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
ChEMBL
ChemSpider
ECHA InfoCard 100.027.589
UNII
  • 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 checkY
    Key: VWUDFIOZFAFOMW-QUOOOCNJSA-N checkY
  • 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
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).
☒N verify (what is checkY☒N ?)
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

References

  1. 1 2 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.
  3. 1 2 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. https://www.caymanchem.com/pdfs/11315.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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