All Publications

  • Toward Point-of-Care Detection of Mycobacterium tuberculosis: A Brighter Solvatochromic Probe Detects Mycobacteria within Minutes. JACS Au Kamariza, M., Keyser, S. G., Utz, A., Knapp, B. D., Ealand, C., Ahn, G., Cambier, C. J., Chen, T., Kana, B., Huang, K. C., Bertozzi, C. R. 2021; 1 (9): 1368-1379


    There is an urgent need for point-of-care tuberculosis (TB) diagnostic methods that are fast, inexpensive, and operationally simple. Here, we report on a bright solvatochromic dye trehalose conjugate that specifically detects Mycobacterium tuberculosis (Mtb) in minutes. 3-Hydroxychromone (3HC) dyes, known for having high fluorescence quantum yields, exhibit shifts in fluorescence intensity in response to changes in environmental polarity. We synthesized two analogs of 3HC-trehalose conjugates (3HC-2-Tre and 3HC-3-Tre) and determined that 3HC-3-Tre has exceptionally favorable properties for Mtb detection. 3HC-3-Tre-labeled mycobacterial cells displayed a 10-fold increase in fluorescence intensity compared to our previous reports on the dye 4,4-N,N-dimethylaminonapthalimide (DMN-Tre). Excitingly, we detected fluorescent Mtb cells within 10 min of probe treatment. Thus, 3HC-3-Tre permits rapid visualization of mycobacteria that ultimately could empower improved Mtb detection at the point-of-care in low-resource settings.

    View details for DOI 10.1021/jacsau.1c00173

    View details for PubMedID 34604847

  • Computation-Guided Rational Design of a Peptide Motif That Reacts with Cyanobenzothiazoles via Internal Cysteine-Lysine Relay JOURNAL OF ORGANIC CHEMISTRY Keyser, S. L., Utz, A., Bertozzi, C. R. 2018; 83 (14): 7467–79


    Site-selective protein modification based on covalent reactions of peptide tags and small molecules is a key capability for basic research as well as for the development of new therapeutic bioconjugates. Here, we describe the computation-guided rational design of a cysteine- and lysine-containing 11-residue peptide sequence that reacts with 2-cyanobenzothiazole (CBT) derivatives. Our data show that the cysteine residue reversibly reacts with the nitrile group on the CBT moiety to form an intermediate thioimidate, which undergoes irreversible SN transfer to the lysine residue, yielding an amidine-linked product. The concepts outlined herein lay a foundation for future development of peptide tags in the context of site-selective modification of lysine residues within engineered microenvironments.

    View details for DOI 10.1021/acs.joc.8b00625

    View details for Web of Science ID 000439761100020

    View details for PubMedID 29771122

  • Synthesis of solvatochromic probes to label the mycobacterial cell wall and their use in studies of host-pathogen interactions Keyser, S., Utz, A., Kamariza, M., Bertozzi, C. AMER CHEMICAL SOC. 2017
  • Synthesis of solvatochromic probes to study the effect of host microenvironment on mycobacterial cell wall dynamics during infection Keyser, S., Utz, A., Bertozzi, C. AMER CHEMICAL SOC. 2017
  • Synthesis of solvatochromic probes to label the mycobacterial cell wall Utz, A., Keyser, S., Bertozzi, C. AMER CHEMICAL SOC. 2017