl. Acidification with CF₃COOH induces decomposition. The order of CO transfer rate to deoxy-Mb and haemoglobin in whole blood is 1 > 2 > 3 > 4 > 5 > 6 >> 7, but it is much faster to whole blood. The haemolytic index of some compounds increases in a similar order: 1 <2 <5 <6; with the exception of 1, the complexes are not toxic to RAW264.7 cells up to a concentration of 100 μM.

Original language	English
Pages (from-to)	89-100
Number of pages	12
Journal	Journal Of Organometallic Chemistry
Volume	760
DOIs	https://doi.org/10.1016/j.jorganchem.2013.12.009
Publication status	Published - 15 Jun 2014

Keywords

CO releasing molecules
CORM
Molybdenum carbonyl

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10.1016/j.jorganchem.2013.12.009

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@article{33cc51adac434b87b9ea19480e9c6a65,

title = "The effect of specific modifications of the amine ligands on the solubility, stability, CO release to myoglobin and whole blood, cell toxicity and haemolytic index of [Mo(CO)4(NR3)2] complexes",

abstract = "A series of cis-[Mo(CO)4(amine)2] complexes (NR 3 = morpholine 1; 4-Me-piperazine, 2; H2NCH 2CH2NH2, 3; H2NCH2CH 2-morpholine (4) R2NCH2CH2- piperazine-4-Me (R = H, 5); R = Me, 6); Me2NCH2CH 2NMe2, 7) was prepared in good yields, in a one-step microwave-assisted synthesis. The X-ray diffraction structures of the complexes 4, 5 and 6 are reported. The stability of the complexes 1-7 in aqueous, aerobic media was studied by UV-Vis spectrophotometry, RP-HPLC and gas chromatography at several pH values. Stability beyond 1 h requires bidentate ligands with at least one tertiary amine ligand and increases in the order 4 <5 <6. Stability is approximately the same at pH 7.5 and pH 3.9 for 5 and 6 in solutions acidified with HCl. Acidification with CF3COOH induces decomposition. The order of CO transfer rate to deoxy-Mb and haemoglobin in whole blood is 1 > 2 > 3 > 4 > 5 > 6 >> 7, but it is much faster to whole blood. The haemolytic index of some compounds increases in a similar order: 1 <2 <5 <6; with the exception of 1, the complexes are not toxic to RAW264.7 cells up to a concentration of 100 μM.",

keywords = "CO releasing molecules, CORM, Molybdenum carbonyl",

author = "Lukas Kromer and Coelho, {Ana Catarina} and Isabel Bento and Marques, {Ana Rita} and Romao, {Carlos Jose}",

note = "WOS:000334295800014",

year = "2014",

month = jun,

day = "15",

doi = "10.1016/j.jorganchem.2013.12.009",

language = "English",

volume = "760",

pages = "89--100",

journal = "Journal Of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier Science Publisher B.V.",

}

The effect of specific modifications of the amine ligands on the solubility, stability, CO release to myoglobin and whole blood, cell toxicity and haemolytic index of [Mo(CO)₄(NR₃)₂] complexes. / Kromer, Lukas ; Coelho, Ana Catarina ; Bento, Isabel; Marques, Ana Rita; Romao, Carlos Jose.

In: Journal Of Organometallic Chemistry, Vol. 760, 15.06.2014, p. 89-100.

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

TY - JOUR

T1 - The effect of specific modifications of the amine ligands on the solubility, stability, CO release to myoglobin and whole blood, cell toxicity and haemolytic index of [Mo(CO)4(NR3)2] complexes

AU - Kromer, Lukas

AU - Coelho, Ana Catarina

AU - Bento, Isabel

AU - Marques, Ana Rita

AU - Romao, Carlos Jose

N1 - WOS:000334295800014

PY - 2014/6/15

Y1 - 2014/6/15

N2 - A series of cis-[Mo(CO)4(amine)2] complexes (NR 3 = morpholine 1; 4-Me-piperazine, 2; H2NCH 2CH2NH2, 3; H2NCH2CH 2-morpholine (4) R2NCH2CH2- piperazine-4-Me (R = H, 5); R = Me, 6); Me2NCH2CH 2NMe2, 7) was prepared in good yields, in a one-step microwave-assisted synthesis. The X-ray diffraction structures of the complexes 4, 5 and 6 are reported. The stability of the complexes 1-7 in aqueous, aerobic media was studied by UV-Vis spectrophotometry, RP-HPLC and gas chromatography at several pH values. Stability beyond 1 h requires bidentate ligands with at least one tertiary amine ligand and increases in the order 4 <5 <6. Stability is approximately the same at pH 7.5 and pH 3.9 for 5 and 6 in solutions acidified with HCl. Acidification with CF3COOH induces decomposition. The order of CO transfer rate to deoxy-Mb and haemoglobin in whole blood is 1 > 2 > 3 > 4 > 5 > 6 >> 7, but it is much faster to whole blood. The haemolytic index of some compounds increases in a similar order: 1 <2 <5 <6; with the exception of 1, the complexes are not toxic to RAW264.7 cells up to a concentration of 100 μM.

AB - A series of cis-[Mo(CO)4(amine)2] complexes (NR 3 = morpholine 1; 4-Me-piperazine, 2; H2NCH 2CH2NH2, 3; H2NCH2CH 2-morpholine (4) R2NCH2CH2- piperazine-4-Me (R = H, 5); R = Me, 6); Me2NCH2CH 2NMe2, 7) was prepared in good yields, in a one-step microwave-assisted synthesis. The X-ray diffraction structures of the complexes 4, 5 and 6 are reported. The stability of the complexes 1-7 in aqueous, aerobic media was studied by UV-Vis spectrophotometry, RP-HPLC and gas chromatography at several pH values. Stability beyond 1 h requires bidentate ligands with at least one tertiary amine ligand and increases in the order 4 <5 <6. Stability is approximately the same at pH 7.5 and pH 3.9 for 5 and 6 in solutions acidified with HCl. Acidification with CF3COOH induces decomposition. The order of CO transfer rate to deoxy-Mb and haemoglobin in whole blood is 1 > 2 > 3 > 4 > 5 > 6 >> 7, but it is much faster to whole blood. The haemolytic index of some compounds increases in a similar order: 1 <2 <5 <6; with the exception of 1, the complexes are not toxic to RAW264.7 cells up to a concentration of 100 μM.

KW - CO releasing molecules

KW - CORM

KW - Molybdenum carbonyl

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U2 - 10.1016/j.jorganchem.2013.12.009

DO - 10.1016/j.jorganchem.2013.12.009

M3 - Article

AN - SCOPUS:84899440033

VL - 760

SP - 89

EP - 100

JO - Journal Of Organometallic Chemistry

JF - Journal Of Organometallic Chemistry

SN - 0022-328X

ER -