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Hydrazino-Pictet-Spengler Ligation as a Biocompatible Method for the Generation of Stable Protein Conjugates
Abstract
Aldehyde- and ketone-functionalized biomolecules have found widespread use in biochemical and biotechnological fields. They are typically conjugated with hydrazide or aminooxy nucleophiles under acidic conditions to yield hydrazone or oxime products that are relatively stable, but susceptible to hydrolysis over time. We introduce a new reaction, the hydrazino-Pictet-Spengler (HIPS) ligation, which has two distinct advantages over hydrazone and oxime ligations. First, the HIPS ligation proceeds quickly near neutral pH, allowing for one-step labeling of aldehyde-functionalized proteins under mild conditions. Second, the HIPS ligation product is very stable (>5 days) in human plasma relative to an oxime-linked conjugate (∼1 day), as demonstrated by monitoring protein-fluorophore conjugates by ELISA. Thus, the HIPS ligation exhibits a combination of product stability and speed near neutral pH that is unparalleled by current carbonyl bioconjugation chemistries.
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Cited by
Oximes and Hydrazones in Bioconjugation: Mechanism and Catalysis
Kölmel, D. K., & Kool, E. T. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00090 · Cited by 699
Sequencing abasic sites in DNA at single-nucleotide resolution
Liu, Z. J., Martínez Cuesta, S., van Delft, P., & Balasubramanian, S. (2019) · Nature Chemistry · doi:10.1038/s41557-019-0279-9 · Cited by 83
Tandem-Cleavage Linkers Improve the In Vivo Stability and Tolerability of Antibody–Drug Conjugates
Chuprakov, S., Ogunkoya, A. O., Barfield, R. M., Bauzon, M., Hickle, C., Kim, Y. C., Yeo, D., Zhang, F., Rabuka, D., & Drake, P. M. (2021) · Bioconjugate Chemistry · doi:10.1021/acs.bioconjchem.1c00029 · Cited by 80
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Metadata
- Authors
- Agarwal, P., Kudirka, R., Albers, A. E., Barfield, R. M., de Hart, G. W., Drake, P. M., Jones, L. C., & Rabuka, D.
- Venue
- Bioconjugate Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-06-03
- Volume
- 24
- Issue
- 6
- Pages
- 846-851
- ISSN
- 1043-1802 (ISSN-L)
- 1520-4812
- OpenAlex
- W2327630133
- Cited by
- 160
- References
- 0
- FWCI
- 7.98
- Type
- journal article
- Language
- en
- Open access
- closed
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- Agarwal, P., Kudirka, R., Albers, A. E., Barfield, R. M., de Hart, G. W., Drake, P. M., Jones, L. C., & Rabuka, D. (2013). Hydrazino-Pictet-Spengler Ligation as a Biocompatible Method for the Generation of Stable Protein Conjugates. Bioconjugate Chemistry. https://doi.org/10.1021/bc400042a
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