Synonym
Kinamycin C; KinamycinC; Kinamycin-C;
IUPAC/Chemical Name
5H-Benzo(b)carbazole-5-carbonitrile, 1,2,4-tris(acetyloxy)-1,2,3,4,6,11-hexahydro-3,7-dihydroxy-3-methyl-6,11-dioxo-, (1-alpha,2-beta,3-alpha,4-alpha)-
InChi Key
BQWLWNOFIHHESO-SBFWRKJZSA-N
InChi Code
InChI=1S/C24H20N2O10/c1-9(27)34-21-16-15-17(20(32)14-12(19(15)31)6-5-7-13(14)30)26(8-25)18(16)22(35-10(2)28)24(4,33)23(21)36-11(3)29/h5-7,21-23,30,33H,1-4H3/t21-,22+,23+,24+/m1/s1
SMILES Code
N#CN1C(C(C2=C(O)C=CC=C23)=O)=C(C4=C1[C@H](OC(C)=O)[C@](C)(O)[C@@H](OC(C)=O)[C@@H]4OC(C)=O)C3=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
496.43
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: Hasinoff BB, Wu X, Yalowich JC, Goodfellow V, Laufer RS, Adedayo O, Dmitrienko GI. Kinamycins A and C, bacterial metabolites that contain an unusual diazo group, as potential new anticancer agents: antiproliferative and cell cycle effects. Anticancer Drugs. 2006 Aug;17(7):825-37. PubMed PMID: 16926632.
2: Omura S, Nakagawa A, Yamada H, Hata T, Furusaki A. Structures and biological properties of Kinamycin A, B, C, and D. Chem Pharm Bull (Tokyo). 1973 May;21(5):931-40. PubMed PMID: 4727361.
3: Lei X, Porco JA Jr. Total synthesis of the diazobenzofluorene antibiotic (-)-kinamycin C1. J Am Chem Soc. 2006 Nov 22;128(46):14790-1. PubMed PMID: 17105273.
4: Nicolaou KC, Li H, Nold AL, Pappo D, Lenzen A. Total synthesis of kinamycins C, F, and J. J Am Chem Soc. 2007 Aug 29;129(34):10356-7. Epub 2007 Aug 4. PubMed PMID: 17676854.
5: Scully SS, Porco JA Jr. Studies toward the synthesis of the epoxykinamycin FL-120B': discovery of a decarbonylative photocyclization. Org Lett. 2012 May 18;14(10):2646-9. doi: 10.1021/ol3010563. Epub 2012 May 9. PubMed PMID: 22571279; PubMed Central PMCID: PMC3433630.