| Identification | Back Directory | [Name]
HEMATOPORPHYRIN | [CAS]
14459-29-1 | [Synonyms]
hp
Photodyn
NSC-59265
A-259H10.2
HEMATOPORPHYRIN
HEMATOPORPHYRINE
HAEMATOPORPHYRIN
hematoporphyrinix
HematoporphyrineBase
HeMatoporphyrin >=45%
HEMATOPORPHYRIN IX BASE
hematoporphyrin free base
ANTI-HPR antibody produced in mouse
1,3,5,8-Tetramethyl-2,4-bis(α-hydroxyethyl)porphine-6,7-dipropionic acid
7,12-bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-18-porphinedipropionicacid
1,3,5,8-tetramethyl-2,4-bis(alpha-hydroxyethyl)prophine-6,7-dipropionicacid
21h,23h-porphine-2,18-dipropanoicacid,7,12-bis(1-hydroxyethyl)-3,8,13,17-te
8,13-BIS(1-HYDROXYETHYL)-3,7,12,17-TETRAMETHYL-21H,23H-PORPHINE-2,18-DIPROPIONIC ACID
7,12-bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-21H,23H-Porphine-2,18-dipropanoic acid
7,12-Bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-21H,23H-porphyrin-2,18-dipropionic acid
21H,23H-Porphine-2,18-dipropanoic acid, 7,12-bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-
3-[18-(2-carboxyethyl)-7,12-bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-22,23-dihydroporphin-2-yl]propionic acid
3-[18-(2-carboxyethyl)-7,12-bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoic acid | [EINECS(EC#)]
238-450-7 | [Molecular Formula]
C34H38N4O6 | [MDL Number]
MFCD00005077 | [MOL File]
14459-29-1.mol | [Molecular Weight]
598.69 |
| Chemical Properties | Back Directory | [Melting point ]
172.5°C | [Boiling point ]
649.58°C (rough estimate) | [density ]
1.328 | [refractive index ]
1.6000 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
DMSO (Sparingly), Methanol (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [color ]
Purple to Black | [biological source]
mouse | [Merck ]
13,4653 | [Stability:]
Light Sensitive | [EPA Substance Registry System]
21H,23H-Porphine-2,18-dipropanoic acid, 7,12-bis(1-hydroxyethyl)-3,8,13,17-tetramethyl- (14459-29-1) |
| Hazard Information | Back Directory | [Uses]
antidepressant, antineoplastic | [Definition]
ChEBI: A dicarboxylic acid that is protoporphyrin in which the vinyl groups at positions 7 and 12 are replaced by 1-hydroxyethyl groups. | [Hazard]
Toxic. Reported to be preferentially
absorbed by cancerous tissues, making them fluoresce under UV light. | [Chemical Properties]
Red-purple crystals, soluble in ethanol, slightly soluble in ether and chloroform, insoluble in water. | [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[3].
| Animal Model: | Wistar albino rats of both sexes (20 d; 60-80 g) bearing a subcutaneous solid Yoshida hepatoma AH-130[3] | | Dosage: | 5, 10 mg/kg | | Administration: | I.p. daily during the initial 10 days and biweekly for the next 2 months | | Result: | No tumor could be palpated a few days after exposure of the rats to light.
The skin healed completely and regrowth of the hair occurred.
Massive coagulation necrosis of the tumor 24 h after phototreatment (×40). |
| [IC 50]
Human Endogenous Metabolite | [Purification Methods]
Purify it by dissolving it in EtOH Hematoporphyrin and adding H2O or Et2O to give deep red crystals. It has also been recrystallised from MeOH. UV has max at 615.5, 565, 534.4 and 499.5nm in 0.1N NaOH, and 597, 619, 634, 653, 683 and 701nm in 2N HCl [Falk Porphyrins and Metalloporphyrins Elsevier, NY, p 175 1964, LCCCNo 63-19821.] It is used in the affinity chromatographic purification of Heme proteins [Olsen Methods Enzymol 123 324 1986]. The O-methyl-dimethyl ester has m 203-206o (from CHCl3/MeOH), and the O,O'-dimethyl-dimethyl ester has m 145o (from CHCl3/MeOH). [Paul Acta Chem Scand 5 389 1951, Beilstein 26 III/IV 3157, and 3158 for the HCl.] |
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