Synonym
Carminomycinone; CCRIS7634; CCRIS-7634; CCRIS 7634
IUPAC/Chemical Name
5,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-1,6,8,10,11-pentahydroxy-, (8S-cis)-
InChi Key
XYDJGVROLWFENK-GIPWTMENSA-N
InChi Code
InChI=1S/C20H16O8/c1-7(21)20(28)5-9-13(11(23)6-20)19(27)15-14(17(9)25)16(24)8-3-2-4-10(22)12(8)18(15)26/h2-4,11,22-23,25,27-28H,5-6H2,1H3/t11-,20+/m1/s1
SMILES Code
O=C(C1=C2C(O)=C3[C@H](O)C[C@](O)(C(C)=O)CC3=C1O)C4=CC=CC(O)=C4C2=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
384.34
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Capobianco ML, De Champdoré M, Francini L, Lena S, Garbesi A, Arcamone F. New TFO conjugates containing a carminomycinone-derived chromophore. Bioconjug Chem. 2001 Jul-Aug;12(4):523-8. doi: 10.1021/bc000139z. PMID: 11459456.
2: El Khadem HS, Swartz DL. Synthesis of 2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone as well as 2'-deoxy-D-erythro- pentopyranosyldaunomycinone, -carminomycinone, and -epsilon-pyrromycinone. J Med Chem. 1981 Jan;24(1):112-5. doi: 10.1021/jm00133a023. PMID: 7205866.
3: Essery JM, Doyle TW, Schreiber RH. Synthesis and antitumor properties of 7-deoxy-7-[(cis- and trans-3-aminocyclohexane)thio]carminomycinone. J Med Chem. 1979 Nov;22(11):1425-8. doi: 10.1021/jm00197a029. PMID: 160462.
4: Olsuf'eva EN, Povarov LS. Sintez i svoĭstva proizvodnykh karminomitsinona [Synthesis and properties of carminomycinone derivatives]. Antibiotiki. 1977 Dec;22(12):1085-8. Russian. PMID: 596853.
5: Kende AS, Tsay YG, Mills JE. Letter: Total synthesis of (+/-)-daunomycinone and (+/-)-carminomycinone. J Am Chem Soc. 1976 Mar 31;98(7):1967-9. doi: 10.1021/ja00423a056. PMID: 1254856.
6: Connors NC, Strohl WR. Partial purification and properties of carminomycin 4-O-methyltransferase from Streptomyces sp. strain C5. J Gen Microbiol. 1993 Jun;139 Pt 6:1353-62. doi: 10.1099/00221287-139-6-1353. PMID: 8360627.
7: Tanaka H, Yoshioka T, Shimauchi Y, Matsushita Y, Matsuzawa Y, Oki T, Ishikura T. Chemical modification of anthracycline antibiotics IV. Synthesis of new anthracyclines with trisaccharide. J Antibiot (Tokyo). 1982 Mar;35(3):312-20. doi: 10.7164/antibiotics.35.312. PMID: 6951827.
8: Paranosenkova VI, Karpov VL. Biosintez rubomitsina. Glikozilirovanie ekzogennykh rubomitsina i karminomitsinona kul'turoi produtsenta rubomitsina [Biosynthesis of rubomycin. The glycosylation of exogenous rubomycin one and carminomycin one by a rubomycin-producing culture]. Antibiotiki. 1977 Jan;22(1):37-41. Russian. PMID: 843071.
9: Wu GS, Gard A, Rosazza JP. Microbial transformations of natural antitumor agents. 13. Conversions of 13-blocked anthracyclinones. J Antibiot (Tokyo). 1980 Jul;33(7):705-10. doi: 10.7164/antibiotics.33.705. PMID: 7190964.
10: Aleksandrova LG, Rubasheva LM, Zbarskiĭ VB, Brazhnikova MG. Opredelenie karminomitsina v ego preparatakh metodom vysokoéffektivnoĭ zhidkostnoĭ khromatografii [Determination of carminomycin in its preparations by high- performance liquid chromatography]. Antibiot Khimioter. 1988 Aug;33(8):574-8. Russian. PMID: 3196114.
