Synonym
Kidamycin; Iyomycin-F;
IUPAC/Chemical Name
(Z)-2-(but-2-en-2-yl)-10-(4-(dimethylamino)-5-hydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)-8-(4-(dimethylamino)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)-11-hydroxy-5-methyl-4H-naphtho[2,3-h]chromene-4,7,12-trione
InChi Key
MFTJRTUKCOVIMD-BOPFTXTBSA-N
InChi Code
InChI=1S/C39H48N2O9/c1-11-17(2)26-15-25(42)29-18(3)12-23-31(37(29)50-26)36(46)32-30(35(23)45)21(27-14-24(40(7)8)33(43)19(4)48-27)13-22(34(32)44)28-16-39(6,41(9)10)38(47)20(5)49-28/h11-13,15,19-20,24,27-28,33,38,43-44,47H,14,16H2,1-10H3/b17-11-
SMILES Code
O=C1C=C(/C(C)=C\C)OC2=C1C(C)=CC(C3=O)=C2C(C4=C3C(C5CC(N(C)C)C(O)C(C)O5)=CC(C6CC(C)(N(C)C)C(O)C(C)O6)=C4O)=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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
688.82
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: Fei Z, McDonald FE. Stereo- and regioselective glycosylations to the bis-C-arylglycoside of kidamycin. Org Lett. 2007 Aug 30;9(18):3547-50. Epub 2007 Aug 11. PubMed PMID: 17691798; PubMed Central PMCID: PMC4604443.
2: Fei Z, McDonald FE. Synthesis of the aglycones of altromycins and kidamycin from a common intermediate. Org Lett. 2005 Aug 18;7(17):3617-20. PubMed PMID: 16092833; PubMed Central PMCID: PMC1388187.
3: Takeshima H, Okamoto M, Komiyama K, Umezawa I. Mechanism of action of acetyl kidamycin. I. Interaction with DNA. Biochim Biophys Acta. 1976 Jan 5;418(1):24-8. PubMed PMID: 942683.
4: Umezawa I, Komiyama K, Takeshima H, Hata T, Kono M. A new antitumor antibiotic, kidamycin. IV. Pharmacokinetics of acetyl-kidamycin. J Antibiot (Tokyo). 1973 Nov;26(11):669-75. PubMed PMID: 4792114.
5: Kanda N. A new antitumor antibiotic, kidamycin. I. Isolation, purification and properties of kidamycin. J Antibiot (Tokyo). 1971 Sep;24(9):599-606. PubMed PMID: 5132247.
6: Kanda N. A new antitumor antibiotic, kidamycin. 3. Preparation and properties of acetyl kidamycin. J Antibiot (Tokyo). 1972 Oct;25(10):557-60. PubMed PMID: 4648310.
7: Kanda N, Kono M, Asano K. A new antitumor antibiotic, kidamycin. II. Experimental treatment of cancer with kidamycin. J Antibiot (Tokyo). 1972 Oct;25(10):553-6. PubMed PMID: 4648309.
8: Fujita H, Sawabe T, Hanawa Y, Kimura K. [In vivo distribution of daunomycin, acetyl kidamycin, actinomycin D and chromomycin A3]. Gan No Rinsho. 1971 Mar;17(3):196-204. Japanese. PubMed PMID: 5102102.
9: Okamoto M, Takeshima H, Komiyama K, Umezawa I. Mechanism of action of acetyl kidamycin. II. Inhibition of RNA synthesis in HeLa cells. J Antibiot (Tokyo). 1976 Dec;29(12):1334-8. PubMed PMID: 1010801.
10: Kumazawa M, Inada S, Namiki M, Ishii S, Tago K. Mechanism of action of antitumor agents on bacteria. II. Effect of acetyl-kidamycin on nucleic acids. Kitasato Arch Exp Med. 1974 Sep;47(3):79-88. PubMed PMID: 4218625.
11: O'Keefe BM, Mans DM, Kaelin DE Jr, Martin SF. Total synthesis of isokidamycin. J Am Chem Soc. 2010 Nov 10;132(44):15528-30. doi: 10.1021/ja107926f. PubMed PMID: 20958036; PubMed Central PMCID: PMC2974561.
12: Fredenhagen A, Séquin U. The photodeactivation of hedamycin, an antitumor antibiotic of the pluramycin type. J Antibiot (Tokyo). 1985 Feb;38(2):236-41. PubMed PMID: 3997668.
13: O'Keefe BM, Mans DM, Kaelin DE Jr, Martin SF. Studies Toward the Syntheses of Pluramycin Natural Products. The First Total Synthesis of Isokidamycin. Tetrahedron. 2011 Sep 2;67(35):6524-6538. PubMed PMID: 21804649; PubMed Central PMCID: PMC3145363.
14: Sun D, Hansen M, Clement JJ, Hurley LH. Structure of the altromycin B (N7-guanine)-DNA adduct. A proposed prototypic DNA adduct structure for the pluramycin antitumor antibiotics. Biochemistry. 1993 Aug 17;32(32):8068-74. PubMed PMID: 8347608.
15: Kaelin DE Jr, Lopez OD, Martin SF. General strategies for the synthesis of the major classes of C-aryl glycosides. J Am Chem Soc. 2001 Jul 18;123(28):6937-8. PubMed PMID: 11448205.
