Tunable pH-Sensitive Linker for Controlled Release

Bioconjugate Chemistry

Volumn 27, Issue 3, 2016, Pages 824-830

  Choy, Cindy J ^a   Geruntho, Jonathan J ^a   Davis, Austen L ^a   Berkman, Clifford E ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONTROLLED DRUG DELIVERY; MOLECULES; PH EFFECTS; PH SENSORS; PHYSIOLOGICAL MODELS; SCAFFOLDS; TARGETED DRUG DELIVERY;

ACIDIC GROUPS; CONTROLLED RELEASE; DRUG MOLECULES; DRUG RELEASE; ENZYMATIC ACTION; PH SENSITIVE; PH VALUE; PHOSPHORAMIDATES; TUNABLES; VARIOUS PH;

HYDROLYSIS;

AMINE; ANTINEOPLASTIC AGENT; BENZYL ALCOHOL DERIVATIVE; NITROGEN DERIVATIVE; PHOSPHINE DERIVATIVE; PHOSPHITE; PHOSPHORAMIDIC ACID DERIVATIVE; PHOSPHORUS DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; DELAYED RELEASE FORMULATION;

ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED DRUG RELEASE; CONTROLLED RELEASE FORMULATION; CONTROLLED STUDY; COVALENT BOND; DRUG STABILITY; ELECTROPHILICITY; ENDOSOME; HYDROGENOLYSIS; HYDROLYSIS; KINETICS; NUCLEOPHILICITY; PH; PKA; PROTON TRANSPORT; STANDARD; SYNTHESIS; TRANSESTERIFICATION; CHEMISTRY; DELAYED RELEASE FORMULATION;

ANTINEOPLASTIC AGENTS; DELAYED-ACTION PREPARATIONS; HYDROGEN-ION CONCENTRATION;

EID: 84962285894     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/acs.bioconjchem.6b00027     Document Type: Article

References (32)

1. Albers, A. E., Garofalo, A. W., Drake, P. M., Kudirka, R., de Hart, G. W., Barfield, R. M., Baker, J., Banas, S., and Rabuka, D. (2014) Exploring the effects of linker composition on site-specifically modified antibody-drug conjugates Eur. J. Med. Chem. 88, 3 10.1016/j.ejmech.2014.08.062
2. Chari, R. V., Miller, M. L., and Widdison, W. C. (2014) Antibody-drug conjugates: An emerging concept in cancer therapy Angew. Chem., Int. Ed. 53, 3796-827 10.1002/anie.201307628
3. Nyman, E. S. and Hynninen, P. H. (2004) Research advances in the use of tetrapyrrolic photosensitizers for photodynamic therapy J. Photochem. Photobiol., B 73, 1-28 10.1016/j.jphotobiol.2003.10.002
4. Panowski, S., Bhakta, S., Raab, H., Polakis, P., and Junutula, J. R. (2014) Site-specific antibody drug conjugates for cancer therapy mAbs 6, 34-45 10.4161/mabs.27022
5. Lyon, R. P., Setter, J. R., Bovee, T. D., Doronina, S. O., Hunter, J. H., Anderson, M. E., Balasubramanian, C. L., Duniho, S. M., Leiske, C. I., Li, F., and Senter, P. D. (2014) Self-hydrolyzing maleimides improve the stability and pharmacological properties of antibody-drug conjugates Nat. Biotechnol. 32, 1059-62 10.1038/nbt.2968
6. Pillow, T. H., Tien, J., Parsons-Reponte, K. L., Bhakta, S., Li, H., Staben, L. R., Li, G., Chuh, J., Fourie-O'Donohue, A., Darwish, M., Yip, V., Liu, L., Leipold, D. D., Su, D., Wu, E., Spencer, S. D., Shen, B. Q., Xu, K., Kozak, K. R., Raab, H., Vandlen, R., Lewis Phillips, G. D., Scheller, R. H., Polakis, P., Sliwkowski, M. X., Flygare, J. A., and Junutula, J. R. (2014) Site-Specific Trastuzumab Maytansinoid Antibody-Drug Conjugates with Improved Therapeutic Activity through Linker and Antibody Engineering J. Med. Chem. 57, 7890-9 10.1021/jm500552c
7. Tumey, L. N., Charati, M., He, T., Sousa, E., Ma, D., Han, X., Clark, T., Casavant, J., Loganzo, F., Barletta, F., Lucas, J., and Graziani, E. I. (2014) Mild Method for Succinimide Hydrolysis on ADCs: Impact on ADC Potency, Stability, Exposure, and Efficacy Bioconjugate Chem. 25, 1871-80 10.1021/bc500357n
8. Behrens, C. R. and Liu, B. (2014) Methods for site-specific drug conjugation to antibodies mAbs 6, 46-53 10.4161/mabs.26632
9. Francisco, J. A., Cerveny, C. G., Meyer, D. L., Mixan, B. J., Klussman, K., Chace, D. F., Rejniak, S. X., Gordon, K. A., DeBlanc, R., Toki, B. E., Law, C. L., Doronina, S. O., Siegall, C. B., Senter, P. D., and Wahl, A. F. (2003) cAC10-vcMMAE, an anti-CD30-monomethyl auristatin E conjugate with potent and selective antitumor activity Blood 102, 1458-65 10.1182/blood-2003-01-0039
10. Flygare, J. A., Pillow, T. H., and Aristoff, P. (2013) Antibody-drug conjugates for the treatment of cancer Chem. Biol. Drug Des. 81, 113-21 10.1111/cbdd.12085
11. Foehrenbacher, A., Patel, K., Abbattista, M. R., Guise, C. P., Secomb, T. W., Wilson, W. R., and Hicks, K. O. (2013) The Role of Bystander Effects in the Antitumor Activity of the Hypoxia-Activated Prodrug PR-104 Front. Oncol. 3, 263 10.3389/fonc.2013.00263
12. Wu, W., Luo, Y., Sun, C., Liu, Y., Kuo, P., Varga, J., Xiang, R., Reisfeld, R., Janda, K. D., Edgington, T. S., and Liu, C. (2006) Targeting cell-impermeable prodrug activation to tumor microenvironment eradicates multiple drug-resistant neoplasms Cancer Res. 66, 970-80 10.1158/0008-5472.CAN-05-2591
13. Dosio, F., Brusa, P., and Cattel, L. (2011) Immunotoxins and Anticancer Drug Conjugate Assemblies: The Role of the Linkage between Components Toxins 3, 848-883 10.3390/toxins3070848
14. Tuma, R. S. (2011) Enthusiasm for Antibody-Drug Conjugates Journal of the National Cancer Institute 103, 1493-1494 10.1093/jnci/djr422
15. Sassoon, I. and Blanc, V. (2013) Antibody-drug conjugate (ADC) clinical pipeline: A review Methods Mol. Biol. 1045, 1-27 10.1007/978-1-62703-541-5-1
16. Ducry, L. and Stump, B. (2010) Antibody-drug conjugates: Linking cytotoxic payloads to monoclonal antibodies Bioconjugate Chem. 21, 5-13 10.1021/bc9002019
17. Nolting, B. (2013) Linker technologies for antibody-drug conjugates Methods Mol. Biol. 1045, 71-100 10.1007/978-1-62703-541-5-5
18. Ganguly, T. (2013) in Department of Chemistry; Washington State University, Pullman, WA.
19. Ganguly, T., Dannoon, S., Hopkins, M. R., Murphy, S., Cahaya, H., Blecha, J. E., Jivan, S., Drake, C. R., Barinka, C., Jones, E. F., VanBrocklin, H. F., and Berkman, C. E. (2015) A high-affinity [(18)F]-labeled phosphoramidate peptidomimetic PSMA-targeted inhibitor for PET imaging of prostate cancer Nucl. Med. Biol. 42, 780-7 10.1016/j.nucmedbio.2015.06.003
20. Ley, C. R., Beattie, N. R., Dannoon, S., Regan, M., VanBrocklin, H., and Berkman, C. E. (2015) Synthesis and evaluation of constrained phosphoramidate inhibitors of prostate-specific membrane antigen Bioorg. Med. Chem. Lett. 25, 2536-9 10.1016/j.bmcl.2015.04.047
21. Capon, B. (1975) Neighbouring Group Participation, in Proton-Transfer Reactions (Caldin, E. F. and Gold, V., Eds.) pp 339-384, Springer: United States.
22. Kirby, A. J., Lima, M. F., da Silva, D., Roussev, C. D., and Nome, F. (2006) Efficient Intramolecular General Acid Catalysis of Nucleophilic Attack on a Phosphodiester J. Am. Chem. Soc. 128, 16944-16952 10.1021/ja066439u
23. Fersht, A. R. and Kirby, A. J. (1967) Intramolecular general acid catalysis of ester hydrolysis by the carboxylic acid group J. Am. Chem. Soc. 89, 5961-5962 10.1021/ja00999a045
24. Orth, E. S., Brandao, T. A. S., Souza, B. S., Pliego, J. R., Vaz, B. G., Eberlin, M. N., Kirby, A. J., and Nome, F. (2010) Intramolecular Catalysis of Phosphodiester Hydrolysis by Two Imidazoles J. Am. Chem. Soc. 132, 8513-8523 10.1021/ja1034733
25. Bender, M. L. and Lawlor, J. M. (1963) Isotopic and Kinetic Studies of the Mechanism of Hydrolysis of Salicyl Phosphate. Intramolecular General Acid Catalysis J. Am. Chem. Soc. 85, 3010-3017 10.1021/ja00902a031
26. Benkovic, S. J. and Sampson, E. J. (1971) Structure-reactivity correlation for the hydrolysis of phosphoramidate monoanions J. Am. Chem. Soc. 93, 4009-4016 10.1021/ja00745a032
27. Benkovic, S. J. and Schray, K. J. (1978) The Mechanism of Phosphoryl Transfer, in Transition States of Biochemical Processes (Gandour, R. D. and Schowen, R. L., Eds.) Springer: United States.
28. Gilard, V., Martino, R., Malet-Martino, M., Niemeyer, U., and Pohl, J. (1999) Chemical stability and fate of the cytostatic drug ifosfamide and its N-dechloroethylated metabolites in acidic aqueous solutions J. Med. Chem. 42, 2542-60 10.1021/jm980587g
29. Zakirova, N. F., Shipitsyn, A. V., Jasko, M. V., Prokofjeva, M. M., Andronova, V. L., Galegov, G. A., Prassolov, V. S., and Kochetkov, S. N. (2012) Phosphoramidate derivatives of acyclovir: Synthesis and antiviral activity in HIV-1 and HSV-1 models in vitro Bioorg. Med. Chem. 20, 5802-9 10.1016/j.bmc.2012.08.008
30. Koizumi, T. and Haake, P. (1973) Acid-catalyzed and alkaline hydrolyses of phosphinamides. Lability of phosphorus-nitrogen bonds in acid and the mechanisms of reaction J. Am. Chem. Soc. 95, 8073-8079 10.1021/ja00805a021
31. Kalogiannis, M., Hsu, E., Willie, J. T., Chemelli, R. M., Kisanuki, Y. Y., Yanagisawa, M., and Leonard, C. S. (2011) Cholinergic modulation of narcoleptic attacks in double orexin receptor knockout mice PLoS One 6, e18697 10.1371/journal.pone.0018697
32. Hoerter, J. A. and Walter, N. G. (2007) Chemical modification resolves the asymmetry of siRNA strand degradation in human blood serum RNA 13, 1887-93 10.1261/rna.602307