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cGMP Pathways
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ALX-153-055 Revised 25-May-07
Carnosine
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SYNONYMS β-Alanyl-L-histidine
PRODUCT LINE Nitric Oxide Pathway
PRODUCT CATEGORY Guanylyl Cyclases, Guanosine Phosphate Metabolism / Related Products
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ALX-153-055-G001   1 g 55.00 USD Add To Cart
Product Specification
SEQUENCE: H-β-Ala-His-OH
FORMULA: C9H14N4O3
MW: 226.2
CAS NUMBER: 305-84-0
PURITY: ≥98%
APPEARANCE: White to off-white powder.
SOLUBILITY: Soluble in 80% acetic acid (10mg/ml).
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

Product Description
Antioxidant. Inhibits soluble guanylyl cyclase (sGC) by interacting with the heme iron to form a chelate complex.
Product Specific Literature References
Carnosine as a regulator of soluble guanylate cyclase: I.S. Severina, et al.; Biochemistry (Mosc) 65, 783 (2000) Abstract; Full Text
Further Categories Containing This Product:
Antioxidants, Flavonoids & Free Radical Scavengers Other Products
 
 
ALX-270-034 Revised 10-Jun-08
ODQ
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SYNONYMS 1H-[1,2,4]Oxadiazole[4,3-a]quinoxalin-1-one
PRODUCT LINE Nitric Oxide Pathway
PRODUCT CATEGORY Guanylyl Cyclases, Guanosine Phosphate Metabolism / Related Products
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Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-270-034-M010   10 mg 46.00 USD Add To Cart
ALX-270-034-M050   50 mg 185.00 USD Add To Cart
Product Specification
FORMULA: C9H5N3O2
MW: 187.2
CAS NUMBER: 41443-28-1
PURITY: ≥98%
APPEARANCE: Off-white to yellow powder.
SOLUBILITY: Soluble in DMSO (5mg/ml), ethyl acetate or 100% ethanol (1.2mg/ml); insoluble in water.
SHIPPING: AMBIENT
LONG TERM STORAGE: +4°C
USE/STABILITY: Solutions may decompose slowly.
HANDLING: Protect from light.
HAZARD: IRRITANT.

Product Description
Potent and selective inhibitor of nitric oxide (NO)-sensitive guanylyl cyclase.
Product Specific Literature References
Nitric oxide-dependent long-term potentiation is blocked by a specific inhibitor of soluble guanylyl cyclase: C.L. Boulton, et al.; Neuroscience 69, 699 (1995) Abstract
Novel guanylyl cyclase inhibitor, ODQ reveals role of nitric oxide, but not of cyclic GMP in endothelin-1 secretion: F. Brunner, et al.; FEBS Lett. 376, 262 (1995) Abstract
Potent and selective inhibition of nitric oxide-sensitive guanylyl cyclase by 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one: J. Garthwaite, et al.; Mol. Pharmacol. 48, 184 (1995) Abstract
cGMP mediates the vascular and platelet actions of nitric oxide: confirmation using an inhibitor of the soluble guanylyl cyclase: M.A. Moro, et al.; PNAS 93, 1480 (1996) Abstract
Characterization of 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one as a heme-site inhibitor of nitric oxide-sensitive guanylyl cyclase: A. Schrammel, et al.; Mol. Pharmacol. 50, 1 (1996) Abstract
The nitric oxide-cyclic GMP pathway and synaptic plasticity in the rat superior cervical ganglion: E. Southam, et al.; Br. J. Pharmacol. 119, 527 (1996) Abstract
A comparative study of the effects of three guanylyl cyclase inhibitors on the L-type Ca2+ and muscarinic K+ currents in frog cardiac myocytes: N. Abi-Gerges, et al.; Br. J. Pharmacol. 121, 1369 (1997) Abstract
Selective guanylyl cyclase inhibitor reverses nitric oxide-induced vasorelaxation: L.J. Olson, et al.; Hypertension 29, 254 (1997) Abstract
Effects of a novel inhibitor of guanylyl cyclase on dilator responses of mouse cerebral arterioles: C.G. Sobey & F.M. Faraci; Stroke 28, 837 (1997) Abstract
Comparison of two soluble guanylyl cyclase inhibitors, methylene blue and ODQ, on sodium nitroprusside-induced relaxation in guinea-pig trachea: T.L. Hwang, et al.; Br. J. Pharmacol 125, 1158 (1998) Abstract
Endothelial heme oxygenase-1 induction by hypoxia. Modulation by inducible nitric-oxide synthase and S-nitrosothiols: R. Motterlini, et al.; J. Biol. Chem. 275, 13613 (2000) Abstract; Full Text
 
 
ALX-270-210 Revised 06-Feb-05
NS-2028
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SYNONYMS 4H-8-Bromo-1,2,4-oxadiazolo(3,4-d)benz(b)(1,4)oxazin-1-one
PRODUCT LINE Nitric Oxide Pathway
PRODUCT CATEGORY Guanylyl Cyclases, Guanosine Phosphate Metabolism / Related Products
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ALX-270-210-M001   1 mg 30.00 USD Add To Cart
ALX-270-210-M005   5 mg 90.00 USD Add To Cart
ALX-270-210-M025   25 mg 360.00 USD Add To Cart
Product Specification
FORMULA: C9H5N2O3Br
MW: 269.1
PURITY: ≥98%
APPEARANCE: Off-white powder.
SOLUBILITY: Soluble in DMSO, 100% ethanol or chloroform.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

Product Description
Potent and selective inhibitor of nitric oxide (NO)-sensitive soluble guanylyl cyclase (sGC). Inhibits also the basal, the YC-1 and the coenhanced sGC activity.
Product Specific Literature References
Characterization of NS 2028 as a specific inhibitor of soluble guanylyl cyclase: S.P. Olesen, et al.; Br. J. Pharmacol. 123, 299 (1998) Abstract
Vascular smooth muscle contraction is an independent regulator of endothelial nitric oxide production: L. Bang, et al.; Scand. Cardiovasc. J. 33, 33 (1999) Abstract
Isometric contraction induces the Ca2+-independent activation of the endothelial nitric oxide synthase: I. Fleming, et al.; PNAS 96, 1123 (1999) Abstract
 
 
ALX-420-025 Revised 26-Jun-08
YC-1
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SYNONYMS 3-(5'-Hydroxymethyl-2'-furyl)-1-benzylindazole
PRODUCT LINE Nitric Oxide Pathway
PRODUCT CATEGORY Guanylyl Cyclases, Guanosine Phosphate Metabolism / Related Products
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ALX-420-025-M001   1 mg 20.00 USD Add To Cart
ALX-420-025-M005   5 mg 65.00 USD Add To Cart
ALX-420-025-M025   25 mg 260.00 USD Add To Cart
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Product Specification
FORMULA: C19H16N2O2
MW: 304.4
CAS NUMBER: 170632-47-0
PURITY: ≥98% (HPLC)
APPEARANCE: White to pale yellow powder.
SOLUBILITY: Soluble in DMSO, methanol or dichloromethane.
SHIPPING: AMBIENT
LONG TERM STORAGE: +4°C
HANDLING: Protect from light.
IDENTITY: Identity determined by 1H-NMR.

Product Description

Nitric oxide (NO) independent, superoxide-sensitive stimulator of soluble guanylyl cyclase (sGC). Inhibits platelet adhesion to collagen. Non-specific phosphodiesterase inhibitor. YC-1 inhibits HIF-α activity in tumors resulting in blocked angiogenesis and an inhibition of tumor growth.
Inhibits Na+ channel.
Binds to [3H]BW202W92.
Product Specific Literature References
YC-1, a novel activator of platelet guanylate cyclase: F.N. Ko, et al.; Blood 84, 4226 (1994) Abstract
YC-1 inhibited human platelet aggregation through NO-independent activation of soluble guanylate cyclase: C.C. Wu, et al.; Br. J. Pharmacol 116, 1973 (1995) Abstract
Effect of YC-1, an NO-independent, superoxide-sensitive stimulator of soluble guanylyl cyclase, on smooth muscle responsiveness to nitrovasodilators: A. Mülsch, et al.; Br. J. Pharmacol. 120, 681 (1997) Abstract
Activation of soluble guanylyl cyclase by YC-1 in aortic smooth muscle but not in ventricular myocardium from rat: J.W. Wegener, et al.; Br. J. Pharmacol. 122, 1523 (1997) Abstract
Differential effects of isoliquiritigenin and YC-1 in rat aortic smooth muscle: J.W. Wegener & H. Nawrath; Eur. J. Pharmacol. 323, 89 (1997) Abstract
Inhibition of platelet adhesion to collagen by cGMP-elevating agents: C.-C. Wu, et al.; BBRC 231, 412 (1997) Abstract
Mechanism of YC-1-induced activation of soluble guanylyl cyclase: A. Friebe & D. Koesling; Mol. Pharmacol. 53, 123 (1998) Abstract; Full Text
Nitric oxide-sensitive guanylyl cyclase inhibits acetylcholine release and excitatory motor transmission in the guinea-pig ileum: K. Hebeiss & H. Kilbinger; Neuroscience 82, 623 (1998) Abstract
Synergistic activation of soluble guanylate cyclase by YC-1 and carbon monoxide: implications for the role of cleavage of the iron-histidine bond during activation by nitric oxide: J.R. Stone & M.A. Marletta; Chem. Biol. 5, 255 (1998) Abstract
Generation and characterization of a stable soluble guanylate cyclase-overexpressing CHO cell line: E.M. Becker, et al.; Nitric Oxide 3, 55 (1999) Abstract
Soluble guanylyl cyclase activator YC-1 protects white matter axons from nitric oxide toxicity and metabolic stress, probably through Na(+) channel inhibition: G. Garthwaite, et al.; Mol. Pharmacol. 61, 97 (2002) Abstract
A Novel Drug Binding Site on Voltage-Gated Sodium Channels in Rat Brain: D. R. Riddall, et al.; Mol. Pharmacol. 69, 278 (2006) Abstract
General Literature References
[1] YC-1: a potential anticancer drug targeting hypoxia-inducible factor 1: E.J. Yeo, et al.; J. Natl. Cancer Inst. 95, 516 (2003) Abstract
Further Categories Containing This Product:
Hypoxia-inducible Factor [HIF] / Related Products • Phosphodiesterases / Related Products
 
 
ALX-420-030 Revised 24-Sep-08
BAY 41-2272
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SYNONYMS 3-(4-Amino-5-cyclopropylpyrimidine-2-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine
PRODUCT LINE Nitric Oxide Pathway
PRODUCT CATEGORY Guanylyl Cyclases, Guanosine Phosphate Metabolism / Related Products
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ALX-420-030-M005   5 mg 92.00 USD Add To Cart
ALX-420-030-M025   25 mg 358.00 USD Add To Cart
Product Specification
FORMULA: C20H17FN6
MW: 360.4
CAS NUMBER: 256376-24-6
PURITY: ≥98%
APPEARANCE: White to off-white needles.
SOLUBILITY: Soluble in DMSO, dichloromethane, 100% ethanol or 2-pyrrolidone; practically insoluble in water.
SHIPPING: AMBIENT
LONG TERM STORAGE: +4°C
HAZARD: IRRITANT.

Product Description
NO-independent activator of soluble guanylyl cyclase (sGC) [1,2]. Activates both isoforms α1β1 and α1β2 of sGC [3]. While the related compound YC-1 (Prod. No. ALX-420-025) also acts as a non-specific phosphodiesterase inhibitor, BAY 41-2272 has no effect on phosphodiesterases. Stimulation of sGC is not blocked by high concentrations of NO scavengers (e.g. PTIO, Prod. No. ALX-430-007) and the combination of  BAY 41-2272 with the NO donor DEA NONOate (Prod. No. ALX-430-034) potentiates the activation of sGC. Although BAY 41-2272 alone is not as strong a stimulator of sGC as NO, concentrations as low as 10-100nM stimulate sGC to a level that would be expected to cause biologically important increases in cGMP [1]. ODQ (Prod. No. ALX-270-034), a potent and selective inhibitor of sGC, completely inhibited the effect of BAY 41-2272 [1]. The activity of BAY 41-2272 is described in selected literature references [4-6].
Product Specific Literature References
[1] NO-independent regulatory site on soluble guanylate cyclase: J.P. Stasch, et al.; Nature 410, 212 (2001) Abstract
[2] NO-independent regulatory site of direct sGC stimulators like YC-1 and BAY 41-2272: E.M. Becker, et al.; BMC Pharmacol. 1, 13 (2001) Abstract; Full Text
NO-independent stimulators of soluble guanylate cyclase: A. Straub, et al.; Bioorg. Med. Chem. Lett. 11, 781 (2001) Abstract
[3] BAY 41-2272 activates two isoforms of nitric oxide-sensitive guanylyl cyclase: M. Koglin, et al.; BBRC 292, 1057 (2002) Abstract
[4] Cardiorenal and humoral properties of a novel direct soluble guanylate cyclase stimulator BAY 41-2272 in experimental congestive heart failure: G. Boerrigter, et al.; Circulation 107, 686 (2003) Abstract
[5] BAY 41-2272: a stimulator of soluble guanylyl cyclase induces nitric oxide-dependent penile erection in vivo: E. Bischoff, et al.; Urology 61, 464 (2003) Abstract
[6] Macrophage endothelial nitric oxide synthase auto-regulates cellular activation and pro-inflammatory protein expression: L. Connelly, et al.; J. Biol. Chem 278, 26480 (2003) Abstract; Full Text
Antiinflammatory activity of soluble guanylate cyclase: cGMP-dependent down-regulation of P-selectin expression and leukocyte recruitment: A. Ahluwalia, et al.; PNAS 101, 1386 (2004) Abstract; Full Text
Identification of residues crucially involved in soluble guanylate cyclase activation: C. Rothkegel, et al.; FEBS Lett. 580, 4205 (2006) Abstract
 
 
ALX-430-041 Revised 17-Sep-08
Protoporphyrin IX (free acid)
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SYNONYMS 8,13-Divinyl-3,7,12,17-tetramethyl-21H,23H-porphine-2,18-dipropionic acid
PRODUCT LINE Oxidative Stress
PRODUCT CATEGORY Porphyrins
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Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-430-041-M300   300 mg 50.00 USD Add To Cart
ALX-430-041-G001   1 g 90.00 USD Add To Cart
Product Specification
FORMULA: C34H34N4O4
MW: 562.6
CAS NUMBER: 553-12-8
MERCK INDEX: 14: 7897
PURITY: ≥97% (HPLC)
APPEARANCE: Purple to dark brown solid.
SOLUBILITY: Soluble in conc. HCl, DMSO (10mg/ml) or 100% ethanol (10mg/ml).
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Protect from light.
HAZARD: IRRITANT.
IDENTITY: Identity determined by NMR.

Product Description
Protoporphyrin IX free acid, as distinct from its zinc salt (which inhibits heme oxygenase), activates soluble guanylyl cyclase (sGC) by binding directly to the enzyme. A useful reagent in cases where the use of nitric oxide (NO) or nitric oxide donors is undesirable.
Product Specific Literature References
H. Verweij & J. Van Steveninck; Photochem. Photobiol. 35, 265 (1982)
Guanylate cyclase from bovine lung. A kinetic analysis of the regulation of the purified soluble enzyme by protoporphyrin IX, heme, and nitrosyl-heme: M.S. Wolin, et al.; J. Biol. Chem. 257, 13312 (1982) Abstract; Full Text
Porphyrins and chlorophylls as probes for fluoroimmunoassays [letter]: J.L. Hendrix; Clin. Chem. 29, 1003 (1983) Abstract
Photodynamic intramolecular crosslinking of myoglobin: J. van Steveninck and T.M.A.R. Dubbelman; Biochim. Biophys. Acta 791, 98 (1984)
Further Categories Containing This Product:
Guanylyl Cyclases, Guanosine Phosphate Metabolism / Related Products
 
 
ALX-430-049 Revised 25-May-07
Zinc(II) Protoporphyrin IX
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PRODUCT LINE Oxidative Stress
PRODUCT CATEGORY Porphyrins
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ALX-430-049-M005   5 mg 20.00 USD Add To Cart
ALX-430-049-M025   25 mg 60.00 USD Add To Cart
ALX-430-049-M100   100 mg 180.00 USD Add To Cart
Product Specification
FORMULA: C34H32N4O4Zn
MW: 626.0
CAS NUMBER: 15442-64-5
PURITY: ≥95% (TLC)
APPEARANCE: Dark red solid.
SOLUBILITY: Soluble in pyridine, dimethyl formamide or DMSO. Colloidal in aqueous base;  slightly soluble in aqueous base/organic solvent mixtures.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
USE/STABILITY: Stable for at least 3 years after receipt when stored at -20°C. Product may be unstable in solution if exposed to light.
HANDLING: Protect from light and moisture.

Product Description
Potent and selective inhibitor of heme oxygenase, the enzyme that generates carbon monoxide (CO). Inhibits soluble guanylyl cyclase. Produces a time- and concentration-dependent inactivation of all three isoforms of nitric oxide synthase (IC50=0.8µM, 4.0µM, and 5.0µM for nNOS (NOS I), iNOS (NOS II) and eNOS (NOS III), respectively). Does not cross the blood-brain barrier.
Product Specific Literature References
Inhibition of platelet aggregation by carbon monoxide is mediated by activation of guanylate cyclase: B. Brune & V. Ullrich; Mol. Pharmacol. 32, 497 (1987) Abstract
Does endogenous zinc protoporphyrin modulate carbon monoxide formation from heme? Implications for long-term potentiation, memory, and cognitive function: G.S. Marks, et al.; Can. J. Physiol.Pharmacol. 71, 753 (1993) Abstract
Nitric oxide and carbon monoxide produce activity-dependent long-term synaptic enhancement in hippocampus: M. Zhuo, et al; Science 260, 1946 (1993) Abstract
Preischemic but not postischemic zinc protoporphyrin treatment reduces infarct size and edema accumulation after temporary focal cerebral ischemia in rats: C. Kadoya, et al.; Stroke 26, 1035 (1995) Abstract; Full Text
Inhibition by zinc protoporphyrin-IX of receptor-mediated relaxation of the rat aorta in a manner distinct from inhibition of haem oxygenase: L. Ny, et al.; Br. J. Pharmacol. 115, 186 (1995) Abstract
Heme oxygenase inhibitor zinc protoporphyrin IX causes an activation of nitric oxide synthase in the rabbit internal anal sphincter: S. Chakder, et al.; J. Pharmacol. Exp. Ther. 277, 1376 (1996) Abstract
Inhibition of nitric oxide synthase isoforms by porphyrins: D.J. Wolff, et al.; Arch. Biochem. Biophys. 333, 27 (1996) Abstract
Pitfalls using metalloporphyrins in carbon monoxide research: L. Grundemar and L. Ny; TIPS 18, 193 (1997), (Review) Abstract
Induction of heme oxygenase-1 expression in vascular smooth muscle cells. A link to endotoxic shock: S.F. Yet, et al.; J. Biol. Chem. 272, 4295 (1997) Abstract; Full Text
Effect of heme oxygenase inhibitors on soluble guanylyl cyclase activity: L. Serfass and J.N. Burstyn; Arch. Biochem. Biophys. 359, 8 (1998) Abstract
Mechanism of inhibition of VIP-induced LES relaxation by heme oxygenase inhibitor zinc protoporphyrin IX: S. Rattan, et al.; Am. J. Physiol. 276, G138 (1999) Abstract; Full Text
Further Categories Containing This Product:
Heme Oxygenase / Related Products • Guanylyl Cyclases, Guanosine Phosphate Metabolism / Related Products • NOS Inhibitors (NOS Induction & Enzyme Activity)
 
 
ALX-430-086 Revised 13-Dec-06
DD1
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SYNONYMS 3-Bromo-3,4,4-trimethyl-3,4-dihydrodiazete 1,2-dioxide
PRODUCT LINE Nitric Oxide Pathway
PRODUCT CATEGORY Nitric Oxide Donors
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ALX-430-086-M010   10 mg 30.00 USD Add To Cart
ALX-430-086-M050   50 mg 90.00 USD Add To Cart
Product Specification
FORMULA: C5H9BrN2O2
MW: 209.0
PURITY: ≥98%
APPEARANCE: Crystals.
SOLUBILITY: Soluble in DMSO, 100% ethanol or water (10mM).
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

Product Description
Guanylyl cyclase activator. Cell permeable thiol-induced nitric oxide donor with strong vasodilator effects.
Product Specific Literature References
Kinetics of nitric oxide liberation by 3,4-dihydro-1,2-diazete 1,2- dioxides and their vasodilatory properties in vitro and in vivo: D.I. Utepbergenov, et al.; BBRC 214, 1023 (1995) Abstract
Thiol-induced nitric oxide release from 3-halogeno-3,4-dihydrodiazete 1,2-dioxides: I.A. Kirilyuk, et al.; J. Med. Chem. 41, 1027 (1998) Abstract
Geldanamycin leads to superoxide formation by enzymatic and non-enzymatic redox cycling. Implications for studies of Hsp90 and endothelial cell nitric-oxide synthase: S. Dikalov, et al.; J. Biol. Chem. 277, 25480 (2002) Abstract; Full Text
Inflammatory cytokines induce apoptosis of corneal endothelium through nitric oxide: P. Sagoo, et al.; Invest. Ophthalmol. Vis. Sci. 45, 3964 (2004) Abstract; Full Text
Further Categories Containing This Product:
Guanylyl Cyclases, Guanosine Phosphate Metabolism / Related Products
 
 
ALX-430-087 Revised 23-Feb-05
DD2
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SYNONYMS 3-Bromo-4-methyl-3,4-hexamethylene-3,4-dihydrodiazete 1,2-dioxide
PRODUCT LINE Nitric Oxide Pathway
PRODUCT CATEGORY Nitric Oxide Donors
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Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-430-087-M010   10 mg 30.00 USD