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Rose bengal

January 01, 1970

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.[1] 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.

Rose bengal
Names
Preferred IUPAC name
4,5,6,7-Tetrachloro-3′,6′-dihydroxy-2′,4′,5′,7′-tetraiodo-3H-spiro[[2]benzofuran-1,9′-xanthen]-3-one
Other names
* C.I. 45440
  • C.I. Acid Red 94
Identifiers
  • 4159-77-7 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1160160 Y
ChemSpider
  • 62647
ECHA InfoCard 100.021.813
EC Number
  • 223-993-4
  • 69439
UNII
  • BIU7Q7W2SH
  • DTXSID0048426
  • InChI=1S/C20H4Cl4I4O5/c21-9-7-8(10(22)12(24)11(9)23)20(33-19(7)31)3-1-5(25)15(29)13(27)17(3)32-18-4(20)2-6(26)16(30)14(18)28/h1-2,29-30H
    Key: IICCLYANAQEHCI-UHFFFAOYSA-N
  • O=C(O1)C2=C(C(Cl)=C(Cl)C(Cl)=C2Cl)C31C4=C(C(I)=C(O)C(I)=C4)OC5=C(I)C(O)=C(I)C=C53
Properties
C20H4Cl4I4O5
Molar mass 973.67 g/mol
1,017.65 g/mol (sodium salt)
Pharmacology
S01JA02 (WHO)
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Rose bengal solid and solution in water

A form of rose bengal is also being studied as a treatment for certain cancers and skin conditions. The cancer formulation of the drug, known as PV-10, is currently undergoing clinical trials for melanoma,[2] breast cancer.[3] and neuroendocrine tumors. The company also has formulated a drug based on rose bengal for the treatment of eczema and psoriasis; this drug, PV-10, is currently in clinical trials as well.[2]

History and etymology edit

Rose bengal was originally prepared in 1882 by Swiss chemist Robert Ghnem, as an analogue of fluorescein.[4] Rudolf Nietzki at the University of Basel identified the principal constituents of rose bengal as iodine derivatives of di- and tetra-chlorofluorescein.[5] The compound was originally used as a wool dye.[6] Its name derives from rose (flower) and Bengal (region); it is printed as rose bengal or Rose Bengal in the scientific literature.[7]

Chemical applications edit

 
Optical microscopy image of the undescribed species of Spinoloricus from Loricifera stained with rose bengal.

Despite its complicated photochemistry involving several species,[8] rose bengal is also used in synthetic chemistry as a visible light photoredox catalyst[9] and to generate singlet oxygen from triplet oxygen. The singlet oxygen can then undergo a variety of useful reactions, particularly [2 + 2] cycloadditions with alkenes and similar systems.

Derivatives and salts edit

Rose bengal can be used to form many derivatives that have important medical functions. One such derivative was created so to be sonosensitive but photoinsensitive, so that with a high intensity focused ultrasound, it could be used in the treatment of cancer. The derivative was formed by amidation of rose bengal, which turned off the fluorescent and photosensitive properties of rose bengal, leading to a usable compound, named in the study as RB2.[10]

 
rose bengal disodium salt

Salts of rose bengal include C20H2Cl4I4Na2O5 (CAS 632-69-9). This sodium salt is a dye, which has its own unique properties and uses.[11]

Biological applications edit

 
Before Brucella Rose Bengal Test application
 
After Brucella Rose Bengal Test application

PV-10 (an injectable form of rose bengal) was found to cause an observable response in 60% of tumors treated, according to researchers in a phase II melanoma study. Locoregional disease control was observed in 75% of patients. Also confirmed was a "bystander effect", previously observed in the phase I trial, whereby untreated lesions responded to treatment as well, potentially due to immune system response. These data were based on the interim results (in 2009) of the first 40 patients treated in an 80-patient study.[3][needs update] As of April 2016 a phase-3 study of PV-10 as a single agent therapy for patients with locally advanced cutaneous melanoma (Clinical Trials ID NCT02288897) is enrolling patients.[2]

Rose bengal has been shown to not just prevent the growth and spread of ovarian cancer, but also to cause apoptotic cell death of the cancer cells. This has been proven in vitro, in order to prove that rose bengal is still a possible option in the treatment of cancer, and further research should be done.[12]

Rose bengal has been used to treat colon cancer. In one such study,[13] a protective immune response was generated from immunogenic cell death.

Rose bengal is also used in animal models of ischemic stroke (photothrombotic stroke models) in biomedical research. A bolus of the compound is injected into the venous system. Then the region of interest (e.g., the cerebral cortex) is exposed and illuminated by LASER light of 561 nm. A thrombus is formed in the illuminated blood vessels, causing a stroke in the dependent brain tissue.[14][15]

Rose bengal has been used for 50 years to diagnose liver and eye cancer. Rose bengal dye is mixed with the homogenate of Brucella and pH of the solution is maintained at 3.8, and this dye is used to diagnose Brucellosis by agglutinating the suspected serum. Rose bengal is slightly irritating and toxic to the eye.[6] It has also been used as an insecticide.[16][17]

Rose bengal is able to stain cells whenever the surface epithelium is not being properly protected by the preocular tear film, because rose bengal has been proven to not be able to stain cells because of the protective functioning of these preocular tear films.[18] This is why rose bengal is often useful as a stain in diagnosing certain medical issues, such as conjunctival and lid disorders.[19]

Rose bengal has been used for ocular surface staining to study the efficacy of punctal plugs in the treatment of keratoconjunctivitis sicca.[20]

Rose bengal is being researched as an agent in creating nano sutures.[21] Wounds are painted on both sides with it and then illuminated with an intense light. This links the tiny collagen fibers together sealing the wound.[22][23][24] Healing is faster and the seal reduces chances of infection.[25][26]

Rose bengal is used to suppress bacterial growth in several microbiological media, including Cooke's rose bengal agar.

Rose bengal has been used as a protoplasm stain to discriminate between living and dead micro-organisms, particularly Foraminifera, since the 1950s when Bill Walton developed the technique.[27]

Rose bengal acetate can act as a photosensitiser and may have potential in photodynamic therapy to treat some cancers.[28]

References edit

  1. ^ "Rose Bengal Compound Summary". PubChem.
  2. ^ a b c Provectus Biopharmaceuticals Reports Data On PV-10 in Combination Therapy and T Cell Mediated Immunity Presented at American Association for Cancer Research (AACR) Annual Meeting 2016. April 2016
  3. ^ a b Metastatic Melanoma PV-10 Trial Results Encouraging Says Drug Company, Medical News Today, 9 June 2009
  4. ^ Alexander W (2010). "American Society of Clinical Oncology, 2010 Annual Meeting and Rose Bengal: From a Wool Dye to a Cancer Therapy". Pharmacy and Therapeutics. 35 (8): 469–474. PMC 2935646. PMID 20844697.
  5. ^ Orellana C. "Rose Bengal The pink eye stain that might be a cancer treatment".
  6. ^ a b Orellana C. "Rose Bengal--the Pink Eye Stain that might be a Cancer Treatment".
  7. ^ Senning, Alexander (2006). Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology. Elsevier. p. 344. ISBN 978-0-08-048881-3.
  8. ^ Ludvíková L, Friš P, Heger D, Šebej P, Wirz J, Klán P (2016). "Photochemistry of rose bengal in water and acetonitrile: a comprehensive kinetic analysis". Physical Chemistry Chemical Physics. 18 (24): 16266–16273. Bibcode:2016PCCP...1816266L. doi:10.1039/C6CP01710J. ISSN 1463-9076. PMID 27253480.
  9. ^ Romero NA, Nicewicz DA (2016-09-14). "Organic Photoredox Catalysis". Chemical Reviews. 116 (17): 10075–10166. doi:10.1021/acs.chemrev.6b00057. ISSN 0009-2665. PMID 27285582.
  10. ^ Kim Y, Valentina Rubio, Jianjun Qi, Rongmin Xia, Zheng-Zheng Shi, Leif Peterson, Ching-Hsuan Tung, Brian E. O'Neill (2012). "Cancer treatment using an optically inert rose bengal derivative combined with pulsed focused ultrasound". AIP Conference Proceedings. 1481 (1): 175. Bibcode:2012AIPC.1481..175K. doi:10.1063/1.4757330. Published as Kim YS, Rubio V, Qi J, Xia R, Shi ZZ, Peterson L, Tung CH, O'Neill BE (2011). "Cancer treatment using an optically inert Rose Bengal derivative combined with pulsed focused ultrasound". J Control Release. 156 (3): 315–22. doi:10.1016/j.jconrel.2011.08.016. PMC 3230682. PMID 21871506.
  11. ^ "Rose Bengal Sodium Salt". Sigma-Aldrich. Sigma Aldrich Co. Retrieved 12 November 2013.
  12. ^ Koevary S (2012). "Selective toxicity of rose bengal to ovarian cancer cells in vitro". International Journal of Physiology, Pathophysiology and Pharmacology. 4 (2): 99–107. PMC 3403562. PMID 22837809.
  13. ^ Qin J (2017). "Colon cancer cell treatment with rose bengal generates a protective immune response via immunogenic cell death". Cell Death and Disease. 8 (2): e2584. doi:10.1038/cddis.2016.473. PMC 5386459. PMID 28151483.
  14. ^ Salber D, et al. (2006). "Differential uptake of [18F]FET and [3H]l-methionine in focal cortical ischemia". Nuclear Medicine and Biology. 33 (8): 1029–1035. doi:10.1016/j.nucmedbio.2006.09.004. PMID 17127177.
  15. ^ Watson BD, Dietrich WD, Busto R, Wachtel MS, Ginsberg MD (1985). "Induction of reproducible brain infarction by photochemically initiated thrombosis". Ann Neurol. 17 (5): 497–504. doi:10.1002/ana.410170513. PMID 4004172. S2CID 37827695.
  16. ^ Capinera JL, Squitier JM (2000). "Insecticidal Activity of Photoactive Dyes to American and Migratory Grasshoppers (Orthoptera: Acrididae)". Journal of Economic Entomology. 93 (3): 662–666. doi:10.1603/0022-0493-93.3.662. PMID 10902313. S2CID 25514306.
  17. ^ Martin P, Mischke S, Schroder R (1998). "Compatibility of Photoactive Dyes with Insect Biocontrol Agents". Biocontrol Science and Technology. 8 (4): 501–508. Bibcode:1998BioST...8..501M. doi:10.1080/09583159830018.
  18. ^ Feenstra R, Tseng, S (July 1992). "What is actually stained by rose bengal?". Arch Ophthalmol. 110 (7): 984–993. doi:10.1001/archopht.1992.01080190090035. PMID 1637285.
  19. ^ Yokoi N (2012). "Vital staining for disorders of conjunctiva and lids". Atarashii Ganka. 29: 1599–1605.
  20. ^ Ervin AM, Wojciechowski R, Schein O (June 26, 2017). "Punctal occlusion for dry eye syndrome". Cochrane Database Syst Rev. 9 (6): CD006775. doi:10.1002/14651858.CD006775.pub3. PMC 5568656. PMID 28649802.
  21. ^ Chan B, Chan O, So K (2008). "Effects of photochemical crosslinking on the microstructure of collagen and a feasibility study on controlled protein release". Acta Biomaterialia. 4 (6): 1627–1636. doi:10.1016/j.actbio.2008.06.007. PMID 18640085.
  22. ^ O’Neill A.C., Winograd J.M, Zeballos J.M., Johnson T.S., Randolph M.A., Bujold K.E., Kochevar I.E., Redmond R.W. (2007). "Microvascular anastomosis using a photochemical tissue bonding technique". Lasers in Surgery and Medicine. 39 (9): 716–722. doi:10.1002/lsm.20548. PMID 17960755. S2CID 46712914.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  23. ^ Mulroy L., Kim J., Wu I., Scharper P., Melki S.A., Azar D.A., Redmond R.W., Kochevar I.E. (2000). "Photochemical keratodesmos for repair of lamellar corneal incisions". Invest Ophthalmol Vis Sci. 41 (11): 3335–3340. PMID 11006222.
  24. ^ Proano C.E., Mulroy L., Erika Jones E., Azar D.A., Redmond R.W., Kochevar I.E. (2004). "Characterization of paracellular penetration routes". Invest Ophthalmol Vis Sci. 38 (11): 2177–2181. PMID 9344340.
  25. ^ Laser Show in the Surgical Suite, Technology Review, March/April 2009
  26. ^ Laser Show in the Surgical Suite, Technology Review, 02.11.2009
  27. ^ Walton W (1952). "Techniques for recognition of living foraminifera". Contrib. Cushman Found. Foraminiferal Res. 3: 56–60.
  28. ^ Panzarini E, Inguscio V, Fimia GM, Dini L (2014). "Rose Bengal acetate photodynamic therapy (RBAc-PDT) induces exposure and release of Damage-Associated Molecular Patterns (DAMPs) in human HeLa cells". PLOS ONE. 9 (8): e105778. Bibcode:2014PLoSO...9j5778P. doi:10.1371/journal.pone.0105778. PMC 4139382. PMID 25140900.

External links edit

January 01, 1970
rose, bengal, tetrachloro, tetraiodofluorescein, stain, belongs, class, organic, compounds, called, xanthenes, sodium, salt, commonly, used, drops, stain, damaged, conjunctival, corneal, cells, thereby, identify, damage, stain, also, used, preparation, foramin. 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 1 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 Rose bengal Names Preferred IUPAC name 4 5 6 7 Tetrachloro 3 6 dihydroxy 2 4 5 7 tetraiodo 3H spiro 2 benzofuran 1 9 xanthen 3 one Other names C I 45440 C I Acid Red 94 Identifiers CAS Number 4159 77 7 Y 3D model JSmol Interactive image ChEMBL ChEMBL1160160 Y ChemSpider 62647 ECHA InfoCard 100 021 813 EC Number 223 993 4 PubChem CID 69439 UNII BIU7Q7W2SH CompTox Dashboard EPA DTXSID0048426 InChI InChI 1S C20H4Cl4I4O5 c21 9 7 8 10 22 12 24 11 9 23 20 33 19 7 31 3 1 5 25 15 29 13 27 17 3 32 18 4 20 2 6 26 16 30 14 18 28 h1 2 29 30HKey IICCLYANAQEHCI UHFFFAOYSA N SMILES O C O1 C2 C C Cl C Cl C Cl C2Cl C31C4 C C I C O C I C4 OC5 C I C O C I C C53 Properties Chemical formula C 20H 4Cl 4I 4O 5 Molar mass 973 67 g mol1 017 65 g mol sodium salt Pharmacology ATC code S01JA02 WHO Hazards GHS labelling Pictograms Signal word Warning Hazard statements H315 H319 H335 Precautionary statements P261 P264 P271 P280 P302 P352 P304 P340 P305 P351 P338 P312 P321 P332 P313 P337 P313 P362 P403 P233 P405 P501 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Rose bengal solid and solution in water A form of rose bengal is also being studied as a treatment for certain cancers and skin conditions The cancer formulation of the drug known as PV 10 is currently undergoing clinical trials for melanoma 2 breast cancer 3 and neuroendocrine tumors The company also has formulated a drug based on rose bengal for the treatment of eczema and psoriasis this drug PV 10 is currently in clinical trials as well 2 Contents 1 History and etymology 2 Chemical applications 2 1 Derivatives and salts 3 Biological applications 4 References 5 External linksHistory and etymology editRose bengal was originally prepared in 1882 by Swiss chemist Robert Ghnem as an analogue of fluorescein 4 Rudolf Nietzki at the University of Basel identified the principal constituents of rose bengal as iodine derivatives of di and tetra chlorofluorescein 5 The compound was originally used as a wool dye 6 Its name derives from rose flower and Bengal region it is printed as rose bengal or Rose Bengal in the scientific literature 7 Chemical applications edit nbsp Optical microscopy image of the undescribed species of Spinoloricus from Loricifera stained with rose bengal Despite its complicated photochemistry involving several species 8 rose bengal is also used in synthetic chemistry as a visible light photoredox catalyst 9 and to generate singlet oxygen from triplet oxygen The singlet oxygen can then undergo a variety of useful reactions particularly 2 2 cycloadditions with alkenes and similar systems Derivatives and salts edit Rose bengal can be used to form many derivatives that have important medical functions One such derivative was created so to be sonosensitive but photoinsensitive so that with a high intensity focused ultrasound it could be used in the treatment of cancer The derivative was formed by amidation of rose bengal which turned off the fluorescent and photosensitive properties of rose bengal leading to a usable compound named in the study as RB2 10 nbsp rose bengal disodium salt Salts of rose bengal include C20H2Cl4I4Na2O5 CAS 632 69 9 This sodium salt is a dye which has its own unique properties and uses 11 Biological applications edit nbsp Before Brucella Rose Bengal Test application nbsp After Brucella Rose Bengal Test application PV 10 an injectable form of rose bengal was found to cause an observable response in 60 of tumors treated according to researchers in a phase II melanoma study Locoregional disease control was observed in 75 of patients Also confirmed was a bystander effect previously observed in the phase I trial whereby untreated lesions responded to treatment as well potentially due to immune system response These data were based on the interim results in 2009 of the first 40 patients treated in an 80 patient study 3 needs update As of April 2016 update a phase 3 study of PV 10 as a single agent therapy for patients with locally advanced cutaneous melanoma Clinical Trials ID NCT02288897 is enrolling patients 2 Rose bengal has been shown to not just prevent the growth and spread of ovarian cancer but also to cause apoptotic cell death of the cancer cells This has been proven in vitro in order to prove that rose bengal is still a possible option in the treatment of cancer and further research should be done 12 Rose bengal has been used to treat colon cancer In one such study 13 a protective immune response was generated from immunogenic cell death Rose bengal is also used in animal models of ischemic stroke photothrombotic stroke models in biomedical research A bolus of the compound is injected into the venous system Then the region of interest e g the cerebral cortex is exposed and illuminated by LASER light of 561 nm A thrombus is formed in the illuminated blood vessels causing a stroke in the dependent brain tissue 14 15 Rose bengal has been used for 50 years to diagnose liver and eye cancer Rose bengal dye is mixed with the homogenate of Brucella and pH of the solution is maintained at 3 8 and this dye is used to diagnose Brucellosis by agglutinating the suspected serum Rose bengal is slightly irritating and toxic to the eye 6 It has also been used as an insecticide 16 17 Rose bengal is able to stain cells whenever the surface epithelium is not being properly protected by the preocular tear film because rose bengal has been proven to not be able to stain cells because of the protective functioning of these preocular tear films 18 This is why rose bengal is often useful as a stain in diagnosing certain medical issues such as conjunctival and lid disorders 19 Rose bengal has been used for ocular surface staining to study the efficacy of punctal plugs in the treatment of keratoconjunctivitis sicca 20 Rose bengal is being researched as an agent in creating nano sutures 21 Wounds are painted on both sides with it and then illuminated with an intense light This links the tiny collagen fibers together sealing the wound 22 23 24 Healing is faster and the seal reduces chances of infection 25 26 Rose bengal is used to suppress bacterial growth in several microbiological media including Cooke s rose bengal agar Rose bengal has been used as a protoplasm stain to discriminate between living and dead micro organisms particularly Foraminifera since the 1950s when Bill Walton developed the technique 27 Rose bengal acetate can act as a photosensitiser and may have potential in photodynamic therapy to treat some cancers 28 References edit Rose Bengal Compound Summary PubChem a b c Provectus Biopharmaceuticals Reports Data On PV 10 in Combination Therapy and T Cell Mediated Immunity Presented at American Association for Cancer Research AACR Annual Meeting 2016 April 2016 a b Metastatic Melanoma PV 10 Trial Results Encouraging Says Drug Company Medical News Today 9 June 2009 Alexander W 2010 American Society of Clinical Oncology 2010 Annual Meeting and Rose Bengal From a Wool Dye to a Cancer Therapy Pharmacy and Therapeutics 35 8 469 474 PMC 2935646 PMID 20844697 Orellana C Rose Bengal The pink eye stain that might be a cancer treatment a b Orellana C Rose Bengal the Pink Eye Stain that might be a Cancer Treatment Senning Alexander 2006 Elsevier s Dictionary of Chemoetymology The Whys and Whences of Chemical Nomenclature and Terminology Elsevier p 344 ISBN 978 0 08 048881 3 Ludvikova L Fris P Heger D Sebej P Wirz J Klan P 2016 Photochemistry of rose bengal in water and acetonitrile a comprehensive kinetic analysis Physical Chemistry Chemical Physics 18 24 16266 16273 Bibcode 2016PCCP 1816266L doi 10 1039 C6CP01710J ISSN 1463 9076 PMID 27253480 Romero NA Nicewicz DA 2016 09 14 Organic Photoredox Catalysis Chemical Reviews 116 17 10075 10166 doi 10 1021 acs chemrev 6b00057 ISSN 0009 2665 PMID 27285582 Kim Y Valentina Rubio Jianjun Qi Rongmin Xia Zheng Zheng Shi Leif Peterson Ching Hsuan Tung Brian E O Neill 2012 Cancer treatment using an optically inert rose bengal derivative combined with pulsed focused ultrasound AIP Conference Proceedings 1481 1 175 Bibcode 2012AIPC 1481 175K doi 10 1063 1 4757330 Published as Kim YS Rubio V Qi J Xia R Shi ZZ Peterson L Tung CH O Neill BE 2011 Cancer treatment using an optically inert Rose Bengal derivative combined with pulsed focused ultrasound J Control Release 156 3 315 22 doi 10 1016 j jconrel 2011 08 016 PMC 3230682 PMID 21871506 Rose Bengal Sodium Salt Sigma Aldrich Sigma Aldrich Co Retrieved 12 November 2013 Koevary S 2012 Selective toxicity of rose bengal to ovarian cancer cells in vitro International Journal of Physiology Pathophysiology and Pharmacology 4 2 99 107 PMC 3403562 PMID 22837809 Qin J 2017 Colon cancer cell treatment with rose bengal generates a protective immune response via immunogenic cell death Cell Death and Disease 8 2 e2584 doi 10 1038 cddis 2016 473 PMC 5386459 PMID 28151483 Salber D et al 2006 Differential uptake of 18F FET and 3H l methionine in focal cortical ischemia Nuclear Medicine and Biology 33 8 1029 1035 doi 10 1016 j nucmedbio 2006 09 004 PMID 17127177 Watson BD Dietrich WD Busto R Wachtel MS Ginsberg MD 1985 Induction of reproducible brain infarction by photochemically initiated thrombosis Ann Neurol 17 5 497 504 doi 10 1002 ana 410170513 PMID 4004172 S2CID 37827695 Capinera JL Squitier JM 2000 Insecticidal Activity of Photoactive Dyes to American and Migratory Grasshoppers Orthoptera Acrididae Journal of Economic Entomology 93 3 662 666 doi 10 1603 0022 0493 93 3 662 PMID 10902313 S2CID 25514306 Martin P Mischke S Schroder R 1998 Compatibility of Photoactive Dyes with Insect Biocontrol Agents Biocontrol Science and Technology 8 4 501 508 Bibcode 1998BioST 8 501M doi 10 1080 09583159830018 Feenstra R Tseng S July 1992 What is actually stained by rose bengal Arch Ophthalmol 110 7 984 993 doi 10 1001 archopht 1992 01080190090035 PMID 1637285 Yokoi N 2012 Vital staining for disorders of conjunctiva and lids Atarashii Ganka 29 1599 1605 Ervin AM Wojciechowski R Schein O June 26 2017 Punctal occlusion for dry eye syndrome Cochrane Database Syst Rev 9 6 CD006775 doi 10 1002 14651858 CD006775 pub3 PMC 5568656 PMID 28649802 Chan B Chan O So K 2008 Effects of photochemical crosslinking on the microstructure of collagen and a feasibility study on controlled protein release Acta Biomaterialia 4 6 1627 1636 doi 10 1016 j actbio 2008 06 007 PMID 18640085 O Neill A C Winograd J M Zeballos J M Johnson T S Randolph M A Bujold K E Kochevar I E Redmond R W 2007 Microvascular anastomosis using a photochemical tissue bonding technique Lasers in Surgery and Medicine 39 9 716 722 doi 10 1002 lsm 20548 PMID 17960755 S2CID 46712914 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Mulroy L Kim J Wu I Scharper P Melki S A Azar D A Redmond R W Kochevar I E 2000 Photochemical keratodesmos for repair of lamellar corneal incisions Invest Ophthalmol Vis Sci 41 11 3335 3340 PMID 11006222 Proano C E Mulroy L Erika Jones E Azar D A Redmond R W Kochevar I E 2004 Characterization of paracellular penetration routes Invest Ophthalmol Vis Sci 38 11 2177 2181 PMID 9344340 Laser Show in the Surgical Suite Technology Review March April 2009 Laser Show in the Surgical Suite Technology Review 02 11 2009 Walton W 1952 Techniques for recognition of living foraminifera Contrib Cushman Found Foraminiferal Res 3 56 60 Panzarini E Inguscio V Fimia GM Dini L 2014 Rose Bengal acetate photodynamic therapy RBAc PDT induces exposure and release of Damage Associated Molecular Patterns DAMPs in human HeLa cells PLOS ONE 9 8 e105778 Bibcode 2014PLoSO 9j5778P doi 10 1371 journal pone 0105778 PMC 4139382 PMID 25140900 External links editRose Bengal at the U S National Library of Medicine Medical Subject Headings MeSH Absorption and extinction data Retrieved from https en wikipedia org w index php title Rose bengal amp oldid 1213343664, wikipedia, wiki, book, books, library,

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