Hematoporphyrin dihydrochloride

Hematoporphyrin dihydrochloride (Hematoporphyrin IX dihydrochloride), a photosensitizer, is a substrate for affinity chromatography of heme-binding proteins. Hematoporphyrin dihydrochloride can induce apoptosis in U87 glioma cells and decrease tumor growth in vivo when exposed to red light.

Product information

CAS Number: 17696-69-4

Molecular Weight: 671.61

Formula: C34H40Cl2N4O6

Synonym:

Hematoporphyrin IX dihydrochloride

Chemical Name: 3-[20-(2-carboxyethyl)-9, 14-bis(1-hydroxyethyl)-5, 10, 15, 19-tetramethyl-21, 22, 23, 24-tetraazapentacyclo[16.2.1.1, .1, .1, ]tetracosa-1, 3, 5, 7, 9, 11(23), 12, 14, 16, 18(21), 19-undecaen-4-yl]propanoic acid dihydrochloride

Smiles: Cl.Cl.CC1=C(C(C)O)C2=CC3=NC(=CC4NC(C=C5N=C(C=C1N2)C(C)=C5CCC(O)=O)=C(CCC(O)=O)C=4C)C(C(C)O)=C3C

InChiKey: QCLJGYHFHNRFIL-UDHHKLSBSA-N

InChi: InChI=1S/C34H38N4O6.2ClH/c1-15-21(7-9-31(41)42)27-14-28-22(8-10-32(43)44)16(2)24(36-28)12-29-34(20(6)40)18(4)26(38-29)13-30-33(19(5)39)17(3)25(37-30)11-23(15)35-27;;/h11-14,19-20,36-37,39-40H,7-10H2,1-6H3,(H,41,42)(H,43,44);2*1H/b23-11-,24-12-,25-11-,26-13-,27-14-,28-14-,29-12-,30-13-;;

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : ≥ 50 mg/mL (74.45 mM)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Hematoporphyrin (20-120 nM; 60 min) dose-dependently inhibits cell viability in U87 and U251 glioma cells, with IC50s of 85 and 166 nM, respectively. Hematoporphyrin (85 nM; 60 min) induces cell apoptosis via induction of ROS in U87 cells. Hematoporphyrin (85 nM; 60 min) induces morphological changes of U87 cells under the red light, including shrinking, fragmentation.

In Vivo:

Hematoporphyrin (5-10 mg/kg; i.p. for 2 months) with the irradiation of red light rapidly decreases the tumor size of rats, due to necrosis caused both by direct action of the photoactivated porphyrin on the tumor cells and by secondary effects on blood vessels.

References:

1. Olsen, K.W., Affinity chromatography of heme-binding proteins: synthesis and characterization of hematin- and hematoporphyrin-agarose. Methods Enzymol, 1986. 123: p. 324-31.
2. Yuan SX, et, al. Underlying mechanism of the photodynamic activity of hematoporphyrin‑induced apoptosis in U87 glioma cells. Int J Mol Med. 2018 Apr;41(4):2288-2296.
3. Tomio L, et, al. Effect of hematoporphyrin and red light on AH-130 solid tumors in rats. Acta Radiol Oncol. 1983;22(1):49-53.

Products are for research use only. Not for human use.