Hemin

Names

[ Name ]:
Hemin

[Synonym ]:
Iron, chloro[7,12-diethenyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoato(2-)-κN,κN]-
Hemin
Chloro(protoporphyrinato)iron(III)
MFCD00010726
Chloro[3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-2,18-porphyrindiyl-κN,N)dipropanoato(2-)]iron
Ferriprotoporphyrin chloride
7,12-Diethenyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoic acid
Ferriheme chloride
Ferriprotoporphyrin IX chloride
Chloroprotoporphyrin IX iron(III)
EINECS 240-140-1

Biological Activity

[Description]:

Hemin is an iron-containing porphyrin. Hemin is an Heme oxygenase (HO)-1 inducer.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Autophagy >> Mitophagy

Research Areas >> Cardiovascular Disease

[Target]

Heme oxygenase[1]

[In Vitro]

Hemin and PGJ2, used as positive controls, strongly increase both expression and activity of HMOX after 4 and 12 h, respectively. Indeed, a significant effect is found of 30 μM Hemin on cell proliferation in all used cell lines after 48 h, which is dose-dependent. Hemin treatment decreases cell proliferation to 62±5 %, 51±3 %, and 38±8 % in PA-TU-8902, BxPC-3 and MiaPaCa-2 cancer cells, respectively, with p<0.0001 for all comparisons. Furthermore, enhancement of anti-proliferative effects of statins is observed by Hemin, documented as decreased cell proliferation after 48 h of co-treatment[1].

[In Vivo]

Following the i.p. administration of Hemin (100 μmol/kg), the HO-1 level in the renal cortex begins to increase gradually. The HO-1 level reaches its peak 24 h after Hemin preconditioning. HO-1 is expressed mainly in the renal tubules. The HO-2 level in the kidney does not change following Hemin preconditioning[2].

[Cell Assay]

For the cell proliferation assay, cells are seeded into 96 well (5-12.5×104 cells per mL according to the cell line) and kept at 37°C and 5 % CO2. After 24 h, cells are treated with statins or/and Hemin, followed by the MTT test as a general cell proliferation assay[1].

[Animal admin]

Mice[2] Eight- to ten-week-old male BABL/c mice are used for the ischemia-reperfusion (I/R) experiments. The animals are divided into five groups as follows: (1) the sham group undergo isolation of the bilateral renal arteries without clamping; (2) the vehicle group receive an intraperitoneal (i.p.) injection of 4 mL/kg PBS as a vehicle control (with IRI); (3) the Hemin-preconditioned group receive Hemin, a potent inducer of HO-1, at 100 μmol/kg i.p.; (4) the Hemin plus ZnPP group receive zinc protoporphyrin IX, an inhibitor of HO-1 activity, at 5 mg/kg i.p. 6 h after receiving 100 μmol/kg Hemin i.p.; and (5) the Hemin plus PD98059 group receive PD98059, an inhibitor of ERK1/2 activity, at 10 mg/kg i.p. 6 h after receiving 100 μmol/kg Hemin i.p. Both inhibitors are administered i.p. 2 h before I/R, whereas Hemin was administered 8 h before I/R.

[References]

[1]. Vanova K, et al. Heme oxygenase is not involved in the anti-proliferative effects of statins on pancreatic cancer cells. BMC Cancer. 2016 May 12;16:309.

[2]. Chen HH, et al. Heme oxygenase-1 ameliorates kidney ischemia-reperfusion injury in mice through extracellular signal-regulated kinase 1/2-enhanced tubular epithelium proliferation. Biochim Biophys Acta. 2015 Oct;1852(10 Pt A):2195-201.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
300 °C

[ Molecular Formula ]:
C₃₄H₃₂ClFeN₄O₄

[ Molecular Weight ]:
651.940

[ Exact Mass ]:
651.146179

[ PSA ]:
109.18000

[ LogP ]:
4.29920

[ Storage condition ]:
2-8°C

[ Stability ]:
Stable. Incompatible with strong oxidizing agents. Combustible.

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
N,Xi

[ Risk Phrases ]:
R10:Flammable. R19:May form explosive peroxides. R50:Very Toxic to aquatic organisms. R36:Irritating to the eyes.

[ Safety Phrases ]:
24/25-22-36-26

[ RIDADR ]:
UN 3272 3/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
LJ8080000

[ Packaging Group ]:
III

[ Hazard Class ]:
3

Articles

Enhancing the anti-inflammatory activity of chalcones by tuning the Michael acceptor site.

Org. Biomol. Chem. 13(10) , 3040-7, (2015)

Inflammatory signaling pathways orchestrate the cellular response to infection and injury. These pathways are known to be modulated by compounds that alkylate cysteinyl thiols. One class of phytochemi...

Kinetics of serotonin oxidation by heme-Aβ relevant to Alzheimer's disease.

J. Biol. Inorg. Chem. 19(8) , 1355-65, (2014)

Serotonin (5-HT) is an essential neurotransmitter for cognitive functions and formation of new memories. A deficit in 5-HT dependent neuronal activity is somewhat specific for Alzheimer's disease. Met...

Trypanocidal Activity of Long Chain Diamines and Aminoalcohols.

Molecules 20 , 11554-68, (2015)

Thirteen aminoalcohols and eight diamines were obtained and tested against Trypanosoma cruzi epimastigotes strains MG, JEM and CL-B5 clone. Some of them were equal or more potent (1.0-6.6 times) than ...