Synonym
NSC176323; NSC 176323; NSC-176323; 9-Methoxycamptothecin
IUPAC/Chemical Name
(S)-4-ethyl-4-hydroxy-10-methoxy-1,12-dihydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H)-dione
InChi Key
XVMZDZFTCKLZTF-NRFANRHFSA-N
InChi Code
InChI=1S/C21H18N2O5/c1-3-21(26)14-8-16-18-11(7-12-15(22-18)5-4-6-17(12)27-2)9-23(16)19(24)13(14)10-28-20(21)25/h4-8,26H,3,9-10H2,1-2H3/t21-/m0/s1
SMILES Code
O=C1[C@](O)(CC)C(C=C23)=C(CO1)C(N2CC4=C3N=C5C=CC=C(OC)C5=C4)=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
378.38
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: Wang H, Ao M, Liu W, Bai Y, Zhu Y, Yu L. Topoisomerases inhibitory activities and DNA binding properties of 9-methoxycamptothecin from Nothapodytes nimmoniana (J. Graham) Mabberly. Nat Prod Res. 2017 Nov 13:1-5. doi: 10.1080/14786419.2017.1402312. [Epub ahead of print] PubMed PMID: 29130341.
2: Wang H, Ao M, Wu J, Yu L. TNFα and Fas/FasL pathways are involved in 9-Methoxycamptothecin-induced apoptosis in cancer cells with oxidative stress and G2/M cell cycle arrest. Food Chem Toxicol. 2013 May;55:396-410. doi: 10.1016/j.fct.2012.12.059. Epub 2013 Jan 29. PubMed PMID: 23369935.
3: Liao N, Zhang P, Ao M, Wang J, Shi Y, Yu L. 9-methoxycamptothecin from Nothapodytes foetida induces apoptosis in murine sarcoma S180 cells. Z Naturforsch C. 2011 Sep-Oct;66(9-10):471-6. PubMed PMID: 22191212.
4: Shweta S, Zuehlke S, Ramesha BT, Priti V, Mohana Kumar P, Ravikanth G, Spiteller M, Vasudeva R, Uma Shaanker R. Endophytic fungal strains of Fusarium solani, from Apodytes dimidiata E. Mey. ex Arn (Icacinaceae) produce camptothecin, 10-hydroxycamptothecin and 9-methoxycamptothecin. Phytochemistry. 2010 Jan;71(1):117-22. doi: 10.1016/j.phytochem.2009.09.030. Epub 2009 Oct 26. PubMed PMID: 19863979.
5: Puri SC, Handa G, Bhat BA, Gupta VK, Amna T, Verma N, Anand R, Dhar KL, Qazi GN. Separation of 9-methoxycamptothecin and camptothecin from Nothapodytes foetida by semipreparative HPLC. J Chromatogr Sci. 2005 Aug;43(7):348-50. PubMed PMID: 16176645.
6: Zhou BN, Hoch JM, Johnson RK, Mattern MR, Eng WK, Ma J, Hecht SM, Newman DJ, Kingston DG. Use of COMPARE analysis to discover new natural product drugs: isolation of camptothecin and 9-methoxycamptothecin from a new source. J Nat Prod. 2000 Sep;63(9):1273-6. PubMed PMID: 11000035.
7: Gunasekera SP, Badawi MM, Cordell GA, Farnsworth NR, Chitnis M. Plant anticancer agents X. Isolation of camptothecin and 9-methoxycamptothecin from Ervatamia heyneana. J Nat Prod. 1979 Sep-Oct;42(5):475-7. PubMed PMID: 521817.
