Disulfide linkage: A potent strategy in tumor-targeting drug discovery

Current Medicinal Chemistry

Volumn 19, Issue 18, 2012, Pages 2976-2983

  Wang, J ^a   Li, S ^a   Luo, T ^a   Wang, C ^a   Zhao, J ^a  

^a HENAN UNIVERSITY   (China)

Author keywords

Antibody; Antitumor drug; Conjugate; Disulfide; Drug delivery; Drug design; Drug release; Endogenous glutathione; Reduction; Tumor targeting

Indexed keywords

ANTIBODY CONJUGATE; CANTUZUMAB MERTANSINE; DISULFIDE; GEMTUZUMAB OZOGAMICIN; MAYTANSINE; TRASTUZUMAB;

DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENCY; DRUG RELEASE; DRUG TARGETING; HUMAN; NONHUMAN; REVIEW;

EID: 84861898494     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986712800672030     Document Type: Review

References (44)

1. Jaracz, S.; Chen, J.; Kuznetsova, L.V.; Ojima, I. Recent advances in tumortargeting anticancer drug conjugates. Bioorg. Med. Chem., 2005, 13, 5043-5054.
2. Chen, J.; Jaracz, S.; Zhao, X.; Chen, S.; Ojima, I. Antibody-based toxin conjugates for cancer therapy. Exp. Opin. Drug Deliv., 2005, 2, 873-890.
3. Wu, X.; Ojima, I. Tumor specific novel taxoid-monoclonal antibody conjugates. Curr. Med. Chem., 2004, 11, 429-438.
4. Ojima, I.; Geng, X.; Wu, X.; Qu, C.; Borella, C.P.; Xie, H.; Wilhelm, S.D.; Leece, B.A.; Bartle, L.M.; Goldmacher, V.S.; Chari, R.V.J. Tumor-specific novel taxoidmonoclonal antibody conjugates. J. Med. Chem., 2002, 45, 5620-5623.
5. Leamon, C.P.; Reddy, J.A. Folate-targeted chemotherapy. Advanced Drug Delivery Reviews, 2004, 56, 1127-1141.
6. Lu, Y.; Low, P.S. Folate-mediated delivery of macromolecular anticancer therapeutic agents. Advanced Drug Delivery Reviews, 2002, 54, 675-693.
7. Wang, J.; Luo, T.; Li, S.; Zhao, J. The powerful applications of polyunsaturated fatty acids in improving the therapeutic efficacy of anticancer drugs. Exp. Opin. Drug Deliv., 2012, 9, 1-7.
8. Bedikian, A.Y.; Deconti, R.C.; Conry, R.; Agarwala, S.; Papadopoulos, N.; Kim, K.B.; Ernstoff, M. Phase 3 study of docosahexaenoic acid-paclitaxel versus dacarbazine in patients with metastatic malignant melanoma. Annals of Oncology, 2011, 22, 787-793.
9. Kuznetsova, L.V.; Chen, L.; Sun, L.; Wu, X.; Pepe, A.; Veith, J.M.; Bernacki, R.J.; Ojima, I. Syntheses and evaluation of novel fatty acid- 2ndgeneration taxoid conjugates as promising anticancer agents. Bioorg. Med. Chem. Lett., 2006, 16, 974-977.
10. Wang, Y.; Li, L.; Jiang, W.; Yang, Z.; Zhang, Z. Synthesis and preliminary antitumor activity evaluation of a DHA and doxorubicin conjugate. Bioorg. Med. Chem. Lett., 2006, 16, 2974-2977.
11. Bradley, M.O.; Webb, N.L.; Anthony, F.H.; Devanesan, P.; Witman, P.A.; Hemamalinl, S.; Chander, M.C.; Baker, S.D.; He, L.; Horwitz, S.B.; Swindell, C.S. Tumor targeting by covalent conjugation of a natural fatty acid to paclitaxel. Clinical Cancer Research, 2001, 7, 3229-3238.
12. Chu, T.C.; Marks, J.W.; Lavery, L.A.; Faulkner, S.; Rosenblum, M.G.; Ellington, A.D.; Levy, M. Aptamer:toxin conjugates that specifically target prostate tumor cells. Cancer Res., 2006, 66, 5989-5992.
13. Nagy, A.; Schally, A.V.; Halmos, G.; Armatis, P.; Cai, R.Z.; Csernus, V.; Kovacs, M.; Koppan, M.; Szepeshazi, K.; Kahan, Z. Synthesis and biological evaluation of cytotoxic analogs of somatostatin containing doxorubicin or its intensely potent derivative, 2-pyrrolinodoxorubicin. Proc. Natl. Acad. Sci. U S A, 1998, 95, 1794-1799.
14. Luo, Y.; Bernshaw, N.J.; Lu, Z.R.; Kopecek, J.; Prestwich, G.D. Targeted delivery of doxorubicin by HPMA copolymer-hyaluronan bioconjugates. Pharmaceutical Research, 2002, 19, 396-402.
15. Garnett, M. Targeted drug conjugates: principles and progress. Advanced Drug Delivery Reviews, 2001, 53, 171-216.
16. Leriche, G.; Chisholm, L.;Wagner, A. Cleavable linkers in chemical biology. Bioorg. Med. Chem., 2012, 20, 571-582.
17. Chari, R.V.J. Targeted cancer therapy: Conferring specificity to cytotoxic drugs. Accounts of Chemical Research, 2008, 41, 98-107.
18. Ojima, I. Guided molecular missiles for tumor-targeting chemotherapy-case studies using the second-generation taxoids as warheads. Accounts of Chemical Research, 2008, 41, 108-119.
19. Saitoa, G.; Swanson, J. A.; Lee, K.D. Drug delivery strategy utilizing conjugation via reversible disulfide linkages: role and site of cellular reducing activities. Advanced Drug Delivery Reviews, 2003, 55, 199-215.
20. Bulmus, V.; Woodward, M.; Lin, L.; Murthy, N.; Stayton, P.; Hoffman, A. A new pH-responsive and glutathione-reactive, endosomal membranedisruptive polymeric carrier for intracellular delivery of biomolecular drugs. J. Controlled Release, 2003, 93, 105-120.
21. Trimble, S.P.; Marquardt, D.; Anderson, D.C. Use of designed peptide linkers and recombinant hemoglobin mutants for drug delivery: in vitro release of an angiotensin II analog and kinetic modeling of delivery. Bioconjugate Chem., 1997, 8, 416-423.
22. Meister, A.; Anderson, M. Glutathione. Annu. Rev. Biochem., 1983, 52, 711-760.
23. Meng, F.; Hennink, W.E.; Zhong, Z. Reductionsensitive polymers and bioconjugates for biomedical applications. Biomaterials, 2009, 30, 2180-2198.
24. Thorpe, P.E.; Wallace, P.M.; Knowles, P.P.; Relf, M.G.; Brown, A.N.F.; Watson, G.J.; Knyba, R.E.; Wawrzynczak, E.J.; Blakey, D.C. New coupling agents for the synthesis of immunotoxins containing a hindered disulfide bond with improved stability in vivo. Cancer Res., 1987, 47, 5924-5931.
25. Kuppusamy, P.; Afeworki, M.; Shankar, R.A.; Coffin, D.; Krishna, M.C.; Hahn, S.M.; Mitchell, J. B.; Zweier, J.L. In vivo electron paramagnetic resonance imaging of tumor heterogeneity and oxygenation in a murine model. Cancer Res., 1998, 58, 1562-1568.
26. Meister, A. Glutathione deficiency produced by inhibition of its synthesis, and its reversal: applications in research and therapy. Pharmacol. Ther., 1991, 51, 155-194.
27. Austin, C.D.; Wen, X.; Gazzard, L.; Nelson, C.; Scheller, R.H.; Scales, S.J. Oxidizing potential of endosomes and lysosomes limits intrcellular cleavage of disulfide-based antibody-drug conjugates. Proc. Natl. Acad. Sci. U S A, 2005, 102, 17987-17992.
28. Erickson, H.K.; Park, P.U.; Widdison, W.C.; Kovtun, Y.V.; Garrett, L.M.; Hoffman, K.; Lutz, R.J.; Goldmacher, V.S.; Blattler, W.A. Antibodymaytansinoid conjugates are activated in targeted cancer cells by lysosomal degradation and linkerdependent intracellular processing. Cancer Res., 2006, 66, 4426-4433.
29. Liu, C.; Tadayoni, B.M.; Bourret, L.A.; Mattocks, K.M.; Derr, S.M.; Widdison, W.C.; Kedersha, N. L.; Ariniello, P.D.; Goldmacher, V.S.; Lambert, J.M.; Blattler, W.A.; Chari, R.V.J. Eradication of large colon tumor xenografts by targeted delivery of maytansinoids. Proc. Natl. Acad. Sci. U S A, 1996, 93, 8618-8623.
30. Kovtun, Y.V.; Audette, C.A.; Ye, Y.; Xie, H.; Ruberti, M.F.; Phinney, S.J.; Leece, B.A.; Chittenden, T.; Blattler, W.A.; Goldmacher, V.S. Antibodydrug conjugates designed to eradicate tumors with homogeneous and heterogeneous expression of the target antigen. Cancer Res., 2006, 66, 3214-3221.
31. Tolcher, A.W.; Ochoa, L.; Hammond, L.A.; Patnaik, A.; Edwards, T.; Takimoto, C.; Smith, L.; de Bono, J.; Schwartz, G.; Mays, T.; Jonak, Z.L.; Johnson, R.; DeWitte, M.; Martino, H.; Audette, C.; Maes, K.; Chari, R.V.J.; Lambert, J.M.; Rowinsky, E.K. Cantuzumab mertansine, a maytansinoid immunoconjugate directed to the CanAg antigen: A phase I, pharmacokinetic, and biologic correlative study. J. Clin. Oncol., 2003, 21, 211-222.
32. Lewis Phillips, G.D.; Li, G.; Dugger, D.L.; Crocker, L.M.; Parsons, K.L.; Mai, E.; Blattler, W.A.; Lambert, J.M.; Chari, R.V.J.; Lutz, R.J.; Wong, W.L.T.; Jacobson, F.S.; Koeppen, H.; Schwall, R.H.; Kenkare-Mitra, S.R.; Spencer, S.D.; Sliwkowski, M.X. Targeting HER2-positive breast cancer with trastuzumab-DM1, an antibody-cytotoxic drug conjugate. Cancer Res., 2008, 68, 9280-9290.
33. Chari, R.V.J.; Jackel, K.A.; Bourret, L.A.; Derr, S.M.; Tadayoni, B.M.; Mattocks, K.M.; Shah, S.A.; Liu, C.; Blattler, W.A.; Goldmacher, V.S. Enhancement of the selectivity and antitumor efficacy of a CC-1065 analog through immunoconjugate formation. Cancer Res., 1995, 55, 4079-4084.
34. Kaul, S.; Igwemezie, L.N.; Stewart, D.J.; Fields, S.Z.; Kosty, M.; Levithan, N.; Bukowski, R.; Gandara, D.; Goss, G.; O'Dwyer, P. Pharmacokinetics and bioequivalence of etoposide following intravenous administration of etoposide phosphate and etoposide in patients with solid tumors. J. Clin. Oncol., 1995, 13, 2835-2841.
35. Hamann, P.R.; Hinman, L.M.; Hollander, I.; Beyer, C.F.; Lindh, D.; Holcomb, R.; Hallett, W.; Tsou, H.R.; Upeslacis, J.; Shochat, D.; Mountain, A.; Flowers, D.A.; Bernstein, I. Gemtuzumab ozogamicin, a potent and selective anti-CD33 antibody-calicheamicin conjugate for treatment of acute myeloid leukemia. Bioconjugate Chem., 2002, 13, 47-58.
36. Bross, P.F.; Beitz, J.; Chen, G.; Chen, X.H.; Duffy, E.; Kieffer, L.; Roy, S.; Sridhara, R.; Rahman, A.; Williams, G.; Pazdur, R. Approval summary: Gemtuzumab ozogamicin in relapsed acute myeloid leukemia. Clin. Cancer Res., 2001, 7, 1490-1496.
37. Ojima, I. Use of fluorine in the medicinal chemistry and chemical biology of bioactive compounds-A case study on fluorinated taxane anticancer agents. Chem. Biol. Chem., 2004, 5, 628-635.
38. Gartner, C.A.; Elias, J.E.; Bakalarski, C.E.; Gygi, S.P. Catch-and-release reagents for broadscale quantitative proteomics analyses. J. Proteome Res., 2007, 6, 1482-1491.
39. Henne, W.A.; Doorneweerd, D.D.; Hilgenbrink, A.R.; Kularatne, S.A.; Low, P.S. Synthesis and activity of a folate peptide camptothecin prodrug. Bioorg. Med. Chem. Lett., 2006, 16, 5350-5355.
40. Vlahov, I.R.; Santhapuram, H.K.; Kleindl, P.J.; Howard, S.J.; Stanford, K.M.; Leamon, C.P. Design and regioselective aynthesis of a new generation of targeted chemotherapeutics. Part 1: EC145, a folic acid conjugate of desacetylvinblastine monohydrazide. Bioorg. Med. Chem. Lett., 2006, 16, 5093-5096.
41. Dubikovskaya, E.A.; Thorne, S. H.; Pillow, T.H.; Contag, C.H.; Wender, P.A. Proc. Natl. Acad. Sci. U S A, 2008, 105, 12128.
42. Zhang, W.; Song, J.; Mu, L.; Zhang, B.; Liu, L.; Xing, Y.; Wang, K.; Li, Z.; Wang, R. Improving anticancer activity and selectivity of camptothecin through conjugation with releasable substance P. Bioorg. Med. Chem. Lett., 2011, 21, 1452-1455.
43. Fan, W.; Wu, Y.; Li, X.K.; Yao, N.; Li, X.; Yu, Y.G.; Hai, L. Design, synthesis and biological evaluation of brain-specific glucosyl thiamine disulfide prodrugs of naproxen. Eur. J. Med. Chem., 2011, 46, 3651-3661.
44. Santra, S.; Kaittanis, C.; Santiesteban, O.J.; Perez, J.M. Cell-specific, activatable, and theranostic prodrug for dual-targeted cancer imaging and therapy. J. Am. Chem. Soc., 2011, 133, 16680-16688.