Fluorescein

Last updated
Fluorescein
Fluorescein 2.svg
Fluorescein-3D-balls.png
Fluorescein-sample.jpg
Names
Pronunciation /flʊəˈrɛsi.ɪn,flʊəˈrɛsiːn/
IUPAC name
3′,6′-dihydroxyspiro[isobenzofuran-1(3H),9′-[9H]xanthen]-3-one
Other names
Resorcinolphthalein, C.I. 45350, solvent yellow 94, D&C yellow no. 7, angiofluor, Japan yellow 201, soap yellow
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.017.302 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 219-031-8
KEGG
MeSH Fluorescein
PubChem CID
UNII
  • InChI=1S/C20H12O5/c21-11-5-7-15-17(9-11)24-18-10-12(22)6-8-16(18)20(15)14-4-2-1-3-13(14)19(23)25-20/h1-10,21-22H Yes check.svgY
    Key: GNBHRKFJIUUOQI-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C20H12O5/c21-11-5-7-15-17(9-11)24-18-10-12(22)6-8-16(18)20(15)14-4-2-1-3-13(14)19(23)25-20/h1-10,21-22H
    Key: GNBHRKFJIUUOQI-UHFFFAOYAZ
  • c1ccc2c(c1)C(=O)OC23c4ccc(cc4Oc5c3ccc(c5)O)O
Properties
C20H12O5
Molar mass 332.311 g·mol−1
Melting point 314 to 316 °C (597 to 601 °F; 587 to 589 K)
Slightly
Pharmacology
S01JA01 ( WHO )
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H319
P305, P338, P351
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Fluorescein is an organic compound and dye based on the xanthene tricyclic structural motif, formally belonging to triarylmethine dyes family. It is available as a dark orange/red powder slightly soluble in water and alcohol. It is used as a fluorescent tracer in many applications. [1]

Contents

The color of its aqueous solutions is green by reflection and orange by transmission (its spectral properties are dependent on pH of the solution), [2] as can be noticed in bubble levels, for example, in which fluorescein is added as a colorant to the alcohol filling the tube in order to increase the visibility of the air bubble contained within. More concentrated solutions of fluorescein can even appear red (because under these conditions nearly all incident emission is re-absorbed by the solution).

It is on the World Health Organization's List of Essential Medicines. [3]

Uses

Fluorescein sodium, the sodium salt of fluorescein, is used extensively as a diagnostic tool in the field of ophthalmology and optometry, where topical fluorescein is used in the diagnosis of corneal abrasions, corneal ulcers and herpetic corneal infections. It is also used in rigid gas permeable contact lens fitting to evaluate the tear layer under the lens. It is available as sterile single-use sachets containing lint-free paper applicators soaked in fluorescein sodium solution. [4]

The thyroxine ester of fluorescein is used to quantify the thyroxine concentration in blood. [1]

Fluorescein is also known as a color additive (D&C Yellow no. 7). The disodium salt form of fluorescein is known as uranine or D&C Yellow no. 8.

Fluorescein is a precursor to the red dye eosin Y by bromination. [1]

Safety

Oral and intravenous use of fluorescein can cause adverse reactions, including nausea, vomiting, hives, acute hypotension, anaphylaxis and related anaphylactoid reaction, [5] [6] causing cardiac arrest [7] and sudden death due to anaphylactic shock. [8] [9]

Intravenous use has the most reported adverse reactions, including sudden death, but this may reflect greater use rather than greater risk. Both oral and topical uses have been reported to cause anaphylaxis, [10] [11] including one case of anaphylaxis with cardiac arrest (resuscitated) following topical use in an eye drop. [7] Reported rates of adverse reactions vary from 1% to 6%. [12] [13] [14] [15] The higher rates may reflect study populations that include a higher percentage of persons with prior adverse reactions. The risk of an adverse reaction is 25 times higher if the person has had a prior adverse reaction. [14] The risk can be reduced with prior (prophylactic) use of antihistamines [16] and prompt emergency management of any ensuing anaphylaxis. [17] A simple prick test may help to identify persons at greatest risk of adverse reaction. [15]

Chemistry

Fluorescein under UV illumination Florescein.jpg
Fluorescein under UV illumination
Fluorescence excitation and emission spectra of fluorescein Fluorescein-spectra3.svg
Fluorescence excitation and emission spectra of fluorescein

The fluorescence of this molecule is very intense; peak excitation occurs at 495  nm and peak emission at 520 nm. Values for the deprotonated form in basic solution.[ citation needed ]

Fluorescein has a pKa of 6.4, [2] and its ionization equilibrium leads to pH-dependent absorption and emission over the range of 5 to 9. Also, the fluorescence lifetimes of the protonated and deprotonated forms of fluorescein are approximately 3 and 4 ns, which allows for pH determination from nonintensity based measurements. The lifetimes can be recovered using time-correlated single photon counting or phase-modulation fluorimetry. Upon exhaustive irradiation with visible light fluorescein decomposes to release phthalic and formic acids and carbon monoxide, effectively acting as a photoCORM. The remaining resorcinol rings react with singlet oxygen formed in situ to give oxidized, ring-opened products. [18]

Fluorescein has an isosbestic point (equal absorption for all pH values) at 460 nm.

Derivatives

Fluorescein isothiocyanate and 6-FAM phosphoramidite FITC FAM.png
Fluorescein isothiocyanate and 6-FAM phosphoramidite

Many derivatives of fluorescein are known. Examples are:

In oligonucleotide synthesis, several phosphoramidite reagents containing protected fluorescein, e.g. 6-FAM phosphoramidite 2, [19] are used for the preparation of fluorescein-labeled oligonucleotides.

The extent to which fluorescein dilaurate is broken down to yield lauric acid can be detected as a measure of pancreatic esterase activity.

Synthesis

Approximately 250 tons were produced in the year 2000. The method involves the fusion of phthalic anhydride and resorcinol, [1] similar to the route described by Adolf von Baeyer in 1871. [20] In some cases, acids such as zinc chloride and methanesulfonic acid are employed to accelerate the Friedel-Crafts reaction. [21] [22]

Preparation of Fluorescein.svg

Research

Fluorescein is a fluorophore commonly used in microscopy, in a type of dye laser as the gain medium, in forensics and serology to detect latent blood stains, and in dye tracing. Fluorescein has an absorption maximum at 494 nm and emission maximum of 512 nm (in water). The major derivatives are fluorescein isothiocyanate (FITC) and, in oligonucleotide synthesis, 6-FAM phosphoramidite.

Biosciences

In cellular biology, the isothiocyanate derivative of fluorescein is often used to label and track cells in fluorescence microscopy applications (for example, flow cytometry). Additional biologically active molecules (such as antibodies) may also be attached to fluorescein, allowing biologists to target the fluorophore to specific proteins or structures within cells. This application is common in yeast display.

Fluorescein can also be conjugated to nucleoside triphosphates and incorporated into a probe enzymatically for in situ hybridisation. The use of fluorescein amidite, shown below right, allows one to synthesize labeled oligonucleotides for the same purpose. Yet another technique termed molecular beacons makes use of synthetic fluorescein-labeled oligonucleotides. Fluorescein-labelled probes can be imaged using FISH, or targeted by antibodies using immunohistochemistry. The latter is a common alternative to digoxigenin, and the two are used together for labelling two genes in one sample. [23]

Fluorescein drops being instilled for an eye examination Fluorescin in dropper.jpg
Fluorescein drops being instilled for an eye examination

Intravenous or oral fluorescein is used in fluorescein angiography in research and to diagnose and categorize vascular disorders including retinal disease, macular degeneration, diabetic retinopathy, inflammatory intraocular conditions, and intraocular tumors. It is also being used increasingly during surgery for brain and spine tumors. [24]

Diluted fluorescein dye has been used to localise multiple muscular ventricular septal defects during open heart surgery and confirm the presence of any residual defects. [25]

The Gemini 4 spacecraft releases dye into the water, to aid location after splashdown, June 1965. Gemini 4 Recovery with Green Marker Dye - GPN-2000-001409.jpg
The Gemini 4 spacecraft releases dye into the water, to aid location after splashdown, June 1965.

Earth sciences

Fluorescein is used as a rather conservative flow tracer in hydrological tracer tests to help in understanding of water flow of both surface waters and groundwater. The dye can also be added to rainwater in environmental testing simulations to aid in locating and analyzing any water leaks, and in Australia and New Zealand as a methylated spirit dye.

As fluorescein solution changes its color depending on concentration, [26] it has been used as a tracer in evaporation experiments.

One of its more recognizable uses was in the Chicago River, where fluorescein was the first substance used to dye the river green on St. Patrick's Day in 1962. In 1966, environmentalists forced a change to a vegetable-based dye to protect local wildlife. [27]

Fluorescein dye solutions, typically 15% active, are commonly used as an aid to leak detection during hydrostatic testing of subsea oil and gas pipelines and other subsea infrastructure. Leaks can be detected by divers or ROVs carrying an ultraviolet light.

Plant science

Fluorescein has often been used to track water movement in groundwater to study water flow and observe areas of contamination or obstruction in these systems. The fluorescence that is created by the dye makes problem areas more visible and easily identified. A similar concept can be applied to plants because the dye can make problems in plant vasculature more visible. In plant science, fluorescein, and other fluorescent dyes, have been used to monitor and study plant vasculature, particularly the xylem, which is the main water transportation pathway in plants. This is because fluorescein is xylem-mobile and unable to cross plasma membranes, making it particularly useful in tracking water movement through the xylem. [28] Fluorescein can be introduced to a plant's veins through the roots or a cut stem. The dye is able to be taken up into the plant the same way as water and moves from the roots to the top of the plant due to a transpirational pull. [29] The fluorescein that has been taken up into the plant can be visualized under a fluorescent microscope.

See also

Related Research Articles

<span class="mw-page-title-main">Fluorescent tag</span>

In molecular biology and biotechnology, a fluorescent tag, also known as a fluorescent label or fluorescent probe, is a molecule that is attached chemically to aid in the detection of a biomolecule such as a protein, antibody, or amino acid. Generally, fluorescent tagging, or labeling, uses a reactive derivative of a fluorescent molecule known as a fluorophore. The fluorophore selectively binds to a specific region or functional group on the target molecule and can be attached chemically or biologically. Various labeling techniques such as enzymatic labeling, protein labeling, and genetic labeling are widely utilized. Ethidium bromide, fluorescein and green fluorescent protein are common tags. The most commonly labelled molecules are antibodies, proteins, amino acids and peptides which are then used as specific probes for detection of a particular target.

<span class="mw-page-title-main">Fluorophore</span> Agents that emit light after excitation by light

A fluorophore is a fluorescent chemical compound that can re-emit light upon light excitation. Fluorophores typically contain several combined aromatic groups, or planar or cyclic molecules with several π bonds.

<span class="mw-page-title-main">Fluorescein angiography</span> Technique for examining the circulation of the retina and choroid of the eye

Fluorescein angiography (FA), fluorescent angiography (FAG), or fundus fluorescein angiography (FFA) is a technique for examining the circulation of the retina and choroid using a fluorescent dye and a specialized camera. Sodium fluorescein is added into the systemic circulation, the retina is illuminated with blue-green light at a wavelength of 490 nanometers, and an angiogram is obtained by photographing the fluorescent green light that is emitted by the dye. The fluorescein is administered intravenously in intravenous fluorescein angiography (IVFA) and orally in oral fluorescein angiography (OFA). The test is a dye tracing method.

<span class="mw-page-title-main">Rhodamine</span> Family of derivatives of xanthene used as dyes, indicators and fluorescent tracers

Rhodamine is a family of related dyes, a subset of the triarylmethane dyes. They are derivatives of xanthene. Important members of the rhodamine family are rhodamine 6G, rhodamine 123, and rhodamine B. They are mainly used to dye paper and inks, but they lack the lightfastness for fabric dyeing.

The Alexa Fluor family of fluorescent dyes is a series of dyes invented by Molecular Probes, now a part of Thermo Fisher Scientific, and sold under the Invitrogen brand name. Alexa Fluor dyes are frequently used as cell and tissue labels in fluorescence microscopy and cell biology. Alexa Fluor dyes can be conjugated directly to primary antibodies or to secondary antibodies to amplify signal and sensitivity or other biomolecules.

<span class="mw-page-title-main">Fluorescein isothiocyanate</span> Chemical compound

Fluorescein isothiocyanate (FITC) is a derivative of fluorescein used in wide-ranging applications including flow cytometry. First described in 1942, FITC is the original fluorescein molecule functionalized with an isothiocyanate reactive group (−N=C=S), replacing a hydrogen atom on the bottom ring of the structure. It is typically available as a mixture of isomers, fluorescein 5-isothiocyanate (5-FITC) and fluorescein 6-isothiocyanate (6-FITC). FITC is reactive towards nucleophiles including amine and sulfhydryl groups on proteins. It was synthesized by Robert Seiwald and Joseph Burckhalter in 1958.

<span class="mw-page-title-main">Texas Red</span> Chemical compound

Texas Red or sulforhodamine 101 acid chloride is a red fluorescent dye, used in histology for staining cell specimens, for sorting cells with fluorescent-activated cell sorting machines, in fluorescence microscopy applications, and in immunohistochemistry. Texas Red fluoresces at about 615 nm, and the peak of its absorption spectrum is at 589 nm. The powder is dark purple. Solutions can be excited by a dye laser tuned to 595-605 nm, or less efficiently a krypton laser at 567 nm. The absorption extinction coefficient at 596 nm is about 85,000 M−1cm−1.

<span class="mw-page-title-main">Rhodamine B</span> Chemical compound

Rhodamine B is a chemical compound and a dye. It is often used as a tracer dye within water to determine the rate and direction of flow and transport. Rhodamine dyes fluoresce and can thus be detected easily and inexpensively with fluorometers.

<span class="mw-page-title-main">Rose bengal</span> Tetrachloro-tetraiodo-fluorescein used as stain

Rose bengal (4,5,6,7-tetrachloro-2',4',5',7'-tetraiodofluorescein) is a stain. Rose bengal belongs to the class of organic compounds called xanthenes. Its sodium salt is commonly used in eye drops to stain damaged conjunctival and corneal cells and thereby identify damage to the eye. The stain is also used in the preparation of Foraminifera for microscopic analysis, allowing the distinction between forms that were alive or dead at the time of collection.

<span class="mw-page-title-main">6-Carboxyfluorescein</span> Chemical compound

6-Carboxyfluorescein (6-FAM) is a fluorescent dye with an absorption wavelength of 495 nm and an emission wavelength of 517 nm. A carboxyfluorescein molecule is a fluorescein molecule with a carboxyl group added. They are commonly used as a tracer agents. It is used in the sequencing of nucleic acids and in the labeling of nucleotides.

Dye tracing is a method of tracking and tracing various flows using dye as a flow tracer when added to a liquid. Dye tracing may be used to analyse the flow of the liquid or the transport of objects within the liquid. Dye tracking may be either qualitative, showing the presence of a particular flow, or quantitative, when the amount of the traced dye is measured by special instruments.

The DyLight Fluor family of fluorescent dyes are produced by Dyomics in collaboration with Thermo Fisher Scientific. DyLight dyes are typically used in biotechnology and research applications as biomolecule, cell and tissue labels for fluorescence microscopy, cell biology or molecular biology.

<span class="mw-page-title-main">Dansyl chloride</span> Chemical compound

Dansyl chloride or 5-(dimethylamino)naphthalene-1-sulfonyl chloride is a reagent that reacts with primary amino groups in both aliphatic and aromatic amines to produce stable blue- or blue-green–fluorescent sulfonamide adducts. It can also be made to react with secondary amines. Dansyl chloride is widely used to modify amino acids; specifically, protein sequencing and amino acid analysis. Dansyl chloride may also be denoted DNSC. Likewise, a similar derivative, dansyl amide is known as DNSA.

<span class="mw-page-title-main">Phloxine</span> Chemical compound

Phloxine B is a water-soluble red dye used for coloring drugs and cosmetics in the United States and coloring food in Japan. It is derived from fluorescein, but differs by the presence of four bromine atoms at positions 2, 4, 5 and 7 of the xanthene ring and four chlorine atoms in the carboxyphenyl ring. It has an absorption maximum around 540 nm and an emission maximum around 564 nm. Apart from industrial use, phloxine B has functions as an antimicrobial substance, viability dye and biological stain. For example, it is used in hematoxylin-phloxine-saffron (HPS) staining to color the cytoplasm and connective tissue in shades of red.

<span class="mw-page-title-main">Indocyanine green</span> Chemical compound

Indocyanine green (ICG) is a cyanine dye used in medical diagnostics. It is used for determining cardiac output, hepatic function, liver and gastric blood flow, and for ophthalmic and cerebral angiography. It has a peak spectral absorption at about 800 nm. These infrared frequencies penetrate retinal layers, allowing ICG angiography to image deeper patterns of circulation than fluorescein angiography. ICG binds tightly to plasma proteins and becomes confined to the vascular system. ICG has a half-life of 150 to 180 seconds and is removed from circulation exclusively by the liver to bile.

<span class="mw-page-title-main">Fluo-3</span> Chemical compound

Fluo-3 is a fluorescence indicator of intracellular calcium (Ca2+), developed by Roger Y. Tsien. It is used to measure Ca2+ inside living cells in flow cytometry, and confocal laser scanning microscopy using visible light excitation (compatible with argon laser sources operating at 488 nm). Fluo-3 and derivatives (Fluo-4, Fluo-5 etc) have also been widely used with two-photon excitation microscopy. Fluo-3 is an essentially nonfluorescent compound, but upon binding of Ca2+ its fluorescence increases sharply with an emission maximum at 525 nm suitable for conventionally used detectors designed for fluorescein isothiocyanate (FITC) measurements. This large change in fluorescence coupled with a good yield of photons provides very high contrast which allowed the detection of microscopic Ca2+ release events inside cells called "Calcium sparks". Whereas the salts of fluo-3 are unable to penetrate cells, loading can be achieved using its acetoxymethyl (AM) ester derivative. Once inside the cell, unspecific esterases cleave the ester effectively trapping fluo-3.

<span class="mw-page-title-main">Fluorescence polarization immunoassay</span> Class of invitro biochemical test

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<span class="mw-page-title-main">Indocyanine green angiography</span> Diagnostic procedure

Indocyanine green angiography (ICGA) is a diagnostic procedure used to examine choroidal blood flow and associated pathology. Indocyanine green (ICG) is a water soluble cyanine dye which shows fluorescence in near-infrared (790–805 nm) range, with peak spectral absorption of 800-810 nm in blood. The near infrared light used in ICGA penetrates ocular pigments such as melanin and xanthophyll, as well as exudates and thin layers of sub-retinal vessels. Age-related macular degeneration is the third main cause of blindness worldwide, and it is the leading cause of blindness in industrialized countries. Indocyanine green angiography is widely used to study choroidal neovascularization in patients with exudative age-related macular degeneration. In nonexudative AMD, ICGA is used in classification of drusen and associated subretinal deposits.

<span class="mw-page-title-main">3-Hydroxyisonicotinaldehyde</span> Chemical compound

3-Hydroxyisonicotinaldehyde (HINA), also known as 3-hydroxypyridine-4-carboxaldehyde, is a derivative of pyridine, with hydroxyl and aldehyde substituents. It has been studied as a simple analogue of vitamin B6. In 2020, it was reported as having the lowest molecular weight of all dyes which exhibit green fluorescence.

<span class="mw-page-title-main">Confocal endoscopy</span>

Confocal endoscopy, or confocal laser endomicroscopy (CLE), is a modern imaging technique that allows the examination of real-time microscopic and histological features inside the body. In the word "endomicroscopy", endo- means "within" and -skopein means "to view or observe". CLE, also known as "optical biopsy", can analyse histology and cytology features of a tissue which otherwise is only possible by tissue biopsy. Similar to confocal microscopy, the laser in CLE filtered by the pinhole excites the fluorescent dye through a beam splitter and objective lens. The fluorescent emission then follows similar paths into the detector. A pinhole is used to select emissions from the desired focal plane. Two categories of CLE exist, namely probe-based (pCLE) and the less common endoscopy-based endoscopy (eCLE).

References

  1. 1 2 3 4 Gessner, Thomas; Mayer, Udo (2000). "Triarylmethane and Diarylmethane Dyes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a27_179. ISBN   978-3527306732.
  2. 1 2 Sjöback, Robert; Nygren, Jan; Kubista, Mikael (1995-06-01). "Absorption and fluorescence properties of fluorescein". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 51 (6): L7–L21. Bibcode:1995AcSpA..51L...7S. doi:10.1016/0584-8539(95)01421-P. ISSN   1386-1425.
  3. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  4. ↑ "New Drugs". Can Med Assoc J . 80 (12): 997–998. 1959. PMC   1831125 . PMID   20325960.
  5. ↑ "The diagnosis and management of anaphylaxis. Joint Task Force on Practice Parameters, American Academy of Allergy, Asthma and Immunology, American College of Allergy, Asthma and Immunology, and the Joint Council of Allergy, Asthma and Immunology" (PDF). The Journal of Allergy and Clinical Immunology. 101 (6 Pt 2): S465–528. 1998. doi:10.1016/S0091-6749(18)30566-9. PMID   9673591. Archived (PDF) from the original on 2015-07-24.
  6. ↑ The diagnosis and management of anaphylaxis: an updated practice parameter. Archived 2007-08-05 at the Wayback Machine National Guideline Clearinghouse.
  7. 1 2 El Harrar, N; Idali, B; Moutaouakkil, S; El Belhadji, M; Zaghloul, K; Amraoui, A; Benaguida, M (1996). "Anaphylactic shock caused by application of fluorescein on the ocular conjunctiva". Presse Médicale. 25 (32): 1546–7. PMID   8952662.
  8. ↑ Fineschi V, Monasterolo G, Rosi R, Turillazzi E (1999). "Fatal anaphylactic shock during a fluorescein angiography". Forensic Sci. Int. 100 (1–2): 137–42. doi:10.1016/S0379-0738(98)00205-9. PMID   10356782.
  9. ↑ Hitosugi M, Omura K, Yokoyama T, Kawato H, Motozawa Y, Nagai T, Tokudome S (2004). "An autopsy case of fatal anaphylactic shock following fluorescein angiography: a case report". Med Sci Law. 44 (3): 264–5. doi:10.1258/rsmmsl.44.3.264. PMID   15296251. S2CID   71681503.
  10. ↑ Kinsella FP, Mooney DJ (1988). "Anaphylaxis following oral fluorescein angiography". Am. J. Ophthalmol. 106 (6): 745–6. doi:10.1016/0002-9394(88)90716-7. PMID   3195657.
  11. ↑ Gómez-Ulla F, Gutiérrez C, Seoane I (1991). "Severe anaphylactic reaction to orally administered fluorescein". Am. J. Ophthalmol. 112 (1): 94. doi:10.1016/s0002-9394(14)76222-1. PMID   1882930.
  12. ↑ Kwan AS, Barry C, McAllister IL, Constable I (2006). "Fluorescein angiography and adverse drug reactions revisited: the Lions Eye experience". Clin. Experiment. Ophthalmol. 34 (1): 33–8. doi:10.1111/j.1442-9071.2006.01136.x. PMID   16451256. S2CID   32809716.
  13. ↑ Jennings BJ, Mathews DE (1994). "Adverse reactions during retinal fluorescein angiography". J Am Optom Assoc. 65 (7): 465–71. PMID   7930354.
  14. 1 2 Kwiterovich KA, Maguire MG, Murphy RP, Schachat AP, Bressler NM, Bressler SB, Fine SL (1991). "Frequency of adverse systemic reactions after fluorescein angiography. Results of a prospective study". Ophthalmology. 98 (7): 1139–42. doi: 10.1016/s0161-6420(91)32165-1 . PMID   1891225.
  15. 1 2 Matsuura M, Ando F, Fukumoto K, Kyogane I, Torii Y, Matsuura M (1996). "[Usefulness of the prick test for anaphylactoid reaction in intravenous fluorescein administration]". Nippon Ganka Gakkai Zasshi (in Japanese). 100 (4): 313–7. PMID   8644545.
  16. ↑ Ellis PP, Schoenberger M, Rendi MA (1980). "Antihistamines as prophylaxis against side reactions to intravenous fluorescein". Trans Am Ophthalmol Soc. 78: 190–205. PMC   1312139 . PMID   7257056.
  17. ↑ Yang CS, Sung CS, Lee FL, Hsu WM (2007). "Management of anaphylactic shock during intravenous fluorescein angiography at an outpatient clinic". J Chin Med Assoc. 70 (8): 348–9. doi: 10.1016/S1726-4901(08)70017-0 . PMID   17698436.
  18. ↑ Martínek, Marek; Ludvíková, Lucie; Šranková, Mária; Navrátil, Rafael; Muchová, Lucie; Huzlík, Jiří; Vítek, Libor; Klán, Petr; Šebej, Peter (2022-11-03). "Common xanthene fluorescent dyes are visible-light activatable CO-releasing molecules". Organic & Biomolecular Chemistry. 21 (1): 93–97. doi:10.1039/D2OB01823C. ISSN   1477-0539. PMID   36326159. S2CID   253266074.
  19. ↑ Brush, C. K. "Fluorescein Labelled Phosphoramidites". U.S. patent 5,583,236 . Priority date July 19, 1991.
  20. ↑ Baeyer, Adolf (1871) "Uber ein neue Klasse von Farbstoffen" Archived 2016-06-29 at the Wayback Machine (On a new class of dyes), Berichte der Deutschen chemischen Gesellschaft zu Berlin, 4 : 555-558; see p. 558.
  21. ↑ Sun, W. C.; Gee, K. R.; Klaubert, D. H.; Haugland, R. P. (1997). "Synthesis of Fluorinated Fluoresceins". The Journal of Organic Chemistry. 62 (19): 6469–6475. doi:10.1021/jo9706178.
  22. ↑ Burgess, Kevin; Ueno, Yuichiro; Jiao, Guan-Sheng (2004). "Preparation of 5- and 6-Carboxyfluorescein". Synthesis. 2004 (15): 2591–2593. doi:10.1055/s-2004-829194.
  23. ↑ Noga E. J., Udomkusonsri, P. (2002). "Fluorescein: A Rapid, Sensitive, Nonlethal Method for Detecting Skin Ulceration in Fish" (PDF). Vet Pathol. 39 (6): 726–731(6). doi:10.1354/vp.39-6-726. PMID   12450204. S2CID   46010136. Archived from the original (PDF) on 2007-09-28. Retrieved 2007-07-16.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  24. ↑ Cardali, Salvatore Massimiliano; Ricciardo, Giuseppe; Garufi, Giada; Raffa, Giovanni; Messineo, Francesco; Scalia, Gianluca; Conti, Alfredo; Germanò, Antonino (2022). "Fluorescein-guided surgery for intradural spinal tumors: A single-center experience". Brain and Spine. 2: 100908. doi:10.1016/j.bas.2022.100908. PMC   9560644 . PMID   36248155.
  25. ↑ Mathew, Thomas (2014). "Use of Fluorescein Dye to Identify Residual Defects". Ann Thorac Surg. 97 (1): e27-8. doi:10.1016/j.athoracsur.2013.10.059. ISSN   0003-4975. PMID   24384220.
  26. ↑ Käss, W. Tracing Technique in Geohydrology. Rotterdam: Balkema.
  27. ↑ The Story Behind Dyeing the River Green. Greenchicagoriver.com. Retrieved on 2014-08-28.
  28. ↑ Salih, Anya; Tjoelker, Mark G.; Renard, Justine; Pfautsch, Sebastian (2015-03-01). "Phloem as Capacitor: Radial Transfer of Water into Xylem of Tree Stems Occurs via Symplastic Transport in Ray Parenchyma". Plant Physiology. 167 (3): 963–971. doi:10.1104/pp.114.254581. ISSN   0032-0889. PMC   4348778 . PMID   25588734.
  29. ↑ Duran-Nebreda S, Bassel G (July 2017). "Fluorescein Transport Assay to Assess Bulk Flow of Molecules Through the Hypocotyl in Arabidopsis thaliana". Bio-Protocol. 8 (7): e2791. doi: 10.21769/bioprotoc.2791 . PMC   8275252 . PMID   34286014.
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