Table 1. Summary of the Photophysical Properties of the Switchable Photoprobes 8–19a.
| compound | λmax (E) [nm] | λmax (Z) [nm] | λiso [nm] | t1/2 [days]b | PSS (E → Z)d (%) | PSS (Z → E)d (%) |
|---|---|---|---|---|---|---|
| 8 | 328 | 430 | 277, 395 | 5.5 | 94 | 72 |
| 9 | 330 | 428 | 281, 391 | 3.0 | 93 | 77 |
| 10 | 332 | 430 | 285, 393 | 1.7 (1.0c) | 86 | 81 |
| 11 | 333 | 430 | 285, 396 | 1.2 | 87 | 85 |
| 12 | 330 | 430 | 281, 390 | 3.0 (1.4c) | 95 | 74 |
| 13 | 332 | 425 | 285, 405 | 0.5 | 85 | 79 |
| 14 | 332 | 430 | 285, 400 | 1.4 | 81 | 86 |
| 15 | 320 | 440 | 277, 380 | 2.7 | 88 | 69 |
| 16 | 320 | 430 | 277, 390 | 3.1 | 89 | 83 |
| 17 | 323 | 425 | 274, 375 | 28.6 | 93 | 88 |
| 18 | 340 | 427 | 293, 403 | 6.6 | 94 | 82 |
| 19 | 333 | 431 | 285, 402 | 54.5 | 93 | 87 |
Isomerization was obtained by irradiation with 340 nm (Z-isomer) and 420 nm for 8–17 and 528 nm for 18 and 19 (E-isomer), respectively. Concentration: 20 μM in HEPES buffer (25 mM HEPES, 2.5 mM CaCl2, 1 mM MgCl2, pH = 7.4) + 0.1% DMSO.
Preirradiation with 340 nm, measured at 25 °C.
Measured at 37 °C.
Prior irradiation with 340 nm (Z-isomer) and 420 nm for 8–17 and 528 nm for 18 and 19 (E-isomer), respectively, for 2 min to ensure the ratio at the PSS. PSS determination was done by analytical C18-RP-HPLC at the appropriate isosbestic points.