Quantitative structure–activity and quantitative structure–property relationship approaches as alternative skin sensitization risk assessment methods

References

• Abramowitz, R., and S. H. Yalkowsky. 1990. Melting point, boiling point, and symmetry. Pharm. Res. 7:942–47.
   PubMed Web of Science ®Google Scholar
• Acree, W. E., Jr. 1991. Thermodynamic properties of organic compounds: Enthalpy of fusion and melting point temperature compilation. Thermochim. Acta 1:37–56. doi:10.1016/0040-6031(91)87098-H.
   Google Scholar
• Ambrose, D., J. E. Connett, J. H. S. Green, J. L. Hales, A. J. Head, and J. F. Martin. 1975. Thermodynamic properties of organic oxygen compounds. 42. Physical and thermodynamic properties of benzaldehyde. J. Chem. Thermodyn. 7:1143–57. doi:10.1016/0021-9614(75)90035-X.
   Web of Science ®Google Scholar
• Ambrose, D., and R. Townsend. 1963. Thermodynamic properties of organic oxygen compounds. Part IX. The critical properties and vapour pressures, above five atmospheres, of six aliphatic alcohols. J. Chem. Soc. 54:3614–25. doi:10.1039/jr9630003614.
   Google Scholar
• Andon, R. J. L., J. F. Counsell, and J. F. Martin. 1963. Thermodynamic properties of organic oxygen compounds. Part II. The thermodynamic properties from 10 to 330K of isopropyl alcohol. Trans. Faraday Soc. 59:1555–58. doi:10.1039/TF9635901555.
   Google Scholar
• Andrews, D. H., G. Lynn, and J. Johnston. 1926. The heat capacities and heat of crystallization of some isomeric aromatic compounds. J. Am. Chem. Soc. 48:1274–87. doi:10.1021/ja01416a022.
   Google Scholar
• Api, A. M., D. Basketter, and J. Lalko. 2015. Correlation between experimental human and murine skin sensitization induction thresholds. Cutan. Ocul. Toxicol. 34:298–302. doi:10.3109/15569527.2014.979425.
   PubMed Web of Science ®Google Scholar
• Ashcroft, S. J. 1976. Vapor pressures and enthalpies of vaporization of benzyl halides. J. Chem. Eng. Data 21:397–298. doi:10.1021/je60071a009.
   Web of Science ®Google Scholar
• Basketter, D., and I. Kimber. 2001. Predictive tests for irritants and allergens and their use in quantitative risk assessment. In Textbook of contact dermatitis, R. J. G. Rycroft et al. (eds.), 227–36. Berlin, Germany: Springer-Verlag.
   Google Scholar
• Basketter, D. A., F. Gerberick, and I. Kimber. 2007. The local lymph node assay and the assessment of relative potency: Status of validation. Contact Derm. 57:70–75. doi:10.1111/j.1600-0536.2007.01141.
   PubMed Web of Science ®Google Scholar
• Basketter, D. A., L. J. Lea, A. Dickens, D. Briggs, I. Pate, R. J. Dearman, and I. Kimber. 1999. A comparison of statistical approaches to the derivation of EC3 values from local lymph node assay dose responses. J. Appl. Toxicol. 19:261–66.
   PubMed Web of Science ®Google Scholar
• Basketter, D. A., C. K. Smith Pease, and G. Y. Patlewicz. 2003. Contact allergy: The local lymph node assay for the prediction of hazard and risk. Clin. Exp. Dermatol. 28:218–21.
   PubMed Web of Science ®Google Scholar
• Bos, J. D., and M. M. Meinardi. 2000. The 500 Dalton rule for the skin penetration of chemical compounds and drugs. Exp. Dermatol. 9:165–69.
   PubMed Web of Science ®Google Scholar
• Braeuning, C., A. Braeuning, H. Mielke, A. Holzwarth, and M. Peiser. 2018. Evaluation and improvement of QSAR predictions of skin sensitization for pesticides. SAR QSAR Environ. Res. 29:823–46. doi:10.1080/1062936X.2018.1518261.
   PubMed Web of Science ®Google Scholar
• Bret-Dibat, P., and A. Lichanot. 1989. Thermodynamic properties of positional isomers of disubstituted benzene in condensed phase. Thermochim. Acta 147:261–71. doi:10.1016/0040-6031(89)85181-0.
   Web of Science ®Google Scholar
• Casey, W. M. 2016. Advances in the development and validation of test methods in the United States. Toxicol. Res. 32:9–14. doi:10.5487/TR.2016.32.1.009.
   PubMed Web of Science ®Google Scholar
• Chang, S. S., J. A. Horman, and A. B. Bestul. 1967. Heat capacities and related thermal data for diethyl phthalate crystal, glass, and liquid to 360K. J. Res. Natl. Bur. Stand. 71:293–305. doi:10.6028/jres.071A.036.
   Google Scholar
• Chickos, J. S., C. M. Braton, D. G. Hesse, and G. F. Liebman. 1991. Estimating entropies and enthalpies of fusion of organic compounds. J. Org. Chem. 56:927–38. doi:10.1021/jo00003a007.
   Web of Science ®Google Scholar
• Choi, S. M., T. H. Roh, D. S. Lim, S. Kacew, H. S. Kim, and B. M. Lee. 2018. Risk assessment of benzalkonium chloride in cosmetic products. J. Toxicol. Environ. Health B 21:8–23. doi:10.1080/10937404.2017.1408552.
   PubMed Web of Science ®Google Scholar
• Clever, H. L., and E. F. Westrum Jr. 1970. Dimethylsulfoxide and dimethylsulfone. Heat capacities, enthalpies of fusion, and thermodynamic properties. J. Phys. Chem. 74:1309–17. doi:10.1021/j100701a027.
   Web of Science ®Google Scholar
• Counsell, J. F., J. L. Hales, and J. F. Martin. 1965. Thermodynamic properties of organic oxygen compounds. Part 16. Butyl alcohol. Trans. Faraday Soc. 61:1869–75. doi:10.1039/TF9656101869.
   Google Scholar
• Danish QSAR Database. 2018. Database search. http://qsar.food.dtu.dk.
   Google Scholar
• DeWit, H. G. M., J. C. A. Offringa, C. G. De Kruif, and J. C. Van Miltenburg. 1983. Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen and sulfur. III. Molar heat capacities measured by differential scanning calorimetry. Thermochim. Acta 65:43–51. doi:10.1016/0040-6031(83)80006-9.
   Web of Science ®Google Scholar
• Domalski, E. S., and E. D. Hearing. 1996. Heat capacities and entropies of organic compounds in the condensed phase. Volume III. J. Phys. Chem. Ref. Data 25:1–525. doi:10.1063/1.555985.
   Web of Science ®Google Scholar
• Donnelly, J. R., L. A. Drewes, R. L. Johnson, W. D. Munslow, K. K. Knapp, and G. W. Sovocool. 1990. Purity and heat of fusion data for environmental standards as determined by differential scanning calorimetry. Thermochim. Acta 2:155–87. doi:10.1016/0040-6031(90)80476-F.
   Google Scholar
• Douslin, D. R., and H. M. Huffman. 1946. Low-temperature thermal data on the five isometric hexanes. J. Am. Chem. Soc. 68:1704–08. doi:10.1021/ja01213a006.
   Web of Science ®Google Scholar
• Du, H., J. Wang, Z. Hu, X. Yao, and X. Zhang. 2008. Prediction of fungicidal activities of rice blast disease based on least-squares support vector machines and project pursuit regression. J. Agric. Food Chem. 56:10785–92. doi:10.1021/jf8022194.
   PubMed Web of Science ®Google Scholar
• Dzhafarov, O. I., K. A. Karasharli, and A. M. Kuliev. 1982. Study of the real heat capacity of N,N-dimethyl-1,3-propanediamine in the range 12–300K. Azerbaijan Chem. J. 3:111–13.
   Google Scholar
• EC (European Commission). 2011. Review of QSAR models and software tools for predicting acute and chronic systemic toxicity. http://publications.jrc.ec.europa.eu/repository/bitstream/JRC61930/eur_24639_en.pdf.
   Google Scholar
• EC (European Commission). 2013. Full EU ban on animal testing for cosmetics enters into force. Brussels, Belgium: Europa EU.
   Google Scholar
• ECETOC (European Centre for Ecotoxicology and Toxicology of Chemicals). 2003a. Contact sensitisation: Classification according to potency. Technical Report No. 87, European Centre for Ecotoxicology and Toxicology of Chemicals, Brussels, Belgium.
   Google Scholar
• ECETOC (European Centre for Ecotoxicology and Toxicology of Chemicals). 2003b. Contact sensitisation: Classification according to potency: A commentary. Document No. 43, European Centre for Ecotoxicology and Toxicology of Chemicals, Brussels, Belgium.
   Google Scholar
• Fine, D. H., and P. Gray. 1967. Explosive decomposition of solid benzoyl peroxide. Combust Flame 11:71–78. doi:10.1016/0010-2180(67)90010-7.
   Web of Science ®Google Scholar
• Gallis, H. E., G. J. K. van Den Berg, and H. A. J. Oonk. 1996. Thermodynamic properties of crystalline d-limonene determined by adiabatic calorimetry. J. Chem. Eng. Data 41:1303–06. doi:10.1021/je960094l.
   Web of Science ®Google Scholar
• Garner, W. E., and F. C. Randall. 1924. Alternation in the heats of crystallization of the normal monobasic fatty acids. Part I. J. Chem. Soc. 125:881–96. doi:10.1039/CT9242500881.
   Google Scholar
• Gerberick, G. F., C. A. Ryan, R. J. Dearman, and I. Kimber. 2007a. Local lymph node assay (LLNA) for detection of sensitization capacity of chemicals. Methods 41:54–60. doi:10.1016/j.ymeth.2006.07.006.
   PubMed Web of Science ®Google Scholar
• Gerberick, G. F., C. A. Ryan, P. S. Kern, H. Schlatter, R. J. Dearman, I. Kimber, G. Y. Patlewicz, and D. A. Basketter. 2005. Compilation of historical local lymph node data for evaluation of skin sensitization alternative methods. Dermatitis 16:157–202.
   PubMed Web of Science ®Google Scholar
• Gerberick, G. F., J. D. Vassallo, L. M. Foertsch, B. B. Price, J. G. Chaney, and J. P. Lepoittevin. 2007b. Quantification of chemical peptide reactivity for screening contact allergens: A classification tree model approach. Toxicol. Sci. 97:417–27. doi:10.1093/toxsci/kfm064.
   PubMed Web of Science ®Google Scholar
• Guha, R., D. Dutta, P. C. Jurs, and T. Chen. 2006. Local lazy regression: Making use of the neighborhood to improve QSAR predictions. J. Chem. Inf. Model. 46:1836–47. doi:10.1021/ci060064e.
   PubMed Web of Science ®Google Scholar
• Han, S. M., G. G. Lee, and K. K. Park. 2012. Skin sensitization study of bee venom (Apis mellifera L.) in guinea pigs. Toxicol. Res. 28:1–4. doi:10.5487/TR.2012.28.1.001.
   PubMedGoogle Scholar
• Hildenbrand, D. L., R. A. McDonald, W. R. Kramer, and D. R. Stull. 1959. Thermodynamic and spectroscopic study of vinylidene chloride. I. Thermodynamic properties of the solid, liquid, and ideal gas. J. Chem. Phys. 30:930–34. doi:10.1063/1.1730128.
   Web of Science ®Google Scholar
• Hoffman, J. D., and B. F. Decker. 1953. Solid state phase changes in long chain compounds. J. Phys. Chem. 57:520–29. doi:10.1021/j150506a009.
   Web of Science ®Google Scholar
• Inoue, A., and K. Horikoshi. 1989. A Pseudomonas thrives in high concentrations of toluene. Nature 338:264–66. doi:10.1038/338264a0.
   Web of Science ®Google Scholar
• Interagency Coordinating Committee on the Validation of Alternative Methods (ICCVAM). 2011. Usefulness and limitations of the murine local lymph node assay for potency categorization of chemicals causing allergic contact dermatitis in humans. https://ntp.niehs.nih.gov/iccvam/docs/immunotox_docs/llna-pot/tmer.pdf.
   Google Scholar
• Katritzkya, A. R., D. A. Dobcheva, and M. Karelson. 2014. Physical, chemical, and technological property correlation with chemical structure: The potential of QSPR. Z. Naturforsch C. 4:373–84.
   Google Scholar
• Kern, P. S., G. F. Gerberick, C. A. Ryan, I. Kimber, A. Aptula, and D. A. Basketter. 2010. Local lymph node data for the evaluation of skin sensitization alternatives: A second compilation. Dermatitis 21:8–32.
   PubMed Web of Science ®Google Scholar
• Kestens, K., G. Auclair, K. Drozdzewska, A. Held, G. Roebben, and T. Linsinger. 2010. Thermodynamic property values of selected polycyclic aromatic hydrocarbons measured by differential scanning calorimetry. J. Therm. Anal. Calorim. 99:245–61. doi:10.1007/s10973-009-0440-6.
   Web of Science ®Google Scholar
• Kim, K. B., Y. W. Kim, S. K. Lim, T. H. Roh, D. Y. Bang, S. M. Choi, D. S. Lim, Y. J. Kim, S. H. Baek, M. K. Kim, et al. 2017. Risk assessment of zinc oxide, a cosmetic ingredient used as a UV filter of sunscreens. J. Toxicol. Environ. Health B 20:155–82. doi:10.1080/10937404.2017.1290516.
   PubMed Web of Science ®Google Scholar
• Kim, M. K., K. B. Kim, K. Yoon, S. Kacew, H. S. Kim, and B. M. Lee. 2018. IL-1α and IL-1β as alternative biomarkers for risk assessment and the prediction of skin sensitization potency. J. Toxicol. Environ. Health A 81:830–43. doi:10.1080/15287394.2018.1494474.
   PubMed Web of Science ®Google Scholar
• Kimber, I., D. A. Basketter, G. F. Gerberick, and R. J. Dearman. 2002. Allergic contact dermatitis. Int. Immunopharmacol. 2:201–11.
   PubMed Web of Science ®Google Scholar
• Kimber, I., M. Cumberbatch, R. J. Dearman, M. Bhushan, and C. E. Griffiths. 2000. Cytokines and chemokines in the initiation and regulation of epidermal Langerhans cell mobilization. Br. J. Dermatol. 142:401–12.
   PubMed Web of Science ®Google Scholar
• Kimber, I., J. Hilton, R. J. Dearman, G. F. Gerberick, C. A. Ryan, D. A. Basketter, L. Lea, R. V. House, G. S. Ladics, S. E. Loveless, et al. 1998. Assessment of the skin sensitization potential of topical medicaments using the local lymph node assay: An interlaboratory evaluation. J. Toxicol. Environ. Health A 53:563–79.
   PubMed Web of Science ®Google Scholar
• Lachapelle, J. M. 2014. Allergic contact dermatitis: Clinical aspects. Rev. Environ. Health 29:185–94. doi:10.1515/reveh-2014-0055.
   PubMedGoogle Scholar
• Lee, B. M., and S. Kacew. 2018. Advances in toxicological research and risk assessment. J. Toxicol. Environ. Health A 81:240. doi:10.1080/15287394.2018.1439689.
   PubMed Web of Science ®Google Scholar
• Lee, M. J., Y. K. Chang, H. M. Lin, and C. H. Chen. 1997. Solid-liquid equilibria for 4-methoxyphenol with catechol, ethylenediamine, or piperazine. J. Chem. Eng. Data 42:349–52. doi:10.1021/je960201b.
   Web of Science ®Google Scholar
• Lim, D. S., T. H. Roh, M. K. Kim, Y. C. Kwon, S. M. Choi, S. J. Kwack, K. B. Kim, S. Yoon, H. S. Kim, and B. M. Lee. 2018a. Non-cancer, cancer, and dermal sensitization risk assessment of heavy metals in cosmetics. J. Toxicol. Environ. Health A 81:432–52. doi:10.1080/15287394.2018.1451191.
   PubMed Web of Science ®Google Scholar
• Lim, D. S., T. H. Roh, M. K. Kim, Y. C. Kwon, S. M. Choi, S. J. Kwack, K. B. Kim, S. Yoon, H. S. Kim, and B. M. Lee. 2018b. Risk assessment of N-nitrosodiethylamine (NDEA) and N-nitrosodiethanolamine (NDELA) in cosmetics. J. Toxicol. Environ. Health A 81:465–80. doi:10.1080/15287394.2018.1460782.
   PubMed Web of Science ®Google Scholar
• Liu, P., and W. Long. 2009. Current mathematical methods used in QSAR/QSPR studies. Int. J. Mol. Sci. 10:1978–98. doi:10.3390/ijms10051978.
   PubMed Web of Science ®Google Scholar
• Lv, X. C., X. H. Gao, Z. C. Tan, Y. S. Li, and L. X. Sun. 2008. Molar heat capacity and thermodynamic properties of 1,2-cyclohexane dicarboxylic anhydride [C8H10O3]. J. Therm. Anal. Calorim. 92:523–27. doi:10.1007/s10973-007-8445-5.
   Web of Science ®Google Scholar
• Matos, M. A. R., C. C. S. Sousa, M. S. Miranda, V. M. F. Morais, and J. F. Liebman. 2009. Energetics of coumarin and chromone. J. Phys. Chem. B 113:11216–21. doi:10.1021/jp9026942.
   PubMed Web of Science ®Google Scholar
• McCullough, J. P., D. R. Douslin, J. F. Messerly, I. A. Hossenlopp, T. C. Kincheloe, and G. Waddington. 1957. Pyridine: Experimental and calculated chemical thermodynamic properties between 0 and 1500 K.; A revised vibrational assignment. J. Am. Chem. Soc. 79:4289–95. doi:10.1021/ja01573a014.
   Web of Science ®Google Scholar
• Mentado, J., F. Henoc, and A. Patricia. 2008. Combustion energies and formation enthalpies of 2-SH-benzazoles. J. Chem. Thermodyn. 7:1106–09. doi:10.1016/j.jct.2008.02.018.
   Google Scholar
• NAFTA(North American Free Trade Agreement) Technical Working Group on Pesticides. 2012. Quantitative structure activity relationship guidance document. https://www.epa.gov/sites/production/files/2016-01/documents/qsar-guidance.pdf.
   Google Scholar
• NCBI(National Center for Biotechnology Information). 2019. PubChem compound. https://www.ncbi.nlm.nih.gov.
   Google Scholar
• Nepal, M. R., Y. Kang, M. J. Kang, D. H. Nam, and T. C. Jeong. 2018. A β-galactosidase-expressing E. coli culture as an alternative test to identify skin sensitizers and nonsensitizers. J. Toxicol. Environ. Health A 81:288–301. doi:10.1080/15287394.2018.1440187.
   PubMed Web of Science ®Google Scholar
• NIH (National Institutes of Health). 2009. Recommended performance standards: Murine local lymph node assay. NIH Publication No. 09-7357. https://ntp.niehs.nih.gov/iccvam/docs/immunotox_docs/llna-ps/llnaperfstds.pdf.
   Google Scholar
• NIST (National Institute of Standards and Technology). 2018. Chemistry webbook. https://webbook.nist.gov/chemistry.
   Google Scholar
• OECD (Organisation for Economic Co-operation and Development). 2012. The adverse outcome pathway for skin sensitisation initiated by covalent binding to proteins. Part 1: Scientific evidence. https://www.oecd-ilibrary.org/environment/oecd-series-on-testing-and-assessment_20777876.
   Google Scholar
• Pacor, P. 1967. Applicability of the DuPont 900 DTA apparatus in quantitative differential thermal analysis. Anal. Chim. Acta. 37:200–08. doi:10.1016/S0003-2670(01)80660-7.
   Web of Science ®Google Scholar
• Parks, G. S., H. M. Huffman, and M. Barmore. 1933. Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc. 55:2733–40. doi:10.1021/ja01334a016.
   Google Scholar
• Pitzer, K. S., and D. W. Scott. 1943. The thermodynamics and molecular structure of benzene and its methyl derivatives. J. Am. Chem. Soc. 65:803–29. doi:10.1021/ja01245a019.
   Google Scholar
• Rai, U. S., and K. D. Mandal. 1990. Chemistry of organic eutectics: P-phenylenediamine-m-nitrobenzoic acid system involving the 1:2 addition compound. Bull. Chem. Soc. Jpn. 63:1496–502. doi:10.1246/bcsj.63.1496.
   Web of Science ®Google Scholar
• Rao, S. P., and S. Sunkada. 2007. Making sense of boiling points and melting points. Resonance 12:43–57. doi:10.1007/s12045-007-0059-5.
   Google Scholar
• Ryu, H. Y., S. Lee, K. S. Ahn, H. J. Kim, S. S. Lee, H. J. Ko, J. K. Lee, M. H. Cho, M. Y. Ahn, E. M. Kim, et al. 2016. Oral toxicity study and skin sensitization test of a cricket. Toxicol. Res. 32:159–73. doi:10.5487/TR.2016.32.2.159.
   PubMed Web of Science ®Google Scholar
• Sciesinski, J., J. Mayer, T. Wasiutynski, E. Sciesinska, and J. Wójtowicz. 1994. Calorimetric study of cyclooctanol. Phase Transitions 1:15–21.
   Google Scholar
• Stull, D. R. A. 1937. Semi-micro calorimeter for measuring heat capacities at low temperatures. J. Am. Chem. Soc. 59:2726–33. doi:10.1021/ja01291a075.
   Google Scholar
• Takenouchi, O., M. Miyazawa, K. Saito, T. Ashikaga, and H. Sakaguchi. 2013. Predictive performance of the human cell line activation test (h-CLAT) for lipophilic chemicals with high octanol-water partition coefficients. J. Toxicol. Sci. 38:599–609.
   PubMed Web of Science ®Google Scholar
• Temprado-María, M., M. V. Roux, and J. S. Chickos. 2008. Some thermophysical properties of several solid aldehydes. J. Therm. Anal. Calorim. 94:257–62. doi:10.1007/s10973-007-8883-0.
   Web of Science ®Google Scholar
• USEPA (United States Environmental Protection Agency). 2018. Chemistry dashboard. https://comptox.epa.gov/dashboard.
   Google Scholar
• Vasil’ev, V. G., and B. V. Lebedev. 1998. Thermodynamic properties of aliphatic aldehydes and polyaldehydes: Effect of composition and structure. Polym. Sci. Ser. A 40:464–71.
   Google Scholar
• Verevkin, S. P., and S. Schick. 2003. Determination of vapor pressures, enthalpies of sublimation, enthalpies of vaporization, and enthalpies of fusion of a series of chloro-aminobenzenes and chloro-nitrobenzenes. Fluid Phase Equilib 211:161–77. doi:10.1016/S0378-3812(03)00181-X.
   Web of Science ®Google Scholar
• Wassvik, C. M., A. G. Holmén, R. Draheim, P. Artursson, and C. A. S. Bergström. 2008. Molecular characteristics for solid-state limited solubility. J. Med. Chem. 51:3035–39. doi:10.1021/jm701587d.
   PubMed Web of Science ®Google Scholar