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hoechst stain wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 molecular characteristics 2 applications 3 toxicity and safety 4 see also 5 references 6 external links toggle the table of contents hoechst stain 16 languages العربية català čeština español français galego עברית 日本語 nederlands polski русский srpskohrvatski српскохрватски српски srpski türkçe українська 中文 edit links article talk english read edit view history save tools tools move to sidebar hide actions read edit view history save general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia fluorescent dye used to stain dna chemical structure of hoechst dyes hoechst stains are part of a family of blue fluorescent dyes used to stain dna 1 2 these bis benzimides were originally developed by hoechst ag which numbered all their compounds so that the dye hoechst 33342 is the 33 342nd compound made by the company there are three related hoechst stains hoechst 33258 hoechst 33342 and hoechst 34580 the dyes hoechst 33258 and hoechst 33342 are the ones most commonly used and they have similar excitation emission spectra molecular characteristics edit excitation emission spectra of hoechst dyes both dyes are excited by ultraviolet light at around 350 nm and both emit blue cyan fluorescent light around an emission spectrum maximum at 461 nm unbound dye has its maximum fluorescence emission in the 510 540 nm range hoechst stains can be excited with a xenon or mercury arc lamp or with an ultraviolet laser there is a considerable stokes shift between the excitation and emission spectra that makes hoechst dyes useful in experiments in which multiple fluorophores are used the fluorescence intensity of hoechst dyes also increases with the ph of the solvent 3 hoechst dyes are soluble in water and in organic solvents such as dimethyl formamide or dimethyl sulfoxide concentrations can be achieved of up to 10 mg ml aqueous solutions are stable at 2 6 c for at least six months when protected from light for longterm storage the solutions are instead frozen at 20 c or below 3 hoechst 33258 magenta bound to the minor groove of dna green and blue from pdb 264d the dyes bind to the minor groove of double stranded dna with a preference for sequences rich in adenine and thymine although the dyes can bind to all nucleic acids at rich double stranded dna strands enhance fluorescence considerably 4 hoechst dyes are cell permeable and can bind to dna in live or fixed cells thus these stains are often called supravital meaning that live cells survive a treatment with these compounds cells that express specific atp binding cassette transporter proteins can also actively transport these stains out of their cytoplasm citation needed applications edit transmission image of hela cells with overlay of hoechst 33258 staining blue the leftmost cell is in the prometaphase stage of mitosis its chromosomes fluoresce brightly because they contain highly compacted dna fluorescent image of cultivated neutrophils isolated from venous blood of human with alzheimer disease sample was treated with hoechst 33342 dye that is used to stain dna the picture shows the release of dna by a neutrophil as foggy area in the center of the view field indicating the spontaneous activation of neutrophil extracellular traps formation in ad patients that is not usually observed in healthy mates a concentration of 0 1 12 μg ml is commonly used to stain dna in bacteria or eukaryote cells cells are stained for 1 30 min at room temperature or 37 c and then washed to remove unbound dye a green fluorescence of unbound hoechst dye may be observed on samples which are stained with too much dye or which are washed partially 3 hoechst dyes are often used as substitutes for another nucleic acid stain called dapi key differences between hoechst dyes and dapi are hoechst dyes are less toxic than dapi which ensures a higher viability of stained cells 5 the additional ethyl group in certain hoechst dyes hoechst 33342 renders them more cell permeable 6 there are nuclei staining dyes that allow for viability of cells after staining citation needed hoechst 33342 and 33258 are quenched by bromodeoxyuridine brdu which is commonly used to detect dividing cells hoechst 33342 exhibits a 10 fold greater cell permeability than h 33258 cells can integrate brdu in newly synthesized dna as a substitute for thymidine when brdu is integrated into dna it is supposed that the bromine deforms the minor groove so that hoechst dyes cannot reach their optimal binding site binding of hoechst dyes is even stronger to brdu substituted dna however no fluorescence ensues hoechst dyes can be used with brdu to monitor cell cycle progression 7 8 hoechst dyes are commonly used to stain genomic dna in the following applications fluorescence microscopy and immunohistochemistry often with other fluorophores 9 flow cytometry to count or sort out cells an example is the use of hoechst dyes to analyse how many cells of a population are in which phase of the cell cycle 10 detecting dna in the presence of rna in agarose gels 11 automated dna determination 12 chromosome sorting 11 hoechst efflux is also used to study hematopoietic and embryonic stem cells as these cells are able to effectively efflux the dye they can be detected via flow cytometry in what is termed the side population this is done by passing the fluorescence emitted from the excited hoechst through both red and blue filters and plotting hoechst red and blue against each other citation needed toxicity and safety edit because hoechst stains bind to dna they interfere with dna replication during cell division consequently they are potentially mutagenic and carcinogenic so care should be used in their handling and disposal hoechst stain is used to sort sperm in livestock and humans its safety has been debated 13 14 see also edit bisbenzimide carcinogen dapi dna binding protein excited state fluorescence fluorescence microscopy fluorophore flow cytometry hoechst ag immunohistochemistry lexitropsin minor groove mutagen netropsin comparison of nucleic acid simulation software pentamidine quenching fluorescence stokes shift references edit latt sa stetten g juergens la willard hf scher cd july 1975 recent developments in the detection of deoxyribonucleic acid synthesis by 33258 hoechst fluorescence journal of histochemistry and cytochemistry 23 7 493 505 doi 10 1177 23 7 1095650 pmid 1095650 latt sa stetten g january 1976 spectral studies on 33258 hoechst and related bisbenzimidazole dyes useful for fluorescent detection of deoxyribonucleic acid synthesis journal of histochemistry and cytochemistry 24 1 24 33 doi 10 1177 24 1 943439 pmid 943439 1 2 3 hoechst stains pdf invitrogren molecular probes archived from the original pdf on 2009 04 19 portugal j waring mj feb 28 1988 assignment of dna binding sites for 4 6 diamidine 2 phenylindole and bisbenzimide hoechst 33258 a comparative footprinting study biochimica et biophysica acta bba gene structure and expression 949 2 158 68 doi 10 1016 0167 4781 88 90079 6 pmid 2449244 bd bioscience 2009 techniques for immune function analysis pdf 2 ed becton dickinson and company archived from the original pdf on 2012 03 22 retrieved 2011 09 09 bucevičius jonas lukinavičius gražvydas gerasimaitė rūta 2018 04 18 the use of hoechst dyes for dna staining and beyond chemosensors 6 2 18 doi 10 3390 chemosensors6020018 hdl 21 11116 0000 0001 a4fe 8 issn 2227 9040 kubbies m rabinovitch ps january 1983 flow cytometric analysis of factors which influence the brdurd hoechst quenching effect in cultivated human fibroblasts and lymphocytes cytometry 3 4 276 81 doi 10 1002 cyto 990030408 pmid 6185287 breusegem sy clegg rm loontiens fg feb 1 2002 base sequence specificity of hoechst 33258 and dapi binding to five a t 4 dna sites with kinetic evidence for more than one high affinity hoechst 33258 aatt complex journal of molecular biology 315 5 1049 61 doi 10 1006 jmbi 2001 5301 pmid 11827475 iain johnson michelle t z spence ed 2011 molecular probes handbook a guide to fluorescent probes and labeling technologies 11 ed invitrogen isbn 978 0 9829279 1 5 kubbies m 1990 flow cytometric recognition of clastogen induced chromatin damage in g0 g1 lymphocytes by non stoichiometric hoechst fluorochrome binding cytometry 11 3 386 94 doi 10 1002 cyto 990110309 pmid 1692786 1 2 mocharla r mocharla h hodes me dec 23 1987 a novel sensitive fluorometric staining technique for the detection of dna in rna preparations nucleic acids research 15 24 10589 doi 10 1093 nar 15 24 10589 pmc 339970 pmid 2447564 sterzel w bedford p eisenbrand g june 1985 automated determination of dna using the fluorochrome hoechst 33258 analytical biochemistry 147 2 462 7 doi 10 1016 0003 2697 85 90299 4 pmid 2409841 ashwood smith m j 1994 safety of human sperm selection by flow cytometry human reproduction 9 5 oxford university press 757 759 doi 10 1093 oxfordjournals humrep a138589 pmid 7929716 parrilla i vázquez j m cuello c gil ma roca j di berardino d martínez ea 2004 hoechst 33342 stain and u v laser exposure do not induce genotoxic effects in flow sorted boar spermatozoa reproduction 128 5 615 621 doi 10 1530 rep 1 00288 pmid 15509707 external links edit wikimedia commons has media related to hoechst stains spectral traces for fluorescent dyes manual for hoechst stains an online guide to fluorescent probes and commercial labeling technologies retrieved from https en wikipedia org w index php title hoechst_stain oldid 1335564704 categories staining dyes fluorescent dyes dna binding substances hidden categories articles with short description short description is different from wikidata all articles with unsourced statements articles with unsourced statements from september 2011 articles with unsourced statements from july 2015 articles with unsourced statements from january 2015 commons category link is on wikidata this page was last edited on 29 january 2026 at 22 44 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle 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