Publications

Latest publication 12/03/2017

A Stable Heroin Analogue That Can Serve as a Vaccine Hapten to Induce Antibodies

An improved synthesis of a haptenic heroin surrogate 1 (6-AmHap) is reported. The intermediate needed for the preparation of 1 was described in the...

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    [title] => A Stable Heroin Analogue That Can Serve as a Vaccine Hapten to Induce Antibodies
    [paragraph] => A Stable Heroin Analogue That Can Serve as a Vaccine Hapten to Induce Antibodies That Block the Effects of Heroin and Its Metabolites in Rodents and That Cross-React Immunologically with Related Drugs of Abuse
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Authors
A Sulima, R Jalah, JFG. Antoline, OB. Torres, GH. Imler, JR. Deschamp, Z Beck, CR. Alving, AE. Jacobson, KC. Rice, GR. Matyas

 Lab
National Institute on Drug Abuse and the National Institute on Alcohol Abuse and Alcoholism, National Institutes of Health
Journal
Journal of Medicinal Chemistry
Abstract
An improved synthesis of a haptenic heroin surrogate 1 (6-AmHap) is reported. The intermediate needed for the preparation of 1 was described in the route in the synthesis of 2 (DiAmHap). A scalable procedure was developed to install the C-3 amido group. Using the Boc protectng group in 18 allowed preparation of 1 in an overall yield of 53% from 4 and eliminated the necessity of preparing the diamide 13. Hapten 1 was conjugated to tetanus toxoid and mixed with liposomes containing monophosphoryl lipid A as an adjuvant. The 1 vaccine induced high anti-1 IgG levels that reduced heroin-induced antinociception and locomotive behavioral changes following repeated subcutaneous and intravenous heroin challenges in mice and rats. Vaccinated mice had reduced heroin-induced hyperlocomotion following a 50 mg/kg heroin challenge. The 1 vaccine-induced antibodies bound to heroin and other abused opioids, including hydrocodone, oxycodone, hydromorphone, oxymorphone, and codeine.
BIOSEB Instruments Used
Thermal Place Preference, 2 Temperatures Choice Nociception Test (BIO-T2CT)
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                    [name] => Thermal Place Preference- 2 Temperatures Choice Nociception Test
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An operator independent test to study pain thresholds in rodents (mouse and rat) by assessing temperature preference (thermal comfort zone) - a new tool for your analgesia/nociception research opening new fields of investigation, and an ideal solution for nociceptive and analgesic drugs screening. Now comes with a brand new software, allowing tracking activity and faster temperature transitions!

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