Zinc protoporphyrin

Zinc protoporphyrin
Names
IUPAC name
Zinc(II) 3-[18-(2-carboxylatoethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid monohydrate
Other names
Zinc protoporphyrin IX
Identifiers
3D model (JSmol)
4932319, 8184206
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.035.853
EC Number
  • 239-455-7
403138
KEGG
MeSH zinc+protoporphyrin
UNII
  • InChI=1S/C34H34N4O4.Zn/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;
    Key: FUTVBRXUIKZACV-RGGAHWMASA-L
  • dianion: InChI=1S/C34H34N4O4.Zn/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-4
    Key: FUTVBRXUIKZACV-UHFFFAOYSA-J
  • CC1=C(CCC(O)=O)C2=[N]3C1=Cc1c(C)c(C=C)c4C=C5C(C)=C(C=C)C6=[N]5[Zn]3(n14)n1c(=C6)c(C)c(CCC(O)=O)c1=C2
  • dianion: CC1=C(C2=CC3=C(C(=C([N-]3)C=C4C(=C(C(=N4)C=C5C(=C(C(=N5)C=C1[N-]2)C)C=C)C)C=C)C)CCC(=O)[O-])CCC(=O)[O-].[Zn+2]
Properties
C34H32N4O4Zn
Molar mass 626.032 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Zinc protoporphyrin (ZPP) refers to coordination complexes of zinc and protoporphyrin IX. It is a red-purple solid that is soluble in water. The complex and related species are found in red blood cells when heme production is inhibited by lead and/or by lack of iron.[1]

Clinical utility

Measurement of zinc protoporphyrin in red cells has been used for screening for lead poisoning[2][3] and for iron deficiency.[1][4]

Zinc protoporphyrin levels can be elevated as the result of a number of conditions, for instance:[2]

The fluorescent properties of ZPP in intact red cells allows the ZPP/heme molar ratio to be measured quickly, at low cost, and in a small sample volume.[6]

History

Porphyrin complexes of zinc have been known since the 1930s.[1] In 1974 ZPP was identified as a major non-heme porphyrin formed in red cells as the result of lead poisoning or iron deficiency.,[7] It was already known at this time that non-heme protoporphyrin IX levels were elevated in these conditions, but prior investigators had used acidic extraction methods in their assays that converted ZPP to unbound Protoporphyrin IX.[8] The early literature on quantifying zinc-PP levels may be unreliable.[1][4]

Early-stage cancer research

ZnPP is under in vitro research for its potential effects on cancer cells.[9][10] ZnPP is a competitive inhibitor of heme oxygenase, which is a cytoprotective enzyme with higher expression in cancerous tissues.[11] In vitro, ZnPP suppression of heme oxygenase reduces cell viability of cancer cells and increases cytotoxicity in cancer cells.[11]

In preliminary human studies conducted in 2014, ZnPP in combination with anticancer drugs increased cytotoxicity of cancer cells.[12] Tumors from several types of cancer showed a susceptibility to ZnPP due to increased expression of heme oxygenase.[12]

ZnPP has been encapsulated in nanoparticles with a specialized coating for drug delivery inside the body.[9] ZnPP did not show any reduced inhibitory potential on heme oxygenase when loaded into nanoparticles.[9]

References

  1. ^ a b c d Labbé RF, Vreman HJ, Stevenson DK (December 1999). "Zinc protoporphyrin: A metabolite with a mission". Clinical Chemistry. 45 (12): 2060–2072. doi:10.1093/clinchem/45.12.2060. PMID 10585337.
  2. ^ a b Martin CJ, Werntz CL, Ducatman AM (December 2004). "The interpretation of zinc protoporphyrin changes in lead intoxication: a case report and review of the literature". Occupational Medicine. 54 (8): 587–591. doi:10.1093/occmed/kqh123. PMID 15576877.
  3. ^ Verschoor M, Herber R, Zielhuis R, Wibowo A (1987). "Zinc protoporphyrin as an indicator of lead exposure: precision of zinc protoporphyrin measurements". International Archives of Occupational and Environmental Health. 59 (6): 613–621. Bibcode:1987IAOEH..59..613V. doi:10.1007/BF00377923. PMID 3679557. S2CID 7583183.
  4. ^ a b Crowell R, Ferris AM, Wood RJ, Joyce P, Slivka H (July 2006). "Comparative effectiveness of zinc protoporphyrin and hemoglobin concentrations in identifying iron deficiency in a group of low-income, preschool-aged children: practical implications of recent illness". Pediatrics. 118 (1): 224–232. doi:10.1542/peds.2006-0156. PMID 16818569. S2CID 8050501.
  5. ^ Casanova-González MJ, Trapero-Marugán M, Jones EA, Moreno-Otero R (September 2010). "Liver disease and erythropoietic protoporphyria: a concise review". World Journal of Gastroenterology. 16 (36): 4526–31. doi:10.3748/wjg.v16.i36.4526. PMC 2945483. PMID 20857522.
  6. ^ Blumberg WE, Eisinger J, Lamola AA, Zuckerman DM (February 1977). "The hematofluorometer". Clinical Chemistry. 23 (2 PT. 1): 270–274. doi:10.1093/clinchem/23.2.270. PMID 832391.
  7. ^ Lamola AA, Yamane T (December 1974). "Zinc protoporphyrin in the erythrocytes of patients with lead intoxication and iron deficiency anemia". Science. 186 (4167): 936–938. Bibcode:1974Sci...186..936L. doi:10.1126/science.186.4167.936. PMID 4469690. S2CID 24011145.
  8. ^ Piomelli S (June 1973). "A micromethod for free erythrocyte porphyrins: the FEP test". The Journal of Laboratory and Clinical Medicine. 81 (6): 932–940. PMID 4710372.
  9. ^ a b c Kongpetch S, Kukongviriyapan V, Prawan A, Senggunprai L, Kukongviriyapan U, Buranrat B (2012-04-13). Sim RB (ed.). "Crucial role of heme oxygenase-1 on the sensitivity of cholangiocarcinoma cells to chemotherapeutic agents". PLOS ONE. 7 (4) e34994. Bibcode:2012PLoSO...734994K. doi:10.1371/journal.pone.0034994. PMC 3325916. PMID 22514698.
  10. ^ Rouhani H, Sepehri N, Montazeri H, et al. (August 2014). "Zinc protoporphyrin polymeric nanoparticles: potent heme oxygenase inhibitor for cancer therapy". Pharmaceutical Research. 31 (8): 2124–2139. doi:10.1007/s11095-014-1313-7. PMID 24558012. S2CID 254885235.
  11. ^ a b Kang KA, Maeng YH, Zhang R, Yang YR, Piao MJ, Kim KC, et al. (August 2012). "Involvement of heme oxygenase-1 in Korean colon cancer". Tumour Biology. 33 (4): 1031–1038. doi:10.1007/s13277-012-0336-0. PMID 22302482. S2CID 18067203.
  12. ^ a b Yin H, Fang J, Liao L, Maeda H, Su Q (June 2014). "Upregulation of heme oxygenase-1 in colorectal cancer patients with increased circulation carbon monoxide levels, potentially affects chemotherapeutic sensitivity". BMC Cancer. 14 (1) 436. doi:10.1186/1471-2407-14-436. PMC 4075569. PMID 24927633.
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