Structure-Toxicity
Relationships of Polycyclic Aromatic Hydrocarbons
using Molecular Quantum Similarity
Ana Gallegos, David
Robert and Ramon Carbó-Dorca
The establishment of quantitative structure-activity
relationships (QSAR) models for the toxicity of polycyclic aromatic
hydrocarbons (PAHs) is described. Two properties: in vitro percutaneous
absorption in rat skin and discrete levels of carcinogenic activity are
examined using molecular quantum similarity measures (MQSM). The results show
that MQSM produce comparable, or even better, results than other approaches
using physicochemical, topological and quantum-chemical molecular descriptors.
furthermore, a careful analysis puts into evidence that most of the information
characterized by the original descriptors is in fact contained in the molecular
density functions, the basis of MQSM. The present paper, together with several
other ones reported by our laboratory, prove that MQSM might be appropriate
theoretical tools for QSAR and computer-aided drug design, comparable to other
highly predictive QSAR methodologies.
Submitted.
Data complementary to the paper: Structures and coordinates of
the different molecular sets.
(1) PERCUTANEOUS ABSORPTION OF PAHs
|
MOL and AMPAC files for the 60 PAHs set |
||
|
Molecule |
MOL file |
AMPAC file |
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Coronene |
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Dibenzo[a,l]pyrene |
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9,10-diphenylanthracene |
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Perylene |
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Dibenzo[a,i]pyrene |
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3-methylcholanthrene |
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9-benzylidenefluorene |
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7,10-dimethylbenzo[a]pyrene |
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Indeno(1,2,3-cd)pyrene |
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Dibenz[a,h]anthracene |
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Benzo[e]pyrene |
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Benzo[g,h,i]perylene |
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9-p-tolylfluorene |
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6-ethylchrysene |
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9-cynnamylfluorene |
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6- methylbenz[a]anthracene |
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Benzo[k]fluoranthene |
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Benzo[a]pyrene |
||
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3-ethylpyrene |
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1-methyl-7-isopropylphenanthrene |
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2-(tert-butyl)anthracene |
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9-phenylanthracene |
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3-methylcholanthrene |
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10-methylbenz[a]anthracene |
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5-methylbenz[a]anthracene |
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9,10-dihydroanthracene |
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9-phenylfluorene |
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1,2,3,6,7,8-hexahydropyrene |
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n-butylpyrene |
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5,6-dihydro-4H-dibenz[a,k,l]anthracene |
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3-ethylfluoranthene |
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Triphenylene |
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7,8,9,10-tetrahydroacephenanthrene |
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2,3-benztriphenylene |
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Benzo[c]phenanthrene |
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1-methylpyrene |
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3,9-dimethylbenz[a]anthracene |
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2,3-benzofluorene |
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1,2-benzofluorene |
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9-benzylfluorene |
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9-m-tolylfluorene |
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Pyrene |
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2-ethylanthracene |
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10-methylbenzo[a]pyrene |
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1-methylanthracene |
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2-methylfluoranthene |
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3,6-dimethylphenanthrene |
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Benzo[a]anthracene |
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Fluorene |
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2-methylphenanthrene |
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9-ethylfluorene |
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1-methylphenanthrene |
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9,10-dihydrophenanthrene |
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9-vinylanthracene |
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Anthracene |
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Fluoranthene |
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1-methylfluorene |
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2-methylanthracene |
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4H-cyclopenta(d,e,f)phenanthrene |
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Phenanthrene |
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|
|
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Data
originally taken from the paper: Roy, T.A.; Krueger, A.J.; Mackerer, C.R.;
Neil, W.; Arroyo, A.M.; Yang, J.J. SAR QSAR Environ. Res., 1998,
9, 171-185.
(2) CARCINOGENIC ACTIVITY OF PAHs
|
MOL and AMPAC files for the 60 PAHs set |
||
|
Molecule |
MOL file |
AMPAC file |
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Dibenzo[3,4:9,10]pyrene |
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Benzo[3,4]pyrene |
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Dibenzo[3,4:8,9]pyrene |
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Dibenzo[3,4:6,7]pyrene |
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Dibenzo[1,2:3,4]pyrene |
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Naphto[2,3:3,4]pyrene |
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Dibenzo[1,2:5,6]anthracene |
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Tribenzo[3,4:6,7:8,9]pyrene |
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Dibenzo[1,2:3,4]phenanthrene |
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Tribenzo[3,4:6,7:9,10]pyrene |
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Dibenzo[1,2:5,6]phenanthrene |
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Benzo[1,2]anthracene |
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Chrysene |
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Benzo[3,4]phenanthrene |
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Dibenzo[1,2:7,8]anthracene |
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Dibenzo[1,2:3,4]anthracene |
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Benzo[1,2]pyrene |
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Phenanthrene |
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Triphenylene |
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Benzo[1,2]naphthacene |
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Dibenzo[3,4:5,6]phenanthrene |
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Picene |
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Tribenzo[1,2:3,4:5,6]anthracene |
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Dibenzo[1,2:5,6]pyrene |
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Phenanthra[2,3:1,2]anthracene |
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Benzo[1,2]pentacene |
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Anthanthrene |
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Benzene |
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Naphtalene |
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Pyrene |
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Benzo[ghi]perylene |
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Coronene |
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7,12-dimethylbenz[a]anthracene |
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6,12-dimethylbenz[a]anthracene |
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6,8,12-trimethylbenz[a]anthracene |
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2-methylbenzo[a]pyrene |
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4-methylbenzo[a]pyrene |
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11-methylbenzo[a]pyrene |
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12-methylbenzo[a]pyrene |
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1-methylbenzo[a]pyrene |
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4,5-dimethylbenzo[a]pyrene |
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3-methylbenzo[a]pyrene |
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1,2-dimethylbenzo[a]pyrene |
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2,3-dimethylbenzo[a]pyrene |
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3,12-dimethylbenzo[a]pyrene |
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1,3-dimethylbenzo[a]pyrene |
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1,4-dimethylbenzo[a]pyrene |
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5-methylbenzo[c]phenanthrene |
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5-methylchrysene |
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6,8-dimethylbenz[a]anthracene |
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7-methylbenz[a]anthracene |
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5-methylbenzo[a]pyrene |
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7-methylbenzo[a]pyrene |
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6-methylbenzo[a]pyrene |
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1,6-dimethylbenzo[a]pyrene |
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3,6-dimethylbenzo[a]pyrene |
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4-methylbenzo[c]phenanthrene |
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3-methylbenzo[c]phenanthrene |
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6-methylbenzo[c]phenanthrene |
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6-methylbenz[a]anthracene |
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12-methylbenz[a]anthracene |
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6-methylanthanthrene |
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6,12-dimethylanthanthrene |
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1-methylbenzo[c]phenanthrene |
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2-methylbenzo[c]phenanthrene |
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10-methylbenzo[a]pyrene |
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6-methylchrysene |
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3-methylbenz[a]anthracene |
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1-methylbenz[a]anthracene |
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11-methylbenz[a]anthracene |
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9-methylbenz[a]anthracene |
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2-methylbenz[a]anthracene |
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5-methylbenz[a]anthracene |
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8-methylbenz[a]anthracene |
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2-methylpyrene |
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4-methylpyrene |
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1-methylpyrene |
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7,10-dimethylbenzo[a]pyrene |
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6,10-dimethylbenzo[a]pyrene |
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8-methylbenzo[a]pyrene |
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|
9-methylbenzo[a]pyrene |
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|
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Data
originally taken from the paper: Vendrame, R.; Braga, R.S.; Takahata, Y.;
Galvao, D.S. J. Chem. Inf. Comput. Sci., 1999, 39,
1094-1104.