WO2015142130A1 - Procédé de détection de porphyrine dans un échantillon biologique par lc-ms/ms - Google Patents

Procédé de détection de porphyrine dans un échantillon biologique par lc-ms/ms Download PDF

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WO2015142130A1
WO2015142130A1 PCT/KR2015/002779 KR2015002779W WO2015142130A1 WO 2015142130 A1 WO2015142130 A1 WO 2015142130A1 KR 2015002779 W KR2015002779 W KR 2015002779W WO 2015142130 A1 WO2015142130 A1 WO 2015142130A1
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porphyrin
biological sample
blood
samples
methanol
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PCT/KR2015/002779
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Young Shin Lee
Seung Woo Kang
Yeoun Hur
Sang Beom Han
Ju Hee Jung
Kwang Jin Kim
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Inernational Scientific Standards, Inc.
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Publication of WO2015142130A1 publication Critical patent/WO2015142130A1/fr

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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/62—Detectors specially adapted therefor
    • G01N30/72—Mass spectrometers
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/72—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood pigments, e.g. haemoglobin, bilirubin or other porphyrins; involving occult blood
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
    • G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
    • G01N2030/8813—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample biological materials
    • G01N2030/8822—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample biological materials involving blood
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2560/00—Chemical aspects of mass spectrometric analysis of biological material
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/62—Detectors specially adapted therefor
    • G01N30/72—Mass spectrometers
    • G01N30/7233—Mass spectrometers interfaced to liquid or supercritical fluid chromatograph

Definitions

  • the present invention relates to a method for detecting porphyrin by using LC-MS/MS (Liquid Chromatography coupled to Tandem Mass Spectrometry).
  • porphyrin makes up heme, which is a component of hemoglobin. Porphyrin is also a component of cytochrome, which plays an important role in oxidation and reduction in vivo. Further, porphyrin is a component of chlorophyll, which is involved in photosynthesis.
  • Porphyrin is related to various diseases.
  • a typical example of porphyrin-related disease is porphyria, which is caused by accumulation of porphyrin and iron in internal organs caused by the lack of enzymes involved in the synthesis of heme due to inherited or acquired genetic defects.
  • the common symptoms of Porphyria are neurovisceral or cutaneous symptoms. Neurovisceral symptoms appear after puberty and are more common in women, and include acute seizures, abdominal pain, and damaged sensorimotor nervous systems. Cutaneous symptoms, which appear after 30s in most cases, include excessive peeling, blisters and scars after being exposed to sunlight. Hepatopathy associated with the accumulation of porphyrin may appear together.
  • porphyrin is receiving attention as a biomarker of autism or autistic spectrum disorder.
  • concentration of porphyrin such as coproporphyrin, hexacarboxylporphyrin and pentacarboxylporphyrin is high in the urine of children with autism.
  • excessive amount of porphyrin causes heavy metal such as mercury to remain longer in vivo and triggers autism in result.
  • chelators such as DMSA or ALA improved the symptoms of autism.
  • Porphyrin is excreted in urine, feces and bile, and is particularly released in a large amount in the urine. Porphyrin is also present in blood, but its amount is too small to detect in tests. Tests for porphyrin are usually performed by using LC-MS/MS. However, it is hard to detect a small amount of porphyrin with conventional methods.
  • the purpose of the present invention is to provide a method for detecting porphyrin in a biological sample using LC-MS/MS, wherein the method includes pretreating the biological sample with a mixed solution of methanol and strong acid.
  • the present invention provides a method for detecting porphyrin in a biological sample, comprising: 1) obtaining a biological sample from a subject; 2) pretreating the biological sample with a mixed solution of methanol and strong acid; and 3) analyzing the pretreated biological sample by using LC-MS/MS.
  • the subject may be a human.
  • the pre-treatment of 2) may be performed by bringing the biological sample into contact with the mixed solution of methanol and strong acid or mixing the biological sample with the mixed solution of methanol and strong acid.
  • porphyrin commonly denotes compounds having the following basic structure and derivatives thereof.
  • porphyrin may vary. Protoporphyrin, harderoporphyrin, coproporphyrin, pentacarboxylporphyrin, hexacarboxylporphyrin, heptacarboxylporphyrin, and uroporphyrin, etc. are generally present in blood, and excreted in urine and feces. They are all referred to as porphyrin. Furthermore, there are type I, II, and III for each porphyrin, and they are all referred to as porphyrin.
  • porphyrin include one or more carboxyl groups.
  • protoporphyrin has two carboxyl groups
  • harderoporphyrin has three carboxyl groups
  • coproporphyrin has four carboxyl groups
  • pentacarboxylporphyrin has five carboxyl groups
  • hexacarboxylporphyrin has six carboxyl groups
  • heptacarboxylporphyrin has seven carboxyl groups
  • uroporphyrin has eight carboxyl groups.
  • the porphyrin is more soluble to water and more likely to be excreted in urine. Porphyrins with 4 carboxyl groups tend to be excreted in urine or feces, and harderoporphyrin or protoporphyrin tend to be excreted in feces.
  • LC-MS/MS Liquid Chromatography coupled to Tandem Mass Spectrometry
  • LC-MS Liquid Chromatography coupled to Tandem Mass Spectrometry
  • a sample is injected into the column by using HPLC and the components contained in the sample are separated. Then the components enter the Mass spectrometer and are ionized, and show signal peaks at different times, from which the corresponding materials may be identified.
  • LC-MS/MS which has more than one (typically two) mass spectrometers, enables more accurate analysis of materials. Since LC-MS/MS is capable of separating materials in samples and identifying the materials, it is widely used in analysis of a variety of materials.
  • the method of the present invention includes pretreating the obtained biological sample with the mixed solution of methanol and strong acid, and thereby porphyrin is esterified so that the carboxyl group is substituted with a methyl ester group and the produced water is removed, ultimately enabling precise detection of porphyrin.
  • the method for the present invention is able to detect a small amount of porphyrin, it is more useful when the amount of biological sample to be obtained is small.
  • One example where only a small amount of sample can be obtained is the case of newborn infants. Since the newborn infants are small in size and very sensitive to stimulation, the number of times obtaining biological samples and the amount of obtainable biological samples are limited.
  • the method of the present invention it is possible to detect porphyrin in a droplet of blood, which is about 3 ⁇ L.
  • the subjects include but not limited to a baby within one month of birth, more preferably seven days of birth, and much more preferably 72 hours of birth.
  • One example the method of the present invention can be utilized is the neonatal screening tests.
  • Some of congenital metabolic disorders may cause irreparable damage upon late diagnosis but such damage may be prevented by treating in early stage.
  • the Korean Government supports neonatal screening tests for six kinds of congenital metabolic disorders with high incidence rate, and most parents additionally perform tests for the other dozens of diseases. These tests are carried out in a manner that the blood is drawn from the heel of a 3 ⁇ 7 day-old baby, dropped on a blood filter paper, dried, and analyzed in lab.
  • the blood filter paper contains only about 3 ⁇ L of blood. Since the method of the present invention enables the detection of porphyrin using blood of the blood filter paper, there is no need to obtain more biological sample from a subject to detect porphyrin.
  • the porphyrins include but not limited to porphyrins with four or more carboxyl groups, such as coproporphyrin, pentacarboxylporphyrin, hexacarboxylporphyrin, heptacarboxylporphyrin, or uroporphyrin.
  • the method of the present invention is effective in detecting porphyrin from a biological sample containing a small amount of porphyrin.
  • the biological samples in 1) include but not limited to blood, for example, whole blood, plasma and serum.
  • the biological samples in 1) include but not limited to urine, feces, and bile.
  • the mixing ratio of methanol and strong acid in 2) is 9:1 ⁇ 8:2 (v/v), and preferably 9:1.
  • the mixing ratio is not limited thereto.
  • 1) may include:
  • eluting the biological sample in c) may be conducted by bringing formic acid into contact with the blood filter paper on which the biological sample was dropped.
  • formic acid enables effective elution of the blood contained in the porous blood filter paper.
  • 0.5 M formic acid in distilled water can be used.
  • concentration of the solution which can be used in the method herein is not limited thereto.
  • the present invention By using the present invention, a small amount of porphyrin can be detected effectively. Accordingly, it is possible to detect porphyrin from biological samples containing a small amount of porphyrin such as blood. Even in the case where the number of times obtaining biological samples and the amount of obtainable biological samples are very limited, such as newborn infants, a precise detection of porphyrin is possible. Therefore, the method of the present invention can be utilized for early diagnosis of porphyrin-related diseases.
  • FIG. 1 is a schematic illustration of a blood filter paper
  • FIG. 2A illustrates the structures of coproporphyrin (CP), pentacarboxylporphyrin (PP), hexacarboxylporphyrin (HexaP), heptacarboxylporphyrin (HeptaP), uroporphyrin (UP), and coproporphyrin I- 15 N 4
  • FIG. 2B illustrates the structures of their esterified forms
  • FIG. 3A illustrates the results of mass analysis of CP, PP, HexaP, HeptaP, and UP
  • FIG.3B illustrates the results of mass analysis of their esterified forms
  • FIG. 4A illustrates the results of analysis of LC-MS/MS of a blank
  • FIG. 4B illustrates the results of analysis of LC-MS/MS of a 50 nmol/L CPTE calibration solution
  • FIG. 5A illustrates the results of analysis of LC-MS/MS of a blank
  • FIG. 5B illustrates the results of analysis of LC-MS/MS of a 50 nmol/L PPPE calibration solution
  • FIG. 6A illustrates the results of analysis of LC-MS/MS of a blank
  • FIG. 6B illustrates the results of analysis of LC-MS/MS of a 50 nmol/L HexaPHE calibration solution
  • FIG. 7A illustrates the results of analysis of LC-MS/MS of a blank
  • FIG. 7B illustrates the results of analysis of LC-MS/MS of a 50 nmol/L HeptaPHE calibration solution
  • FIG. 8A illustrates the results of analysis of LC-MS/MS of a blank
  • FIG. 8B illustrates the results of analysis of LC-MS/MS of a 50 nmol/L UPOE calibration solution.
  • Example 1 Testing instruments, testing devices, and materials
  • LC-MS/MS used in the Examples herein includes the mass spectrometers and columns listed in the following Table 1.
  • testing devices used in the Examples herein are as in the Table 2 below.
  • CP, PP, HexaP, HeptaP, and UP which were purchased from Frontier Scientific, were added to the blood prepared in (1), and solutions containing the above compounds at a concentration of 10 nmol/L respectively were prepared.
  • Each of the prepared solutions was dropped on a blood filter paper schematically illustrated in FIG. 1, and dried at room temperature for at least 3 hours out of sunlight to prepare control samples (dried blood spot samples). Then 200 ⁇ L of 0.5 M formic acid in DW was added to the control sample to elute the compounds from the blood filter paper.
  • CP, PP, HexaP, HeptaP, and UP which were purchased from Frontier Scientific, were added to the blood prepared in (1), and solutions containing the above compounds at a concentration of 10 nmol/L respectively were prepared.
  • Each of the prepared solutions was dropped on a blood filter paper schematically illustrated in FIG. 1, and dried at room temperature for at least 3 hours out of sunlight to prepare testing samples (dried blood spot samples).
  • CP, PP, HexaP, HeptaP, UP and coproporphyrin I- 15 N 4 were esterified via the reaction mechanism below to coproporphyrin tetramethyl ester (CPTE), pentacarboxylporphyrin pentamethyl ester (PPPE), hexacarboxylporphyrin hexamethyl ester (HexaPHE), heptacarboxylporphyrin heptamethyl ester (HeptaPHE), uroporphyrin octamethyl ester (UPOE), and coproporphyrin I- 15 N 4 tetramethyl ester, respectively.
  • CPTE coproporphyrin tetramethyl ester
  • PPPE pentacarboxylporphyrin pentamethyl ester
  • HexaPHE hexacarboxylporphyrin hexamethyl ester
  • HeptaPHE heptacar
  • the X axis represents time (min) and the Y axis represents the concentration (cps).
  • Each peak corresponds to CPTE, PPPE, HexaPHE, HeptaPHE, and UPOE from the right. Since the mass of each compound is increased upon esterification, the peaks of FIG. 3B were shifted rightward compared to FIG. 3A.
  • Calibration standards and quality control (QC) samples were prepared as follows, and measured to check system suitability, specificity, carry-over, accuracy and precision, thereby evaluating whether the tests of Example 3 were appropriately performed.
  • CP 0.75 mg of CP, 0.86 mg of PP, 0.91 mg of HexaP, 0.96 mg of HeptaP, and 1.00 mg of UP were weighed, dissolved in 100 mL of 6 M formic acid in DW, to prepare 10,000 nmol/L stock solutions for CP, PP, HexaP, HeptaP, and UP, respectively. The stock solutions were then frozen and stored.
  • the working solutions for CP, PP, HexaP, HeptaP, and UP prepared in (1) were subjected to serial dilution with 6 M formic acid as shown in Table 7 below, to prepare QC solutions.
  • the kinds of solutions taken in Table 7 below ((A), (E), (F)) are as represented in Table 6.
  • QH denotes high-concentration QC solution (H: High)
  • QM denotes medium-concentration QC solution (M: Medium)
  • QL denotes low-concentration QC solution (L: Low)
  • LLOQ denotes a QC solution having a concentration corresponding to the lowest limit of quantification.
  • Each of the prepared calibration solutions was dropped on the blood filter paper as schematically illustrated in FIG. 1, and dried at room temperature for at least 3 hours out of sunlight to prepare calibration standards (dried blood spot samples).
  • the suitability of the present tester to ensure objectivity of the tests of Example 3 was evaluated as below. S1, among the calibration standards, and QL, among the QC samples, were injected into LC-MS/MS to ensure sensitivity. As an acceptance criterion for system suitability, the precision (CV, %) of the peak area ratio of each of CPTE, PPPE, HexaPHE, HeptaPHE, and UPOE relative to the internal standard is 10% or less in principle, but was set to 15% in the present tests because five kinds of materials were analyzed simultaneously.
  • the sample was determined to be free of any material interfering the subject material.
  • FIGS. 4A to 8A show the results of mass analysis of the blanks
  • FIGS. 4B to 8B show the results of analysis of each compound.
  • the blank does not include any material showing a peak at 8.59 min, which corresponds to the peak of CPTE.
  • FIGS. 5A and 5B it can be understood that the blank does not include any material showing a peak at 7.64 min, which corresponds to the peak of PPPE.
  • FIGS. 4A to 8A show the results of mass analysis of the blanks
  • FIGS. 4B to 8B show the results of analysis of each compound.
  • the blank does not include any material showing a peak at 8.59 min, which corresponds to the peak of CPTE.
  • the blank does not include any material showing a peak at 7.64 min, which corresponds to the peak of PPPE.
  • the blank does not include any material showing a peak at 6.88 min, which corresponds to the peak of HexaPHE.
  • FIGS. 7A and 7B it can be understood that the blank does not include any material showing a peak at 6.24 min, which corresponds to the peak of HeptaPHE.
  • FIGS. 8A and 8B it can be understood that the blank does not include any material showing a peak at 5.77 min, which corresponds to the peak of UPOE. Accordingly, the porphyrin-free whole blood used in the tests did not include any material that interfere CPTE, PPPE, HexaPHE, HeptaPHE, and UPOE.
  • a calibration curve was drawn, from which correlation coefficients were determined.
  • An acceptance criterion is as follows: a deviation from the nominal concentration at LOQ has to be within 20% and a deviation from the nominal concentration at a concentration other than LOQ has to be within 15%, where r (correlation coefficient) has to be 0.98 or more.
  • the correlation coefficient (r) in the concentration range of 0.2 ⁇ 50 nmol/L is 0.9982 ⁇ 0.9999 for CPTE, 0.9815 ⁇ 0.9999 for PPPE, 0.9958 ⁇ 0.9999 for HexaPHE, 0.9938 ⁇ 0.9986 for HeptaPHE, and 0.9980 ⁇ 0.9990 for UPOE, all of which were equal to or higher than the acceptance criterion, and the accuracy results satisfied the acceptance criterion.
  • the specific numerical values thereof are provided in Tables 12 to 16 below.
  • Accuracy was expressed as a percentage (%) of the value obtained in such a manner that the numerical values obtained from injecting QC samples into LC-MS/MS were substituted into the calibration curves to give the mean concentration that was then divided by the concentration of the actual QC samples as known. Five tests were performed per day using QH, QM, QL, and LLOQ samples to calculate intra-day accuracy, and the tests were repeated for five days to calculate inter-day accuracy.
  • the precision was expressed as a percentage (%) of the value obtained in such a manner that the numerical values resulting from injecting the QC samples in LC-MS/MS were divided by the mean value of the peak area ratios of CPTE, PPPE, HexaPHE, HeptaPHE, and UPOE and coproporphyrin tetramethyl ester I- 15 N 4 as the internal standard. Five tests were performed per day using QH, QM, QL, and LLOQ samples to calculate intra-day precision, and the tests were repeated for five days to calculate inter-day precision.
  • CPTE precision of CPTE was 4.35%, 4.76%, 9.20% and 6.48% at LLOQ, QL, QM and QH, respectively.
  • accuracy of CPTE was 114.63%, 109.10%, 88.06% and 106.51% at LLOQ, QL, QM and QH, respectively.
  • the specific numerical values thereof are provided in Table 17 below.
  • the precision of PPPE was 4.14%, 7.58%, 5.93% and 5.39% at LLOQ, QL, QM and QH, respectively, and the accuracy of PPPE was 108.69%, 103.64%, 92.87% and 93.32% at LLOQ, QL, QM and QH, respectively.
  • the specific numerical values thereof are provided in Table 18 below.
  • HexaPHE The precision of HexaPHE was 11.53%, 4.88%, 2.63% and 2.28% at LLOQ, QL, QM and QH, respectively, and the accuracy of HexaPHE was 94.13%, 86.06%, 86.74% and 85.20% at LLOQ, QL, QM and QH, respectively.
  • the specific numerical values thereof are provided in Table 19 below.
  • HeptaPHE The precision of HeptaPHE was 17.79%, 7.57%, 14.27% and 13.15% at LLOQ, QL, QM and QH, respectively, and the accuracy of HeptaPHE was 104.07%, 101.50%, 93.47% and 103.24% at LLOQ, QL, QM and QH, respectively.
  • the specific numerical values thereof are provided in Table 20 below.
  • the precision of UPOE was 4.35%, 4.76%, 9.20% and 6.48% at LLOQ, QL, QM and QH, respectively, and the accuracy of UPOE was 114.63%, 109.10%, 88.06% and 106.51% at LLOQ, QL, QM and QH, respectively.
  • the specific numerical values thereof are provided in Table 21 below.
  • CPTE precision of CPTE was 4.80%, 12.11%, 12.71% and 7.14% at LLOQ, QL, QM and QH, respectively.
  • accuracy of CPTE was 114.72%, 103.08%, 97.49% and 109.05% at LLOQ, QL, QM and QH, respectively.
  • the specific numerical values thereof are provided in Table 22 below.
  • the precision of PPPE was 3.99%, 10.61%, 6.46% and 8.85% at LLOQ, QL, QM and QH, respectively.
  • the accuracy of PPPE was 111.49%, 102.53%, 101.14% and 102.60% at LLOQ, QL, QM and QH, respectively.
  • the specific numerical values thereof are provided in Table 23 below.
  • the precision of HexaPHE was 8.30%, 6.91%, 10.91% and 12.62% at LLOQ, QL, QM and QH, respectively.
  • the accuracy of HexaPHE was 99.32%, 94.33%, 100.69% and 103.69% at LLOQ, QL, QM and QH, respectively.
  • the specific numerical values thereof are provided in Table 24 below.
  • HeptaPHE The precision of HeptaPHE was 9.11%, 12.37%, 13.37% and 10.55% at LLOQ, QL, QM and QH, respectively.
  • the accuracy of HeptaPHE was 106.66%, 104.24%, 100.13% and 104.72% at LLOQ, QL, QM and QH, respectively.
  • the specific numerical values thereof are provided in Table 25 below.

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Abstract

La présente invention concerne un procédé de détection de prophyrine par LC-MS/MS par prétraitement d'un échantillon biologique. Ce procédé est très efficace dans la détection d'une faible quantité de porphyrine. En conséquence, il est possible de détecter la porphyrine dans des échantillons biologiques qui contiennent une faible quantité de porphyrine tels que du sang. De plus, même dans le cas où le nombre de fois que l'obtention d'échantillons biologiques et la quantité d'échantillons biologiques pouvant être obtenue sont très limités, tels que des nourrissons, une détection précise de la porphyrine est possible. Par conséquent, ce procédé peut être utilisé pour un diagnostic précoce de maladies liées à la porphyrine.
PCT/KR2015/002779 2014-03-21 2015-03-20 Procédé de détection de porphyrine dans un échantillon biologique par lc-ms/ms WO2015142130A1 (fr)

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
WO2017082915A1 (fr) * 2015-11-12 2017-05-18 Halliburton Energy Services, Inc. Détection de porphyrines dans des formations souterraines
GB2557801A (en) * 2015-11-12 2018-06-27 Haliburton Energy Services Inc Detection of porphyrins in subterranean formations

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