Quinone-methide species, a gateway to functional molecular systems: From self-immolative dendrimers to long-wavelength fluorescent dyes

Accounts of Chemical Research

Volumn 47, Issue 10, 2014, Pages 2970-2984

  Gnaim, Samer ^a   Shabat, Doron ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84908102018     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar500179y     Document Type: Article

References (61)

1. Carl, P. L.; Chakravarty, P. K.; Katzenellenbogen, J. A. A novel connector linkage applicable in prodrug design J. Med. Chem. 1981, 24, 479-480
2. Blencowe, C. A.; Russell, A. T.; Greco, F.; Hayes, W.; Thornthwaite, D. W. Self-immolative linkers in polymeric delivery systems Polym. Chem. 2011, 2, 773-790
3. Amir, R. J.; Popkov, M.; Lerner, R. A.; Barbas, C. F.; Shabat, D. Prodrug activation gated by a molecular "OR" logic trigger Angew. Chem., Int. Ed. 2005, 44, 4378-4381
4. Gopin, A.; Rader, C.; Shabat, D. New chemical adaptor unit designed to release a drug from a tumor targeting device by enzymatic triggering Biorg. Med. Chem. 2004, 12, 1853-1858
5. Gopin, A.; Pessah, N.; Shamis, M.; Rader, C.; Shabat, D. A chemical adaptor system designed to link a tumor-targeting device with a prodrug and an enzymatic trigger Angew. Chem., Int. Ed. 2003, 42, 327-332
6. Shabat, D.; Amir, R. J.; Gopin, A.; Pessah, N.; Shamis, M. Chemical adaptor systems Chem.-Eur. J. 2004, 10, 2626-2634
7. Amir, R. J.; Pessah, N.; Shamis, M.; Shabat, D. Self-immolative dendrimers Angew. Chem., Int. Ed. 2003, 42, 4494-4499
8. Perry, R.; Amir, R. J.; Shabat, D. Substituent-dependent disassembly of self-immolative dendrimers New J. Chem. 2007, 31, 1307-1312
9. Erez, R.; Shabat, D. The azaquinone-methide elimination: comparison study of 1,6-and 1,4-eliminations under physiological conditions Org. Biomol. Chem. 2008, 6, 2669-2672
10. de Groot, F. M. H.; Albrecht, C.; Koekkoek, R.; Beusker, P. H.; Scheeren, H. W. "Cascade-release dendrimers" liberate all end groups upon a single triggering event in the dendritic core Angew. Chem., Int. Ed. 2003, 42, 4490-4494
11. Szalai, M. L.; Kevwitch, R. M.; McGrath, D. V. Geometric disassembly of dendrimers: Dendritic amplification J. Am. Chem. Soc. 2003, 125, 15688-15689
12. Sagi, A.; Segal, E.; Satchi-Fainaro, R.; Shabat, D. Remarkable drug-release enhancement with an elimination-based AB(3) self-immolative dendritic amplifier Biorg. Med. Chem. 2007, 15, 3720-3727
13. Shamis, M.; Shabat, D. Single-triggered AB(6) self-immolative dendritic amplifiers Chem.-Eur. J. 2007, 13, 4523-4528
14. Avital-Shmilovici, M.; Shabat, D. Enzymatic activation of hydrophobic self-immolative dendrimers: The effect of reporters with ionizable functional groups Bioorg. Med. Chem. Lett. 2009, 19, 3959-3962
15. Amir, R. J.; Danieli, E.; Shabat, D. Receiver-amplifier, self-immolative dendritic device Chem.-Eur. J. 2007, 13, 812-821
16. Amir, R. J.; Shabat, D. Self-immolative dendrimer biodegradability by multi-enzymatic triggering Chem. Commun. 2004, 1614-1615
17. Amir, R. J.; Shabat, D. Domino dendrimers Adv. Polym. Sci. 2006, 192, 59-94
18. Shabat, D. Self-immolative dendrimers as novel drug delivery platforms J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1569-1578
19. Erez, R.; Segal, E.; Miller, K.; Satchi-Fainaro, R.; Shabat, D. Enhanced cytotoxicity of a polymer-drug conjugate with triple payload of paclitaxel Biorg. Med. Chem. 2009, 17, 4327-4335
20. Shamis, M.; Lode, H. N.; Shabat, D. Bioactivation of self-immolative dendritic prodrugs by catalytic antibody 38C2 J. Am. Chem. Soc. 2004, 126, 1726-1731
21. Gopin, A.; Ebner, S.; Attali, B.; Shabat, D. Enzymatic activation of second-generation dendritic prodrugs: Conjugation of self-immolative dendrimers with poly(ethylene glycol) via click chemistry Bioconjugate Chem. 2006, 17, 1432-1440
22. Haba, K.; Popkov, M.; Shamis, M.; Lerner, R. A.; Barbas, C. F.; Shabat, D. Single-triggered trimeric prodrugs Angew. Chem., Int. Ed. 2005, 44, 716-720
23. Grinda, M.; Clarhaut, J.; Renoux, B.; Tranoy-Opalinski, I.; Papot, S. A self-immolative dendritic glucuronide prodrug of doxorubicin MedChemComm 2012, 3, 68-70
24. Tranoy-Opalinski, I.; Legigan, T.; Barat, R.; Clarhaut, J.; Thomas, M.; Renoux, B.; Papot, S. β-Glucuronidase-responsive prodrugs for selective cancer chemotherapy: An update Eur. J. Med. Chem. 2014, 74, 302-313
25. Avital-Shmilovici, M.; Shabat, D. Self-immolative dendrimers: A distinctive approach to molecular amplification Soft Matter 2010, 6, 1073-1080
26. McGrath, D. V. Dendrimer disassembly as a new paradigm for the application of dendritic structures Mol. Pharmaceutics 2005, 2, 253-263
27. Sella, E.; Shabat, D. Self-immolative dendritic probe for direct detection of triacetone triperoxide Chem. Commun. 2008, 5701-5703
28. Danieli, E.; Shabat, D. Molecular probe for enzymatic activity with dual output Biorg. Med. Chem. 2007, 15, 7318-7324
29. Redy, O.; Kisin-Finfer, E.; Sella, E.; Shabat, D. A simple FRET-based modular design for diagnostic probes Org. Biomol. Chem. 2012, 10, 710-715
30. Labruere, R.; Alouane, A.; Le Saux, T.; Aujard, I.; Pelupessy, P.; Gautier, A.; Dubruille, S.; Schmidt, F.; Jullien, L. "Self-Immolative" Spacer for Uncaging with Fluorescence Reporting Angew. Chem., Int. Ed. 2012, 51, 9344-9347
31. Turan, I. S.; Akkaya, E. U. Chemiluminescence Sensing of Fluoride Ions Using a Self-Immolative Amplifier Org. Lett. 2014, 16, 1680-1683
32. Adler-Abramovich, L.; Perry, R.; Sagi, A.; Gazit, E.; Shabat, D. Controlled assembly of peptide nanotubes triggered by enzymatic activation of self-immolative dendrimers ChemBioChem 2007, 8, 859-862
33. Perry-Feigenbaum, R.; Baran, P. S.; Shabat, D. The pyridinone-methide elimination Org. Biomol. Chem. 2009, 7, 4825-4828
34. Sagi, A.; Weinstain, R.; Karton, N.; Shabat, D. Self-immolative polymers J. Am. Chem. Soc. 2008, 130, 5434-5435
35. Peterson, G. I.; Larsen, M. B.; Boydston, A. J. Controlled depolymerization: Stimuli-responsive self-immolative polymers Macromolecules 2012, 45, 7317-7328
36. Weinstain, R.; Sagi, A.; Karton, N.; Shabat, D. Self-immolative comb-polymers: Multiple-release of side-reporters by a single stimulus event Chem.-Eur. J. 2008, 14, 6857-6861
37. Weinstain, R.; Baran, P. S.; Shabat, D. Activity-linked labeling of enzymes by self-immolative polymers Bioconjugate Chem. 2009, 20, 1783-1791
38. Wang, W.; Alexander, C. Self-immolative polymers Angew. Chem., Int. Ed. 2008, 47, 7804-7806
39. Phillips, S. T.; Di Lauro, A. M. Continuous head-to-tail depolymerization: An emerging concept for imparting amplified responses to stimuli-responsive materials ACS Macro Lett. 2014, 3, 298-304
40. Seo, W.; Phillips, S. T. Patterned plastics that change physical structure in response to applied chemical signals J. Am. Chem. Soc. 2010, 132, 9234-9235
41. Wong, A. D.; DeWit, M. A.; Gillies, E. R. Amplified release through the stimulus triggered degradation of self-immolative oligomers, dendrimers, and linear polymers Adv. Drug Delivery Rev. 2012, 64, 1031-1045
42. Olah, M. G.; Robbins, J. S.; Baker, M. S.; Phillips, S. T. End-capped poly(benzyl ethers): Acid and base stable polymers that depolymerize rapidly from head-to-tail in response to specific applied signals Macromolecules 2013, 46, 5924-5928
43. Esser-Kahn, A. P.; Sottos, N. R.; White, S. R.; Moore, J. S. Programmable microcapsules from self-immolative polymers J. Am. Chem. Soc. 2010, 132, 10266-10268
44. Fomina, N.; McFearin, C.; Sermsakdi, M.; Edigin, O.; Almutairi, A. UV and near-IR triggered release from polymeric nanoparticles J. Am. Chem. Soc. 2010, 132, 9540-9542
45. Deshayes, S.; Kasko, A. M. Polymeric biomaterials with engineered degradation J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3531-3566
46. Dewit, M. A.; Gillies, E. R. A cascade biodegradable polymer based on alternating cyclization and elimination reactions J. Am. Chem. Soc. 2009, 131, 18327-18334
47. Sella, E.; Shabat, D. Dendritic chain reaction J. Am. Chem. Soc. 2009, 131, 9934-9936
48. Swiderska, M. A.; Reymond, J. L. A dendritic signal amplifier Nat. Chem. 2009, 1, 527-528
49. Avital-Shmilovici, M.; Shabat, D. Dendritic chain reaction: Responsive release of hydrogen peroxide upon generation and enzymatic oxidation of methanol Biorg. Med. Chem. 2010, 18, 3643-3647
50. Sella, E.; Weinstain, R.; Erez, R.; Burns, N. Z.; Baran, P. S.; Shabat, D. Sulfhydryl-based dendritic chain reaction Chem. Commun. 2010, 46, 6575-6577
51. Perry-Feigenbaum, R.; Sella, E.; Shabat, D. Autoinductive exponential signal amplification: A diagnostic probe for direct detection of fluoride Chem.-Eur. J. 2011, 17, 12123-12128
52. Sella, E.; Lubelski, A.; Klafter, J.; Shabat, D. Two-component dendritic chain reactions: Experiment and theory J. Am. Chem. Soc. 2010, 132, 3945-3952
53. Karton-Lifshin, N.; Shabat, D. Exponential diagnostic signal amplification via dendritic chain reaction: The dendritic effect of a self-immolative amplifier component New J. Chem. 2012, 36, 386-393
54. Baker, M. S.; Phillips, S. T. A two-component small molecule system for activity-based detection and signal amplification: Application to the visual detection of threshold levels of Pd(II) J. Am. Chem. Soc. 2011, 133, 5170-5173
55. Karton-Lifshin, N.; Segal, E.; Omer, L.; Portnoy, M.; Satchi-Fainaro, R.; Shabat, D. A unique paradigm for a turn-ON near-infrared cyanine-based probe: Noninvasive intravital optical imaging of hydrogen peroxide J. Am. Chem. Soc. 2011, 133, 10960-10965
56. Karton-Lifshin, N.; Albertazzi, L.; Bendikov, M.; Baran, P. S.; Shabat, D. "Donor-two-acceptor" dye design: A distinct gateway to NIR fluorescence J. Am. Chem. Soc. 2012, 134, 20412-20420
57. Kisin-Finfer, E.; Shabat, D. New repertoire of "donor-two-acceptor" NIR fluorogenic dyes Biorg. Med. Chem. 2013, 21, 3602-3608
58. Redy-Keisar, O.; Kisin-Finfer, E.; Ferber, S.; Satchi-Fainaro, R.; Shabat, D. Synthesis and use of QCy7-derived modular probes for the detection and imaging of biologically relevant analytes Nat. Protoc. 2014, 9, 27-36
59. Redy, O.; Shabat, D. Modular theranostic prodrug based on a FRET-activated self-immolative linker J. Controlled Release 2012, 164, 276-282
60. Weinstain, R.; Segal, E.; Satchi-Fainaro, R.; Shabat, D. Real-time monitoring of drug release Chem. Commun. 2010, 46, 553-555
61. Wang, R. E.; Costanza, F.; Niu, Y.; Wu, H.; Hu, Y.; Hang, W.; Sun, Y.; Cai, J. Development of self-immolative dendrimers for drug delivery and sensing J. Controlled Release 2012, 159, 154-163