A smart tumor targeting peptide–drug conjugate, pHLIP-SS-DOX: synthesis and cellular uptake on MCF-7 and MCF-7/Adr cells

References

• Ai S, Duan J, Liu X, et al. (2011). Biological evaluation of a novel doxorubicin-peptide conjugate for targeted delivery to EGF receptor-overexpressing tumor cells. Mol Pharm 8:375–86
   PubMed Web of Science ®Google Scholar
• Andreev OA, Dupuy AD, Segala M, et al. (2007). Mechanism and uses of a membrane peptide that targets tumors and other acidic tissues in vivo. Proc Natl Acad Sci USA 104:7893–8
   PubMed Web of Science ®Google Scholar
• Andreev OA, Karabadzhak AG, Weerakkody D, et al. (2010). pH (low) insertion peptide (pHLIP) inserts across a lipid bilayer as a helix and exits by a different path. Proc Natl Acad Sci USA 107:4081–6
   PubMed Web of Science ®Google Scholar
• Aroui S, Brahim S, Waard MD, Kenani A. (2010). Cytotoxicity, intracellular distribution and uptake of doxorubicin and doxorubicin coupled to cell-penetrating peptides in different cell lines: a comparative study. Biochem Biophys Res Commun 391:419–25
   PubMed Web of Science ®Google Scholar
• Bao Y, Guo Y, Zhuang X, et al. (2014). D-alpha-tocopherol polyethylene glycol succinate-based redox-sensitive paclitaxel prodrug for overcoming multidrug resistance in cancer cells. Mol Pharm 11:3196–209
   PubMed Web of Science ®Google Scholar
• Bechara C, Sagan S. (2013). Cell-penetrating peptides: 20 years later, where do we stand? Febs Lett 587:1693–702
   PubMed Web of Science ®Google Scholar
• Burstein EA, Vedenkina NS, Ivkova MN. (1973). Fluorescence and the location of tryptophan residues in protein molecules. Photochem Photobiol 18:263–79
   PubMed Web of Science ®Google Scholar
• Chen W, Shi Y, Feng H, et al. (2012). Preparation of copolymer paclitaxel covalently linked via a disulfide bond and its application on controlled drug delivery. J Phys Chem B 116:9231–7
   PubMed Web of Science ®Google Scholar
• Chhikara BS, St JN, Mandal D, et al. (2011). Fatty acyl amide derivatives of doxorubicin: synthesis and in vitro anticancer activities. Eur J Med Chem 46:2037–42
   PubMed Web of Science ®Google Scholar
• Chuan X, Song Q, Lin J, et al. (2014). Novel free-paclitaxel-loaded redox-responsive nanoparticles based on a disulfide-linked poly(ethylene glycol)-drug conjugate for intracellular drug delivery: synthesis, characterization, and antitumor activity in vitro and in vivo. Mol Pharm 11:3656–70
   PubMed Web of Science ®Google Scholar
• Drachuk I, Shchepelina O, Lisunova M, et al. (2012). pH-responsive layer-by-layer nanoshells for direct regulation of cell activity. ACS Nano 6:4266–78
   PubMed Web of Science ®Google Scholar
• Dubikovskaya EA, Thorne SH, Pillow TH, et al. (2008). Overcoming multidrug resistance of small-molecule therapeutics through conjugation with releasable octaarginine transporters. Proc Natl Acad Sci USA 105:12128––33
   PubMed Web of Science ®Google Scholar
• Fendos J, Engelman D. (2012). pHLIP and acidity as a universal biomarker for cancer. Yale J Biol Med 85:29–35
   PubMedGoogle Scholar
• Geng Q, Sun X, Gong T, Zhang ZR. (2012). Peptide–drug conjugate linked via a disulfide bond for kidney targeted drug delivery. Bioconjug Chem 23:1200–10
   PubMed Web of Science ®Google Scholar
• Girotti AW, Minotti G. (2013). Development of a tumor-specific photoactivatable doxorubicin prodrug. Photochem Photobiol 89:1009–10
   PubMed Web of Science ®Google Scholar
• Greenfield NJ. (2006). Using circular dichroism spectra to estimate protein secondary structure. Nat Protoc 1:2876–90
   PubMed Web of Science ®Google Scholar
• Guillemard V, Uri SH. (2004). Prodrug chemotherapeutics bypass p-glycoprotein resistance and kill tumors in vivo with high efficacy and target-dependent selectivity. Oncogene 23:3613–21
   PubMed Web of Science ®Google Scholar
• He X, Li J, An S, Jiang C. (2013). pH-sensitive drug-delivery systems for tumor targeting. Ther Deliv 4:1499–510
   PubMedGoogle Scholar
• Hunt JF, Rath P, Rothschild KJ, Engelman DM. (1997). Spontaneous, pH-dependent membrane insertion of a transbilayer alpha-helix. Biochemistry-US 36:15177–92
   PubMed Web of Science ®Google Scholar
• KCR Thapa B, Xu P. (2012). pH and redox dual responsive nanoparticle for nuclear targeted drug delivery. Mol Pharm 9:2719–29
   PubMed Web of Science ®Google Scholar
• Kono K, Kojima C, Hayashi N, et al. (2008). Preparation and cytotoxic activity of poly(ethylene glycol)-modified poly(amidoamine) dendrimers bearing adriamycin. Biomaterials 29:1664–75
   PubMed Web of Science ®Google Scholar
• Koo AN, Lee HJ, Kim SE, et al. (2008). Disulfide-cross-linked PEG-poly(amino acid)s copolymer micelles for glutathione-mediated intracellular drug delivery. Chem Commun (Camb) 48:6570–2
   PubMed Web of Science ®Google Scholar
• Kratz F, Beyer U, Roth T, et al. (1998). Transferrin conjugates of doxorubicin: synthesis, characterization, cellular uptake, and in vitro efficacy. J Pharm Sci 87:338–46
   PubMed Web of Science ®Google Scholar
• Kuppusamy P, Li H, Ilangovan G, et al. (2002). Noninvasive imaging of tumor redox status and its modification by tissue glutathione levels. Cancer Res 62:307–12
   PubMed Web of Science ®Google Scholar
• Liang JF, Yang VC. (2005). Synthesis of doxorubicin-peptide conjugate with multidrug resistant tumor cell killing activity. Bioorg Med Chem Lett 15:5071–5
   PubMed Web of Science ®Google Scholar
• Maksimenko A, Dosio F, Mougin J, et al. (2014). A unique squalenoylated and nonpegylated doxorubicin nanomedicine with systemic long-circulating properties and anticancer activity. Proc Natl Acad Sci USA 111:E217–26
   PubMed Web of Science ®Google Scholar
• Mali SM, Ganesh KM, Katariya MM, Gopi HN. (2014). HBTU mediated 1-hydroxybenzotriazole (HOBt) conjugate addition: synthesis and stereochemical analysis of beta-benzotriazole N-oxide substituted gamma-amino acids and hybrid peptides. Org Biomol Chem 12:8462–72
   PubMed Web of Science ®Google Scholar
• Milletti F. (2012). Cell-penetrating peptides: classes, origin, and current landscape. Drug Discov Today 17:850–60
   PubMed Web of Science ®Google Scholar
• Minko T, Kopeckova P, Pozharov V, Kopecek J. (1998). HPMA copolymer bound adriamycin overcomes MDR1 gene encoded resistance in a human ovarian carcinoma cell line. J Control Release 54:223–33
   PubMed Web of Science ®Google Scholar
• Mura S, Nicolas J, Couvreur P. (2013). Stimuli-responsive nanocarriers for drug delivery. Nat Mater 12:991–1003
   PubMed Web of Science ®Google Scholar
• Nasrollahi SA, Taghibiglou C, Azizi E, Farboud ES. (2012). Cell-penetrating peptides as a novel transdermal drug delivery system. Chem Biol Drug Des 80:639–46
   PubMed Web of Science ®Google Scholar
• Ohkawa K, Hatano T, Tsukada Y, Matsuda M. (1993). Chemotherapeutic efficacy of the protein-doxorubicin conjugates on multidrug resistant rat hepatoma cell line in vitro. Br J Cancer 67:274–8
   PubMed Web of Science ®Google Scholar
• Pan YJ, Chen YY, Wang DR, et al. (2012). Redox/pH dual stimuli-responsive biodegradable nanohydrogels with varying responses to dithiothreitol and glutathione for controlled drug release. Biomaterials 33:6570–9
   PubMed Web of Science ®Google Scholar
• Reshetnyak YK, Andreev OA, Segala M, et al. (2008). Energetics of peptide (pHLIP) binding to and folding across a lipid bilayer membrane. Proc Natl Acad Sci USA 105:15340–5
   PubMed Web of Science ®Google Scholar
• Reshetnyak YK, Segala M, Andreev OA, Engelman DM. (2007). A monomeric membrane peptide that lives in three worlds: in solution, attached to, and inserted across lipid bilayers. Biophys J 93:2363–72
   PubMed Web of Science ®Google Scholar
• Santra S, Kaittanis C, Santiesteban OJ, Perez JM. (2011). Cell-specific, activatable, and theranostic prodrug for dual-targeted cancer imaging and therapy. J Am Chem Soc 133:16680–8
   PubMed Web of Science ®Google Scholar
• Shi NQ, Gao W, Xiang B, Qi XR. (2012). Enhancing cellular uptake of activable cell-penetrating peptide–doxorubicin conjugate by enzymatic cleavage. Int J Nanomed 7:1613–21
   PubMed Web of Science ®Google Scholar
• Soudy R, Chen C, Kaur K. (2013). Novel peptide–doxorubucin conjugates for targeting breast cancer cells including the multidrug resistant cells. J Med Chem 56:7564–73
   PubMed Web of Science ®Google Scholar
• Szwed M, Kania KD, Jozwiak Z. (2014). Relationship between therapeutic efficacy of doxorubicin–transferrin conjugate and expression of P-glycoprotein in chronic erythromyeloblastoid leukemia cells sensitive and resistant to doxorubicin. Cell Oncol (Dordr) 37:421–8
   PubMed Web of Science ®Google Scholar
• Tetin SY, Prendergast FG, Venyaminov SY. (2003). Accuracy of protein secondary structure determination from circular dichroism spectra based on immunoglobulin examples. Anal Biochem 321:183–7
   PubMed Web of Science ®Google Scholar
• Thevenin D, An M, Engelman DM. (2009). pHLIP-mediated translocation of membrane-impermeable molecules into cells. Chem Biol 16:754–62
   PubMed Web of Science ®Google Scholar
• Vasconcelos L, Parn K, Langel U. (2013). Therapeutic potential of cell-penetrating peptides. Ther Deliv 4:573–91
   PubMedGoogle Scholar
• Wilson JT, Keller S, Manganiello MJ, et al. (2013). pH-responsive nanoparticle vaccines for dual-delivery of antigens and immunostimulatory oligonucleotides. ACS Nano 7:3912–25
   PubMed Web of Science ®Google Scholar
• Wu Q, Yang Z, Nie Y, et al. (2014). Multi-drug resistance in cancer chemotherapeutics: mechanisms and lab approaches. Cancer Lett 347:159–66
   PubMed Web of Science ®Google Scholar
• Xie H, Braha O, Gu LQ, et al. (2005). Single-molecule observation of the catalytic subunit of cAMP-dependent protein kinase binding to an inhibitor peptide. Chem Biol 12:109–20
   PubMed Web of Science ®Google Scholar
• Yoo HS, Lee KH, Oh JE, Park TG. (2000). In vitro and in vivo anti-tumor activities of nanoparticles based on doxorubicin-PLGA conjugates. J Control Release 68:419–31
   PubMed Web of Science ®Google Scholar
• Zhang W, Song J, Zhang B, et al. (2011). Design of acid-activated cell penetrating peptide for delivery of active molecules into cancer cells. Bioconjug Chem 22:1410–15
   PubMed Web of Science ®Google Scholar
• Zhao BX, Zhao Y, Huang Y, et al. (2012). The efficiency of tumor-specific pH-responsive peptide-modified polymeric micelles containing paclitaxel. Biomaterials 33:2508–20
   PubMed Web of Science ®Google Scholar