Professional Education

  • Bachelor of Science, University of Western Ontario (2009)
  • Master of Science, University of Western Ontario (2011)
  • Doctor of Philosophy, University of California Santa Barbara (2018)

Stanford Advisors

All Publications

  • Tuning the Diels-Alder Reaction for Bioconjugation to Maleimide Drug-Linkers BIOCONJUGATE CHEMISTRY St Amant, A. H., Lemen, D., Florinas, S., Mao, S., Fazenbaker, C., Zhong, H., Wu, H., Gao, C., Christie, R., de Alanie, J. 2018; 29 (7): 2406–14


    The thiol-maleimide linkage is widely used for antibody-drug conjugate (ADC) production; however, conjugation of maleimide-drugs could be improved by simplified procedures and reliable conjugate stability. Here, we report the evaluation of electron-rich and cyclic dienes that can be appended to antibodies and reacted with maleimide-containing drugs through the Diels-Alder (DA) reaction. Drug conjugation is fast and quantitative due to reaction acceleration in water, and the linkage is more stable in serum than in the corresponding thiol-maleimide adduct with the same drug. ADCs produced using the DA reaction (DAADCs) are effective in vitro and in vivo, demonstrating the utility of this reaction in producing effective biotherapeutics. Given the large number of commercially available maleimide compounds, this conjugation approach could be readily applied to the production of a wide range of antibody (or protein) conjugates.

    View details for DOI 10.1021/acs.bioconjchem.8b00320

    View details for Web of Science ID 000439531800029

    View details for PubMedID 29932647

  • Endo and Exo Diels-Alder Adducts: Temperature-Tunable Building Blocks for Selective Chemical Functionalization JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Discekici, E. H., St Amant, A. H., Nguyen, S. N., Lee, I., Hawker, C. J., de Alaniz, J. 2018; 140 (15): 5009–13


    The development and application of a novel endo furan-protected maleimide building block is reported. The endo isomer undergoes deprotection at temperatures ∼50 °C below the exo derivative. This enables a simple and powerful approach to quantitatively and selectively introduce functional maleimide groups via temperature modulation.

    View details for DOI 10.1021/jacs.8b01544

    View details for Web of Science ID 000430642000013

    View details for PubMedID 29613783

    View details for PubMedCentralID PMC6205238

  • Novel Methods of Determining Urinary Calculi Composition: Petrographic Thin Sectioning of Calculi and Nanoscale Flow Cytometry Urinalysis SCIENTIFIC REPORTS Gavin, C. T., Ali, S. N., Tailly, T., Olvera-Posada, D., Alenezi, H., Power, N. E., Hou, J., Amant, A., Luyt, L. G., Wood, S., Wu, C., Razvi, H., Leong, H. S. 2016; 6: 19328


    Accurate determination of urinary stone composition has significant bearing on understanding pathophysiology, choosing treatment modalities and preventing recurrence. A need exists for improved methods to determine stone composition. Urine of 31 patients with known renal calculi was examined with nanoscale flow cytometry and the calculi collected during surgery subsequently underwent petrographic thin sectioning with polarized and fluorescent microscopy. Fluorescently labeled bisphosphonate probes (Alendronate-fluorescein/Alendronate-Cy5) were developed for nanoscale flow cytometry to enumerate nanocrystals that bound the fluorescent probes. Petrographic sections of stones were also imaged by fluorescent and polarized light microscopy with composition analysis correlated to alendronate +ve nanocrystal counts in corresponding urine samples. Urine samples from patients with Ca(2+) and Mg(2+) based calculi exhibited the highest alendronate +ve nanocrystal counts, ranging from 100-1000 nm in diameter. This novel urine based assay was in agreement with composition determined by petrographic thin sections with Alendronate probes. In some cases, high alendronate +ve nanocrystal counts indicated a Ca(2+) or Mg(2+) composition, as confirmed by petrographic analysis, overturning initial spectrophotometric diagnosis of stone composition. The combination of nanoscale flow cytometry and petrographic thin sections offer an alternative means for determining stone composition. Nanoscale flow cytometry of alendronate +ve nanocrystals alone may provide a high-throughput means of evaluating stone burden.

    View details for DOI 10.1038/srep19328

    View details for Web of Science ID 000368160300001

    View details for PubMedID 26771074

    View details for PubMedCentralID PMC4725893

  • Direct synthesis of anilines and nitrosobenzenes from phenols ORGANIC & BIOMOLECULAR CHEMISTRY St Amant, A. H., Frazier, C. P., Newmeyer, B., Fruehauf, K. R., de Alaniz, J. 2016; 14 (24): 5520–24


    A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution ((i)SOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.

    View details for DOI 10.1039/c6ob00073h

    View details for Web of Science ID 000378933400020

    View details for PubMedID 26848022

  • Synthesis and Evaluation of Optical and PET GLP-1 Peptide Analogues for GLP-1R Imaging MOLECULAR IMAGING Azad, B., Rota, V., Yu, L., McGirr, R., Amant, A., Lee, T., Dhanvantari, S., Luyt, L. G. 2015; 14
  • Cascade rearrangement of furylcarbinols with hydroxylamines: practical access to densely functionalized cyclopentane derivatives ORGANIC & BIOMOLECULAR CHEMISTRY Veits, G. K., Wenz, D. R., Palmer, L. I., St Amant, A. H., Hein, J. E., de Alaniz, J. 2015; 13 (31): 8465–69


    This article describes the aza-Piancatelli rearrangement with hydroxylamines to 4-aminocyclopentenones and subsequent transformations that highlight the versatility of the cyclopentene scaffold and the value of the hydroxylamine nucleophile in this transformation.

    View details for DOI 10.1039/c5ob00944h

    View details for Web of Science ID 000358733100012

    View details for PubMedID 26154503

  • A solid-phase CuAAC strategy for the synthesis of PNA containing nucleobase surrogates. Artificial DNA, PNA & XNA St Amant, A. H., Engbers, C., Hudson, R. H. 2013; 4 (1): 4–10


    The synthesis of an azide containing PNA monomer is described. The monomer was incorporated into two PNA sequences for the purpose of synthesizing an intercalating fluorophore-labeled PNA and a metal binding hairpin using a solid phase copper catalyzed azide-alkyne Huisgen cycloaddition (CuAAC). Click chemistry was performed using 2-ethynylfluorene or 1-ethynylpyrene to add a fluorophore to the PNA, which were tested for their ability to recognize an abasic site on a DNA target. A PNA hairpin possessing azide monomers at each termini was synthesized and reacted with 2-ethynylpyridine to form a hairpin that is stabilized by Ni²⁺.

    View details for DOI 10.4161/adna.23982

    View details for PubMedID 23422048

    View details for PubMedCentralID PMC3654728

  • Synthesis and oligomerization of Fmoc/Boc-protected PNA monomers of 2,6-diaminopurine, 2-aminopurine and thymine ORGANIC & BIOMOLECULAR CHEMISTRY St Amant, A. H., Hudson, R. E. 2012; 10 (4): 876–81


    A Boc-protecting group strategy for Fmoc-based PNA (peptide nucleic acid) oligomerization has been developed for thymine, 2,6-diaminopurine (DAP) and 2-aminopurine (2AP). The monomers may be used interchangeably with standard Fmoc PNA monomers. The DAP monomer was incorporated into a PNA and was found to selectively bind to T (ΔT(m)≥ +6 °C) in a complementary DNA strand. The 2AP monomer showed excellent discrimination of T (ΔT(m)≥ +12 °C) over the other nucleobases. 2AP also acted as a fluorescent probe of the PNA:DNA duplexes and displayed fluorescence quenching dependent on the opposite base.

    View details for DOI 10.1039/c1ob06582c

    View details for Web of Science ID 000298751900026

    View details for PubMedID 22159214

  • Click fleximers: a modular approach to purine base-expanded ribonucleoside analogues ORGANIC & BIOMOLECULAR CHEMISTRY St Amant, A. H., Bean, L. A., Guthrie, J., Hudson, R. E. 2012; 10 (32): 6521–25


    The synthesis of nucleoside analogues incorporating 4-(5-pyrimidinyl)-1,2,3-triazole aglycons as expanded purine nucleobase mimics were accessed using the copper-catalyzed azide-alkyne Huisgen cycloaddition between a ribosyl azide and 5-alkynylpyrimidines. Depending on the nature of the alkyne employed, other nucleoside analogues that possess fluorescence or potential metal-binding properties were prepared. Computational studies were undertaken on the purine analogues and indicate that the heterocycles of the unfused nucleobase prefer a coplanar arrangement and the anti-glycosidic conformer is favoured in most instances.

    View details for DOI 10.1039/c2ob25678a

    View details for Web of Science ID 000306854600010

    View details for PubMedID 22752020