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((more citations needed|date=March 2018))

((Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 414067478
| ImageFile = Chromomycin A3.svg
| ImageSize = 250px
| IUPACName = (6''S'',7''S'')-6-[(4-''O''-Acetyl-2,6-dideoxy-3-''C''-methyl-α-<small>L</small>-''arabino''-hexopyranosyl)-(1→3)-(2,6-dideoxy-β-<small>D</small>-''arabino''-hexopyranosyl)-(1→3)-2,6-dideoxy-β-<small>D</small>-''arabino''-hexopyranosyloxy]-7-[(1''S'')-5-deoxy-1-''O''-methyl-<small>D</small>-''threo''-pent-2-ulos-1-''C''-yl]-4,10-dihydroxy-3-methyl-5-oxo-5,6,7,8-tetrahydroanthracen-2-yl (2,6-dideoxy-4-''O''-methyl-<small>D</small>-''lyxo''-hexopyranosyl)-(1→3)-2,6-dideoxy-<small>D</small>-''lyxo''-hexopyranoside 4-acetate
| SystematicName = (1<sup>2</sup>''S'',1<sup>4</sup>''S'',1<sup>5</sup>''S'',1<sup>6</sup>''S'',3<sup>2</sup>''S'',3<sup>4</sup>''R'',3<sup>5</sup>''R'',3<sup>6</sup>''R'',5<sup>2</sup>''S'',5<sup>4</sup>''R'',5<sup>5</sup>''R'',5<sup>6</sup>''R'',7<sup>2</sup>''S'',7<sup>3</sup>''S'',9<sup>2</sup>''S'',9<sup>4</sup>''R'',9<sup>5</sup>''S'',9<sup>6</sup>''R'',11<sup>2</sup>''R'',11<sup>4</sup>''R'',11<sup>5</sup>''R'',11<sup>6</sup>''R'')-7<sup>3</sup>-[(1''S'',3''S'',4''R'')-3,4-Dihydroxy-1-methoxy-2-oxopentyl]-1<sup>4</sup>,3<sup>5</sup>,5<sup>5</sup>,7<sup>8</sup>,7<sup>9</sup>,11<sup>4</sup>-heptahydroxy-11<sup>5</sup>-methoxy-1<sup>4</sup>,1<sup>6</sup>,3<sup>6</sup>,5<sup>6</sup>,7<sup>7</sup>,9<sup>6</sup>,11<sup>6</sup>-heptamethyl-7<sup>1</sup>-oxo-7<sup>1</sup>,7<sup>2</sup>,7<sup>3</sup>,7<sup>4</sup>-tetrahydro-2,4,6,8,10-pentaoxa-1,11(2),3,5(4,2),9(2,4)-pentakis(oxana)-7(2,6)-anthracenaundecaphane-1<sup>5</sup>,9<sup>5</sup>-diyl diacetate
| OtherNames = Toyomycin
|Section1=((Chembox Identifiers
| Abbreviations =
| InChI = 1S/C56H80O27/c1-20-32(78-38-18-35(51(25(6)75-38)83-55(67)68)81-36-15-31(59)50(70-10)24(5)74-36)14-29-12-28-13-30(52(71-11)49(66)44(61)21(2)57)53(48(65)42(28)47(64)41(29)43(20)60)82-39-17-33(45(62)23(4)73-39)79-37-16-34(46(63)22(3)72-37)80-40-19-56(9,69)54(26(7)76-40)77-27(8)58/h12,14,21-26,30-31,33-40,44-46,50-54,57,59-64,69H,13,15-19H2,1-11H3,(H,67,68)/t21-,22-,23-,24-,25-,26+,30+,31-,33-,34-,35-,36-,37+,38+,39+,40+,44+,45-,46-,50+,51+,52+,53+,54+,56+/m1/s1
| InChIKey = VWUDFIOZFAFOMW-QUOOOCNJBW
| StdInChI_Ref = ((stdinchicite|correct|chemspider))
| StdInChI = 1S/C56H80O27/c1-20-32(78-38-18-35(51(25(6)75-38)83-55(67)68)81-36-15-31(59)50(70-10)24(5)74-36)14-29-12-28-13-30(52(71-11)49(66)44(61)21(2)57)53(48(65)42(28)47(64)41(29)43(20)60)82-39-17-33(45(62)23(4)73-39)79-37-16-34(46(63)22(3)72-37)80-40-19-56(9,69)54(26(7)76-40)77-27(8)58/h12,14,21-26,30-31,33-40,44-46,50-54,57,59-64,69H,13,15-19H2,1-11H3,(H,67,68)/t21-,22-,23-,24-,25-,26+,30+,31-,33-,34-,35-,36-,37+,38+,39+,40+,44+,45-,46-,50+,51+,52+,53+,54+,56+/m1/s1
| StdInChIKey_Ref = ((stdinchicite|correct|chemspider))
| StdInChIKey = VWUDFIOZFAFOMW-QUOOOCNJSA-N
| InChIKey1 = VWUDFIOZFAFOMW-QUOOOCNJSA-N
| CASNo_Ref = ((cascite|correct|??))
| CASNo = 7059-24-7
| UNII_Ref = ((fdacite|correct|FDA))
| UNII = DVW027E7NL
| EINECS =
| PubChem = 656673
| ChemSpiderID_Ref = ((chemspidercite|correct|chemspider))
| ChemSpiderID = 16735739
| SMILES =
| ChEMBL_Ref = ((ebicite|changed|EBI))
| ChEMBL = 216639
| RTECS =
| MeSHName =
| ChEBI_Ref = ((ebicite|correct|EBI))
| ChEBI =
| KEGG_Ref = ((keggcite|correct|kegg))
| KEGG =
))
|Section2=((Chembox Properties
| C=57 | H=82 | O=26
| Appearance =
| Density =
| MeltingPt =
| MeltingPt_notes =
| BoilingPt =
| BoilingPt_notes =
| Solubility =
| SolubleOther =
| Solvent =
| pKa =
| pKb =
| IsoelectricPt =
| SpecRotation =
| RefractIndex =
| Viscosity =
| Dipole =
 ))
|Section3=((Chembox Structure
| CrystalStruct =
| Coordination =
| MolShape =
 ))
|Section4=((Chembox Thermochemistry
| DeltaHf =
| DeltaHc =
| Entropy =
| HeatCapacity =
 ))
|Section5=((Chembox Pharmacology
| AdminRoutes =
| Bioavail =
| Metabolism =
| HalfLife =
| ProteinBound =
| Excretion =
| Legal_status =
| Legal_US =
| Legal_UK =
| Legal_AU =
| Legal_CA =
| Pregnancy_category =
| Pregnancy_AU =
| Pregnancy_US =
 ))
|Section6=((Chembox Explosive
| ShockSens =
| FrictionSens =
| DetonationV =
| REFactor =
 ))
|Section7=((Chembox Hazards
| ExternalSDS =
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-S =
| FlashPt =
| AutoignitionPt =
| ExploLimits =
| PEL =
 ))
|Section8=((Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunction =
| OtherFunction_label =
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))

'''Chromomycin A3 (CMA<sub href="Natural anthraquinone">3</sub>)''' or '''Toyomycin''' is an [[Natural anthraquinone|anthraquinone]] [[antibiotic]] [[glycoside]] produced by the [[Industrial fermentation|fermentation]] of a certain strain of ''[[Streptomyces|Streptomyces griseus]]'' (No. 7).<ref name=":0">((Cite journal|last1=Kamiyama|first1=M.|last2=Kaziro|first2=Y.|date=January 1966|title=Mechanism of action of chromomycin A3. 1. Inhibition of nucleic acid metabolism in Bacillus subtilis cells|journal=Journal of Biochemistry|volume=59|issue=1|pages=49–56|issn=0021-924X|pmid=4957278|doi=10.1093/oxfordjournals.jbchem.a128257))</ref>

__TOC__
== Fluorescence properties ==
In the presence of [[Mg²⁺|Mg<sup>2+</sup>]] [[ion]]s, Chromomycin A<sub>3</sub> binds reversibly to [[DNA]], preferentially to contiguous [[Guanine|G]]/[[Cytosine|C]] [[base pair]]s.<ref>((Cite journal|last=Kamiyama|first=M.|date=May 1968|title=Mechanism of action of chromomycin A3. 3. On the binding of chromomycin A3 with DNA and physiochemical properties of the complex|journal=Journal of Biochemistry|volume=63|issue=5|pages=566–572|issn=0021-924X|pmid=4972707|doi=10.1093/oxfordjournals.jbchem.a128814))</ref><ref name=":12">((Cite journal|last1=Van Dyke|first1=M. W.|last2=Dervan|first2=P. B.|date=1983-05-10|title=Chromomycin, mithramycin, and olivomycin binding sites on heterogeneous deoxyribonucleic acid. Footprinting with (methidiumpropyl-EDTA)iron(II)|journal=Biochemistry|volume=22|issue=10|pages=2373–2377|issn=0006-2960|pmid=6222762|doi=10.1021/bi00279a011))</ref>

When bound to DNA, Chromomycin A<sub>3</sub> has a maximum [[excitation wavelength]] of 445 [[Nanometre|nm]] ([[blue]]), and a maximum emission wavelength of 575&nbsp;nm ([[yellow]]).<ref>https://www.caymanchem.com/pdfs/11315.pdf ((Bare URL PDF|date=March 2022))</ref>

== Uses ==
* [[in-vitro]] [[Cell membrane|membrane]]-impermeant G/C-specific [[Fluorescence|fluorescent]] DNA-binding dye.<ref name=":12" />
* [[in-vitro]] [[antibiotic]] of [[Gram-positive bacteria|gram-positive]] [[bacteria]], through inhibition of the incorporation of [[Phosphate|P<sub>i</sub>]] in the [[RNA]].<ref name=":0" />
* [[in-vitro]] [[anticancer drug]] that inhibits [[RNA synthesis]].<ref>((Cite journal|last1=Kajiro|first1=Y.|last2=Kamiyama|first2=M.|date=October 1967|title=Mechanism of action of chromomycin A3. II. Inhibition of RNA polymerase reaction|journal=Journal of Biochemistry|volume=62|issue=4|pages=424–429|issn=0021-924X|pmid=5587590|doi=10.1093/oxfordjournals.jbchem.a128685))</ref>
* Evaluation of [[male fertility]]: Chromomycin A<sub>3</sub> and [[protamine]]s compete for the same [[binding site]]s in the DNA, so CMA<sub>3</sub> positivity in [[spermatozoa]] reflects protamine deficiency (affecting sperm morphology and decreasing fertility).<ref>((Cite journal|last1=Iranpour|first1=Farhad Golshan|last2=Nasr-Esfahani|first2=Mohammad Hosein|last3=Valojerdi|first3=Mojtaba Rezazadeh|last4=Al-Taraihi|first4=Taki Mohammad Taki|date=2000-01-01|title=Chromomycin A3 Staining as a Useful Tool for Evaluation of Male Fertility|journal=Journal of Assisted Reproduction and Genetics|language=en|volume=17|issue=1|pages=60–66|doi=10.1023/a:1009406231811|pmid=10754785|issn=1058-0468|pmc=3455193))</ref><ref>((Cite journal|last1=Nijs|first1=Martine|last2=Creemers|first2=Eva|last3=Cox|first3=Annemie|last4=Franssen|first4=Kim|last5=Janssen|first5=Mia|last6=Vanheusden|first6=Elke|last7=Jonge|first7=Christopher De|last8=Ombelet|first8=Willem|title=Chromomycin A3 staining, sperm chromatin structure assay and hyaluronic acid binding assay as predictors for assisted reproductive outcome|journal=Reproductive BioMedicine Online|volume=19|issue=5|pages=671–684|doi=10.1016/j.rbmo.2009.07.002|date=November 2009|pmid=20021715|doi-access=free))</ref>

== References ==
<references />

((Anthraquinone))

[[Category:Antibiotics]]
[[Category:Anthraquinone glycosides]]


((Antibiotic-stub))

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