# Porphyrin

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Type of chemical compound

Not to be confused with [Perforin](/source/Perforin) or [Porphyran](/source/Porphyran).

[Porphine](/source/Porphine), the parent of porphyrin

**Porphyrins** ([/ˈpɔːrfərɪns/](https://en.wikipedia.org/wiki/Help:IPA/English) [*POR-fər-ins*](https://en.wikipedia.org/wiki/Help:Pronunciation_respelling_key)) are [heterocyclic](/source/Heterocyclic_compound), [macrocyclic](/source/Macrocyclic), [organic compounds](/source/Organic_compound), composed of four modified [pyrrole](/source/Pyrrole) subunits interconnected at their [α carbon](/source/Alpha_and_beta_carbon) atoms via [methine](/source/Methine) bridges (=CH−). In [vertebrates](/source/Vertebrate), an essential member of the porphyrin group is [heme](/source/Heme), which is a component of [hemoproteins](/source/Hemoprotein), whose functions include carrying [oxygen](/source/Oxygen) in the [bloodstream](/source/Circulatory_system). In [plants](/source/Plants), an essential porphyrin derivative is [chlorophyll](/source/Chlorophyll), which is involved in [light harvesting](/source/Light-harvesting_complex) and [electron transfer](/source/Electron_transfer) in [photosynthesis](/source/Photosynthesis).

The parent of porphyrins is [porphine](/source/Porphine), a rare chemical compound of exclusively theoretical interest. Substituted porphines are called porphyrins.[1] With a total of 26 π-electrons the porphyrin ring structure is a coordinated [aromatic](/source/Aromaticity) system.[2] One result of the large [conjugated system](/source/Conjugated_system) is that porphyrins absorb strongly in the visible region of the electromagnetic spectrum, i.e. they are deeply colored. The name "porphyrin" derives from [Greek](/source/Greek_language) πορφύρα*(porphyra)* 'purple'.[3]

## Structure

[Porphyrin complexes](/source/Porphyrin_complexes) consist of a square planar MN4 core. The periphery of the porphyrins, consisting of sp2-hybridized carbons, generally display small deviations from planarity. "Ruffled" or saddle-shaped porphyrins is attributed to interactions of the system with its environment.[4] Additionally, the metal is often not centered in the N4 plane.[5] For free porphyrins, the two pyrrole protons are mutually trans and project out of the N4 plane.[6] These nonplanar distortions are associated with altered chemical and physical properties. [Chlorophyll](/source/Chlorophyll)-rings are more distinctly nonplanar, but they are more saturated than porphyrins.[7]

## Complexes of porphyrins

Main article: [Transition metal porphyrin complexes](/source/Transition_metal_porphyrin_complexes)

Concomitant with the displacement of two N-*H* protons, porphyrins bind metal ions in the N4 "pocket". The metal [ion](/source/Ion) usually has a charge of 2+ or 3+. A schematic equation for these syntheses is shown, where M = metal ion and L = a [ligand](/source/Ligand):

- H2porphyrin + [ML*n*]2+ → M(porphyrinate)L*n*−4 + 4 L + 2 H+

	- Representative porphyrins and derivatives

		- Derivatives of [protoporphyrin IX](/source/Protoporphyrin_IX) are common in nature, the precursor to [hemes](/source/Heme).

		- [Octaethylporphyrin](/source/Octaethylporphyrin) (H2OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP2− is highly symmetrical.

		- [Tetraphenylporphyrin](/source/Tetraphenylporphyrin) (H2TPP)is another synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, TPP2− is highly symmetrical. Another difference is that its methyne centers are occupied by phenyl groups.

		- Simplified view of [heme](/source/Heme), a complex of a protoporphyrin IX

		- A nanoring of 40 porphyrin molecules, model

		- A nanoring of 40 porphyrin molecules, [STM image](/source/Scanning_tunneling_microscope)

## Ancient porphyrins

A geoporphyrin, also known as a petroporphyrin, is a porphyrin of geologic origin.[8] They can occur in [crude oil](/source/Crude_oil), [oil shale](/source/Oil_shale), coal, or sedimentary rocks.[8][9] [Abelsonite](/source/Abelsonite) is possibly the only geoporphyrin mineral, as it is rare for porphyrins to occur in isolation and form crystals.[10]

The field of [organic geochemistry](/source/Organic_geochemistry) had its origins in the isolation of porphyrins from petroleum. These findings helped establish the biological origins of petroleum.[11][12] Petroleum is sometimes "fingerprinted" by analysis of trace amounts of nickel and [vanadyl](/source/Vanadyl) porphyrins. Metalloporphyrins in general are highly stable organic compounds, and the detailed structures of the extracted derivatives made clear that they originated from chlorophyll.

## Biosynthesis

In non-photosynthetic [eukaryotes](/source/Eukaryotes) such as animals, insects, fungi, and [protozoa](/source/Protozoa), as well as the α-proteobacteria group of bacteria, the [committed step](/source/Committed_step) for porphyrin [biosynthesis](/source/Biosynthesis) is the formation of [δ-aminolevulinic acid](/source/Aminolevulinic_acid) (δ-ALA, 5-ALA or dALA) by the reaction of the [amino acid](/source/Amino_acid) [glycine](/source/Glycine) with [succinyl-CoA](/source/Succinyl-CoA) from the [citric acid cycle](/source/Citric_acid_cycle). In [plants](/source/Plants), [algae](/source/Algae), [bacteria](/source/Bacteria) (except for the α-proteobacteria group) and [archaea](/source/Archaea), it is produced from [glutamic acid](/source/Glutamic_acid) via glutamyl-tRNA and [glutamate-1-semialdehyde](/source/Glutamate-1-semialdehyde). The enzymes involved in this pathway are [glutamyl-tRNA synthetase](/source/Aminoacyl_tRNA_synthetases%2C_class_I), [glutamyl-tRNA reductase](/source/Glutamyl-tRNA_reductase), and [glutamate-1-semialdehyde 2,1-aminomutase](/source/Glutamate-1-semialdehyde_2%2C1-aminomutase). This pathway is known as the C5 or Beale pathway.

Two molecules of dALA are then combined by [porphobilinogen synthase](/source/Porphobilinogen_synthase) to give [porphobilinogen](/source/Porphobilinogen) (PBG), which contains a pyrrole ring. Four PBGs are then combined through [deamination](/source/Deamination) into [hydroxymethyl bilane](/source/Hydroxymethyl_bilane) (HMB), which is [hydrolysed](/source/Hydrolysation) to form the circular tetrapyrrole [uroporphyrinogen III](/source/Uroporphyrinogen_III). This molecule undergoes a number of further modifications. Intermediates are used in different species to form particular substances, but, in humans, the main end-product [protoporphyrin IX](/source/Protoporphyrin_IX) is combined with iron to form heme. Bile pigments are the breakdown products of heme.

The following scheme summarizes the biosynthesis of porphyrins, with references by EC number and the [OMIM](/source/OMIM) database. The [porphyria](/source/Porphyria) associated with the deficiency of each enzyme is also shown:

Heme B biosynthesis pathway and its modulators. Major enzyme deficiences are also shown.

Enzyme Location Substrate Product Chromosome EC OMIM Disorder ALA synthase Mitochondrion Glycine, succinyl CoA δ-Aminolevulinic acid 3p21.1 2.3.1.37 125290 X-linked dominant protoporphyria, X-linked sideroblastic anemia ALA dehydratase Cytosol δ-Aminolevulinic acid Porphobilinogen 9q34 4.2.1.24 125270 aminolevulinic acid dehydratase deficiency porphyria PBG deaminase Cytosol Porphobilinogen Hydroxymethyl bilane 11q23.3 2.5.1.61 176000 acute intermittent porphyria Uroporphyrinogen III synthase Cytosol Hydroxymethyl bilane Uroporphyrinogen III 10q25.2-q26.3 4.2.1.75 606938 congenital erythropoietic porphyria Uroporphyrinogen III decarboxylase Cytosol Uroporphyrinogen III Coproporphyrinogen III 1p34 4.1.1.37 176100 porphyria cutanea tarda, hepatoerythropoietic porphyria Coproporphyrinogen III oxidase Mitochondrion Coproporphyrinogen III Protoporphyrinogen IX 3q12 1.3.3.3 121300 hereditary coproporphyria Protoporphyrinogen oxidase Mitochondrion Protoporphyrinogen IX Protoporphyrin IX 1q22 1.3.3.4 600923 variegate porphyria Ferrochelatase Mitochondrion Protoporphyrin IX Heme 18q21.3 4.99.1.1 177000 erythropoietic protoporphyria

## Laboratory synthesis

Main article: [Rothemund reaction](/source/Rothemund_reaction)

Brilliant crystals of *meso*-tetratolylporphyrin, prepared from [4-methylbenzaldehyde](/source/4-methylbenzaldehyde) and pyrrole in refluxing [propionic acid](/source/Propionic_acid)

A common synthesis for porphyrins is the [Rothemund reaction](/source/Rothemund_reaction), first reported in 1936,[13][14] which is also the basis for more recent methods described by Adler and Longo.[15] The general scheme is a [condensation](/source/Condensation_reaction) and [oxidation](/source/Organic_oxidation_reaction) process starting with pyrrole and an [aldehyde](/source/Aldehyde).

## Potential applications

### Photodynamic therapy

Porphyrins have been evaluated in the context of [photodynamic therapy](/source/Photodynamic_therapy) (PDT) since they strongly absorb light, which is then converted to heat in the illuminated areas.[16] This technique has been applied in [macular degeneration](/source/Macular_degeneration) using [verteporfin](/source/Verteporfin).[17]

PDT is considered a noninvasive cancer treatment, involving the interaction between light of a determined frequency, a photo-sensitizer, and oxygen. This interaction produces the formation of a highly reactive oxygen species (ROS), usually singlet oxygen, as well as superoxide anion, free hydroxyl radical, or hydrogen peroxide.[18] These high reactive oxygen species react with susceptible cellular organic biomolecules such as; lipids, aromatic amino acids, and nucleic acid heterocyclic bases, to produce oxidative radicals that damage the cell, possibly inducing apoptosis or even necrosis.[19]

### Molecular electronics and sensors

Porphyrin-based compounds are of interest as possible components of [molecular electronics](/source/Molecular_electronics) and photonics.[20] Synthetic porphyrin dyes have been incorporated in prototype [dye-sensitized solar cells](/source/Dye-sensitized_solar_cells).[21][22]

### Biological applications

Porphyrins have been investigated as possible anti-inflammatory agents[23] and evaluated on their anti-cancer and anti-oxidant activity.[24] Several porphyrin-peptide conjugates were found to have antiviral activity against HIV *in vitro*.[25]

### Toxicology

Heme biosynthesis is used as [biomarker](/source/Biomarker) in environmental toxicology studies. While excess production of porphyrins indicate [organochlorine](/source/Organochlorine) exposure, [lead](/source/Lead) inhibits [ALA dehydratase](/source/ALA_dehydratase) enzyme.[26]

## Gallery

		- Lewis structure for *meso*-tetraphenylporphyrin

		- [UV–vis](/source/Ultraviolet%E2%80%93visible_spectroscopy) readout for *meso*-tetraphenylporphyrin

		- Light-activated porphyrin. Monatomic oxygen. Cellular aging.

## Related species

### In nature

Several heterocycles related to porphyrins are found in nature, almost always bound to metal ions. These include

N4-macrocycle Cofactor name metal comment chlorin chlorophyll magnesium several versions of chlorophyll exist (sidechain; exception being chlorophyll c) bacteriochlorin bacteriochlorophyll (in part) magnesium several versions of bacteriochlorophyll exist (sidechain; some use a usual chlorin ring) sirohydrochlorin (an isobacteriochlorin) siroheme iron Important cofactor in sulfur assimilation biosynthetic intermediate en route to cofactor F430 and B12 corrin vitamin B12 cobalt several variants of B12 exist (sidechain) corphin Cofactor F430 nickel highly reduced macrocycle

### Synthetic

A **benzoporphyrin** is a porphyrin with a benzene ring fused to one of the pyrrole units. e.g. [verteporfin](/source/Verteporfin) is a benzoporphyrin derivative.[27]

#### Non-natural porphyrin isomers

Porphycene, first porphyrin isomer, synthesised from bipyrrole dialdehyde through [McMurry coupling reaction](/source/McMurry_reaction)

The first synthetic porphyrin [isomer](/source/Isomer) was reported by Emanual Vogel and coworkers in 1986.[28] This isomer [18]porphyrin-(2.0.2.0) is named as **porphycene**, and the central N4 Cavity forms a [rectangle](/source/Rectangle) shape as shown in figure.[29] Porphycenes showed interesting [photophysical](/source/Photochemistry) behavior and found versatile compound towards the [photodynamic therapy](/source/Photodynamic_therapy).[30] This result was followed by the preparation of [18]porphyrin-(2.1.0.1), named it as **corrphycene** or **porphycerin**.[31] Other non-natural porphyrins include [18]porphyrin-(2.1.1.0) and [18]porphyrin-(3.0.1.0) or **isoporphycene**.[32] The **N-confused porphyrins** feature one of the pyrrolic subunits with the nitrogen atoms facing outwards from the core of the macrocycle.[33][34]

Various reported Isomers of porphyrin

## See also

- [Porphyria](/source/Porphyria) – Metabolic disorders in which porphyrins build up in the body

- [Heme](/source/Heme) – Chemical coordination complex of an iron ion chelated to a porphyrin

- [Cytochrome P450](/source/Cytochrome_P450) – A class of enzymes containing heme

- [Chlorophyll](/source/Chlorophyll) – Closely related to porphyrin

- [Corroles](/source/Corrole) – A closely related class of molecules, including [vitamin B12](/source/Vitamin_B12)

- [Cofactor F430](/source/Cofactor_F430) contains porphyrin.

- [Phthalocyanine](/source/Phthalocyanine) and [tetrapyrazinoporphyrazine](/source/Tetrapyrazinoporphyrazine) are nitrogen-substituted porphyrins.

- [Tetraanthraporphyrin](/source/Tetraanthraporphyrin) – Extended porphyrin

## References

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## External links

Wikimedia Commons has media related to [Porphyrins](https://commons.wikimedia.org/wiki/Category:Porphyrins).

Look up ***[porphyrin](https://en.wiktionary.org/wiki/Special:Search/porphyrin)*** in Wiktionary, the free dictionary.

- *[Journal of Porphyrins and Phthalocyanines](https://www.worldscientific.com/worldscinet/jpp)*

- [Handbook of Porphyrin Science](https://web.archive.org/web/20100331125114/http://www.worldscibooks.com/chemistry/7376.html)

- [Porphynet – an informative site about porphyrins and related structures](https://web.archive.org/web/20180709131903/http://www.porphyrin.net/)

v t e Types of tetrapyrroles Bilanes (Linear) Bilirubin Biliverdin Stercobilinogen Stercobilin Urobilinogen Urobilin Phytobilins Phytochromobilin Phycobilins Phycoerythrobilin Phycocyanobilin Phycourobilin Phycoviolobilin Macrocycle Corrinoids Adenosylcobalamin Cyanocobalamin Methylcobalamin Pseudovitamin B12 Porphyrins Protoporphyrins Heme (b, c, a, o) Magnesium protoporphyrin Protoporphyrin IX Pterobilin Zinc protoporphyrin Phytoporphyrins Chlorophyll c Protochlorophyllide Reduced porphyrins Porphyrinogens Uroporphyrinogen (I, III) Coproporphyrinogen (I, III) Protoporphyrinogen IX Chlorins Chlorophyllide (a, b) Chlorophyll (a, b) Pheophytin (a, b) Bacteriochlorophyll c Bacteriochlorins Bacteriochlorophyll a Isobacteriochlorins Siroheme Sirohydrochlorin Corphins Cofactor F430

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Adapted from the Wikipedia article [Porphyrin](https://en.wikipedia.org/wiki/Porphyrin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Porphyrin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.