HOME＞ケージド化合物のデータリスト＞Bhc-cGMP

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Bhc-cGMP

(6-Bromo-7-hydroxycoumarin-4-yl)methyl guanosine 3',5'-cyclic monophosphate, axial isomer, Bhc-cGMP (ax); equatorial isomer, Bhc-cGMP (eq)

Structure (axial isomer)		Absorption Spectrum
Photochemical and Photophysical Properties
substrate	λ^a(ε)^b	φ_dis^c	φ_app^d	φε^e	s^f	t_1/2^g
Bhc-cGMP (ax)	377 (14 800)	0.075	0.116	1 260	580	1 240
Bhc-cGMP (eq)	372 (17 000)	0.117	0.116	1 260	430	420
[a] Absorption maximum (nm) measured in K-MOPS (pH 7.2). [b] Molar absorptivity (M-1cm-1). [c] Quantum yields for the disappearance of the starting materials upon irradiation (350 nm). Samples (10 uM) in K-MOPS (pH 7.2) were photolysed with two RPR 350 nm lamps. [d] Quantum yields for the appearance of the cyclic nucleotides upon irradiation (350 nm). [e] The product of quantum yields for the disappearance and molar absorptivity at 350 nm. [f] Solubility (uM) in K-MOPS (pH 7.2) containing 1% DMSO. [g] Half-life (h) in the dark. Samples (10 uM) in K-MOPS (pH 7.2) were placed in the dark at room temperature.

Spectroscopic Properties

axial isomer: 31P NMR d (DMSO-d6) -5.06; 1H NMR d (DMSO-d6) 10.52 (1H, s), 7.90 (1H, s), 7.60 (1H, s), 6.44 (2H, s), 6.32 (1H, s), 6.19 (1H, s), 5.90 (1H, s), 5.79 (1H, s), 5.25 (2H, d, J = 7 Hz), 4.8-4.5 (2H, m), 4.2-4.0 (4H, m), equatorial isomer: 31P NMR d (DMSO-d6) -3.90; 1H NMR d (DMSO-d6) 10.53 (1H, s), 7.94 (1H, s), 7.78 (1H, s), 6.66 (1H, s), 6.58 (2H, s), 6.27 (1H, s), 6.14 (1H, s), 5.84 (1H, s), 5.32 (2H, d, J = 7 Hz), 5.15 (1H, m), 4.70 (1H, m), 4.56-4.40 (3H, m); HRMS (FAB+) Calcd for C20H18O10N579BrP: 597.9975. Found: 598.0023.

References

synthesis
1) T. Furuta, H. Takeuchi, M. Isozaki, Y. Takahashi, M. Sugimoto, M. Kanehara, T. Watanabe, K. Noguchi, T. M. Dore, T. Kurahashi, M. Iwamura, R. Y. Tsien, Bhc-cNMPs as either water-soluble or membrane-permeant photo-releasable cyclic nucleotides for both one and two-photon excitation, ChemBioChem, 5, 1119-1128 (2004).

application
1) T. Nishigaki, C. D. Wood, Y. Tatsu, N. Yumoto, T. Furuta, D. Ellias, K. Shiba, S. A. Baba, A. Darszon, A sea urchin jelly peptide induces a cGMP-mediated decrease in sperm intracellular Ca2+ before its increase, Dev. Biol. 272, 376-388 (2004).