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The Effect of Organometallic and Quaternary Ammonium Compounds on the Growth of Microorganisms Lowell Lawrence Wallen Iowa State College

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The Effect of Organometallic and Quaternary Ammonium Compounds on the Growth of Microorganisms Lowell Lawrence Wallen Iowa State College Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1954 The effect of organometallic and quaternary ammonium compounds on the growth of microorganisms Lowell Lawrence Wallen Iowa State College Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Biochemistry Commons Recommended Citation Wallen, Lowell Lawrence, "The effect of organometallic and quaternary ammonium compounds on the growth of microorganisms " (1954). Retrospective Theses and Dissertations. 14151. https://lib.dr.iastate.edu/rtd/14151 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. INFORMATION TO USERS This manuscript has been reproduced from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand corner and continuing from left to right in equal sections with small overiaps. ProQuest Information and Learning 300 North Zeeb Road, Ann Arbor, Ml 48106-1346 USA 800-521-0600 NOTE TO USERS This reproduction is ttie best copy available. UMI' THE EFFECT OF ORGANOMETALLIC AND QUATERNARY AMMONIUM COMPOUNDS ON THE GROWTH OF MICROORGANISMS by Lowell L. Wallen A Dlsaertatlon Submitted to the Graduate Faculty In Partial Fulfillment of The Requirements for the Degree of DOCTOR OF.PHILOSOPHY Ma'Jor. Subject.; • Bloofiemlstry Approved; Signature was redacted for privacy. In Charge of M^^Jor Work Signature was redacted for privacy. Head of Major Department Signature was redacted for privacy. De^n of Graduate College Iowa State College 1954 UMl Number: DP13033 UMI' UMl Microform DP13033 Copyright 2005 by ProQuest Information and Learning Company. All rights reserved. This microform edition is protected against unauthorized copying under Title 17, United States Code. ProQuest Information and Learning Company 300 North Zeeb Road P.O. 60x1346 Ann Arbor, Mi 48106-1346 QD41 \ W I ^ 'I TABLE OF CONTENTS Page I. INTRODUCTION 1 II. RFVIEW OP LITERATURE 5 A. Introduction 5 6. Microorganisms 6 1. SBCcharomyces cerevisiae 6 2. Aspergillus niger 8 3. LaotoDacilIU3~5elbrueckii 8 4. Acetobacter suboxydans. 9 5. Lactobacillus easel 11 6. Clostridium acetobutylicum. 11 C, Organoraetallic Chemotherapy 13 1. History of organoraetallic compounds.. 13 2. Nature of organoraetallic compounds... 15 3. Chemotherapeutic properties of organ­ oraetallic compounds 19 4. Recent studies of organoraetallic chemotherapy 22 D, Quaternary Ammonium Compounds 26 1. History of quaternary ammonium com­ pounds 26 2. Nature of quaternary ammonium com­ pounds 28 3. Recent studies of quaternary ammonium compounds 35 E, Respiration and Metabolism of Microorgan­ isms..... 38 III. MATERIALS 48 A. Cultures 48 B. Ingredients of Media 48 1. Glucose 48 2. Yeast extract 49 3. Peptonized milk 49 4. Corn 49 5. Sorbitol ^ 49 TiH+7 / Ill TABLE OF CONTENTS (continued) Page C. Special Solutions and Chemicals 50 1. Solutions of test compounds 50 2. BAL 50 3. y-Dlethylaminopropanol 50 4. Dlphenylmercury 50 5. Other organic compounds 50 6. Reagents.... 52 IV. •METHODS 53 A. Warburg Apparatus 53 B. Fermentation Procedures 54 1. Aerobes 54 2, Anaerobes 55 C. Analytical Procedures 57 1. Detection of sorbose by chromatography 57 2. Determination of acetone 59 3. Determination of total solvents 59 4. Determination of reducing sugars 59 5. Determination of volatile acids(total) 60 6. Determination of concentrations of organo metal lie intermediates 60 7. Determination of the presence of organometallic intermediates 61 8. Qualitative determination of elements 62 9. Quantitative determination of elements 62 D. Synthetic Procedures 62 1. Nitrogen purification 62 2. Melting points 65 V. EXPERIMENTAL RESULTS 66 A. Synthesis of Organic Compounds 66 1. Preparation of phenylllthlum 66 2. Preparation of triphenyllead lithium . 66 3. Preparation of Y-diethylamlnopropyl chloride 67 4. Preparation of trlphenyl-y-diethyl- amlnopropyllead 68 Iv TABLE OF CONTENTS (continued) Page 5. Preparation of trlphenyl-Y -(diethyl- methylammonlum)-propyllead raethoaulfate 68 6. Preparation of p-tolylllthlum 69 7. Preparation of trlphenyllead chloride... 69 8. Preparation of trlphenyl-p-tolyllead.,.. 69 9. Preparation of trlphenylmethyl chloride. 72 10. Preparation of trlphenylmethyl sodium... 7S 11. Preparation of 4,4,4-triphenyl-n-butyl- dlethylamlne 73 12. Preparation of 4,4,4-trlphenyl-n-'butyl- diethyl-raethylaramonium methosulfate.... 73 13. Preparation of n-propyldiethylaralne 77 14. Preparation of raethyldlethyl-n-propyl- ammonium methosulfate 78 B. Preliminary Experiments 79 1. Solvents and solubility.. 79 8. Effect of the presence of yeast extract on glucose analyses 80 3, Exposure of media containing an organo- lead detergent to air-borne microorgan­ isms 82 4, Growth of an air-borne mold in the pres­ ence of an organolead compound 83a 5. Growth tests of microorganisms in the presence of an organotin compound 84 6. Growth of Saccharomyces cerevisiae in the presence of tetralcis-(p-dimethyl- arainophenyl)-lead tetramethiodide 85 C. Tests Conducted on Microorganisms Using Organic Compounds 86 1. Aspergillus nip-;er 86 2. Saccharomyces cerevisiae. 88 3. Acetobacter suboxydans 142 4. Clostridium acetoDutyllcum 153 5. Lactobacillus easel 162 VI. DISCUSSION AND CONCLUSIONS 167 VII. SUMMARY 180 V TABLE OF CONTENTS (continued) Page VIII. LITERATURE CITED 186 IX. ACKNOWLEDGEMENTS 199 1 I. INTRODUCTION The presence of microorganisms upon the earth is univer­ sal, and they can be found almost anywhere man may search for them. The fact of their existence has not always been known since they are too small to be observed by the naked eye. However, this does not presume that they are of little Importance, for some are endowed with tremendous potentiali­ ties for good and some for evil. They can survive under a great variety of conditions, and in addition, they multiply so rapidly that the destruction of millions of them la often of no consequence to their survival. The man chiefly responsible for enabling microorganisms to be seen was a Dutch linen merchant turned investigator, AntonJ van Leeuwenhoek (1632-1723), who was skilled in the art of making lenses to the extent that he fashioned a type of crude microscope. With such an instrument, van Leeuwenhoek was able to observe microorganisms, which he called "animalcules" (45), Since then, the study of microorganisms has increased in scope, and as a result, the entire overall concept of a bacterial cell is so vast that no single person is able to master it In its entirety. The scope Included in the genesis, lifespan and death of a cell Involves all branches of chem­ istry, as well as physics, genetics, bacteriology, cytology, physiology, and many other branches of science, making it 2 necessary for one who endeavors to work with microorganisms to specialize In a limited area of research and thus add his findings to those of past years to help complete the ever-growing picture. The activity of harmful and undesirable microorganisms has constantly challenged mankind in his attempt to gain mastery over them. Among the primary reasons for this ef­ fort is the control of diseases, many of which are usually attributed to microorganisms. Thus there have been many at­ tempts to destroy these causative agents and therefore rid the world of diseases. This search continues unabated, and has resulted in a tremendous collection of published mate­ rial dealing with methods for controlling or eliminating troublesome and pathogenic microorganisms from the body or wherever they may be found. Chemotherapy is the science of therapeutics which em­ ploys chemical reagents toxic to the organisms, but not toxic (or only slightly so) to the host. Some compounds have Involved a metal atom in their structure and have been very beneficial to man. Metals or their salts have been used for many years since the second century when mercury was employed by the ancients of the medical trade (149), but of more recent note is Salvarsan, an organometallic compound prepared by Paul Ehrlich, which has been used for the treatment of syphilis for many years. Organometallic compounds have been defined very 3 generally as organic compounds which incorporate a metal in their structure. This could include the metal salts of or­ ganic acids, so this generalization usually excludes salts of this kind. A true organometallic compound, in the strict­ est sense, is one in which all normal valences of the metal atom are employed in a oarbon-to-metal bond for each valence. The chemical literature has many references to
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