Synonym
PNU-159682; PNU 159682; PNU159682. metabolite of nemorubicin (MMDX)
IUPAC/Chemical Name
(7S,9S)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-7-(((1S,3R,4aS,9S,9aR,10aS)-9-methoxy-1-methyloctahydro-1H-pyrano[4',3':4,5]oxazolo[2,3-c][1,4]oxazin-3-yl)oxy)-7,9,10,12-tetrahydrotetracen-5(8H)-one
InChi Key
NOGFHSKHNYEVCK-DQTAREDWSA-N
InChi Code
InChI=1S/C32H37NO12/c1-14-29-18(33-7-8-42-31(41-3)30(33)45-29)10-22(43-14)44-20-12-32(39,21(35)13-34)11-17-24(20)28(38)25-16(26(17)36)9-15-5-4-6-19(40-2)23(15)27(25)37/h4-6,14,18,20,22,29-31,34,36,38-39H,7-13H2,1-3H3/t14-,18-,20-,22-,29+,30+,31-,32-/m0/s1
SMILES Code
O=C(C1=C(C2=C(C(O)=C1C3)C[C@@](O)(C(CO)=O)C[C@@H]2O[C@@H]4O[C@H]([C@H]5O[C@@H]6[C@@H](OC)OCCN6[C@H]5C4)C)O)C7=C3C=CC=C7OC
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, not in water
Shelf Life
>2 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
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| Soluble in DMSO, not in water |
0.0 |
100.00 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
627.64
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: Yu SF, Zheng B, Go M, Lau J, Spencer S, Raab H, Soriano R, Jhunjhunwala S,
Cohen R, Caruso M, Polakis P, Flygare J, Polson AG. A Novel Anti-CD22
Anthracycline-Based Antibody-Drug Conjugate (ADC) That Overcomes Resistance to
Auristatin-Based ADCs. Clin Cancer Res. 2015 Jul 15;21(14):3298-306. doi:
10.1158/1078-0432.CCR-14-2035. Epub 2015 Apr 3. PubMed PMID: 25840969.
2: Mazzini S, Scaglioni L, Mondelli R, Caruso M, Sirtori FR. The interaction of
nemorubicin metabolite PNU-159682 with DNA fragments d(CGTACG)(2), d(CGATCG)(2)
and d(CGCGCG)(2) shows a strong but reversible binding to G:C base pairs. Bioorg
Med Chem. 2012 Dec 15;20(24):6979-88. doi: 10.1016/j.bmc.2012.10.033. Epub 2012
Nov 3. PubMed PMID: 23154079.
3: Quintieri L, Fantin M, Palatini P, De Martin S, Rosato A, Caruso M, Geroni C,
Floreani M. In vitro hepatic conversion of the anticancer agent nemorubicin to
its active metabolite PNU-159682 in mice, rats and dogs: a comparison with human
liver microsomes. Biochem Pharmacol. 2008 Sep 15;76(6):784-95. doi:
10.1016/j.bcp.2008.07.003. Epub 2008 Jul 11. PubMed PMID: 18671948.
4: Quintieri L, Geroni C, Fantin M, Battaglia R, Rosato A, Speed W, Zanovello P,
Floreani M. Formation and antitumor activity of PNU-159682, a major metabolite of
nemorubicin in human liver microsomes. Clin Cancer Res. 2005 Feb
15;11(4):1608-17. PubMed PMID: 15746066.
(last updated: 4/21/2016).
