Caged Cyclic Nucleotides

  • Adenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( cAMP-AM )Cat. No.: A 022
  • Adenosine- 3', 5'- cyclic monophosphate, benzyl ester ( cAMP-Bn )Cat. No.: A 065
  • Adenosine- 3', 5'- monophosphorothioate acetoxymethyl ester, Sp- isomer ( Sp-cAMPS-AM )Cat. No.: A 035
  • 6, 7- Bis(carboxymethoxy)coumarin- 4- yl)methyl- adenosine- 3', 5'- cyclic monophosphate ( BCMCM-caged cAMP )Cat. No.: B 016
  • [6, 7- Bis(carboxymethoxy)coumarin- 4- yl]methyl- 8- bromoadenosine- 3', 5'- cyclic monophosphate ( BCMCM-caged 8-Br-cAMP )Cat. No.: B 018
  • [6, 7- Bis(carboxymethoxy)coumarin- 4- yl]methyl- 8- bromoguanosine- 3', 5'- cyclic monophosphate ( BCMCM-caged 8-Br-cGMP )Cat. No.: B 019
  • [6, 7- Bis(carboxymethoxy)coumarin- 4- yl]methyl- guanosine- 3', 5'- cyclic monophosphate ( BCMCM-caged cGMP )Cat. No.: B 017
  • 8- Bromo- 2'- O- methyladenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-Br-2'-O-Me-cAMP-AM )Cat. No.: B 028
  • 8- Bromoadenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-Br-cAMP-AM )Cat. No.: B 020
  • 8- Bromoadenosine- 3', 5'- cyclic monophosphorothioate, Sp- isomer, acetoxymethyl ester ( Sp-8-Br-cAMPS-AM )Cat. No.: B 029
  • 8- Bromoguanosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-Br-cGMP-AM )Cat. No.: B 014
  • 8- Chloroadenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-Cl-cAMP-AM )Cat. No.: C 050
  • 8- (4- Chlorophenylthio)- 2'- O- methyladenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-pCPT-2'-O-Me-cAMP-AM )Cat. No.: C 051
  • 8- (4- Chlorophenylthio)adenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-CPT-cAMP-AM )Cat. No.: C 056
  • 8- (4- Chlorophenylthio)guanosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-pCPT-cGMP-AM )Cat. No.: C 033
  • Cytidine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( cCMP-AM )Cat. No.: C 067
  • N6, 2'- O- Dibutyryladenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( DB-cAMP-AM )Cat. No.: D 008
  • (7- Diethylaminocoumarin- 4- yl)methyladenosine- 3', 5'- cyclic monophosphate ( DEACM-caged cAMP )Cat. No.: D 042
  • (7- Diethylaminocoumarin- 4- yl)methylguanosine- 3', 5'- cyclic monophosphate ( DEACM-caged cGMP )Cat. No.: D 043
  • (7- Dimethylaminocoumarin-4- yl)methyl- 8- bromoadenosine- 3', 5'- cyclic monophosphate ( DMACM-caged 8-Br-cAMP )Cat. No.: D 044
  • (7- Dimethylaminocoumarin-4- yl)methyl- 8- bromoguanosine- 3', 5'- cyclic monophosphate ( DMACM-caged 8-Br-cGMP )Cat. No.: D 045
  • Guanosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( cGMP-AM )Cat. No.: G 002

     

  • Adenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( cAMP-AM )
       Membrane-permeant precursor of the second messenger cyclic AMP. After permeation and metabolic activation by esterases the polar cAMP is released
       which is trapped inside the cell and subsequently metabolized quickly, resulting in a pulse-type signal.
      Schultz et al., J. Biol. Chem., 268, 6316 - 6322 (1993).
    A 022 1 uM/ ~0.4 mg, 5 x 1 uM CAS No.: [159764-93-9]

    Adenosine- 3', 5'- cyclic monophosphate, benzyl ester ( cAMP-Bn )
       Hydrolysis slowly releases the polar cAMP which is trapped inside the cell and subsequently metabolized, resulting in an elevated cAMP level for a prolonged
       period.
       Engels et al., J. Med. Chem., 20, 907 - 911 (1977).
    A 065 1 uM/ ~0.4 mg, 5 x 1 uM CAS No.: [62742-71-6]

    Adenosine- 3', 5'- monophosphorothioate acetoxymethyl ester, Sp- isomer ( Sp-cAMPS-AM )
       Membrane-permeant precursor of the PDE-resistant protein kinase A activator Sp-cAMPS. Metabolic bioactivation by esterases releases the active analogue,
       which is trapped inside the cell. Chemical hydrolysis can produce some cyclic AMP as well.
       Maronde et al., J. Pineal Res., 31, 183 - 185 (2001).
    A 065 1 uM/ ~0.4 mg, 5 x 1 uM CAS No.: [152218-24-1]

    6, 7- Bis(carboxymethoxy)coumarin- 4- yl)methyl- adenosine- 3', 5'- cyclic monophosphate ( BCMCM-caged cAMP )
       BCMCM-caged cAMP is an only weakly fluorescent, caged precursor of the second messenger cyclic AMP, which upon irradiation, releases both cAMP and
       a fluorescent coumarin analogue.
       Hagen et al., Angew. Chem. Int. Ed., 40, 1046 - 1048 (2001).
    B 016 0.1 uM/ ~68 ug, 5 x 0.1 uM CAS No.: [339291-51-9]

    [6, 7- Bis(carboxymethoxy)coumarin- 4- yl]methyl- 8- bromoadenosine- 3', 5'- cyclic monophosphate ( BCMCM-caged 8-Br-cAMP )
       BCMCM-caged 8-Br-cAMP is an only weakly fluorescent, caged precursor of 8-bromo cyclic cAMP, which upon irradiation, releases both 8-Br-cAMP and
       a fluorescent coumarin analogue.
       Hagen et al., Angew. Chem. Int. Ed., 40, 1046 - 1048 (2001).
    B 018 0.1 uM/ ~76 ug, 5 x 0.1 uM CAS No.: [370091-64-8]

    [6, 7- Bis(carboxymethoxy)coumarin- 4- yl]methyl- 8- bromoguanosine- 3', 5'- cyclic monophosphate
       ( BCMCM-caged 8-Br-cGMP )
       BCMCM-caged 8-Br-cGMP is an only weakly fluorescent, caged precursor of 8-bromo cyclic cGMP, which upon irradiation, releases both 8-Br-cGMP and
       a fluorescent coumarin analogue.
       Hagen et al., Angew. Chem. Int. Ed., 40, 1046 - 1048 (2001).
    B 019 0.1 uM/ ~78 ug, 5 x 0.1 uM CAS No.: [370091-68-2]

    [6, 7- Bis(carboxymethoxy)coumarin- 4- yl]methyl- guanosine- 3', 5'- cyclic monophosphate
       ( BCMCM-caged cGMP )
       BCMCM-caged cGMP is an only weakly fluorescent, caged precursor of the second messenger cyclic cGMP, which upon irradiation, releases both cGMP and
       a fluorescent coumarin analogue.
       Hagen et al., Angew. Chem. Int. Ed., 40, 1046 - 1048 (2001).
    B 017 0.1 uM/ ~69 ug, 5 x 0.1 uM CAS No.: [339291-52-0]

    8- Bromo- 2'- O- methyladenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-Br-2'-O-Me-cAMP-AM )
       Extremely membrane-permeant precursor of the specific Epac agonist 8-Br-2'-O-Me-cAMP. After permeation and metabolic activation by esterases the active
       compound is released.
       Protected by patent n° EP 02077219.0 and foreign equivalents, exclusively licensed to BIOLOG LSI for research purposes only.
    B 028   CAS No.: [pending]

    8- Bromoadenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-Br-cAMP-AM )
       A membrane-permeant precursor of the PKA activator 8-Br-cAMP (Cat. No. B 007). Metabolic activation by esterases releases the polar active analogue,
       which is trapped inside the cell.
       Kruppa et al., Bioorg. Med. Chem. Lett., 7, 945 - 948 (1997); Moll et al., J. Neural. Transm., 113, 1015 - 1032 (2006).
    B 020 1 uM/ ~0.5 mg, 5 x 1 uM CAS No.: [190522-24-8]

    8- Bromoadenosine- 3', 5'- cyclic monophosphorothioate, Sp- isomer, acetoxymethyl ester ( Sp-8-Br-cAMPS-AM )
       Membrane-permeant precursor of the PDE-resistant protein kinase A activator Sp-8-Br-cAMPS (Cat. No. B 002). Metabolic bioactivation by esterases
       releases the active analogue, which is trapped inside the cell. Chemical hydrolysis can produce some 8-Br-cAMP as well.
       Maronde et al., J. Pineal Res., 31, 183 - 185 (2001).
    B 029 1 uM/ ~0.5 mg, 5 x 1 uM CAS No.: [pending]

    8- Bromoguanosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-Br-cGMP-AM )
       Membrane-permeant precursor of the PKG activator 8-Br-cGMP (Cat. No. B 004). Metabolic activation by esterases releases the polar active analogue, which
       is trapped inside the cell.
       Schwede et al., Bioorg. Med. Chem. Lett., 10, 571 - 573 (2000).
    B 014 1 uM/ ~0.5 mg, 5 x 1 uM CAS No.: [272445-71-3]

    8- Chloroadenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-Cl-cAMP-AM )
       Membrane-permeant precursor of the PKA activator 8-Cl-cAMP (Cat. No. C 007). Metabolic activation by esterases releases the polar active analogue, which
       is trapped inside the cell.
       J. Kruppa, Ph.D. thesis, University of Bremen, Germany, 1996.
    C 050 1 uM/ ~0.4 mg, 5 x 1 uM CAS No.: [pending]

    8- (4- Chlorophenylthio)- 2'- O- methyladenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester
       ( 8-pCPT-2'-O-Me-cAMP-AM )
       Extremely membrane-permeant precursor of the specific Epac agonist 8-CPT-2'-O-Me-cAMP. After permeation and metabolic activation by esterases
       the active compound is released.
       Vliem et al., ChemBioChem [Epub ahead of print] (2008).
    C 051   CAS No.: [pending]

    8- (4- Chlorophenylthio)adenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-CPT-cAMP-AM )
       Membrane-permeant precursor of the PKA activator 8-CPT-cAMP (Cat. No. C 010). Metabolic activation by esterases releases the active analogue.
       Kruppa et al., Bioorg. Med. Chem. Lett., 7, 945 - 948 (1997).
    C 056 1 uM/ ~0.5 mg, 5 x 1 uM CAS No.: [663941-66-0]

    8- (4- Chlorophenylthio)guanosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( 8-pCPT-cGMP-AM )
       Highly membrane-permeant precursor of the PKG activator 8-pCPT-cGMP (Cat. No. C 009). Metabolic activation by esterases releases the active analogue.
       Schwede et al., Bioorg. Med. Chem. Lett., 10, 571 - 573 (2000).
    C 033 1 uM/ ~0.6 mg, 5 x 1 uM CAS No.: [272445-72-4]

    Cytidine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( cCMP-AM )
       Membrane-permeant, metabolically activatable prodrug form of the potential further second messenger cyclic CMP. After permeation and metabolic activation
       by esterases the polar cCMP is released which is trapped inside the cell and subsequently metabolized quickly, resulting in a pulse-type signal.
    C 067 1 uM/ ~0.4 mg, 5 x 1 uM CAS No.: [pending]

    N6, 2'- O- Dibutyryladenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( DB-cAMP-AM )
       Highly potent and membrane-permeant precursor of DB-cAMP. Releases dibutyryl cAMP after metabolic activation by esterases. Due to further degradation to
       the much more polar monobutyryl cAMP and cAMP the kinase activators are trapped inside the cell.
    D 008 1 uM/ ~0.5 mg, 5 x 1 uM CAS No.: [159910-48-2]

    (7- Diethylaminocoumarin- 4- yl)methyladenosine- 3', 5'- cyclic monophosphate ( DEACM-caged cAMP )
       DEACM-caged cAMP is an only weakly fluorescent, caged precursor of the second messenger cyclic AMP, which upon irradiation, releases both cAMP and
       a fluorescent coumarin analogue. High lipophilicity but still reasonable solubility in aqueous systems.
    D 042 0.1 uM/ ~58 ug, 5 x 0.1 uM CAS No.: [339291-37-1]

    (7- Diethylaminocoumarin- 4- yl)methylguanosine- 3', 5'- cyclic monophosphate ( DEACM-caged cGMP )
       Highly membrane-permeant precursor of the PKG activator 8-pCPT-cGMP. Metabolic activation bDEACM-caged cGMP is an only weakly fluorescent, caged
       precursor of the second messenger cyclic cGMP, which upon irradiation, releases both cGMP and a strongly fluorescent coumarin analogue.
       Hagen et al., Angew. Chem. Int. Ed., 40, 1046 - 1048 (2001).
    D 043 0.1 uM/ ~63 ug, 5 x 0.1 uM CAS No.: [339291-42-8]

    (7- Dimethylaminocoumarin-4- yl)methyl- 8- bromoadenosine- 3', 5'- cyclic monophosphate ( DMACM-caged 8-Br-cAMP )
       DMACM-caged 8-Br-cAMP is an only weakly fluorescent, caged precursor of 8-bromo cyclic AMP, which upon irradiation, releases both 8-Br-cAMP and
       a fluorescent coumarin analogue. High lipophilicity and membrane permeability; thus only limited solubility in aqueous systems.
       Hagen et al., J. Photochem. Photobiol. B: Biol., 53 (1999).
    D 044 0.1 uM/ ~60 ug, 5 x 0.1 uM  

    (7- Dimethylaminocoumarin-4- yl)methyl- 8- bromoguanosine- 3', 5'- cyclic monophosphate ( DMACM-caged 8-Br-cGMP )
       DMACM-caged 8-Br-cGMP is an only weakly fluorescent, caged precursor of 8-bromo cyclic cGMP, which upon irradiation, releases both 8-Br-cGMP and
       a strongly fluorescent coumarin analogue. High lipophilicity and membrane permeability, thus only limited solubility in aqueous systems.
       Hagen et al., J. Photochem. Photobiol. B: Biol., 53 (1999).
    D 045 0.1 uM/ ~60 ug, 5 x 0.1 uM  

    Guanosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester ( cGMP-AM )
       Membrane-permeant precursor of the second messenger cyclic GMP. Metabolic activation by esterases releases the polar active analogue which is trapped
       inside the cell. In contrast to other membrane-permeant and PDE-resistant cGMP analogues, cGMP-AM yields a transient increase (pulse) of cGMP.
       Especially suitable for external triggering of cGMP-regulated phosphodiesterases (PDE II, III & V) where most cGMP analogues are not accepted.
       Hagen et al., J. Photochem. Photobiol. B: Biol., 53 (1999).
    G 002 1 uM/ ~0.4 mg, 5 x 1 uM CAS No.: [164007-71-0]