Generation of Polyclonal Catalytic Antibodies Against Cocaine Using Transition State Analogs of Cocaine Conjugated to Diphtheria Toxoid

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概要

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• Six novel transition state analogs (TSAs) of cocaine (10-14 and 17) and one non-cocaine, p-aminophenyl-phosphonyl ester of cyclohexanol (19), were synthesized and characterized by ^1H- and ^<13>C-NMR and FAB-MS.(1R)-ecgonine methyl ester or cyclohexanol were subjected to phenylphosphonylation in the presence of dicyclohexyl carbodiimde (DCC) and 4-N, N-dimethyl aminopyridine (4-DMAP). TSA-IV (10), however, was synthesized from norcocaine which was protected with dibromoethane to yield 4 before acid hydrolysis, esterification and phenyl-phosphonylation were carried out. TSA-III (11) TSA-I (12) and (19), using various length spacer arms, were coupled with the immunogenic protein, diphtheria toxoid (DT). The TSAs coupled with DT were used to immunize mice and after appropriate boosts their sera were tested for the presence and titer of anti-TSA polyclonal antibodies using ELISA. Preliminary results show that the mice immunized with these TSAs produced high titers of polyclonal catalytic antibodies, except for (19), with the ability to hydrolyze the substrate ^<125>I-4'-iodococaine in an in vitro assay, even in the presence of noncatalytic anti-TSA antibodies.

• 公益社団法人日本薬学会の論文
• 1995-11-15

著者

• Singh Sanjewon

  Department Of Medcinal Chemistry I. M. S. Banaras Hindu University

• Singh Satendra

  Department Of Medicinal Chemistry And Pharmaceutics College Of Pharmacy University Of Oklahoma Healt

• AVOR Kwasi

  Department of Medicinal Chemistry and Pharmaceutics, College of Pharmacy University of Oklahoma Heal

• SEALE Thomas

  Department of Pediatrics, Psychiatry and Behavioral Science, College of Medicine University of Oklah

• BASMADJIAN Garo

  Department of Medicinal Chemistry and Pharmaceutics, College of Pharmacy University of Oklahoma Heal

• SASTRODJOJO Budiono

  Department of Medicinal Chemistry and Pharmaceutics, College of Pharmacy

• SMITH Blaine

  Department of Medicinal Chemistry and Pharmaceutics, College of Pharmacy

• CHANG Fengchun

  Department of Medicinal Chemistry and Pharmaceutics, College of Pharmacy

• MILLS Stanley

  Department of Medicinal Chemistry and Pharmaceutics, College of Pharmacy

• Avor Kwasi

  Department Of Medicinal Chemistry And Pharmaceutics College Of Pharmacy University Of Oklahoma Healt

• Seale Thomas

  Department Of Pediatrics Psychiatry And Behavioral Science College Of Medicine University Of Oklahom

• Smith Blaine

  Department Of Medicinal Chemistry And Pharmaceutics College Of Pharmacy

• Mills Stanley

  Department Of Medicinal Chemistry And Pharmaceutics College Of Pharmacy

• Chang Fengchun

  Department Of Medicinal Chemistry And Pharmaceutics College Of Pharmacy

• Sastrodjojo Budiono

  Department Of Medicinal Chemistry And Pharmaceutics College Of Pharmacy

• Basmadjian Garo

  Department Of Medicinal Chemistry And Pharmaceutics College Of Pharmacy University Of Oklahoma Healt

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• Design and Synthesis of Isoxazole Containing Bioisosteres of Epibatidine as Potent Nicotinic Acetylcholine Receptor Agonists
• Generation of Polyclonal Catalytic Antibodies Against Cocaine Using Transition State Analogs of Cocaine Conjugated to Diphtheria Toxoid

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