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. 2016 Dec 18;30(1):332–366. doi: 10.1021/acs.chemrestox.6b00366

Table 2. Adduct Formation with Albumin (Alb) and/or Plasma Proteins (PP) in Rodents Exposed to Arylamines and Nitroarenes.

  PB-indexa total 14C or 3H-label PB-indexa hydrolyzable adduct Dose [mmol/kg] % of dose boundb Adduct ratio Hb/PPe Adduct ratio Hb/Albe
Benzidine 1632 (PP)i ND (PP)186 0.0011 0.360% 0.5186  
3,3′-Dichlorobenzidine (DCBz) 529 (PP)i 138 (PP)186 0.05 0.166% 0.2186  
1-Nitropyrene 181 (PP)337 adductg,337 0.00004–0.004 0.04%337 0.25338  
Nitrobenzene 136 (PP)61 79 (PP)186 0.2 0.0300% 7.6186  
4-Chloroaniline (4CA) 82 (PP)339 19.7 (PP)186 0.014 0.0181% 29.3i,186  
Acetanilide 70 (PP)61 11.2 (PP)186 0.15 0.0154% 2.5186  
             
2-Aminofluorene   72 (PP)340 0.5 0.0159% 2.38f,340  
2-Nitrofluorene   5.0 (PP)340 0.5 0.0011% 0.32f,340  
1-Aminopyrene   0.44 (PP)340 0.5 0.0001% 0.73f,340  
2-Aminonaphthalene   0.2 (PP)340 0.5 0.00004% 50f,340  
2-Nitronaphthalene   NDh(PP)340     only Hb-adduct340  
Aniline   ND (PP)340 0.5   only Hb-adductf,h,340 42 in humanf,341  
2-Methylaniline (2MA) 297 (Alb)193 ND (Alb)193 0.466 0.0291%   0.94193
4,4′-Methylenebis(2-chloroaniline) (MOCA)192 279 (Alb)192 ND (Alb)192 0.0037 0.027%   1.0192
2-Amino-3-methylimidazo [4,5-f]quinoline (IQ)88,191 223 (Alb) 22.3 (Alb) 0.15 0.022%d   0.33–0.288
4-Aminobiphenyl (4ABP)c220 204 (Alb)c,j   0.012 0.02%   25189
a

Protein binding (PB)-index: (pmol compound/mg protein)/(mmol compound/kg body weight).

b

Calculated with the assumptions: per kg rat there are 0.98 g Alb and or 2.205g plasma proteins (PP).342

c

After pronase digestion: isolation of the adduct with Trp214 (Ala-Trp-Ala-Val).20

d

After pronase digestion: N2-(Pro-Tyr-cysteinesulfinyl-)IQ; 0.014–0.043% of the dose bound to Alb = experimental value.

e

Total binding (= hydrolyzable plus nonhydrolyzable) to Hb devided by total binding to Alb and/or PP.

f

Ratio of hydrolyzable adducts.

g

1-Acetylamino-X,Y-diacetoxy-pyrenes.337

h

ND = not detected

i

Neumann186 used a PB-index expressed as (mmol compound/mol protein)/(mmol/kg body weight). A molecular weight of 68000 was taken for the calculations.339 Therefore, (106/68000)·[(mmol compound/mol PP)/(mmol compound/kg body weight)] yields the values expressed as [(pmol compound/mg PP)/(mmol compound/kg body weight)]. Differences from the experimental results are due to rounding errors.

j

This value was calculated from the percentage of the dose bound to Alb and from the dose.