Zeocin
{{Chembox
| ImageFile = phleomycin D1.svg
| ImageSize = 250px
| SystematicName = (24R,7S,10S,11S,12R,15S,16R,182R,183S,184S,185S,186S,192R,193S,194S,195R,196R)-15-{6-Amino-2-[(1S)-3-amino-1-{[(2S)-2,3-diamino-3-oxopropyl]amino}-3-oxopropyl]-5-methylpyrimidine-4-carboxamido}-14-({4-[(diaminomethylidene)amino]butyl}carbamoyl)-11,184,185,203,205-pentahydroxy-7-[(1R)-1-hydroxyethyl]-186,206-bis(hydroxymethyl)-16-(1H-imidazol-5-yl)-10,12-dimethyl-6,9,14-trioxo-24,25-dihydro-17,19-dioxa-5,8,13-triaza-1(2),2(4,2)-bis([1,3]thiazola)-18(2,3),20(2)-bis(oxana)icosaphan-204-yl carbamate
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 11031-11-1
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII = O0VC1NEK5M
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 159333
| ChEBI = 75046
| ChemSpiderID = 140128
| SMILES = CC1=C(N=C(N=C1N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)C(=O)N[C@@H]([C@H](C2=CN=CN2)O[C@H]3[C@H]([C@H]([C@@H]([C@@H](O3)CO)O)O)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)OC(=O)N)O)C(=O)N[C@H](C)[C@H]([C@H](C)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCCC5=N[C@H](CS5)C6=NC(=CS6)C(=O)NCCCCN=C(N)N)O
| InChI = 1/C55H86N20O21S2/c1-19-32(72-45(75-43(19)58)24(11-30(57)79)67-12-23(56)44(59)85)49(89)74-34(40(25-13-63-18-68-25)94-53-42(38(83)36(81)28(14-76)93-53)95-52-39(84)41(96-55(62)91)37(82)29(15-77)92-52)50(90)69-21(3)35(80)20(2)46(86)73-33(22(4)78)48(88)65-10-7-31-70-27(17-97-31)51-71-26(16-98-51)47(87)64-8-5-6-9-66-54(60)61/h13,16,18,20-24,27-29,33-42,52-53,67,76-78,80-84H,5-12,14-15,17,56H2,1-4H3,(H2,57,79)(H2,59,85)(H2,62,91)(H,63,68)(H,64,87)(H,65,88)(H,69,90)(H,73,86)(H,74,89)(H2,58,72,75)(H4,60,61,66)
| InChIKey = CWCMIVBLVUHDHK-UHFFFAOYAG
| StdInChI = 1S/C55H86N20O21S2/c1-19-32(72-45(75-43(19)58)24(11-30(57)79)67-12-23(56)44(59)85)49(89)74-34(40(25-13-63-18-68-25)94-53-42(38(83)36(81)28(14-76)93-53)95-52-39(84)41(96-55(62)91)37(82)29(15-77)92-52)50(90)69-21(3)35(80)20(2)46(86)73-33(22(4)78)48(88)65-10-7-31-70-27(17-97-31)51-71-26(16-98-51)47(87)64-8-5-6-9-66-54(60)61/h13,16,18,20-24,27-29,33-42,52-53,67,76-78,80-84H,5-12,14-15,17,56H2,1-4H3,(H2,57,79)(H2,59,85)(H2,62,91)(H,63,68)(H,64,87)(H,65,88)(H,69,90)(H,73,86)(H,74,89)(H2,58,72,75)(H4,60,61,66)
| StdInChIKey = CWCMIVBLVUHDHK-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=55|H=86|N=20|O=21|S=2
| Appearance =
| Density =
| MeltingPt =
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| Section3 = {{Chembox Hazards
| MainHazards =
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Zeocin is a trade name for a formulation of phleomycin D1, a glycopeptide antibiotic and one of the phleomycins from Streptomyces verticillus belonging to the bleomycin family of antibiotics.{{cite web |last1=InvivoGen |title=Technical Data Sheet for Zeocin |url=https://www.invivogen.com/sites/default/files/invivogen/products/files/zeocin_tds.pdf}} It is a broad-spectrum antibiotic that is effective against most aerobic organisms including bacteria, filamentous fungi, yeast, plant, and animal cells. It causes cell death by intercalating into DNA and inducing double stranded breaks of the DNA.{{cite journal |vauthors=Ehrenfeld GM, Shipley JB, Heimbrook DC, Sugiyama H, Long EC, van Boom JH, van der Marel GA, Oppenheimer NJ, Hecht SM |year= 1987 |title=Copper-dependent cleavage of DNA by bleomycin |journal= Biochemistry |volume=26 |issue=3|pages=931–42 |pmid= 2436656 |doi=10.1021/bi00377a038}}{{cite journal |vauthors=Chankova SG, Dimova E, Dimitrova M, Bryant PE |year= 2007 |title=Induction of DNA double-strand breaks by zeocin in Chlamydomonas reinhardtii and the role of increased DNA double-strand breaks rejoining in the formation of an adaptive response |journal= Radiation and Environmental Biophysics |volume=46 |issue=4|pages=409–16 |pmid= 17639449 |doi=10.1007/s00411-007-0123-2|s2cid= 40973182 }}
Zeocin is a registered trademark belonging to InvivoGen. {{cite web | url=https://trademarks.justia.com/792/85/zeocin-79285216.html | title=ZEOCIN Trademark of INVIVOGEN - Registration Number 6366745 - Serial Number 79285216 :: Justia Trademarks }}
Properties
Zeocin is blue in colour due to the presence of copper ion Cu2+. This copper-chelated form is inactive. When Zeocin enters a cell, the Cu2+ is reduced to Cu+ and then removed. Subsequently, Zeocin becomes activated and can then bind and cleave DNA. However, the mechanism of action is not yet fully understood.{{cite journal |vauthors=Benko Z, Zhao RY |year= 2011 |title=Zeocin for selection of bleMX6 resistance in fission yeast | url= http://www.biotechniques.com/multimedia/archive/00162/BTN_A_000113706_O_162844a.pdf |journal= BioTechniques |volume=51 |issue=1|pages=57–60 |pmid=21781055 |doi= 10.2144/000113706 |doi-access=free }}
Usage
Zeocin and other related chemicals in the bleomycin family of compounds are primarily used in molecular biology as an antibiotic, especially for the selection of eukaryotic cell lines when used in conjunction with vectors containing a selectable marker for Zeocin resistance. Zeocin is considerably cheaper than phleomycin, works better in minimal media, and is therefore often used preferentially in studies.{{cite journal |vauthors=Benko Z, Zhao RY |year= 2011 |title=Zeocin for selection of bleMX6 resistance in fission yeast | url= http://www.biotechniques.com/multimedia/archive/00162/BTN_A_000113706_O_162844a.pdf |journal= BioTechniques |volume=51 |issue=1|pages=57–60 |pmid=21781055 |doi= 10.2144/000113706 |doi-access=free }}
Resistance to Zeocin is conferred by the product of the Sh ble gene first isolated from Streptoalloteichus hindustanus.{{cite journal |author=Gatignol, A., Durand, H. & Tiraby, G. |year=1988 |title=Bleomycin resistance conferred by a drug-binding protein |journal= FEBS Lett |volume=230 |issue=1–2 |pages=171–175|pmid= 2450783 |doi=10.1016/0014-5793(88)80665-3|s2cid=19925947 |doi-access=free }} The Sh ble gene product binds the antibiotic in a one-to-one ratio so it can no longer cause cleavage of DNA. This resistance gene is used as a selectable marker in some cloning and expression vectors where Zeocin is used as the antibiotic for selection.{{cite journal |vauthors=Pfeifer TA, Hegedus DD, Grigliatti TA, Theilmann DA |title=Baculovirus immediate-early promoter-mediated expression of the Zeocin resistance gene for use as a dominant selectable marker in dipteran and lepidopteran insect cell lines |journal=Gene |year=1997 |volume= 188 |issue=2|pages=183–90 |pmid=9133590 |doi=10.1016/s0378-1119(96)00756-1}}{{cite journal |vauthors=Mulsant P, Gatignol A, Dalens M, Tiraby G |year=1988 |title=Phleomycin resistance as a dominant selectable marker in CHO cells |journal= Somatic Cell and Molecular Genetics |volume= 14 |issue=3|pages=243–52 |pmid=2453083 |doi=10.1007/bf01534585|s2cid=40855423 }}
Plasmids with Zeocin Resistance
pFUSE-Fc plasmid{{cn|date=March 2023}}
References
{{reflist|2}}
External links
- {{cite web |url=https://www.invivogen.com/zeocin |title= Zeocin |date= 25 November 2016 |publisher= InvivoGen |access-date= December 2, 2022}}