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(6-Maleimidocaproyl)hydrazone of doxorubicin. A new derivative for the preparation of immunoconjugates of doxorubicin
Abstract
The (6-maleimidocaproyl)hydrazone of doxorubicin was synthesized and conjugated to several mAbs, including chimeric BR96, via a Michael addition reaction to thiol-containing mAbs. DTT reduction of disulfides present in the mAb was a reliable and general method for generating a consistent number of reactive SH groups. The conjugates, after purification by Bio-Beads, were free of unreacted linker and/or doxorubicin. All conjugates released doxorubicin under acidic conditions that mimic the lysosomal environment, while they were relatively stable at neutral pH. BR96 conjugates showed antigen-specific cytotoxicity.
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Citations
Cited by
Saito, G., Swanson, J. A., & Lee, K.-D. (2003) · Advanced Drug Delivery Reviews · doi:10.1016/s0169-409x(02)00179-5 · Cited by 1,407
Effects of Drug Loading on the Antitumor Activity of a Monoclonal Antibody Drug Conjugate
Hamblett, K. J., Senter, P. D., Chace, D. F., Sun, M. M. C., Lenox, J., Cerveny, C. G., Kissler, K. M., Bernhardt, S. X., Kopcha, A. K., Zabinski, R. F., et al. (2004) · Clinical Cancer Research · doi:10.1158/1078-0432.ccr-04-0789 · Cited by 1,247
Agarwal, P., & Bertozzi, C. R. (2015) · Bioconjugate Chemistry · doi:10.1021/bc5004982 · Cited by 605
Mechanisms of drug release in nanotherapeutic delivery systems
Wong, P. T., & Choi, S. K. (2015) · Chemical Reviews · doi:10.1021/cr5004634 · Cited by 507
Polymeric anticancer drugs with pH-controlled activation
Ulbrich, K. (2004) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2003.10.040 · Cited by 494
Metadata
- Authors
- Willner, D., Trail, P. A., Hofstead, S. J., King, H. D., Lasch, S. J., Braslawsky, G. R., Greenfield, R. S., Kaneko, T., & Firestone, R. A.
- Venue
- Bioconjugate Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1993-11-01
- Volume
- 4
- Issue
- 6
- Pages
- 521-527
- ISSN
- 1043-1802 (ISSN-L)
- 1520-4812
- OpenAlex
- W2055713782
- Cited by
- 225
- References
- 0
- FWCI
- 5.30
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: (6-Maleimidocaproyl)hydrazone of doxorubicin. A new derivative for the preparation of immunoconjugates of doxorubicin. https://app.cochat.ai/papers/10.1021/bc00024a015
- The paper
- Willner, D., Trail, P. A., Hofstead, S. J., King, H. D., Lasch, S. J., Braslawsky, G. R., Greenfield, R. S., Kaneko, T., & Firestone, R. A. (1993). (6-Maleimidocaproyl)hydrazone of doxorubicin. A new derivative for the preparation of immunoconjugates of doxorubicin. Bioconjugate Chemistry. https://doi.org/10.1021/bc00024a015
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
