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ALX-480-093
Revised 07-Feb-08
8-(4-Chlorophenylthio)-2'-O-methyladenosine 3',5'-cyclic Monophosphate . sodium salt
SYNONYMS
8-CPT-2'-O-Me-cAMP . Na
PRODUCT LINE
Signal Transduction
PRODUCT CATEGORY
cAMP Derivatives
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
Add To Cart
ALX-480-093-M001
1 mg
130.00 USD
ALX-480-093-M005
5 mg
520.00 USD
Product Specification
FORMULA:
C
17
H
16
ClN
5
O
6
PS . Na
MW:
484.8 . 23.0
CAS NUMBER:
510774-50-2
PURITY:
≥98% (HPLC)
PURITY DETAIL:
Product is not sterile.
FORMULATION:
White to off-white powder.
SOLUBILITY:
Soluble in water, aqueous buffers, DMSO, dimethyl formamide or methanol.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
HANDLING:
Protect from light. Hygroscopic.
IDENTITY:
Determined by
1
H-NMR, MS and UV (λ
max
: 282nm, ε: 16’000, pH 7).
Product Description
Specific, potent and membrane permeant activator of the Epac cAMP receptor. Activates Epac1 and Epac2, the guanine nucleotide-exchange factors (GEFs) for the small GTPases Rap1 and Rap2. Does not activate protein kinase A (PKA), neither
in vitro
nor
in vivo
and is therefore a valuable tool to specifically discriminate between PKA- and Epac-mediated effects. Since a free 2'-ribose hydroxyl group in cyclic AMP is essential for stimulation of PKA, the methylated structure of 8-CPT-2'-O-Me-cAMP is an extremely poor PKA activator. Its high lipophilicity allows for good membrane permeability in most biosystems and its increased resistance towards phosphodiesterases prevents rapid hydrolysis.
Product Specific Literature References
A novel Epac-specific cAMP analogue demonstrates independent regulation of Rap1 and ERK
:
J.M. Enserink, et al.; Nat. Cell Biol.
4
, 901 (2002)
Abstract
;
Full Text
Epac-selective cAMP analog 8-pCPT-2'-O-Me-cAMP as a stimulus for Ca2+-induced Ca2+ release and exocytosis in pancreatic beta-cells
:
G. Kang, et al.; J. Biol. Chem.
278
, 8279 (2003)
Abstract
;
Full Text
Cyclic AMP induces integrin-mediated cell adhesion through Epac and Rap1 upon stimulation of the {beta}2-adrenergic receptor
:
S. Rangarajan, et al.; J. Cell Biol.
160
, 487 (2003)
Abstract
General Literature References
Signal transduction. New exchange, new target
:
J. Downward; Nature
396
, 416 (1998), Comment
Abstract
Epac is a Rap1 guanine-nucleotide-exchange factor directly activated by cyclic AMP
:
J. de Rooij, et al.; Nature
396
, 474 (1998)
Abstract
A family of cAMP-binding proteins that directly activate Rap1
:
H. Kawasaki, et al.; Science
282
, 2275 (1998)
Abstract
Further Categories Containing This Product:
PKA Activators
•
Guanine-nucleotide Exchange Factors [GEFs]
ALX-480-006
Revised 22-Oct-08
8-Bromoguanosine-3',5'-cyclic Monophosphate . sodium salt
SYNONYMS
8-Br-cGMP . Na
PRODUCT LINE
Signal Transduction
PRODUCT CATEGORY
cGMP Derivatives
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
Add To Cart
ALX-480-006-M010
10 mg
48.00 USD
ALX-480-006-M050
50 mg
145.00 USD
Product Specification
FORMULA:
C
10
H
10
BrN
5
O
7
P . Na
MW:
423.1 . 23.0
CAS NUMBER:
51116-01-9
PURITY:
≥99% (HPLC)
APPEARANCE:
White to off-white powder.
PURITY DETAIL:
Low in fluorescent and colored impurities.
SOLUBILITY:
Soluble in water or aqueous buffers.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
IDENTITY:
Identity determined by
1
H-NMR, MS and UV.
Product Description
Activator of cGMP-dependent protein kinases (PKGs) 1α, 1β and type II and cGMP-gated ion channels (cGMP agonist). Has increased metabolic stability and membrane permeability compared to cGMP (Prod. No.
ALX-480-059
).
Product Specific Literature References
Sodium nitroprusside-induced protein phosphorylation in intact rat aorta is mimicked by 8-bromo cyclic GMP:
R.M. Rapoport, et al.; PNAS
79
, 6470 (1982)
Abstract
The nitric oxide--cyclic GMP pathway and synaptic depression in rat hippocampal slices:
C.L. Boulton, et al.; Eur. J. Neurosci.
6
, 1528 (1994)
Abstract
Nitric oxide in skeletal muscle:
L. Kobzik, et al.; Nature
372
, 546 (1994)
Abstract
Nitric oxide. More jobs for that molecule:
S. Snyder; Nature
372
, 504 (1994)
Abstract
Further Categories Containing This Product:
PKG Activators
ALX-480-026
Revised 03-Aug-06
8-Bromoguanosine 3',5'-cyclic Monophosphothioate, Rp-Isomer . sodium salt (high purity)
SYNONYMS
Rp-8-Br-cGMPS . Na
8-Br-cGMPS . Na, Rp-isomer
PRODUCT LINE
Signal Transduction
PRODUCT CATEGORY
cGMP Derivatives
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
Add To Cart
ALX-480-026-MC05
0.5 mg
90.00 USD
ALX-480-026-M001
1 mg
160.00 USD
Product Specification
FORMULA:
C
10
H
10
BrN
5
O
6
PS . Na
MW:
439.2 . 23.0
CAS NUMBER:
150418-07-8
PURITY:
≥99% (HPLC)
APPEARANCE:
White lyophilized powder.
SOLUBILITY:
Soluble in water.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
Product Description
Inhibitor of cGMP-dependent protein kinase (PKG) 1α and 1β. Resistant to mammalian cyclic nucleotide-dependent phosphodiesterases; no metabolic side effects. Significantly more lipophilic and membrane permeant as compared to cyclic GMP (Prod. No.
ALX-480-059
) or Rp-cGMPS (Prod. No.
ALX-480-072
).
Product Specific Literature References
Nitric oxide regulates luteinizing hormone-releasing hormone secretion:
M. Moretto, et al.; Endocrinology
133
, 2399 (1993)
Abstract
Role of guanylyl cyclase and cGMP-dependent protein kinase in long-term potentiation:
M. Zhuo, et al.; Nature
368
, 635 (1994)
Abstract
Further Categories Containing This Product:
PKG Inhibitors
ALX-480-027
Revised 25-Jun-08
8-Bromoguanosine 3',5'-cyclic Monophosphothioate, Sp-Isomer . sodium salt (high purity)
SYNONYMS
Sp-8-Br-cGMPS . Na
8-Br-cGMPS . Na, Sp-isomer
PRODUCT LINE
Signal Transduction
PRODUCT CATEGORY
cGMP Derivatives
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
Add To Cart
ALX-480-027-M001
1 mg
80.00 USD
ALX-480-027-M005
5 mg
320.00 USD
Product Specification
FORMULA:
C
10
H
10
BrN
5
O
6
PS . Na
MW:
439.2 . 23.0
CAS NUMBER:
153660-03-8
PURITY:
≥99% (HPLC)
APPEARANCE:
White to off-white powder.
SOLUBILITY:
Soluble in water.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
IDENTITY:
Identity determined by MS,
1
H-NMR and UV.
Product Description
Unspecific activator of both cGMP-dependent protein kinase (PKG) 1α and cAMP-dependent protein kinase (PKA). Resistant to cyclic nucleotide phosphodiesterases. Much more lipophilic and membrane permeant as compared to cyclic GMP (Prod. No.
ALX-480-059
) or Sp-cGMPS (Prod. No.
ALX-480-073
).
Product Specific Literature References
Evidence for two intracellular calcium pools in Dictyostelium: the cAMP- induced calcium influx is directed into a NBD-Cl- and 2,5-di-(tert- butyl)1,4-hydroquinone-sensitive pool:
H. Flaadt, et al.; J. Cell Sci.
105
, 1131 (1993)
Abstract
Further Categories Containing This Product:
PKG Activators
•
PKA Activators
ALX-480-031
Revised 08-Oct-08
8-(4-Chlorophenylthio)guanosine 3',5'-cyclic Monophosphate . triethylammonium salt
SYNONYMS
8-pCPT-cGMP . TEA
PRODUCT LINE
Signal Transduction
PRODUCT CATEGORY
cGMP Derivatives
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
Add To Cart
ALX-480-031-M001
1 mg
42.00 USD
ALX-480-031-M005
5 mg
168.00 USD
Product Specification
FORMULA:
C
16
H
14
ClN
5
O
7
PS . C
6
H
15
N
MW:
486.8 . 101.2
CAS NUMBER:
54364-02-2
PURITY:
≥99% (HPLC)
APPEARANCE:
White to off-white powder.
SOLUBILITY:
Soluble in water.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
IDENTITY:
Identity determined by MS, UV and
1
H-NMR.
Product Description
Selective activator of cGMP-dependent protein kinase Iα, Iβ and type II as well as of cGMP-gated ion channels. Higher activation potential as compared to cGMP; excellent cell membrane permeability and phosphodiesterase stability. Preferred alternative to unsuitable analogs such as dibutyryl-cGMP.
Product Specific Literature References
Analysis of the functional role of cGMP-dependent protein kinase in intact human platelets using a specific activator 8-para- chlorophenylthio-cGMP:
E. Butt, et al.; Biochem. Pharmacol.
43
, 2591 (1992)
Abstract
Role of cGMP and cGMP-dependent protein kinase in nitrovasodilator inhibition of agonist-evoked calcium elevation in human platelets:
J. Geiger, et al.; PNAS
89
, 1031 (1992)
Abstract
Further Categories Containing This Product:
PKG Activators
ALX-480-032
Revised 03-Feb-05
8-(4-Chlorophenylthio)guanosine 3',5'-cyclic Monophosphothioate, Rp-Isomer . triethylammonium salt (high purity)
SYNONYMS
Rp-8-pCPT-cGMPS . TEA
8-pCPT-cGMPS . TEA, Rp-Isomer
PRODUCT LINE
Signal Transduction
PRODUCT CATEGORY
cGMP Derivatives
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
Add To Cart
ALX-480-032-C100
100 µg
45.00 USD
ALX-480-032-M001
1 mg
230.00 USD
Product Specification
FORMULA:
C
16
H
15
ClN
5
O
6
PS
2
. C
6
H
15
N
MW:
504.1 . 101.0
CAS NUMBER:
153660-04-9
PURITY:
≥99%
APPEARANCE:
White lyophilized powder.
SOLUBILITY:
Soluble in water.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
Product Description
Potent selective inhibitor of cGMP-dependent protein kinase 1α, 1β and type II. Resistant to mammalian cyclic nucleotide-dependent phosphodiesterases, no metabolic side effects. Significantly more lipophilic and membrane permeant as compared to Rp-cGMPS (Prod. No.
ALX-480-072
) or Rp-8-Br-cGMPS (Prod. No.
ALX-480-026
).
Product Specific Literature References
(Rp)-8-pCPT-cGMPS, a novel cGMP-dependent protein kinase inhibitor:
E. Butt, et al.; Eur. J. Pharmacol.
269
, 265 (1994)
Abstract
The type II isoform of cGMP-dependent protein kinase is dimeric and possesses regulatory and catalytic properties distinct from the type I isoforms:
D.M. Gamm, et al.; J. Biol. Chem.
270
, 27380 (1995)
Abstract
;
Full Text
Antagonists of cyclic nucleotide-gated channels and molecular mapping of their site of action:
R.H. Kramer & G.R. Tibbs; J. Neurosci.
16
, 1285 (1996)
Abstract
Further Categories Containing This Product:
PKG Inhibitors
ALX-480-046
Revised 17-Sep-08
N2,2'-O-Dibutyrylguanosine 3',5'-cyclic Monophosphate . sodium salt
SYNONYMS
Dibutyryl-cGMP . Na
DBcGMP . Na
PRODUCT LINE
Signal Transduction
PRODUCT CATEGORY
cGMP Derivatives
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
Add To Cart
ALX-480-046-M005
5 mg
40.00 USD
ALX-480-046-M025
25 mg
160.00 USD
Product Specification
FORMULA:
C
18
H
23
N
5
O
9
P . Na
MW:
484.4 . 23.0
CAS NUMBER:
51116-00-8
PURITY:
≥97% (HPLC)
APPEARANCE:
White to off-white solid.
SOLUBILITY:
Soluble in water, 100% ethanol, DMSO, dimethyl formamide or methanol.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
IDENTITY:
Identity determined by
1
H-NMR, MS and UV.
Product Description
Activates cGMP-dependent protein kinase (PKG). Cell permeable. For a better and more selective agonist, use 8-pCPT-cGMP (Prod. No.
ALX-480-031
or Prod. No.
ALX-480-088
).
Product Specific Literature References
Analogs of cyclic AMP and cyclic GMP: general methods of synthesis and the relationship of structure to enzymic activity:
R.B. Meyer & J.P. Miller; Life Sci.
14
, 1019 (1974)
Abstract
Relaxation of hormonally stimulated smooth muscular tissues by the 8- bromo derivative of cyclic GMP:
K.D. Schultz, et al.; Naunyn-Schmiedeberg's Arch. Pharmacol.
306
, 1 (1979)
Abstract
Relaxation of vascular and tracheal smooth muscle by cyclic nucleotide analogs that preferentially activate purified cGMP-dependent protein kinase:
S.G. Francis, et al.; Mol. Pharmacol.
34
, 506 (1988)
Abstract
Cyclic GMP analogs inhibit gamma thrombin-induced arachidonic acid release in human platelets:
D.C. Sane, et al.; BBRC
165
, 708 (1989)
Abstract
Analysis of the functional role of cGMP-dependent protein kinase in intact human platelets using a specific activator 8-para-chlorophenylthio-cGMP:
E. Butt, et al.; Biochem. Pharmacol.
43
, 2591 (1992)
Abstract
Further Categories Containing This Product:
PKG Activators
ALX-480-059
Revised 09-Mar-06
Guanosine 3',5'-cyclic Monophosphate . sodium salt
SYNONYMS
cGMP . Na
PRODUCT LINE
Signal Transduction
PRODUCT CATEGORY
cGMP Derivatives
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
Add To Cart
ALX-480-059-M025
25 mg
25.00 USD
ALX-480-059-M100
100 mg
95.00 USD
Product Specification
FORMULA:
C
10
H
11
N
5
O
7
P . Na
MW:
344.2 . 23.0
CAS NUMBER:
40732-48-7
MERCK INDEX:
14:
2709
PURITY:
≥98% (HPLC)
APPEARANCE:
White to off-white solid.
SOLUBILITY:
Soluble in water.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
Product Description
Intracellular messenger implicated in mediating action of nitric oxide (NO) in many cell types. Target receptors for the second messenger guanosine 3',5'-cyclic monophosphate (cGMP) include protein kinase G (PKG) isozymes, cGMP-dependent ion channels as well as cGMP-responsive phosphodiesterases. In presence of corresponding phosphodiesterases cGMP is metabolized rapidly. Suppresses apoptosis.
Product Specific Literature References
Cyclic GMP metabolism and involvement in biological regulation:
N.D. Goldberg & M.K. Haddox; Ann. Rev. Biochem.
46
, 823 (1977)
Abstract
Interleukin-1 beta suppresses apoptosis in rat ovarian follicles by increasing nitric oxide production:
S.Y. Chun, et al.; Endocrinology
136
, 3120 (1995)
Abstract
Further Categories Containing This Product:
Guanylyl Cyclases, Guanosine Phosphate Metabolism / Related Products
•
Apoptosis Inducers & Inhibitors Other Products
ALX-480-070
Revised 05-Dec-04
8-(4-Chlorophenylthio)guanosine-3',5'-cyclic-Monophosphothioate, Sp-Isomer . sodium salt
SYNONYMS
Sp-8-pCPT-cGMPS . Na
8-pCPT-cGMPS . Na, Sp-Isomer
PRODUCT LINE
Signal Transduction
PRODUCT CATEGORY
cGMP Derivatives
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
Add To Cart
ALX-480-070-MC05
0.5 mg
80.00 USD
ALX-480-070-M001
1 mg
140.00 USD
Product Specification
FORMULA:
C
16
H
14
N
5
ClO
6
S
2
P . Na
MW:
502.9 . 23.0
CAS NUMBER:
160385-87-5
PURITY:
≥99%
APPEARANCE:
White lyophilized powder.
SOLUBILITY:
Soluble in water.
SHIPPING:
AMBIENT
LONG TERM STORAGE:
-20°C
Product Description
Potent activator of both cGMP-dependent protein kinase 1α, 1β and type II and cAMP-dependent protein kinase II. Excellent cell membrane permeability and phosphodiesterase stability.
Product Specific Literature References
(Rp)-8-pCPT-cGMPS, a novel cGMP-dependent protein kinase inhibitor:
E. Butt, et al.; Eur. J. Pharmacol.
269
, 265 (1994)
Abstract
The type II isoform of cGMP-dependent protein kinase is dimeric and possesses regulatory and catalytic properties distinct from the type I isoforms:
D.M. Gamm, et al.; J. Biol. Chem.
270
, 27380 (1995)
Abstract
;
Full Text
Further Categories Containing This Product:
PKA Activators
•
PKG Activators
ALX-480-072
Revised 16-Jun-06
Guanosine 3',5'-cyclic Monophosphothioate, Rp-Isomer . sodium salt
SYNONYMS
Rp-cGMPS . Na
cGMPS . Na, Rp-Isomer
PRODUCT LINE
Signal Transduction
PRODUCT CATEGORY
cGMP Derivatives
Ordering Information
Product Numbers:
Format:
Size:
Unit Price:
Quantity:
Add To Cart
ALX-480-072-M001
1 mg
240.00 USD
Product Specification
FORMULA:
