TY - JOUR
T1 - Comparative tumor initiating activities of cyclopentano and methyl derivatives of 5-methylchrysene and chrysene
AU - Amin, S.
AU - Hecht, S. S.
AU - Di Raddo, P.
AU - Harvey, R. G.
N1 - Funding Information:
We thankV eronicaS aa and BijayaM israf or their technicala ssistanceT. his study was supported by Grant No. CA-44377 from the National Cancer Institutea nd Grant No. ES-04266 from the NationalI nstituteo f Environ-mentalH ealthS ciences.T his is paper no. 133 in “A Study of ChemicalC arcinogenesis”.
PY - 1990/5/15
Y1 - 1990/5/15
N2 - Previous studies showed that 5,6-dimethylchrysene (5,6-diMeC) and 5,7-diMec were significantly less tumorigenic than 5-methylchrysene (5-MeC). These results were unexpected based on the known mechanism of metabolic activation of 5-MeC and indicated the presence of critical steric requirements for tumorigenicity at the 6 and 7 positions of 5-MeC. In this study, the structure activity relationships were further extended by comparing the tumor-initiating activities on mouse skin of 5-MeC, 6,7-cyclopentano-5-MeC, 5,6-diMeC, 6,7-diMeC, 5,7-diMeC, chrysene and 6,7-cyclopentanochrysene. 5-MeC was the most tumorigenic compound, with activity significantly higher than all other compounds tested. Among the other compounds, only 5,6-diMeC was significantly tumorigenic. The results demonstrate that substitution of methyl or methylene groups at the 6 or 7 positions of 5-MeC leads to a significant reduction of tumor initiating activity.
AB - Previous studies showed that 5,6-dimethylchrysene (5,6-diMeC) and 5,7-diMec were significantly less tumorigenic than 5-methylchrysene (5-MeC). These results were unexpected based on the known mechanism of metabolic activation of 5-MeC and indicated the presence of critical steric requirements for tumorigenicity at the 6 and 7 positions of 5-MeC. In this study, the structure activity relationships were further extended by comparing the tumor-initiating activities on mouse skin of 5-MeC, 6,7-cyclopentano-5-MeC, 5,6-diMeC, 6,7-diMeC, 5,7-diMeC, chrysene and 6,7-cyclopentanochrysene. 5-MeC was the most tumorigenic compound, with activity significantly higher than all other compounds tested. Among the other compounds, only 5,6-diMeC was significantly tumorigenic. The results demonstrate that substitution of methyl or methylene groups at the 6 or 7 positions of 5-MeC leads to a significant reduction of tumor initiating activity.
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U2 - 10.1016/0304-3835(90)90225-M
DO - 10.1016/0304-3835(90)90225-M
M3 - Article
C2 - 2337893
AN - SCOPUS:0025229039
SN - 0304-3835
VL - 51
SP - 17
EP - 20
JO - Cancer Letters
JF - Cancer Letters
IS - 1
ER -
