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Studies on the Chemical Nature of Bi Nding of Bound STUDIES ON THE CHEMICAL NATURE OF BI NDING OF BOUND ACETYLCHOLINE IN RAT BRAIN by Gregory Kwai- Wah Ko A thesis submitted to the Facul ty of Gradua te Studies and Research in partial fulfilment of the requirements for the degree of Master of Science. Department of Biochemistry, McGill University, Montrea 1, P. Q. April, 1966 -·- AC KNOWLEDGEMENTS 1 wish to express my deepest gratitude to Dr. E .A. Hosein, my research director, for his valuable advice and generous guidance throughout the course of this study 1 and for his critic ism of this thesis. To Dr. J. G. Chabrol, 1 wish to express my cardia 1 thanks for his assistance during the initiation period and for his keen interest in this investigation. To my friend 1 Vivien 1 1 am ob 1iged for her encouragement, patience and for her help in preparing the first draft of this manuscript. Thanks are due to my fami ly for the ir understanding and support. To my sis ter 1 Patty, this thesis is dedicated. 1 wish to express my thanks to Miss Sandra Mac Lean for her collaboration in the colorimetrie assay and for her valuable time and effort in proof-reading this thesis. Grateful acknowledgement is made to Mr. Gabor Kato for his generous supply of acetyl carnitine, and for proof-reoding the bibliography. The skill and core with which Miss Elizabeth Moder typed this thesisarethankfully appreciated. A grant to Dr. E.A. Hosein from the Multiple Sclerosis Society of Canada in a id of this investigation is gratefully acknowledged. -Il- TABLE OF CONTENTS Page AC KNOWLEDGEMENTS •••••••••.••••••••••••••••••••••••• TABLE OF CONTENTS • . • • . • • • • • • • • • . • • • • . • . • • • . • . • . • • • ii LIST OF TABLES • • • • • • • • • • • • • . • • • • • • • • • • • • • • • • • • . • • . • • . • vi i liST OF FIGURES • • • • • • • . • • . • • . • • • • • • • • • • • • . • • . • . • • • • . viii ABBREVIA Tl 0 NS • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • ix INTRODUCTION THE CONCEPTS OF NEUROHUMORAL TRANSMISSION ..... A. The Electrical Theory • • • • • • • • • • • • • • • • • • • • • • • • • • • • 2 B. The Chemical Theory • • • • • • • • • • • • • • • • • • . • • • • • • • • • 3 ACETYLCHOLINE • • • • • • • . • • • . • • • • . • . • . • • . • • • . • • • • . • • . • 4 A. Historical . • • . • . • . • • . • • • . • . • . • • . 4 B. Acetylcholine in the Brain • • • • • • • • • • • • • • • • • • • • • • • 6 C. Nature of Acetylcholine in Tissues • • • • • • • • • • • • • • • • 8 1. The Brain • • • • • • • • • • . • • • • • • . • . • . • . • . • . • . • 8 a. The Concept of 11 Free 11 and 11 Bound 11 Acetyl- choline • . • • • • • • • • . • • • • • • • . • . • • . • . • • • • • • 8 11 11 b. Objections to Acetylcholine being Bound • • 12 c. Physiological Evidence of Acetylcholine being 11 Bound 11 in r;ssues . • • . • . • • . • . • . • . • 15 d. Nature of the Binding Material in "Bound 11 Acetylcholine • • • • • • • • • • • • • • • • • • • • • • • • • . • • 18 e. Cerebroside Sulfate as the Binding Material • in 11 Bound 11 Acetylcholine • • • • • • • • • • • • • • • • • 19 -Ill- Page f. Other Lipids as the Binding Materiel of Acetylcholine • . • • • • • . • . • • • • • • • • • . • • . • • 21 g. Vesicular Storage of 11 Bound 11 Acetylcholine • • 25 h. Synthesis of 11 Bound 11 Acetylcholine in vitro • • • 28 i. Dynamic Equil ibrium between 11 Free 11 and 11 Bound 11 Acetylcholine • • • • • • • • • • • • • • • • • • • • 32 Il. The Heart • • • • . • • • . • • • • • • • . • • • • • • • • • • • • • • • . • . 33 OTHER SUBSTANCES IN TISSUES WITH ACETYLCHOLINE- LI KE ACTIVITY • • • . • . • . • . • . • • • • • • . • • • • . • • • • • • . • • • • . • . • . • • 35 A. Longer Chain Choline Esters • • • • • • • • • • • • • • • • • • .. • • 35 B. Gamma-Butyrobetaine Esters • • • • • • • • • • • • • • • • • • • • • • 38 BIOASSAY OF ACETYLCHOLINE • • • • • • • • •• • •• • • • • • • • ... • • 42 FORMULATION OF PROBLEMS • • • •• •• • •• • • • •• ••• ••• • • • •• • 44a METHODS EXTRACTION OF BRAIN LIPIDS WITH VARIOUS LIPID SOLVENTS 45 A. Alcohol . • • • • . • • • • • • . • . • . • • . • . • . • . • . • . • . • . 45 B. Acetone . • . • . • . • . • . 46 C. Chloroform:Methanol (2: 1 v/v) • • • • • • • • • • • • • • • • • • • • 46 FRACTIONATION OF CRUDE LIPID COMPONENTS OF RAT BRAIN • • • • • • • • • • • • . • . • • • • • • • • • • • • • • • • . • • • • • • • . • • . 49 A. Sep:uation by Solvent Solubility • • • • • • • • • • • • • • • • • • 49 1. Preparation of Filtrates • • • • • • • • • • • • • • • • • • • • • • • 49 Il. Treatment of Filtrates ........................ 50 a. Filtrates I,II,IVand V • •••• ••• ••• •• ••• • •• 50 b • Fi 1tra te Ill • • • • • • • • • • • • • • • • • • • • • • • • • • • • • 51 -iv..: Page B. Separation of Sulphatides from Other Lipids 51 c. Separation by Column Chromatography . ............. 53 1. Alumina . •• •• . • • • • • ••• •• • • . • . • .• •• . • . • • • • . •• 53 Il. Silicic Acid ···••••••••••••••••••••••••••••••• 54 D. Separation by Thin Layer Chromatography ........... 55 1. PreJXlrO ti on of Pla tes •••••••••••••••••••••••••• 56 a. Coating ................................. 56 b. Drying • • . • . • • • . • . • . • • • . • • • . • • . • . • . • • • 56 c. Activation and Application of Substances ..... 56 Il. Development ................................. 57 Ill. Detection ..................................... 58 E. Separation by Paper Chromatography ................. 59 1. Butanoi-Water System • • • • • • • • • • • • • • • • • • • • • • • • • • 59 Il. Chloroform: 2,6-Lutidine:Giacial Acetic Acid (4:4: 1 v/v/v) System • • • • • • • • • • • • • • • • • • • • • • • • • • • éiJ ELUT 10 N • • • • • • • • • • • • • • • • • • • • • • • • . • • • • . • • • • • . • • • • • • • • • • • • • 62 A. Paper Chromatogroms •••••.•••••••••....•.•••••••••• 62 B. Thin Layer Chromatograms •••••••••••••••••••••••••• 63 ASSAY .................................................. 63 A. Bioassay on the Frog Rectus Abdominis Preparation ...... 63 1. Preparation of Bath Fluid •••••••••••••••••••••• 63 Il. Prepara ti on of the Musc le ••••••••••••••••••••• 64 Ill. Standardization of the Muscle ••••••••••••••••• 65 -v- Page IV. Assay . • . • . • . • . • . 66 V. Calcula ti ons . • . • . • . • . • . 67 B. Colorimetrie Determination • • • • • • • • • • • • • • • • • • • • • • • • 68 RESULTS SECTION 1 ACETYLCHOLINE-LIKE ACTIVITY EXTRACTABLE FROM RAT BRAINS WITH VARIOUS LIPID SOL VENTS • • • • • • • • • • • • • .. • • 69 A. Alcohol Extraction .............................. 69 B. Acetone Extraction 70 C. Chloroform:Methanol (2: 1 v/v) Extraction • • • • • • • • • • 71 SECTION Il DETERMINATION OF LIPID FRACTIONS IN ASSOCIATION WITH ACETYLCHOLINE-LIKE ACTIVITY OF RAT BRAIN EX TRACT • • • • • • • • • • • • • . • • • • • • • • • • • • • • • • • • • • • • • • . • • • • • . • • 73 A. Separation by Solvent Solubility • • • • • • • • • • • • • •• •• • 73 B. Separation of Sulphatides from Other Lipids •• • • • • • • • 77 C. Chroma togra ph y Separa ti on • • • • • • • • • • • • • • • • • • • • • • • 79 •· Column Chromatography on Alumina • • • • • • • • • • • • 79 ii. rhin Layer Chromatography • • • • • • • • • • • • • • • .. • • 82 iii. Paper Chromatography in Water-Saturated Butanol 83 •v. Col umn Chroma tography on Si 1 ic ic Ac id • • • • • • • • 85 v. Paper Chromatography in Chloroform: 2,6-Lutidine: Glacial Acetic Acid (4:4:1 v/v/v) System •••••••• 91 -vi- Page SECTION Ill BINDING OF ACETYLCHOLINE-LIKE MATER1AL IN VITRO..... 93 A. Distribution of Pure Acetylcholine-1 and di-Acetyl Carnitine in a Biphasic System in the Presence of Lecithin and Sphingomyet in • • • • • • • • • . • • • • • • • • • • • • • • • • • • • • • • 93 B. Uptake of Pure Acetylcholine by Organ ic Sol vents 95 D1SCUSSION ...•.•••.•..•...•...•.••.....•.•••....•.•.•.• 98 CONCLUSION AND SUMMARY • • • • •• ••• • • • •• • •• ••• •• • • • •• 112 BIBLIOGRAPHY •••••.•••••••••••·•••••••••••••.•••.•.•••••. 114 -vii- LIST OF TABLES ACh-Like Activity from Alcohol and Acetone Extractions of the Rat Brain • • • • • • • • • • • • • • • • • • • • • • • 71 Il ACh- Like Activity of the Water Layer and Chloroform Layer from a Chloroform-Methanol Extract of the Rat Brain, Normal, TCA Treated and Dialyzed ••••••••• 74 Ill Association of ACh-Like Activity with Various Crude Lipid Subfractions from the Rat Brain •••••••••••••• 77 IV Determination of ACh-Like Activity Associating with Sul phatide and Other Lipids ••••••••••••••••••••• 79 v Relative Activity from Fractions Collected by Column Chromatography on Alumina Column ••••••••••••••• 81 VI Distribution of ACh-Like Activity on Paper Chromato­ grams of Chloroform:Methanol Extracts of Rat Brain in !2_-Butanoi-Water System • • • • • • • • • • • • • • • • • • • • • • • • • 85 VIl Distribution of ACh-Like Activity in Fractions of Crude Brain Lipid Separated by Column Chromatography on Silicic Ac id • . • . • . • . • . • • . • • . • . • . • . • • 87 VIII The Expec ted and Experimentally Derived RF of Lipid Fractions from Rat Brain Tissue in Chloroform:Methanol: Glacial Acetic Acid:Water {65:25:8:4) •••••••••••••• 90 IX Comparison of RF of "Marker" Lecithin and Sphingo­ myelin with Fractions 5 and 6 of Column Eluates by Thin Layer Chromatography ••••••••••••••••••••••• 91 X Distribution of ACh-Like Activity on Paper Chromato­ grams of Chloroform:Methanol Extracts of Rat Brain in Chloroform: 2,6- Lutidine:G lac ial Acetic Acid ( 4:4:1 v/v/v) System . • . • • . • . • . • . • . • . • 92 Xl Distribution of Pure ACh-1 and di-Acetyl Carn itine in a Biphasic System in the Presence or Absence of Lecithin and Sphingomyelin
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