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  Y
ChEMBL	ChEMBL216639  N
ChemSpider	16735739  Y
ECHA InfoCard	100.027.589
PubChem CID	656673
UNII	DVW027E7NL  Y
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 Y Key: VWUDFIOZFAFOMW-QUOOOCNJSA-N Y 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). N  verify  (what is  YN ?) 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

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.
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. "Product Information Chromomycin A3 Item No. 11315" (PDF). Cayman Chemical. 28 September 2022. Archived (PDF) from the original on 19 June 2024.
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.