A medusa-like β-cyclodextrin with 1-methyl-2-(2′-carboxyethyl) maleic anhydrides, a potential carrier for pH-sensitive drug delivery

References

• Fleige E, Quadir MA, Haag R. Stimuli-responsive polymeric nanocarriers for the controlled transport of active compounds: concepts and applications. Adv Drug Delivery Rev 2012;64:866–84
   PubMed Web of Science ®Google Scholar
• Lee Y, Kataoka K. Biosignal-sensitive polyion complex micelles for the delivery of biopharmaceuticals. Soft Matter 2009;5:3810–17
   Web of Science ®Google Scholar
• Gupta P, Vermani K, Garg S. Hydrogels: from controlled release to pH-responsive drug delivery. Drug Discovery Today 2002;7:569–79
   PubMed Web of Science ®Google Scholar
• Prasannan A, Tsai H-C, Chen Y-S, Hsiue G-H. A thermally triggered in situ hydrogel from poly(acrylic acid-co-N-isopropylacrylamide) for controlled release of anti-glaucoma drugs. J Mater Chem B 2014;2:1988–97
   Web of Science ®Google Scholar
• Jiang J, Tong X, Zhao Y. A new design for light-breakable polymer micelles. J Am Chem Soc 2005;127:8290–1
   PubMed Web of Science ®Google Scholar
• Lee Y, Fukushima S, Bae Y, et al. A protein nanocarrier from charge-conversion polymer in response to endosomal pH. J Am Chem Soc 2007;129:5362–3
   PubMed Web of Science ®Google Scholar
• Cheng R, Feng F, Meng F, et al. Glutathione-responsive nano-vehicles as a promising platform for targeted intracellular drug and gene delivery. J Controlled Release 2011;152:2–12
   PubMed Web of Science ®Google Scholar
• Miyata T, Uragami T, Nakamae K. Biomolecule-sensitive hydrogels. Adv Drug Delivery Rev 2002;54:79–98
   PubMed Web of Science ®Google Scholar
• Gao W-W, Chan JM, Farokhzad OC. pH-responsive nanoparticles for drug delivery. Mol Pharmaceutics 2010;7:1913–20
   PubMed Web of Science ®Google Scholar
• Wu XL, Kim JH, Koo H, et al. Tumor-targeting peptide conjugated pH-responsive micelles as a potential drug carrier for cancer therapy. Bioconjugate Chem 2010;21:208–13
   PubMed Web of Science ®Google Scholar
• Punnia-Moorthy A. Evaluation of pH changes in inflammation of the subcutaneous air pouch lining in the rat, induced by carrageenan, dextran and Staphylococcus aureus. J Oral Pathol Med 1987;16:36–44
   Web of Science ®Google Scholar
• Bessman AN, Page J, Thomas LJ. In vivo pH of induced soft-tissue abscesses in diabetic and nondiabetic mice. Diabetes 1989;38:659–62
   PubMed Web of Science ®Google Scholar
• Ford C, Hamel J, Stapert D, Yancey R. Establishment of an experimental model of a Staphylococcus aureus abscess in mice by use of dextran and gelatin microcarriers. J Med Microbiol 1989;28:259–66
   PubMed Web of Science ®Google Scholar
• Abhay A, Singh CA, Vamanrao DP, Kumar JN. Poly(amidoamine) (PAMAM) dendritic nanostructures for controlled site-specific delivery of acidic anti-inflammatory active ingredient. AAPS PharmSciTech 2005;6:E536–42
   PubMedGoogle Scholar
• Lee Y, Miyata K, Oba M, et al. Charge-conversion ternary polyplex with endosome disruption moiety: a technique for efficient and safe gene delivery. Angew Chem Int Ed 2008;47:5163–6
   PubMed Web of Science ®Google Scholar
• Rozema DB, Lewis DL, Wakefield DH, et al. Dynamic PolyConjugates for targeted in vivo delivery of siRNA to hepatocytes. PNAS 2007;104:12982–7
   PubMed Web of Science ®Google Scholar
• Lee Y, Ishii T, Cabral H, et al. Charge-conversional polyionic complex micelles-efficient nanocarriers for protein delivery into cytoplasm. Angew Chem Int Ed 2009;48:5309–12
   PubMed Web of Science ®Google Scholar
• Mellman I, Fuchs R, Helenius A. Acidification of the endocytic and exocytic pathways. Annu Rev Biochem 1986;55:663–700
   PubMed Web of Science ®Google Scholar
• Lee Y, Ishii T, Kim HJ, et al. Efficient delivery of bioactive antibodies into the cytoplasm of living cells by charge-conversional polyion complex micelles. Angew Chem Int Ed 2010;49:2552–5
   PubMed Web of Science ®Google Scholar
• Kirby AJ, Lloyd GJ. Structure and efficiency in intramolecular and enzymic catalysis: intramolecular general base catalysis. Catalysis of amide hydrolysis by the carboxy-group of substituted maleamic acids. J Chem Soc Perkin Trans 2 1976:1753–61
   Google Scholar
• Mehta NB, Phillips AP, Lui FF, Brooks RE. Maleamic and citraconamic acids, methyl esters, and imides. J Org Chem 1960;25:1012–15
   Web of Science ®Google Scholar
• Rozema DB, Ekena K, Lewis DL, et al. Endosomolysis by masking of a membrane-active agent (EMMA) for cytoplasmic release of macromolecules. Bioconjugate Chem 2003;14:51–7
   PubMed Web of Science ®Google Scholar
• Davis ME, Brewster ME. Cyclodextrin-based pharmaceutics: past, present and future. Nat Rev Drug Discovery 2004;3:1023–35
   PubMed Web of Science ®Google Scholar
• Cravotto G, Bicchi C, Tagliapietra S, et al. New chiral selectors: design and synthesis of 6-TBDMS-2,3-methyl beta-cyclodextrin 2-2′ thioureido dimer and 6-TBDMS-2,3-methyl (or 2-methyl-3-acetyl) beta-cyclodextrin bearing an (R) Mosher acid moiety. Chirality 2004;16:526–33
   PubMed Web of Science ®Google Scholar
• Motoyama K, Onodera R, Okamatsu A, et al. Potential use of the complex of doxorubicin with folate-conjugated methyl-beta-cyclodextrin for tumor-selective cancer chemotherapy. J Drug Targeting 2014;22:211–19
   PubMed Web of Science ®Google Scholar
• Copolovici DM, Langel K, Eriste E, Langel U. Cell-penetrating peptides: design, synthesis, and applications. ACS Nano 2014;8:1972–94
   PubMed Web of Science ®Google Scholar
• Hakkarainen B, Fujita K, Immel S, et al. 1H NMR studies on the hydrogen-bonding network in mono-altro-beta-cyclodextrin and its complex with adamantane-1-carboxylic acid. Carbohydr Res 2005;340:1539–45
   PubMed Web of Science ®Google Scholar
• Kulkarni A, Deng W, Hyun SH, Thompson DH. Development of a low toxicity, effective pDNA vector based on noncovalent assembly of bioresponsive amino-beta-cyclodextrin:adamantane-poly(vinyl alcohol)-poly(ethylene glycol) transfection complexes. Bioconjugate Chem 2012;23:933–40
   PubMed Web of Science ®Google Scholar
• Naganawa A, Ichikawa Y, Isobe M. Synthetic studies on tautomycin. Synthesis of 2,3-disubstituted maleic anhydride segment. Tetrahedron 1994;50:8969–82
   Web of Science ®Google Scholar
• Humblet V, Misra P, Bhushan KR, et al. Multivalent scaffolds for affinity maturation of small molecule cell surface binders and their Application to Prostate Tumor Targeting. J Med Chem 2009;52:544–50
   PubMed Web of Science ®Google Scholar
• Petrasek Z, Schwille P. Precise measurement of diffusion coefficients using scanning fluorescence correlation spectroscopy. Biophys J 2008;94:1437–48
   PubMed Web of Science ®Google Scholar
• Kim SA, Heinze KG, Schwille P. Fluorescence correlation spectroscopy in living cells. Nat Methods 2007;4:963–73
   PubMed Web of Science ®Google Scholar
• Granadero D, Bordello J, Perez-Alvite MJ, et al. Host-guest complexation studied by fluorescence correlation spectroscopy: adamantane-cyclodextrin inclusion. Int J Mol Sci 2010;11:173–88
   PubMed Web of Science ®Google Scholar
• Smirnov D, Dhall A, Sivanesam K, et al. Fluorescent probes reveal a minimal ligase recognition motif in the prokaryotic ubiquitin-like protein from Mycobacterium tuberculosis. J Am Chem Soc 2013;135:2887–90
   PubMed Web of Science ®Google Scholar
• Suh J, Baek D-J. Intramolecular catalysis of amide hydrolysis by carboxyl and metal ion/proton agents. I. Intramolecular reactions of imidazole or pyridine derivatives of maleamic acid. Bioorg Chem 1981;10:266–76
   Web of Science ®Google Scholar
• Kirby AJ, McDonald RS, Smith CR. Intramolecular catalysis of amide hydrolysis by two carboxy groups. J Chem Soc Perkin Trans 2 1974:1495–504
   Google Scholar
• Monahan SD, Subbotin VM, Budker VG, et al. Rapidly reversible hydrophobization: an approach to high first-pass drug extraction. Chem Biol 2007;14:1065–77
   PubMed Web of Science ®Google Scholar
• Takemoto H, Miyata K, Hattori S, et al. Acidic pH-responsive siRNA conjugate for reversible carrier stability and accelerated endosomal escape with reduced IFNalpha-associated immune response. Angew Chem Int Ed 2013;52:6218–21
   PubMed Web of Science ®Google Scholar
• Wong SC, Wakefield D, Klein J, et al. Hepatocyte targeting of nucleic acid complexes and liposomes by a T7 phage p17 peptide. Mol Pharmaceutics 2006;3:386–97
   PubMed Web of Science ®Google Scholar
• Moore JS, Stupp SI. Room temperature polyesterification. Macromolecules 1990;23:65–70
   Web of Science ®Google Scholar
• Li L, Guo X, Wang J, et al. Polymer networks assembled by host-guest inclusion between adamantyl and β-cyclodextrin substituents on poly(acrylic acid) in aqueous solution. Macromolecules 2008;41:8677–81
   Web of Science ®Google Scholar
• Harries D, Rau DC, Parsegian VA. Solutes probe hydration in specific association of cyclodextrin and adamantane. J Am Chem Soc 2005;127:2184–90
   PubMed Web of Science ®Google Scholar