Honors & Awards

  • Graduate Research Fellow, National Science Foundation (2016)
  • Goldwater Scholar, Barry M. Goldwater Foundation (2014)

Professional Affiliations and Activities

  • Secretary of Education and Outreach, Stanford Polymer Collective (2017 - 2019)

Education & Certifications

  • B.Mus., Oberlin College, Percussion (2015)
  • B.A., Oberlin College, Chemistry and Materials Physics (2015)

Stanford Advisors

  • Yan Xia, Doctoral Dissertation Advisor (AC)

All Publications

  • Tuning the Molecular Weights, Chain Packing, and Gas-Transport Properties of CANAL Ladder Polymers by Short Alkyl Substitutions MACROMOLECULES Lai, H. H., Benedetti, F. M., Jin, Z., Teo, Y., Wu, A. X., De Angelis, M., Smith, Z. P., Xia, Y. 2019; 52 (16): 6294–6302
  • Microporous Polyimides from Ladder Diamines Synthesized by Facile Catalytic Arene-Norbornene Annulation as High-Performance Membranes for Gas Separation CHEMISTRY OF MATERIALS Abdulhamid, M. A., Lai, H. H., Wang, Y., Jin, Z., Teo, Y., Ma, X., Pinnau, I., Xia, Y. 2019; 31 (5): 1767–74
  • Glucuronide-Linked Antibody-Tubulysin Conjugates Display Activity in MDR+ thorn and Heterogeneous Tumor Models MOLECULAR CANCER THERAPEUTICS Burke, P. J., Hamilton, J. Z., Pires, T. A., Lai, H. H., Leiske, C. I., Emmerton, K. K., Waight, A. B., Senter, P. D., Lyon, R. P., Jeffrey, S. C. 2018; 17 (8): 1752–60


    Although antibody-drug conjugates (ADCs) find increasing applications in cancer treatment, de novo or treatment-emergent resistance mechanisms may impair clinical benefit. Two resistance mechanisms that emerge under prolonged exposure include upregulation of transporter proteins that confer multidrug resistance (MDR+) and loss of cognate antigen expression. New technologies that circumvent these resistance mechanisms may serve to extend the utility of next-generation ADCs. Recently, we developed the quaternary ammonium linker system to expand the scope of conjugatable payloads to include tertiary amines and applied the linker to tubulysins, a highly potent class of tubulin binders that maintain activity in MDR+ cell lines. In this work, tubulysin M, which contains an unstable acetate susceptible to enzymatic hydrolysis, and two stabilized tubulysin analogues were prepared as quaternary ammonium-linked glucuronide-linkers and assessed as ADC payloads in preclinical models. The conjugates were potent across a panel of cancer cell lines and active in tumor xenografts, including those displaying the MDR+ phenotype. The ADCs also demonstrated potent bystander activity in a coculture model comprised of a mixture of antigen-positive and -negative cell lines, and in an antigen-heterogeneous tumor model. Thus, the glucuronide-tubulysin drug-linkers represent a promising ADC payload class, combining conjugate potency in the presence of the MDR+ phenotype and robust activity in models of tumor heterogeneity in a structure-dependent manner. Mol Cancer Ther; 17(8); 1752-60. ©2018 AACR.

    View details for DOI 10.1158/1535-7163.MCT-18-0073

    View details for Web of Science ID 000440605000012

    View details for PubMedID 29866744

  • Functionalized Rigid Ladder Polymers from Catalytic Arene-Norbornene Annulation Polymerization ACS MACRO LETTERS Lai, H. H., Teo, Y., Xia, Y. 2017; 6 (12): 1357–61
  • Synthesis of Ladder Polymers: Developments, Challenges, and Opportunities CHEMISTRY-A EUROPEAN JOURNAL Teo, Y., Lai, H. H., Xia, Y. 2017; 23 (57): 14101–12


    Ladder polymers are unique in that their backbones consist of fused rings with adjacent rings having two or more atoms in common. The restriction of bond rotations in rigid ladder polymers greatly limits their conformational freedom, leading to many intriguing and unique properties. As a non-traditional type of polymers, rigid ladder polymers are of great fundamental interest and technical importance as advanced materials for applications such as membrane gas separation and organic electronics. Ladder polymers can be divided into non-conjugated (with kinked conformations) and conjugated (with planar conformations) structures. Their synthesis can be broadly classified into two general strategies: direct ladder polymerization, and zipping of a linear precursor polymer. This Concept article outlines the historical development of ladder polymers and the chemical strategies used for their synthesis; highlights the challenges associated with their synthesis and characterization, and presents opportunities and outlooks for this unique and intriguing type of polymers.

    View details for PubMedID 28810077

  • Norbornyl Benzocyclobutene Ladder Polymers: Conformation and Microporosity JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY Lai, H. H., Liu, S., Xia, Y. 2017; 55 (18): 3075–81

    View details for DOI 10.1002/pola.28640

    View details for Web of Science ID 000406937100024

  • Supramolecular Assembly of Tris(4-carboxyphenyl)arenes: Relationship between Molecular Structure and Solid-State Catenation Motifs CRYSTAL GROWTH & DESIGN Lai, H. W., Wiscons, R. A., Zentner, C. A., Zeller, M., Rowsel, J. L. 2016; 16 (2): 821-833
  • Orientational ortho-H-2 pair interactions in the microporous framework MOF-5 PHYSICAL REVIEW B FitzGerald, S. A., Eckdahl, C. T., McDonald, C. S., Nelson, J. N., Shinbrough, K., Lai, H. W., Rowsell, J. L. 2015; 92 (13)
  • High surface area and Z ' in a thermally stable 8-fold polycatenated hydrogen-bonded framework CHEMICAL COMMUNICATIONS Zentner, C. A., Lai, H. W., Greenfield, J. T., Wiscons, R. A., Zeller, M., Campana, C. F., Talu, O., Fitzgerald, S. A., Rowsell, J. L. 2015; 51 (58): 11642-11645


    1,3,5-Tris(4-carboxyphenyl)benzene assembles into an intricate 8-fold polycatenated assembly of (6,3) hexagonal nets formed through hydrogen bonds and π-stacking. One polymorph features 56 independent molecules in the asymmetric unit, the largest Z' reported to date. The framework is permanently porous, with a BET surface area of 1095 m(2) g(-1) and readily adsorbs N2, H2 and CO2.

    View details for DOI 10.1039/c5cc04219d

    View details for Web of Science ID 000357618200024

    View details for PubMedID 26099041

  • Conformational Preferences of N,N-Dimethylsuccinamate as a Function of Alkali and Alkaline Earth Metal Salts: Experimental Studies in DMSO and Water As Determined by H-1 NMR Spectroscopy JOURNAL OF PHYSICAL CHEMISTRY A Lai, H. W., Liu, A. T., Emenike, B. U., Carroll, W. R., Roberts, J. D. 2014; 118 (11): 1965-1970


    The fraction of gauche conformers of N,N-dimethylsuccinamic acid (1) and its Li(+), Na(+), K(+), Mg(2+), Ca(2+), and N(Bu)4(+) salts were estimated in DMSO and D2O solution by comparing the experimental vicinal proton-proton couplings determined by (1)H NMR spectroscopy with those calculated using the Haasnoot, de Leeuw, and Altona (HLA) equation. In DMSO, the gauche preferences were found to increase with decreasing Ahrens ionic radius of the metal counterion. The same trend was not seen in D2O, where the gauche fraction for all of the metallic salts were estimated to be approximately statistical or less. This highlights the importance of metal chelation on the conformation of organic molecules in polar aprotic media, which has implications for protein folding.

    View details for DOI 10.1021/jp4106508

    View details for Web of Science ID 000333381700001

    View details for PubMedID 24506581