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1 article(s) from Lin, Lucy

A chemically contiguous hapten approach for a heroin–fentanyl vaccine

Yoshihiro Natori,
Candy S. Hwang,
Lucy Lin,
Lauren C. Smith,
Bin Zhou and
Kim D. Janda

Beilstein J. Org. Chem. 2019, 15, 1020–1031, doi:10.3762/bjoc.15.100

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Graphical Abstract

Figure 1: Graphical summary of chemically contiguous opioid vaccine approach. A) Illustration of chemically c...

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Figure 2: The chemically contiguous heroin–fentanyl haptens designed in this study. Grouping was based on the...

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Figure 3: Heroin intermediates used to synthesize HF-1 through HF-9.

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Scheme 1: General outline of HF-1, HF-2, HF-3, HF-7 synthesis from fentanyl intermediate 5 and heroin interme...

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Scheme 2: Synthesis of fentanyl intermediate 5. Reaction conditions: a) phthalic anhydride, AcOH, reflux, 81%...

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Scheme 3: General outline of HF-5, HF-8, HF-9 synthesis from fentanyl intermediates 28 and 46, and heroin int...

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Scheme 4: Parallel synthesis of fentanyl domains 25 and 34, for HF-4 and HF-6, respectively.

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Scheme 5: General strategy and coupling partners for the chemically contiguous series. ^aGeneral conditions fo...

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Figure 4: Vaccination, titer assessment, and bleed schedule.

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Figure 5: Summary of behavioral data for most promising chemically contiguous vaccine HF-7, compared to singu...

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Figure 6: Summary of behavioral data for phenethyl-linked haptens HF-4 and HF-6. Bars represent mean ± SEM.

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Figure 7: Correlation plots of dual hapten vaccines comparing week 5 and 8 ELISA midpoint titers to ED₅₀ valu...

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Published 03 May 2019

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