Copper-8-hydroxyquinoline

Copper(II), di-/Lt-bromobis[bromo(pyridine)-structure, 2, 108 Copper 8-hydroxyquinolinate biocidal activity mechanism, 1, 401 fungicide, 1, 399 Copper nitrotetrazole as propellants, 5, 837 Copper phthalocyanine, 1, 333-334 colour and constitution, 1, 345 Coproporphyrin, 4, 382 Coproporphyrin, dehydro-, 4, 382... 

Copper 8-hydroxyquinolinate (21) is one of the oldest preservatives, used primarily as a fabric mildewcide for military applications. Although it is stable and has low human toxicity and low cost, it is limited in applications by its intense green color. 

The lipophilic nature of the organic ligands of copper 8-hydroxyquinolinate (21) helps to transport the copper atom into the cell. Once there, dissociation to the active species (27) is thought to occur (equation 9) the biocidal action may be due to the coordination of (27) with metal-binding sites of cell enzymes (B-69Mill500). 

Chloroallyl)-3,5,7-triaza-l-azoniaadamantane chloride Copper 8-hydroxyquinolinate... 

SYNS BIOQUIN BIOQUIN 1 BIS(8-QUINOUNATO)COPPER BIS(8-QUINOLINOL-ATO)COPPER BIS(8-QUINOLINOLATO-NLo )-COPPER CELLU-QUIN COPPER-8 COPPER HYDROXYQUINOLATE COPPER-8-HYDROXY-QUINOLATE COPPER-8-HYDROXYQUINOLINATE COPPER-8-HYDROXYQUINOLINE COPPER OXINATE COPPER (2-I-) OXINATE COPPER OXINE... 

Lipid-soluble metal complexes such as copper xanthates (from mineral flotation plants), copper 8-hydroxyquinolinate (agricultural fungicide) or alkyl-mercury compounds are particularly toxic forms of heavy metals because they diffuse rapidly through a biomembrane and carry both metal and ligand into the cell. ... 

Copper, [1,3,8,16,18,24-hexabromo-2,4,9,10,11,15,17,22,23,25-decachlo-rophthalocyaninato (2])]-. See Pigment green 36 Copper hydroxy quinolate Copper-8-hydroxyquinolinate Copper-8-hy-droxyquinoline. See Copper 8-quinolinolate... 

Synonyms Bis (8-oxyquinoline) copper Bis (8-quinolinato) copper Bis (quinolin-8-olato) copper Copper-8 Copper hydroxy quinolate Copper-8-hydroxyquinolinate Copper-8-hydroxyquinoline Copper oxinate Copper oxyquinolate Copper oxyquinoline Copper quinolate Copper-8-quinolate Cupric-8-hydroxyquinolate 8-Hydroxyquinoline copper complex Oxime copper Oxine copper... 

The prerequisite for the toxic effect of heavy metals is penetration of the cell wall. For this, certain carriers are needed to transport the heavy metals through lipophilic centres in the cell membrane. Oxines, 2-mercapto-pyridine-N-oxides (III. 11) and dialkyl-dithiocarbamates (III.9) are examples of compounds capable of complexing heavy metal ions such as Cu ions and transporting them into the microbe cell. The carriers named are also toxic, as such, to micro-organisms. But, as a copper carrier, copper-8-hydroxyquinoline is about 100 times more effective than 8-hydroxyquinoline (oxine III. 11.4). Once heavy metal ions have overcome the cell wall with the aid of the carrier molecules, they may compete with magnesium, calcium and potassium ions for receptor sites, inhibit enzymes and cause non-specific precipitation of proteins. 

The antimicrobial activity described here is only valid for 8-hydroxyquinoline and not for the seven other possible hydroxyquinolines which are widely inactive and do not, as does 8-hydroxyquinoline, chelate metal cations, e.g. copper, iron and zinc. Contrary to Oxine the corresponding chelation complexes, e.g. copper 8-hydroxyquinoline (Section 11.5) possess considerable lipid solubility enabling the complex to pass through the cell membrane and then to dissociate into the toxic 8-hydroxyquinoline. However, according to the findings of Block (1983)... 

As is demonstrated in Table 99, Oxine is a broad spectrum microbicide, although it is much more toxic for Gram-positive bacteria than for Gram-negative bacteria. But unfavourable solubility properties and coloration risks have prevented Oxine from becoming an important microbicide for material protection. More popular are the chelate complexes, above all copper 8-hydroxyquinoline (Section 11.5). 

Substance classes Properties — Effectiveness — Applications 11.5 Copper 8-hydroxyquinoline — Oxine copper... 

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