Chemicals & Small Molecules

Zn (II) Protoporphyrin IX is an inhibitor of heme oxygenase (the enzyme that catalyzes the conversion of heme to biliverdin in the heme degradation pathway) and guanylyl cyclase. Heme oxygenase has been implicated in tumor cell resistance to chemotherapy reduction of free radical formation and inflammation and associated with vascular repair.References1) Maines M. D. (1981). "Zinc protoporphyrin is a selective inhibitor of heme oxygenase activity in the neonatal rat." Biochim Biophys Acta 673(3): 339-50.2) Gupta G. J. Kim et al. (1997). "Expression and Purification of Soluble Active Heterodimeric Guanylyl Cyclase from Baculovirus." Protein Expression and Purification 10(3): 325.3) Jozkowicz A. H. Was et al. (2007). "Heme oxygenase-1 in tumors: is it a false friend?" Antioxid Redox Signal 9(12): 2099-117.4) Abraham N. G. and A. Kappas (2005). "Heme oxygenase and the cardiovascular-renal system." Free Radic Biol Med 39(1): 1-25.5) Kim D. H. A. P. Burgess et al. (2008). "Hem

Cu (II) Protoporphyrin IX does not inhibit heme oxygenase (the enzyme that catalyzes the conversion of heme to biliverdin in the heme degradation pathway) and is used as a negative control for Zn (II) Protoporphyrin (an inihibitor of heme oxygenase).  Heme oxygenase has been implicated in tumor cell resistance to chemotherapy reduction of free radical formation and inflammation and associated with vascular repair.References1) Jozkowicz A. H. Was et al. (2007). "Heme oxygenase-1 in tumors: is it a false friend?" Antioxid Redox Signal 9(12): 2099-117.2) Abraham N. G. and A. Kappas (2005). "Heme oxygenase and the cardiovascular-renal system." Free Radic Biol Med 39(1): 1-25.3) Kim D. H. A. P. Burgess et al. (2008). "Heme oxygenase-mediated increases in adiponectin decrease fat content and inflammatory cytokines tumor necrosis factor-alpha and interleukin-6 in Zucker rats and reduce adipogenesis in human mesenchymal stem cells." J Pharmacol Exp Ther 325(3): 833-40.

Sn (IV) Protoporphyrin IX is an inhibitor heme oxygenase (the enzyme that catalyzes the conversion of heme to biliverdin in the heme degradation pathway) but has also been found to stimulate production of the heme oxygenase protein. Contrast the activity of Co (III) Protoporphyrin which has been found to have similar activities to Sn (IV) Protoporphyrin but with a greater enhancement of heme oxygenase synthesis activity such that heme oxygenase activity is actually increased when administered in vivo while in vitro administration inhibits heme oxygenase activity. Heme oxygenase has been implicated in tumor cell resistance to chemotherapy reduction of free radical formation and inflammation and associated with vascular repair.References1) Sardana M. K. and A. Kappas (1987). "Dual control mechanism for heme oxygenase: tin(IV)-protoporphyrin potently inhibits enzyme activity while markedly increasing content of enzyme protein in liver." Proc Natl Acad Sci U S A 84(8): 2464-8.2) Jozkowi

Zn (II) Deuteroporphyrin IX 2 4 bis ethyleneglycol is an inhibitor of heme oxygenase (the enzyme that catalyzes the conversion of heme to biliverdin in the heme degradation pathway) at concentrations as low at 0.5 μM. Heme oxygenase has been implicated in tumor cell resistance to chemotherapy reduction of free radical formation and inflammation and associated with vascular repair.References1) Chernick R. J. P. Martasek et al. (1989). "Sensitivity of human tissue heme oxygenase to a new synthetic metalloporphyrin." Hepatology 10(3): 365-9.2) Jozkowicz A. H. Was et al. (2007). "Heme oxygenase-1 in tumors: is it a false friend?" Antioxid Redox Signal 9(12): 2099-117.3) Abraham N. G. and A. Kappas (2005). "Heme oxygenase and the cardiovascular-renal system." Free Radic Biol Med 39(1): 1-25.4) Kim D. H. A. P. Burgess et al. (2008). "Heme oxygenase-mediated increases in adiponectin decrease fat content and inflammatory cytokines tumor necrosis factor-alpha and interleukin-6 in Z

Biliverdin Hydrochloride is produced from the oxidation of heme in a reaction catalyzed by the enzyme heme oxygenase. Heme oxygenase has been implicated in tumor cell resistance to chemotherapy reduction of free radical formation reduction of inflammation and has been associated with vascular repair. In vivo biliverdin is reduced to bilirubin. Biliverdin Hydrochloride is soluble in basic aqueous solutions (pH > 9 for intitial dissolution) and soluble down to pH 7 once in solution as well as methanol and ethanol if made slightly basic.References1) Seta F. L. Bellner et al. (2006). "Heme Oxygenase-2 Is a Critical Determinant for Execution of an Acute Inflammatory and Reparative Response." The American Journal of Pathology 169(5): 1612.2) Jozkowicz A. H. Was et al. (2007). "Heme oxygenase-1 in tumors: is it a false friend?" Antioxid Redox Signal 9(12): 2099-117.3) Abraham N. G. and A. Kappas (2005). "Heme oxygenase and the cardiovascular-renal system." Free Radic Biol Med 39

Bilirubin dimethyl ester is a natural derivative of bilirubin and is found in normal sera representing an average of 1.75% total sera bilirubin. Bilirubin is a water insoluble tetrapyrrole produced from the reduction of biliverdin in a reaction catalyzed by the enzyme bilirverdin reductase. Water insoluble bilirubin (also called indirect bilirubin) in vivo undergoes glucuronidation in the liver (addition of one or two glucuronic acids through a glycosidic bond) to form the water soluble bilirubin mono or diglucuronide (also called bilirubin conjugate or direct bilirubin).  Bilirubin conjugate is excreted from the liver in bile or is converted to urobilinogen and excreted in the urine as urobilin or in the feces as stercobilin.  Bilirubin dimethyl ester has been found to be converted to bilirubin conjugate via esterase and glucuronidase activity in vivo.References1) Muraca M. and N. Blanckaert (1983). "Liquid-chromatographic assay and identification of mono- and diester conjugates of

Bilirubin is a water insoluble tetrapyrrole produced from the reduction of biliverdin in a reaction catalyzed by the enzyme bilirverdin reductase. In vivo it undergoes glucuronidation in the liver (addition of one or two glucuronic acids through a glycosidic bond) to form the water soluble mono or diglucuronide (also called bilirubin conjugate). The conjugate is excreted from the liver in bile or is converted to urobilinogen and excreted in the urine as urobilin or in the feces as stercobilin.References1) Lee K. S. L. D. Raymond et al. (2007). "Hemin Interactions and Alterations of the Subcellular Localization of Prion Protein." Journal of Biological Chemistry 282(50): 36525-36533.2) Soares M. P. M. P. Seldon et al. (2004). "Heme Oxygenase-1 Modulates the Expression of Adhesion Molecules Associated with Endothelial Cell Activation." The Journal of Immunology 172(6): 3553-3563.3) Huber A. H. B. Zhu et al. (2012). "Fluorescence Sensor for the Quantification of Unbound Bilirubin

Bilirubin Conjugate is a water soluble ditaurate derivative of bilirubin equivalent to bilirubin glucuronide derivatives. Bilirubin glucuronide derivatives are produced in vivo from the glucuronidation (addition of one or two glucuronic acids through a glycosidic bond) of bilirubin (also called indirect bilirubin) in a reaction catalyzed by the enzyme UDP Glucuronidase. The glucuronidation of bilirubin occurs in the liver to form the water soluble bilirubin mono or diglucuronide (also called bilirubin conjugate or direct bilirubin). Bilirubin conjugate is excreted from the liver in bile or is converted to urobilinogen and excreted in the urine as urobilin or in the feces as stercobilin.References1) Maghzal G. J. M.-C. Leck et al. (2009). "Limited Role for the Bilirubin-Biliverdin Redox Amplification Cycle in the Cellular Antioxidant Protection by Biliverdin Reductase." Journal of Biological Chemistry 284(43): 29251-29259.2) MacLean P. D. E. C. Drake et al. (2007). "Bilirubin as a

Urobilin Hydrochloride is produced via the oxidation of urobilinogen a degradation product of bilirubin and excreted in the urine. Bilirubin is a water insoluble tetrapyrrole produced from the reduction of biliverdin in a reaction catalyzed by the enzyme bilirverdin reductase. Water insoluble bilirubin (also called indirect bilirubin) in vivo undergoes glucuronidation in the liver (addition of one or two glucuronic acids through a glycosidic bond) to form the water soluble bilirubin mono or diglucuronide (also called bilirubin conjugate or direct bilirubin). Bilirubin conjugate is excreted from the liver in bile or is converted to mesobilinogen via gut bacteria and then to urobilinogen and excreted in the urine as urobilin or stercobilinogen and excreted in the feces as stercobilin. Urobilin Hydrochloride is soluble in basic aqueous solutions (pH > 9 for intitial dissolution) and soluble down to pH 7 once in solution as well as methanol and ethanol if made slightly basic.Reference