In this work, we developed a water-soluble caging group based on a π-extended BODIPY scaffold able to release carboxylate-containing cargo upon red light illumination (λirr =633 nm). We performed mechanistic studies showing new insights into the principles of the photoreactivity of these cages and demonstrated a significant influence of the structure of a carboxylate cargo on the rate and efficiency of the uncaging process and its side reactions. We used it for selective delivery, visualisation, and photorelease of a signaling lipid in cell plasma and internal membranes. With this approach, we successfully induced Ca2+ release in cells expressing the GPR40 receptor.

Department of Biochemistry and Biotechnology Vasyl Stefanyk Precarpathian National University 57 Shevchenko Str Ivano Frankivsk 76018 Ukraine

Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo náměstí 542 2 Prague 6 160 00 Czech Republic

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P. Klán, T. Šolomek, C. G. Bochet, A. Blanc, R. Givens, M. Rubina, V. Popik, A. Kostikov, J. Wirz, Chem. Rev. 2013, 113, 119-191.

R. Weinstain, T. Slanina, D. Kand, P. Klán, Chem. Rev. 2020, 120, 13135-13272.

L. Josa-Culleré, A. Llebaria, ChemPhotoChem 2021, 5, 296-314.

S. Wäldchen, J. Lehmann, T. Klein, S. van de Linde, M. Sauer, Sci. Rep. 2015, 5, 15348.

A. Alabugin, Photochem. Photobiol. 2019, 95, 722-732.

M. Bojtár, A. Kormos, K. Kis-Petik, M. Kellermayer, P. Kele, Org. Lett. 2019, 21, 9410-9414.

P. Šebej, J. Wintner, P. Müller, T. Slanina, J. Al Anshori, L. A. P. Antony, P. Klán, J. Wirz, J. Org. Chem. 2013, 78, 1833-1843.

R. R. Nani, A. P. Gorka, T. Nagaya, H. Kobayashi, M. J. Schnermann, Angew. Chem. Int. Ed. 2015, 54, 13635-13638;

Angew. Chem. 2015, 127, 13839-13842.

A. P. Gorka, M. J. Schnermann, Curr. Opin. Chem. Biol. 2016, 33, 117-125.

P. P. Goswami, A. Syed, C. L. Beck, T. R. Albright, K. M. Mahoney, R. Unash, E. A. Smith, A. H. Winter, J. Am. Chem. Soc. 2015, 137, 3783-3786.

N. Rubinstein, P. Liu, E. W. Miller, R. Weinstain, Chem. Commun. 2015, 51, 6369-6372.

J. A. Peterson, C. Wijesooriya, E. J. Gehrmann, K. M. Mahoney, P. P. Goswami, T. R. Albright, A. Syed, A. S. Dutton, E. A. Smith, A. H. Winter, J. Am. Chem. Soc. 2018, 140, 7343-7346.

T. Slanina, P. Shrestha, E. Palao, D. Kand, J. A. Peterson, A. S. Dutton, N. Rubinstein, R. Weinstain, A. H. Winter, P. Klán, J. Am. Chem. Soc. 2017, 139, 15168-15175.

J. A. Peterson, D. Yuan, A. H. Winter, J. Org. Chem. 2021, 86, 9781-9787.

P. Shrestha, K. C. Dissanayake, E. J. Gehrmann, C. S. Wijesooriya, A. Mukhopadhyay, E. A. Smith, A. H. Winter, J. Am. Chem. Soc. 2020, 142, 15505-15512.

E. Palao, T. Slanina, L. Muchová, T. Šolomek, L. Vítek, P. Klán, J. Am. Chem. Soc. 2016, 138, 126-133.

A. Takeda, T. Komatsu, H. Nomura, M. Naka, N. Matsuki, Y. Ikegaya, T. Terai, T. Ueno, K. Hanaoka, T. Nagano, Y. Urano, ChemBioChem 2016, 17, 1233-1240.

N. Umeda, H. Takahashi, M. Kamiya, T. Ueno, T. Komatsu, T. Terai, K. Hanaoka, T. Nagano, Y. Urano, ACS Chem. Biol. 2014, 9, 2242-2246.

J. A. Peterson, L. J. Fischer, E. J. Gehrmann, P. Shrestha, D. Yuan, C. S. Wijesooriya, E. A. Smith, A. H. Winter, J. Org. Chem. 2020, 85, 5712-5717.

D. Kand, L. Pizarro, I. Angel, A. Avni, D. Friedmann-Morvinski, R. Weinstain, Angew. Chem. Int. Ed. 2019, 58, 4659-4663;

Angew. Chem. 2019, 131, 4707-4711.

D. Kand, P. Liu, M. X. Navarro, L. J. Fischer, L. Rousso-Noori, D. Friedmann-Morvinski, A. H. Winter, E. W. Miller, R. Weinstain, J. Am. Chem. Soc. 2020, 142, 4970-4974.

R. F. Khairutdinov, N. Serpone, J. Phys. Chem. B 1997, 101, 2602-2610.

D. S. Conceição, D. P. Ferreira, L. F. V. Ferreira, Int. J. Mol. Sci. 2013, 14, 18557-18571.

A. Nadler, D. A. Yushchenko, R. Müller, F. Stein, S. Feng, C. Mulle, M. Carta, C. Schultz, Nat. Commun. 2015, 6, 10056.

K. Sitkowska, M. F. Hoes, M. M. Lerch, L. N. Lameijer, P. van der Meer, W. Szymański, B. L. Feringa, Chem. Commun. 2020, 56, 5480-5483.

Y. Xu, S. Lin, R. He, Y. Zhang, Q. Gao, D. K. P. Ng, J. Geng, Chem. Eur. J. 2021, 27, 11268-11272.

N. Watabe, Y. Ishida, A. Ochiai, Y. Tokuoka, N. Kawashima, J. Oleo Sci. 2007, 56, 73-80.

P. Gaur, O. A. Kucherak, Y. G. Ermakova, V. V. Shvadchak, D. A. Yushchenko, Chem. Commun. 2019, 55, 12288-12291.

G. Milligan, B. Shimpukade, T. Ulven, B. D. Hudson, Chem. Rev. 2017, 117, 67-110.

J. A. Frank, D. A. Yushchenko, N. H. F. Fine, M. Duca, M. Citir, J. Broichhagen, D. J. Hodson, C. Schultz, D. Trauner, Chem. Sci. 2017, 8, 7604-7610.

C. F. Burant, Diabetes Care 2013, 36, S175-S179.

Reversing protonation of weakly basic drugs greatly enhances intracellular diffusion and decreases lysosomal sequestration

Bioorthogonal Chemistry in Cellular Organelles

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