haematoxylin

Haematoxylin
Names
	IUPAC name 7,11b-Dihydroindeno[2,1-c]chromene-3,4,6a,9,10(6H)-pentol
	Other names Hematoxylin; Natural Black 1; Hematoxyline; Hydroxybrazilin; Hydroxybrasilin; C.I. 75290
Identifiers
CAS Registry Number	517-28-2
ChEMBL	ChEMBL477197
ChemSpider	21106443
	InChI InChI=1S/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2/t13?,16-/m0/s1 ; Key: WZUVPPKBWHMQCE-VYIIXAMBSA-N ; InChI=1/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2/t13?,16-/m0/s1; Key: WZUVPPKBWHMQCE-VYIIXAMBBJ ;
Jmol-3D images	Image
MeSH	Hematoxylin
PubChem	10603
	SMILES Oc2cc3C[C@]4(O)COc1c(O)c(O)ccc1C4c3cc2O ;
UNII	YKM8PY2Z55
Properties
Molecular formula	C16H14O6
Molar mass	302.28 g·mol−1
	Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

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関: hematoxylin

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/05/09 18:26:45」(JST)

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Haematein

Haematoxylin, hematoxylin, Natural Black 1, or C.I. 75290 is a compound extracted from the heartwood of the logwood tree.^[1] Hematoxylin is a basic / positive compound that binds to and forms salts with acidic, or basophilic, compounds containing negative charges (such as DNA and RNA which are acidic/negative because the nucleic acid building blocks that come off the phosphate backbone are negatively charged) and stains them dark blue or violet. Haematoxylin and eosin together make up haematoxylin and eosin stain, one of the most commonly used stains in histology. This type of stain is a permanent stain as opposed to temporary stains (e.g. iodine solution in KI). Another common stain is phosphotungstic acid haematoxylin, a mix of haematoxylin with phosphotungstic acid. When oxidized it forms haematein, a compound that forms strongly coloured complexes with certain metal ions, the most notable ones being Fe(III) and Al(III) salts. Metal-haematein complexes are used to stain cell nuclei prior to examination under a microscope. Structures that stain with iron- or aluminium-haematein are often called basophilic, even though the mechanism of the staining is different from that of staining with basic dyes.

In the early 1970s and in 2008, there were shortages of haematoxylin due to interruptions in its extraction from logwood. The price of the compound increased, affecting the cost of diagnostic histopathology, and prompted a search for alternative nuclear stains. Before the use of any alternatives became firmly established, haematoxylin returned to the market, though at a higher price, and resumed its place in histopathology. Several synthetic dyes have been recommended as replacements, notably celestine blue (CI 51050), gallocyanine (CI 51030), gallein (CI 45445) and eriochrome cyanine R (also called chromoxane cyanine R and solochrome cyanine (CI 43820). All four have Fe(III) as the mordant. Another alternative is the aluminium complex of oxidized brazilin, which differs from haematoxylin by only one hydroxyl group.

Staining solutions

Mouse skin showing hematoxylin (nuclear/purple) and eosin (cytosolic/pink).

These stains are commonly employed for histological studies. The mordants used to demonstrate nuclear and cytoplasmic structures are alum and iron, forming lakes or coloured complexes (dye-mordant-tissue complexes), the colour of which will depend on the salt used. Aluminium salt lakes are usually coloured blue-white, whereas ferric salt lakes are coloured blue-black.

Aluminium solutions

The three main alum haematoxylin solutions employed are Ehrlich's haematoxylin, Harris's haematoxylin, and Mayer's haematoxylin. The name haemalum is preferable to "haematoxylin" for these solutions because haematein, a product of oxidation of haematoxylin, is the compound that combines with aluminium ions to form the active dye-metal complex. Alum haematoxylin solutions impart to the nuclei of cells a light transparent red stain that rapidly turns blue on exposure to any neutral or alkaline liquid.

Alum or potassium aluminium sulfate used as the mordant usually dissociates in an alkaline solution, combining with HO⁻ of water to form insoluble aluminium hydroxide. In the presence of excess acid, aluminium hydroxide cannot be formed, thus causing failure of aluminium haematoxylin dye-lake to form, due to lack of OH⁻ ions. Hence, acid solutions of alum haematoxylin become red. During staining, alum haematoxylin-stained sections are usually passed on to a neutral or alkaline solution (e.g., hard tap water or 1% ammonium hydroxide) in order to neutralize the acid and form an insoluble blue aluminium haematin complex. This procedure is known as blueing.

When tap water is not sufficiently alkaline, or is even acidic and is unsatisfactory for blueing haematoxylin, a tap water substitute consisting of 3.5 g NaHCO₃ and 20 g MgSO₄.7H₂O in one litre of water with thymol (to inhibit formation of moulds), is used to accelerate blueing of thin paraffin sections. Addition of a trace of any alkali to tap or distilled water also provides an effective blueing solution; a few drops of strong ammonium hydroxide or of saturated aqueous lithium carbonate, added immediately before use, are sufficient for a 400 ml staining dish full of water. Use of very cold water slows down the blueing process, whereas warming accelerates it. In fact, the use of water below 10 °C for blueing sections may even produce pink artifact discolourations in the tissue.

Notes

^ Cooksey 2010

References

Brown, G. G. (1978). An Introduction to Histotechnology. Appleton-Century-Crofts, New York.
Cooksey C. (2010) Hematoxylin and related compounds - an annotated bibliography concerning their origin, properties, chemistry and certain applications. Biotechnic & Histochemistry 85(1): 65-82. PMID 19568968
Dapson R., Horobin R.W., Kiernan J.A. (2010) Hematoxylin shortages their causes and duration and other dyes that can replace hemalum in routine hematoxylin and eosin staining. Biotechnic & Histochemistry 85(1): 55-63.
Godwin Avwioro (2011). Histochemical Uses Of Haematoxylin - A Review. JPCS 1:24-34. PDF
Jocelyn H. Bruce-Gregorios, M.D.: Histopathologic Techniques, JMC Press Inc., Quezon City, Philippines, 1974.
Meloan, S. M. & Puchtler, H. 1987. "Harris hematoxylin," what Harris really wrote and the mechanism of hemalum stains. Journal of Histotechnology 10: 257-261.
Puchtler, H., Meloan, S.N. & Waldrop, F.S. 1986. Application of current chemical concepts to metal-haematein and -brazilein stains. Histochemistry 85: 353-364.

External links

Stainsfile

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English Journal

Bixin action in the healing process of rats mouth wounds.

Piva RM, Johann AC, Costa CK, Miguel OG, Rosa ER, de Azevedo-Alanis LR, Trevilatto PC, Ignacio SA, Bettega PV, Gregio AM1.Author information 1Rua Professor Luiz César 873 apto 202, Agua Verde - 80.620-280, Curitiba- Parana- Brazil. ana.gregio@pucpr.br.AbstractOral lesions that manifest as ulcer lesions are quite common and can cause discomfort to the patient. Searching for drugs to accelerate the healing of these lesions is nonstop process. Bixin is a molecule found in annatto (urucum) seeds and is considered a viable therapeutic option to treat such lesions due to its anti-inflammatory, anti-oxidant, and healing properties. Therefore, the present study aimed to evaluate the effect of the bixin solution in the ulcer healing process in the oral mucosa of rats. Ulcers were induced with punches of 0.5 cm in the middle of the dorsum of the tongue of 64 Wistar rats. The animals were randomly divided into 8 groups, in which 4 groups were treated with saline solution, while the other 4 were treated with the bixin solution. The animals were sacrificed in the periods 2, 7, 14, and 21 days after the beginning of the treatment. The species were histologically processed and stained with hematoxylin/eosin and picrosirius. Fibroblasts, reepithelialization, and wound contraction could be observed, as could the quantification of neutrophils, macrophages, plasma cells, lymphocytes, and mature and immature collagen. On the seventh day, the experimental group, when compared to the control group, presented a higher proliferation of fibroblasts, more advanced reepithelialization, and a higher contraction in the wounds. A reduction in the average number of neutrophils in the experimental group, when compared to the control group, could be observed in all periods (p=0.000). Up to two days, the total collagen area was higher (p=0.044) in the experimental group (4139.60±3047.51t han in the control group (1564.81±918.47). The deposition of mature collagen, on the 14(th) day, was higher (p=0.048) in the experimental group (5802.40±3578.18) than in the control group (1737.26±1439.97). The results found in the present study indicate that the bixin solution inhibits the acute inflammatory response with a minor average number of neutrophils and accelerates reepithelialization, wound contraction and collagen maturation, thus illustrating that this solution does in fact represent an important adjuvant in the treatment of ulcers.
Current pharmaceutical biotechnology.Curr Pharm Biotechnol.2014 Oct;14(9):785-91.
Oral lesions that manifest as ulcer lesions are quite common and can cause discomfort to the patient. Searching for drugs to accelerate the healing of these lesions is nonstop process. Bixin is a molecule found in annatto (urucum) seeds and is considered a viable therapeutic option to treat such les
PMID 24372269

Histometric changes and epidermal FGF9 expression in carbon photoenhancer-assisted Nd:YAG laser treatment.

Zheng Z1, Kim J, Choi MJ, Goo B, Chun SI, Cho SB.Author information 1Department of Dermatology and Cutaneous Biology Research Institute, Yonsei University College of Medicine , Seoul , Korea.AbstractFibroblast growth factor (FGF)-9 plays an important role in wound healing. However, the effects of non-ablative laser treatment on the expression of FGF9 have not been fully investigated. Non-ablative 1064-nm quasi-long pulsed and Q-switched Nd:YAG laser treatments were delivered to hairless mice with and without a carbon photoenhancer. For histological and immunohistochemical analyses, sections were stained with hematoxylin and eosin as well as FGF9 antibody. Significantly, increased epidermal and dermal thickness was noted in mice treated with carbon photoenhancer-assisted quasi-long pulsed or Q-switched laser treatments compared to those treated without a carbon photoenhancer. Expression of FGF9 was observed in both the epidermis and dermis in all groups of mice during the healing process. Earlier and more pronounced expression of FGF9 was detected in mice treated with carbon photoenhancer-assisted quasi-long pulsed laser therapy. In addition, two peaks of pronounced FGF9 expression were observed, especially in mice that underwent carbon photoenhancer-assisted 1064-nm quasi-long pulsed Nd:YAG laser treatment. A carbon photoenhancer seems to enhance the effect of quasi-long pulsed and Q-switched Nd:YAG laser treatment. In addition, expression of FGF9 may play an important role in the healing process after laser treatments and could contribute to histometric changes.
The Journal of dermatological treatment.J Dermatolog Treat.2014 Aug;25(4):278-82. doi: 10.3109/09546634.2012.723121. Epub 2012 Sep 19.
Fibroblast growth factor (FGF)-9 plays an important role in wound healing. However, the effects of non-ablative laser treatment on the expression of FGF9 have not been fully investigated. Non-ablative 1064-nm quasi-long pulsed and Q-switched Nd:YAG laser treatments were delivered to hairless mice wi
PMID 22905667

Excellent prognosis of node negative patients after sentinel node procedure in colon carcinoma: A 5-year follow-up study.

Braat AE1, Pol RA2, Oosterhuis JW3, de Vries JE4, Mesker WE5, Tollenaar RA5.Author information 1Department of Surgery, Leiden University Medical Center, Albinusdreef 2, 2333 ZA Leiden, The Netherlands. Electronic address: a.e.braat@lumc.nl.2Department of Surgery, University Medical Center Groningen, Hanzeplein 1, 9700 RB Groningen, The Netherlands.3Department of Surgery, VU Medical Centre, P.O. Box 7075, 1007 MB Amsterdam, The Netherlands.4Department of Surgery, Isala Klinieken, Locatie Sophia, Dokter van Heesweg 2, P.O. Box 10400, 8000 GK Zwolle, The Netherlands.5Department of Surgery, Leiden University Medical Center, Albinusdreef 2, 2333 ZA Leiden, The Netherlands.AbstractAIM: Investigate the prognostic impact and clinical relevance of the sentinel node (SN)-procedure in colon carcinoma.
European journal of surgical oncology : the journal of the European Society of Surgical Oncology and the British Association of Surgical Oncology.Eur J Surg Oncol.2014 Jun;40(6):747-55. doi: 10.1016/j.ejso.2013.10.003. Epub 2013 Oct 23.
AIM: Investigate the prognostic impact and clinical relevance of the sentinel node (SN)-procedure in colon carcinoma.PATIENTS AND METHODS: Between May 2002 and January 2004, the SN-procedure was performed in 55 patients that underwent elective resection for clinically non-advanced colon carcinoma. A
PMID 24220573