Chromomycin A3

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{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 414067478 | ImageFile = Chromomycin A3.svg | ImageClass = skin-invert-image | 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 = (1²''S'',1⁴''S'',1⁵''S'',1⁶''S'',3²''S'',3⁴''R'',3⁵''R'',3⁶''R'',5²''S'',5⁴''R'',5⁵''R'',5⁶''R'',7²''S'',7³''S'',9²''S'',9⁴''R'',9⁵''S'',9⁶''R'',11²''R'',11⁴''R'',11⁵''R'',11⁶''R'')-7³-[(1''S'',3''S'',4''R'')-3,4-Dihydroxy-1-methoxy-2-oxopentyl]-1⁴,3⁵,5⁵,7⁸,7⁹,11⁴-heptahydroxy-11⁵-methoxy-1⁴,1⁶,3⁶,5⁶,7⁷,9⁶,11⁶-heptamethyl-7¹-oxo-7¹,7²,7³,7⁴-tetrahydro-2,4,6,8,10-pentaoxa-1,11(2),3,5(4,2),9(2,4)-pentakis(oxana)-7(2,6)-anthracenaundecaphane-1⁵,9⁵-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 = | OtherCompounds = }} }}

'''Chromomycin A3 (CMA₃)''' or '''Toyomycin''' is an anthraquinone antibiotic glycoside produced by the fermentation of a certain strain of ''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|doi-access=free}}</ref>

__TOC__ == Fluorescence properties == In the presence of Mg²⁺ ions, Chromomycin A₃ binds reversibly to DNA, preferentially to contiguous G/C base pairs.<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|doi-access=free}}</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 A₃ has a maximum excitation wavelength of 445 nm (blue), and a maximum emission wavelength of 575&nbsp;nm (yellow).<ref>{{cite web |url=https://www.caymanchem.com/pdfs/11315.pdf |publisher=Cayman Chemical |title=Product Information Chromomycin A3 Item No. 11315 |date=28 September 2022 |archive-url=https://web.archive.org/web/20240619215013/https://cdn.caymanchem.com/cdn/insert/11315.pdf |archive-date=19 June 2024 |url-status=live}}</ref>

== Uses == * in-vitro membrane-impermeant G/C-specific fluorescent DNA-binding dye.<ref name=":12" /> * in-vitro antibiotic of gram-positive bacteria, through inhibition of the incorporation of P_i 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|doi-access=free}}</ref> * Evaluation of male fertility: Chromomycin A₃ and protamines compete for the same binding sites in the DNA, so CMA₃ 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