Octanol-water partition bioaccumulation

The toxicological or cumulative effect of illicit drugs on the ecosystems has not been studied yet. Moreover, their fate and transport in the environment is to a big extent still unknown. Due to their physical-chemical properties (octanol-water partition coefficient, solubility, etc.) some of them, such as cannabinoids, are likely to bioaccumulate in organisms or concentrate in sediments whereas the rest, much more polar compounds, will tend to stay in aqueous environmental matrices. However, continuous exposure of aquatic organisms to low aquatic concentrations of these substances, some of them still biologically active (e.g., cocaine (CO), morphine (MOR) and MDMA) may cause undesirable effects on the biota. 

Gossett RW, Brown DA, Young DR. 1983. Predicting the bioaccumulation of organic compounds in marine organisms using octanol/water partition coefficients. Mar Pollut Bull 14 387-392. 

Based on the relatively low value of the octanol/water partition coefficient (K° ) for acrylonitrile (log K OW = -0. 92) (Verschueren 1983), it would notbe expected tnat acrylonitrile will strongly bioaccumulate... 

Geyer, H.J., Politzki, G., Freitag, D. (1984) Prediction of ecotoxicological behaviour of chemicals relationship between n-octanol/water partition coefficient and bioaccumulation of organic chemicals by alga chlorella. Chemosphere 13(2), 269-284. 

Fisk, A.T., R.J. Norstrom, C.D. Cymbalisty, and D.C.G. Muir. 1998. Dietary accumulation and depuration of hydrophobic organochlorines bioaccumulation parameters and their relationship with the octanol/water partition coefficient. Environ. Toxicol. Chem. 17 951-961. 

Laskowski [1] has thoroughly reviewed the physico-chemical properties of the SPs, and these are summarized briefly below. SPs are typically of low water solubility (in the low microgram per liter range) and are highly nonpolar (logarithmic octanol water partition coefficients of around 6-7), indicating potential for bioaccumulation. Fish bioconcentration factors (BCF) of several hundred to several thousand are reported however metabolism limits the amount of bioaccumulation,... 

The octanol-water partition coefficient, Kow, is the most widely used descriptor of hydrophobicity in quantitative structure activity relationships (QSAR), which are used to describe sorption to organic matter, soil, and sediments [15], bioaccumulation [104], and toxicity [105 107J. Octanol is an amphiphilic bulk solvent with a molar volume of 0.12 dm3 mol when saturated with water. In the octanol-water system, octanol contains 2.3 mol dm 3 of water (one molecule of water per four molecules of octanol) and water is saturated with 4.5 x 10-3 mol dm 3 octanol. Octanol is more suitable than any other solvent system (for) mimicking biological membranes and organic matter properties, because it contains an aliphatic alkyl chain for pure van der Waals interactions plus the alcohol group, which can act as a hydrogen donor and acceptor. 

Dithiocarbamates and xanthates form particularly stable, neutral complexes with Cu(II), Cd(II) (and also Ni, Hg, Pb), which are membrane permeable and increase the apparent bioaccumulation of these metals [13]. In the series of sulfoxine, oxine, and chloroxine, the hydrophobicity of the neutral and the charged form, as well as of the Cu complex, increases. While the sulfoxine is not hydrophobic and does not modulate copper toxicity [220], the Cu-oxine complex is hydrophobic with an octanol-water partition constant, log Kok, of 1.7 [221] or 2.6 [222]. Chloroxine can be assumed to be even more hydrophobic, but so far its influence on uptake and toxicity has not been investigated. Uptake of Cu2+ into unilamellar liposomes was increased in the presence of 8-hydroxy-chinoline, and decreased again after adding HA [223],... 

The dominant transport process from water is volatilization. Based on mathematical models developed by the EPA, the half-life for M-hexane in bodies of water with any degree of turbulent mixing (e.g., rivers) would be less than 3 hours. For standing bodies of water (e.g., small ponds), a half-life no longer than one week (6.8 days) is estimated (ASTER 1995 EPA 1987a). Based on the log octanol/water partition coefficient (i.e., log[Kow]) and the estimated log sorption coefficient (i.e., log[Koc]) (see Table 3-2), ii-hexane is not expected to become concentrated in biota (Swann et al. 1983). A calculated bioconcentration factor (BCF) of 453 for a fathead minnow (ASTER 1995) further suggests a low potential for -hcxanc to bioconcentrate or bioaccumulate in trophic food chains. 

Food Chain Bioaccumulation. 1,2-Diphenylhydrazine reacts rapidly in water to form azobenzene and other oxidation products (half-life in wastewater is 60 minutes). Because of this and based upon the log octanol/water partition coefficient, no bioaccumulation is expected in any aquatic organism. 

Food Chain Bioaccumulation. 3,3 -Dichlorobenzidine is bioconcentrated by aquatic organisms imder experimental eonditions. Whole-fish BCFs of around 500, with equilibration occurring in 96-168 hours, have been published (Appleton and Sikka 1980). In view of the -octanol/water partition coeffieient for... 

Dichlorobenzene is expected to bioconcentrate in aquatic organisms. The high octanol-water partition coefficient (K, ) value of 2,455 (Leo et al. 1971) also suggests that 1,4-dichlorobenzene has a moderate to high potential for bioaccumulation. A calculated bioconcentration factor (BCF) of 267 was reported for the fathead minnow (Pimephales promelas) (ASTER 1995). Measured mean BCF values of 370 and 720 were experimentally determined for rainbow trout exposed to water concentrations of... 

The logarithm of the n-octanol/water partition coefficient (log Kow is a useful preliminary indicator of the bioconcentration potential of a compound. The calculated log K values for 1,3-DNB and 1,3,5-TNB are 1.52 and 1.18 (Deneer et al. 1987), respectively, suggesting a low potential for bioaccumulation. An experimental bioconcentration factor (BCF) of 1,3-DNB for the guppy, Poecilia reticulata, was reported to be 74.13 (Deneer et al. 1987). This BCF indicates that bioaccumulation in aquatic organisms is not an important fate process. BCF data were not located for 1,3,5-TNB. 

The partition coefficient Kq of an organic compound in the 1-octanol/water system is used to assess the bioaccumulation potential and the distribution pattern of drugs and pollutants. The partition coefficient of imidazole and ILs strongly depends on the hydrogen bond formed by these molecules and is less than one due to the high solubility in water. The low value of the 1-octanol/water partition coefficient is required for new substances, solvents, insecticides to avoid bioaccumulation. Kqw is an extremely important quantity because it is the basis of correlations to calculate bioaccumulation, toxicity, and sorption to soils and sediments. Computing the activity of a chemical in human, fish, or animal lipid, which is where pollutants that are hydrophobic will appear, is a difficult task. Thus, it is simpler to measure the 1-octanol/water partition coefficient. This parameter is used as the primary parameter characterizing hydrophobisity. 

Octanol/Water Partition Coefficient (Kow) — the equilibrium ratio of the concentrations of material partitioned between octanol and water. This coefficient is considered to be an index of the potential of a chemical to be bioaccumulated. Higher values of K, are associated with greater bioaccumulative potential. 

Meylan, W., Howard, P. and Boefhling, R. (1999) Improved method for estimating bioconcentration/bioaccumulation factor from octanol/water partition coefficient. Environ. Toxicol. Chem., 18 (4), 664—672. 

Octanol-water partition coefficient (logP0/w) lipophilicity (logPo/w) usually correlates well with acute aquatic toxicity. For nonionic organic chemicals that are toxic through narcosis, acute and chronic toxicity increases exponentially with increases in logPo/w up to a value of about 5-7. For those with logPo/w >5, bioavailability decreases along with toxicity, but bioaccumulation also increases. Minimal toxicity is likely for chemicals with log/ ( w <2 [32]... 

The mobility and bioavailability of CPs, and thus their bioremediation, are affected by their chemical and physical properties. The solubility of CPs in water decreases as the number of chlorine substituents increases. In addition, the increase in the number of chlorosubstituents in the phenol ring increases the lipophilicity of CPs and thus their tendency to bioaccumulate. The water solubilities, pKa (acidity constant) and pK0W (octanol-water partition constant) values for environmentally important CPs are summarized in Figure 8.1. 

Fig. 14 Bioaccumulation factor (BAF) in Lake Superior lake trout versus octanol-water partition coefficient (.Kow) for 19 toxaphene congeners plus B9-715 and B10-1010 [74], Results for 6 congeners (P31, B8-1413, B9-1679, B9-1046, B9-715 and B10-1010) were estimated assuming water concentrations at the detection limit. The coefficient of variation r2 = 0.35 P< 0.01...

Fig. 6 Log-log plot of estimated bioaccumulation factor vs. octanol-water partition coefficient of PAHs in Lake Erie (data from [137])...

Gill uptake rate relationships. General relationships between the gill uptake rate constant (kj), gill elimination rate constant (k2), fecal egestion rate constant (kE), and the bioconcentration factor, based on chemical equilibrium (BCFeq) and on the truly dissolved chemical concentration in the water (BCFd) and the total chemical concentration in the water (BCFt), the field based bioaccumulation factor based on the truly dissolved chemical concentration in the water (BAF) and the octanol-water partition coefficient Kow. 

Fisk, A T., Bosenberg, B., Cymbalisty, C.D, Stem, G.A., Muir, D.C.G. (1999) Octanol/water partition coefficients of toxaphene congeners determined by the slow-stirring method. Chemosphere 39, 2549-2562 Fisk, AT., Norstrom, R.J., Cymbalisty, C.D, Muir, D.C.G. (1998) Dietary accumulation and depuration of hydrophobic oiganochlo-rines bioaccumulation parameters and their relationship with the octanol/water partition coefficient. Environ. Toxicol. Chem. 17, 951-961. 

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