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Rational development of caged-biotin protein-labeling agents and some applications in live cells.

Terai T, Maki E, Sugiyama S, Takahashi Y, Matsumura H, Mori Y, Nagano T
Chem Biol 18 1261-72 (2011)
Related entries: 3vhh, 3vhi, 3vhm

Cited: 9 times
EuropePMC logo PMID: 22035795

Abstract

Biotin-(strept)avidin complex is widely used in biotechnology because of its extremely high binding constant, but there is no report describing spatiotemporally controlled formation of the complex in live cells. Here, based on X-ray crystal structure analysis and calorimetric data, we designed and synthesized photoreleasable biotins, which show greatly reduced affinity for (strept)avidin, but recover native affinity after UV irradiation. For application at the cell surface, we introduced an amine-reactive moiety into these "caged" biotin molecules. Specific fluorescence imaging of live cells that had been labeled with these agents and then UV-irradiated, was accomplished by addition of streptavidin conjugated with a fluorophore. We also demonstrated the applicability of these compounds for UV-irradiated-cell-specific drug delivery by using caged-biotin-labeled cells, a prodrug, and streptavidin conjugated with a prodrug-activating enzyme.

Articles - 3vgw mentioned but not cited (1)

  1. Structural Characterization of the Avidin Interactions with Fluorescent Pyrene-Conjugates: 1-Biotinylpyrene and 1-Desthiobiotinylpyrene. Strzelczyk P, Plażuk D, Zakrzewski J, Bujacz G. Molecules 21 E1270 (2016)


Reviews citing this publication (1)

  1. Engineering Proteins at Interfaces: From Complementary Characterization to Material Surfaces with Designed Functions. Morsbach S, Gonella G, Mailänder V, Wegner S, Wu S, Weidner T, Berger R, Koynov K, Vollmer D, Encinas N, Kuan SL, Bereau T, Kremer K, Weil T, Bonn M, Butt HJ, Landfester K. Angew Chem Int Ed Engl 57 12626-12648 (2018)

Articles citing this publication (7)

  1. Dynamic blue light-switchable protein patterns on giant unilamellar vesicles. Bartelt SM, Chervyachkova E, Steinkühler J, Ricken J, Wieneke R, Tampé R, Dimova R, Wegner SV. Chem Commun (Camb) 54 948-951 (2018)
  2. Modified recombinant proteins can be exported via the Sec pathway in Escherichia coli. Chen N, Hong FL, Wang HH, Yuan QH, Ma WY, Gao XN, Shi R, Zhang RJ, Sun CS, Wang SB. PLoS One 7 e42519 (2012)
  3. Design and synthesis of biotin analogues reversibly binding with streptavidin. Yamamoto T, Aoki K, Sugiyama A, Doi H, Kodama T, Shimizu Y, Kanai M. Chem Asian J 10 1071-1078 (2015)
  4. Target-activated streptavidin-biotin controlled binding probe. Wu YP, Chew CY, Li TN, Chung TH, Chang EH, Lam CH, Tan KT. Chem Sci 9 770-776 (2018)
  5. Love-Hate ligands for high resolution analysis of strain in ultra-stable protein/small molecule interaction. Fairhead M, Shen D, Chan LK, Lowe ED, Donohoe TJ, Howarth M. Bioorg Med Chem 22 5476-5486 (2014)
  6. Imaging and Quantification of Secreted Peroxynitrite at the Cell Surface by a Streptavidin-Biotin-Controlled Binding Probe. Chung TH, Wu YP, Chew CY, Lam CH, Tan KT. Chembiochem 19 2584-2590 (2018)
  7. Selection methods for proximity-dependent enrichment of ligands from DNA-encoded libraries using enzymatic fusion proteins. Cai B, Mhetre AB, Krusemark CJ. Chem Sci 14 245-250 (2023)


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