Application of Structural Concepts to Evaluate the Potential Carcinogenicity of Natural Products

SAR and QSAR in Environmental Research

Volumn 5, Issue 2, 1996, Pages 79-98

  Rosenkranz, H S ^a   Liu, M ^a   Cunningham, A ^a   Klopman, G ^b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

biophore; carcinogenicity; CASE MULTICASE; natural products; Salmonella

Indexed keywords

BIOPHORE; CARCINOGENICITY; CASE/MULTICASE; DATA BASE; GENOTOXIC; MARGINALS; NATURAL PRODUCTS; RELATIONAL SYSTEMS; STRUCTURAL CONCEPT; STRUCTURE ACTIVITY;

ANTHOCYANIN; CARCINOGEN; PROANTHOCYANIDIN; SELLIGUEAIN A; SWEETENING AGENT;

ANIMAL; ARTICLE; BAGG ALBINO MOUSE; CHEMISTRY; DRUG EFFECT; ELECTROCHEMISTRY; EXPERT SYSTEM; FACTUAL DATABASE; GENETICS; MOUSE; MUTAGEN TESTING; SALMONELLA; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTHOCYANINS; CARCINOGENS; DATABASES, FACTUAL; ELECTROCHEMISTRY; EXPERT SYSTEMS; MICE; MICE, INBRED BALB C; MUTAGENICITY TESTS; PROANTHOCYANIDINS; SALMONELLA; STRUCTURE-ACTIVITY RELATIONSHIP; SWEETENING AGENTS;

EID: 0029686995     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/10629369608031709     Document Type: Article

References (53)

1. Lave, L. B., Ennever, F. K., Rosenkranz, H. S., and Omenn, G. S., 1988. Information value of the rodent bioassay. Nature, 336: 631–633.
2. Klopman, G., and Rosenkranz, H. S., 1994. Prediction of carcinogenicity/mutagenicity using MULTICASE. Mutation Res., 305: 33–46.
3. Baek, N. I., Chung, M. S., Shamon, L., Kardono, L. B.S., Tsauri, S., Padmawinata, K., Pezzuto, J. M., Soejarto, D. D., and Kinghorn, A. D., 1993. Selligueain A, a novel highly sweet proanthocyanidin from the rhizomes o. Selliguea feei. J. Nat. Products, 56: 1532–1538.
4. Klopman, G., 1984. Artificial intelligence approach to structure-activity studies. Computer automated structure evaluation of biological activity of organic molecules. J. Am. Chem. Soc., 106: 7315–7321.
5. Klopman, G., and Rosenkranz, H. S., 1984. Structural requirements for the mutagenicity of environmental nitroarenes. Mutation Res., 126: 227–238.
6. Klopman, G., 1992. MULTICASE 1. A hierarchical computer automated structure evaluation program. Quant. Struct-Act. Relat., 11: 176–184.
7. Klopman, G., and Rosenkranz, H. S., 1991. Quantification of the predictivity of some short term assays for carcinogenicity in rodents. Mutation Res., 253: 237–240.
8. Klopman, G., 1964. A semiempirical treatment of molecular structures. I. Electronegativity and atomic terms. J. Am. Chem. Soc., 86: 1463–1469.
9. Pearson, R. G., 1986. Absolute electronegativity and hardness correlated with molecular orbital theory. Proc. Natl. Acad. Sci. USA, 83: 8440–8441.
10. Houser, J. J., and Klopman, G., 1988. A new tool for the rapid estimation of charge distribution. J. Comput. Chem., 9: 893–904.
11. Houser, J. J., and Klopman, G., 1992. The rapid estimation of charge distribution. II. Heteroatoms. J. Comput. Chem., 13: 990–996.
12. Ashby, J., 1985. Fundamental structural alerts to potential carcinogenicity or non-carcinogenicity. Environ. Mutagenesis, 7: 919–921.
13. Ashby, J., and Tennant, R. W., 1991. Definitive relationships among chemical structure, carcinogenicity and mutagenicity for 301 chemicals tested by the U.S. National Toxicology Program. Mutation Res., 257: 229–306.
14. Ashby, J., and Patton, D., 1993. The influence of chemical structure on the extent and sites of carcinogenesis for 522 rodent carcinogens and 52 different chemical carcinogen exposures. Mutation Res., 286: 3–74.
15. Tennant, R. W., and Ashby, J., 1991. Classification according to chemical structure, mutagenicity to Salmonella and level of carcinogenicity of a further 39 chemicals tested for carcinogenicity by the U.S. National Toxicology Program. Mutation Res., 257: 209–227.
16. Tennant, R. W., Spalding, J., Stasiewicz, S., and Ashby, J., 1990. Prediction of the outcome of rodent carcinogenicity bioassays currently being conducted on 44 chemicals by the National Toxicology Program. Mutagenesis, 5: 3–14.
17. Dunkel, V. C., Zeiger, E., Brusick, D., McCoy, E. C., McGregor, D., Mortelmans, K., Rosenkranz, H. S., and Simmon, V. F., 1984. Reproducibility of microbial mutagenicity assays: I. Tests with Salmonella typhimurium and Escherichia coli using standardized protocol. Environ. Mutagenesis, 6: 1–254. (Suppl. 2)
18. Dunkel, V. C., Zeiger, E., Brusick, D., McCoy, E., McGregor, D., Mortelmans, K., Rosenkranz, H. S., and Simmon, V. F., 1985. Reproducibility of microbial mutagenicity assays: II. Testing of carcinogens and noncarcinogens in Salmonella typhimurium and Escherichia coli. Environ. Mutagenesis, 7: 1–248. (Suppl. 5)
19. Mortelmans, K., Haworth, S., Lawlor, T., Speck, W. T., Tainer, B., and Zeiger, E., 1986. Salmonella mutagenicity tests. II. Results from the testing of 270 chemicals. Environ. Mutagenesis, 8: 1–119.
20. Zeiger, E., 1987. Carcinogenicity of mutagens: Predictive capability of the Salmonella mutagenesis assay for rodent carcinogenicity. Cancer Res., 47: 1287–1296.
21. Zeiger, E., Anderson, B., Haworth, S., Lawlor, T., Mortelmans, K., and Speck, W., 1987. Salmonella mutagenicity tests: III. Results from 255 chemicals. Environ. Mutagenesis, 9: 1–109. (Suppl. 9)
22. Zeiger, E., Anderson, B., Haworth, S., Lawlor, T., and Mortelmans, K., 1988. Salmonella mutagenicity tests: IV. Results from the testing of 300 chemicals. Environ. Molecular Mutagenesis, 11: 1–157. (Suppl. 12)
23. Ashby, J., and Tennant, R. W., 1988. Chemical structure, Salmonella mutagenicity and extent of carcinogenicity as indicators of genotoxic carcinogenesis among 222 chemicals tested in rodents by the U.S. NCI/NTP. Mutation Res., 204: 17–115.
24. Ashby, J., Tennant, R. W., Zeiger, E., and Stasiewicz, S., 1989. Classification according to chemical structure, mutagenicity to Salmonella and level of carcinogenicity of a further 42 chemicals tested for carcinogenicity by the U.S. National Toxicology Program. Mutation Res., 223: 73–103.
25. Matthews, E. J., Spalding, J. W., and Tennant, R. W., 1993. Transformation of BALB/C-3T3 cells: V. Transformation responses of 168 chemicals compared with mutagenicity in Salmonella and carcinogenicity in rodent bioassays. Environ. Health perspect. Suppl., 101: 347–482. (Suppl. 2)
26. Rosenkranz, H. S., and Klopman, G., 1993. Structural relationships between mutagenicity, maximum tolerated dose, and carcinogenicity in rodents. Environ. Molecular Mutagenesis, 21: 193–206.
27. Gold, L. S., Sawyer, C. B., Magaw, R., Backman, G. M., de Veciana, M., Levinson, R., Hooper, N. K., Havender, W. R., Bernstein, L., Peto, R., Pike, M. C., and Ames, B. N., 1984. A carcinogenic potency database of the standardized results of animal bioassays. Environ. Health Perspect., 58: 9–319.
28. Gold, L. S., de Veciana, M., Backman, G. M., Magaw, R., Lopipero, P., Smith, M., Blumenthal, M., Levinson, R., Bernstein, L., and Ames, B. N., 1986. Chronological supplement to the carcinogenic potency database: Standardized results of animal bioassays published through December 1982. Environ. Health perspect., 67: 161–200.
29. Gold, L. S., Slone, T. H., Backman, G. M., Magaw, R., Da Costa, M., Lopipero, P., Blumenthal, M., and Ames, B. N., 1987. Second chronological supplement to the carcinogenic potency database: Standardized results of animal bioassays published through December 1984 and by the National Toxicology Program through May 1986. Environ. Health Perspect., 74: 237–329.
30. Gold, L. S., Slone, T. H., Backman, G. M., Eisenberg, S., Da Costa, M., Wong, M., Manley, N. B., Rohrbach, L., and Ames, B. N., 1990. Third chronological supplement to the carcinogenic potency database: Standardized results of animal bioassays published through December 1986 and by the National Toxicology Program through June 1987. Environ. Health Perspect., 84: 215–286.
31. Gold, L. S., Manley, N. B., Slone, T. H., Garfinkel, G. B., Rohrbach, L., and Ames, B. N., 1993. The fifth plot of the carcinogenic potency database: Results of animal bioassays published in the general literature through 1988 and by the National Toxicology Program through 1989. Environ. Health Perspect., 100: 65–135.
32. Rosenkranz, H. S., and Klopman, G., 1995. “The application of structural concepts for predicting the carcinogenicity of therapeutic agents”. In Burger's Medicinal Chemistry and Drug Discovery. Principles and Practice, Edited by: Wolff, M. E., 223–249. New York: John Wiley & Sons.
33. 50: A proposed general convention for the numerical description of the carcinogenic potency of chemicals in chronic-exposure animal experiments. Environ. Health Perspect., 58: 1–8.
34. Ashby, J., and Tenant, R. W., 1994. Prediction of rodent carcinogenicity for 44 chemicals: Results. Mutagenesis, 9: 7–15.
35. Piegorsch, W. W., and Zeiger, E., 1991. “Measuring intra-assay agreement for the Ames Salmonella assay”. In Lecture Notes in Medical Information. Statistical Methods in Toxicology, Edited by: Rienhoff, O., and Linberg, D. A.B., 35–41. Berlin: Springer.
36. Ashby, J., 1993. Gambling and the conduct of genetic toxicology tests. Mutation Res., 319: 151–153.
37. Gold, L. S., Bernstein, L., Magaw, R., and Slone, T. H., 1989. Interspecies extrapolation in carcinogenesis: Prediction between rats and mice. Environ. Health Perspect., 81: 211–219.
38. IARC. 1992. Mechanisms of Carcinogenesis in Risk Identification, IARC Scientific Publication No. 116 Edited by: Vainio, H., Magee, P., McGregor, D., and McMichael, A. J., Lyon: International Agency for Research on Cancer.
39. Ennever, F. K., Noonan, T. J., and Rosenkranz, H. S., 1987. The predictivity of animal bioassays and short-term genotoxicity tests for carcinogenicity and non-carcinogenicity to humans. Mutagenesis, 2: 73–78.
40. Bartsch, H., and Malaveille, C., 1989. Prevalence of genotoxic chemicals among animal and human carcinogens evaluated in the IARC Monograph Series. Cell Biol. Toxicol., 5: 115–127.
41. Shelby, M. D., 1988. The genetic toxicity of human carcinogens and its implications. Mutation Res., 204: 3–15.
42. Ashby, J., and Morrod, R. S., 1991. Detection of human carcinogens. Nature, 352: 185–186.
43. Williams, G. M., 1987. “Definition of a human cancer hazard”. In Nongenotoxic Mechanisms in Carcinogenesis, Banbury Report 25 Edited by: Butterworth, B. E., and Slaga, T. J., 367–380. Cold Spring Harbor, New York: Cold Spring Harbor Laboratory.
44. Williams, G. M., 1990. Screening procedures for evaluating the potential carcinogenicity of food-packaging chemicals. Regul. Toxicol. Pharmacol., 12: 30–40.
45. Wilson, J. D., 1989. “Assessment of low-exposure risk from carcinogenesis: Implications of the Knudson-Moolgavkar two-critical mutation theory”. In Biologically-Based Methods for Cancer Risk Assessment, Edited by: Travis, C. C., 275–287. Plenum Press.
46. Andersen, M. E., Higginson, J., Krewski, D., Munro, I. C., Pegg, A. E., Rosenkranz, H. S., Solomon, K. R., Weisburger, E., Williams, G. M., and Wogan, G. N., 1990. Safety assessment procedures for indirect food additives. An overview. Regul. Toxicol. Pharmacol., 12: 2–12.
47. Ames, B. N., and Gold, L. S., 1990. Chemical carcinogenesis: Too many rodent carcinogens. Proc. Natl. Acad. Sci., 87: 7772–7776.
48. Cohen, S. M., and Ellwein, L. B., 1990. Cell proliferation in carcinogenesis. Science, 249: 1007–1011.
49. Cohen, S. M., and Ellwein, L. B., 1991. Genetic errors, cell proliferation and carcinogenesis. Cancer Res., 51: 6493–6505.
50. Butterworth, B. E., 1990. Consideration of both genotoxic and nongenotoxic mechanisms in predicting carcinogenic potential. Mutation Res., 239: 117–132.
51. Butterworth, B. E., Popp, J. A., Conolly, R. B., and Goldsworthy, T. L., 1992. “Chemically induced cell proliferation in carcinogenesis”. In Mechanisms of Carcinogenesis in Risk Identification, IARC Scientific Publication No. 116 Edited by: Vainio, H., Magee, P., McGregor, D., and McMichael, A. J., 279–305. Lyon
52. Preston-Martin, S., Pike, M. C., Ross, R. K., Jones, P. A., and Henderson, B. E., 1990. Increased cell division as a cause of human cancer. Cancer Res., 50: 7415–7421.
53. Rosenkranz, H. S., Zhang, Y. P., and Klopman, G., 1995. Risk identification using structural concepts: The potential carcinogenicity of praziquantel. Regul. Toxicol. Pharmacol., 22: 152–161.