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Predicting Toxicity and Degradability of Quadricyclane, Fluorocarbon Ethers and Their Analogs

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Progress Report of the Air Force Project Covering the period 8/1/96 to 7/31//97 Agency No: DOD/F49620-94-1-0401 U of M No: 0756-5140 (1613-189-6090) NRRI Technical Report Number: NRRI/TR-97/15 Predicting Toxicity and Degradability of Quadricyclane, Fluorocarbon Ethers and Their Analogs Submitted By: Subhash C. Basak, Ph.D. Principal Investigator Natural Resources Research Institute 5013 Miller Trunk Highway Duluth, MN 55811 Phone: (218)720-4230 Fax: (218)720-9412 Email: [email protected] Keith B. Lodge, Ph.D. Co-principal Investigator Department of Chemical Engineering University of Minnesota, Duluth Duluth, MN 55812 Joseph Schubauer-Berigan, Ph.D. Principal Investigator of the USC Subcontract NIWB NERR Baruch Marine Laboratory P.O. Box 1630 Georgetown, SC 29442 The University of Minnesota is an equal opportunity educator and employer. Table of Contents Acknowledgments........................................................................................................................2 Objectives.................................................................................................................................... 3 Status of Effort ............................................................................................................................ 3 Accomplishments/New Findings................................................................................................. 4 TASK 1: Development of data bases ............................................................................4 TASK 2: Development of methods to quantify molecular similarity...............................4 TASK 3 Selection of analogs ............................ 5 TASK 4 ..........................................................................................................................5 A. Estimation of properties of the target chemical from the probe-induced subset B. Hierarchical approach to toxicity estimation using topological, geometrical, and quantum chemical parameters Task 5 Measurement of hydrophobicity ......................................................................... 6 Task 6 Microbial degradation studies............................................................................. 7 Task 7 Photochemical Degradation Studies ...............................................................7 Personnel Supported ..................................................................................................................7 Publications.................................................................................................................................. 7 Interactions/transitions ................................................................................................................8 A. Participation/Presentations......................................................................................... 8 B. Consultative and Advisory Functions ......................................................................... 9 C. Transitions ..................................................................................................................9 Honors/Awards.......................................................................................................................... 10 Appendix 1...................................................................................................................................10 Appendix 2...................................................................................................................................10 Acknowledgments During the third year of the Air Force grant I have benefited through interaction with numerous colleagues. I would like to specially mention Dr. Mic Lajiness (Computer-Aided Drug Discovery, The Upjohn Company, Kalamazoo, Ml), Professor A. T. Balaban (Polytechnic Institute, Bucharest, Roumania), Professor K. Balasubramanian (Department of Chemistry and Biochemistry, Arizona State University Tempe, AZ), Professor William C. Herndon, (Department of Chemistry, University of Texas, El Paso), Dr. David Opitz (Department of Computer Science, University of Minnesota, Duluth), Dr. Mark Johnson (Computer-Aided Drug Discovery, The Upjohn Company, Kalamazoo, Ml), and Professor Milan Randic (Department of Mathematics and Computer Science, Drake University, IA) for many fruitful discussions on topics related to quantification of molecular structure, molecular similarity and structure-activity relationships (SAR) pertaining to environmental toxicology. I am thankful to Mr. Greg Grunwald, Applications Programmer of NRRI, for his excellent efforts in developing databases and carrying out computations resulting in many publications supported by the Air Force. Finally, I would like to thank AFOSR for providing us financial support for carrying out the research reported herein. Subhash C. Basak, Ph.D. Principal Investigator 2 Objectives (The same as in the original proposal) In a large number of cases, we have to assess the risk of chemicals and predict the toxic potential of molecules in the face of limited experimental data. Structural criteria and functional criteria (if available) are routinely used to estimate the possible hazard posed by a chemical to the environment and ecosystem. Frequently, no biological or relevant physicochemical properties of the chemical species of interest are available to the risk assessor. In the proposed project, we will develop and implement a number of methods of quantifying molecular similarity of chemicals using techniques of computational and mathematical chemistry. Some of the methods are new and will be based on our own research on the theoretical development and implementation of molecular similarity methods. These techniques will be implemented in a user friendly computer environment of the Silicon Graphics workstation. The similarity methods will be used to select analogs of chemicals of interest to the Air Force, viz., QUADRICYCLANE, FLUOROCARBON ETHERS AND THEIR ANALOGS, from databases containing high quality physicochemical data and toxicity endpoints for large number of chemicals. The databases used in the project will come from three sources: a) public domain databases, b) our own in-house databases, and c) databases acquired from commercial vendors. The set of selected analogs, called probe-induced subsets, will be used to: a) develop structure-activity relationships (SAR), and b) carry out ranking of chemicals. Both of these methods will be used to estimate the hazard of the chemicals of interest. A set of chemicals (five to ten) will be chosen for experimental work with the purpose of evaluating and refining computer models. The set will include quadricyclane and fluorocarbon ethers of interest to the Air Force. It will also include a selection of analogs (probe-induced subset) that are readily available, suitable for experimentation, and for which data are lacking. Experiments will be performed to assess the biodegradability and photochemical degradability of the members of the set. Their toxicity will be tested by MicroTox and MutaTox. In cases where significant degradation is observed, the toxicity of the degradation products will also be tested. Direct measurement of the hydrophobicity (octanol-water partition coefficient) will be performed on the members of the set. Status of Effort A number of novel molecular similarity methods have been developed using topostructural and topochemical parameters which can be computed directly from molecular structure using POLLY. Topological indices (TIs), atom pairs (APs), geometrical parameters, and semiempirical quantum chemical parameters have been used for molecular similarity analysis and development of hierarchical QSAR models. The relative effectiveness of the various similarity techniques in selecting analogs and estimating properties of toxicological importance have been tested on a selected set of properties such as mutagenicity, acute toxicity, lipophilicity (logP, octanol/water), etc. The K nearest neighbor (KNN) method, K=1,2,... 25, has been used in generating probe-induced subsets from different databases. Results show that the KNN method gives the best estimate of properties at K = 5-10 for the properties studied. Seventy-five probe-induced subsets have been generated for Quadricyclane from three different databases: a) STARLIST logP database of Daylight, Inc., containing more than 4,000 3 high quality logP values, for b) the selection was restricted to C7 cmpds Available Chemicals Directory (ACD), containing over 180,000 chemicals which are currently available from suppliers worldwide, and c) a Chemical Abstracts Service database containing about 120,000 diverse chemicals. Some of the selected analogs are being tested in the laboratory in order to determine the utility of analogs in predicting properties of chemicals from the properties of their neighbors in similarity spaces. Accomplishments/New Findings The following is a summary of accomplishments of the various tasks of the project during the reporting period. TASK1: Development of data bases A large number of databases relevant to toxicology have been developed from published literature. These include properties like teratogenicity, inhibition of microsomal and mitochondrial oxygen uptake in rat cerebellum by chemicals, minimum inhibitory concentration of chemicals for DNA gyrase activity in E. Coli, EC50 for AHH receptor activation, Ames mutagenicity, Ito’s test for carcinogenicity, liver carcinogenicity in rat/mice, acute toxicity of various pollutants including
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