Chromomycin A3

Chromomycin A3
Names
	IUPAC name (6S,7S)-6-[(4-O-Acetyl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl)-(1→3)-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyloxy]-7-[(1S)-5-deoxy-1-O-methyl-D-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-D-lyxo-hexopyranosyl)-(1→3)-2,6-dideoxy-D-lyxo-hexopyranoside 4-acetate
	Systematic IUPAC name (12S,14S,15S,16S,32S,34R,35R,36R,52S,54R,55R,56R,72S,73S,92S,94R,95S,96R,112R,114R,115R,116R)-73-[(1S,3S,4R)-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
	Other names Toyomycin
Identifiers
CAS Number	7059-24-7 ;
ChEMBL	ChEMBL216639 ;
ChemSpider	16735739 ;
ECHA InfoCard	100.027.589
PubChem CID	656673;
UNII	DVW027E7NL ;
CompTox Dashboard (EPA)	DTXSID4046363 ;
	InChI 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 Key: VWUDFIOZFAFOMW-QUOOOCNJSA-N ; 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 Key: VWUDFIOZFAFOMW-QUOOOCNJBW; Key: VWUDFIOZFAFOMW-QUOOOCNJSA-N;
Properties
Chemical formula	C57H82O26
Molar mass	1183.257 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Chromomycin A3 (CMA₃) or Toyomycin is an anthraquinone antibiotic glycoside produced by the fermentation of a certain strain of Streptomyces griseus (No. 7).^[1]

Fluorescence properties

In the presence of Mg²⁺ ions, Chromomycin A₃ binds reversibly to DNA, preferentially to contiguous G/C base pairs.^[2]^[3]

When bound to DNA, Chromomycin A₃ has a maximum excitation wavelength of 445 nm (blue), and a maximum emission wavelength of 575 nm (yellow).^[4]

Uses

in-vitro membrane-impermeant G/C-specific fluorescent DNA-binding dye.^[3]
in-vitro antibiotic of gram-positive bacteria, through inhibition of the incorporation of P_i in the RNA.^[1]
in-vitro anticancer drug that inhibits RNA synthesis.^[5]
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).^[6]^[7]

References

^ ^a ^b Kamiyama, M.; Kaziro, Y. (January 1966). "Mechanism of action of chromomycin A3. 1. Inhibition of nucleic acid metabolism in Bacillus subtilis cells". Journal of Biochemistry. 59 (1): 49–56. doi:10.1093/oxfordjournals.jbchem.a128257. ISSN 0021-924X. PMID 4957278.
^ Kamiyama, M. (May 1968). "Mechanism of action of chromomycin A3. 3. On the binding of chromomycin A3 with DNA and physiochemical properties of the complex". Journal of Biochemistry. 63 (5): 566–572. doi:10.1093/oxfordjournals.jbchem.a128814. ISSN 0021-924X. PMID 4972707.
^ ^a ^b Van Dyke, M. W.; Dervan, P. B. (1983-05-10). "Chromomycin, mithramycin, and olivomycin binding sites on heterogeneous deoxyribonucleic acid. Footprinting with (methidiumpropyl-EDTA)iron(II)". Biochemistry. 22 (10): 2373–2377. doi:10.1021/bi00279a011. ISSN 0006-2960. PMID 6222762.
^ https://www.caymanchem.com/pdfs/11315.pdf ^{[bare URL PDF]}
^ Kajiro, Y.; Kamiyama, M. (October 1967). "Mechanism of action of chromomycin A3. II. Inhibition of RNA polymerase reaction". Journal of Biochemistry. 62 (4): 424–429. doi:10.1093/oxfordjournals.jbchem.a128685. ISSN 0021-924X. PMID 5587590.
^ Iranpour, Farhad Golshan; Nasr-Esfahani, Mohammad Hosein; Valojerdi, Mojtaba Rezazadeh; Al-Taraihi, Taki Mohammad Taki (2000-01-01). "Chromomycin A3 Staining as a Useful Tool for Evaluation of Male Fertility". Journal of Assisted Reproduction and Genetics. 17 (1): 60–66. doi:10.1023/a:1009406231811. ISSN 1058-0468. PMC 3455193. PMID 10754785.
^ Nijs, Martine; Creemers, Eva; Cox, Annemie; Franssen, Kim; Janssen, Mia; Vanheusden, Elke; Jonge, Christopher De; Ombelet, Willem (November 2009). "Chromomycin A3 staining, sperm chromatin structure assay and hyaluronic acid binding assay as predictors for assisted reproductive outcome". Reproductive BioMedicine Online. 19 (5): 671–684. doi:10.1016/j.rbmo.2009.07.002. PMID 20021715.

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[:0-1] Kamiyama, M.; Kaziro, Y. (January 1966). "Mechanism of action of chromomycin A3. 1. Inhibition of nucleic acid metabolism in Bacillus subtilis cells". Journal of Biochemistry. 59 (1): 49–56. doi:10.1093/oxfordjournals.jbchem.a128257. ISSN 0021-924X. PMID 4957278.

[2] Kamiyama, M. (May 1968). "Mechanism of action of chromomycin A3. 3. On the binding of chromomycin A3 with DNA and physiochemical properties of the complex". Journal of Biochemistry. 63 (5): 566–572. doi:10.1093/oxfordjournals.jbchem.a128814. ISSN 0021-924X. PMID 4972707.

[:12-3] Van Dyke, M. W.; Dervan, P. B. (1983-05-10). "Chromomycin, mithramycin, and olivomycin binding sites on heterogeneous deoxyribonucleic acid. Footprinting with (methidiumpropyl-EDTA)iron(II)". Biochemistry. 22 (10): 2373–2377. doi:10.1021/bi00279a011. ISSN 0006-2960. PMID 6222762.

[4] ttps://www.caymanchem.com/pdfs/11315.pdf ^{[bare URL PDF]}

[5] Kajiro, Y.; Kamiyama, M. (October 1967). "Mechanism of action of chromomycin A3. II. Inhibition of RNA polymerase reaction". Journal of Biochemistry. 62 (4): 424–429. doi:10.1093/oxfordjournals.jbchem.a128685. ISSN 0021-924X. PMID 5587590.

[6] Iranpour, Farhad Golshan; Nasr-Esfahani, Mohammad Hosein; Valojerdi, Mojtaba Rezazadeh; Al-Taraihi, Taki Mohammad Taki (2000-01-01). "Chromomycin A3 Staining as a Useful Tool for Evaluation of Male Fertility". Journal of Assisted Reproduction and Genetics. 17 (1): 60–66. doi:10.1023/a:1009406231811. ISSN 1058-0468. PMC 3455193. PMID 10754785.

[7] Nijs, Martine; Creemers, Eva; Cox, Annemie; Franssen, Kim; Janssen, Mia; Vanheusden, Elke; Jonge, Christopher De; Ombelet, Willem (November 2009). "Chromomycin A3 staining, sperm chromatin structure assay and hyaluronic acid binding assay as predictors for assisted reproductive outcome". Reproductive BioMedicine Online. 19 (5): 671–684. doi:10.1016/j.rbmo.2009.07.002. PMID 20021715.

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v t e Types of natural anthraquinones
Dihydroxyanthraquinones	Alizarin Aloe emodin Damnacanthal 1,3-Dihydroxyanthraquinone 1,4-Dihydroxyanthraquinone 1,8-Dihydroxyanthraquinone Rhein
Trihydroxyanthraquinones	Parietin Emodin 1,2,4-Trihydroxyanthraquinone 1,3,8-Trihydroxyanthraquinone
Tetrahydroxyanthraquinones	quinalizarin rheoemodin
Misc:	Kermesic acid Carminic acid Senna glycosides