NK-611 free acid | CAS# 105655-99-0 (free acid) | emisynthetic analogue of etoposide

MedKoo Cat#: 414425 | Name: NK-611 free acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

NK-611 free acid is a new semisynthetic analogue of etoposide, which presumably also acts through inhibition of topoisomerase II, and has been found to be more potent against several cancer cell lines in vitro than etoposide.

Chemical Structure

NK-611 free acid

CAS#105655-99-0 (free acid)

Theoretical Analysis

MedKoo Cat#: 414425

Name: NK-611 free acid

CAS#: 105655-99-0 (free acid)

Chemical Formula: C31H37NO12

Exact Mass: 615.2316

Molecular Weight: 615.63

Elemental Analysis: C, 60.48; H, 6.06; N, 2.28; O, 31.19

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

105655-99-0 (free acid); 105760-98-3 (HCl)

Synonym

NK-611 free acid; NK611 free acid; NK 611 free acid; VP19; VP-19; VP 19

IUPAC/Chemical Name

Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 9-((2-deoxy-2-(dimethylamino)-4,6-O-(1R)-ethylidene-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-

InChi Key

ZKSNZYLCOXUJIR-QMWJQCESSA-N

InChi Code

InChI=1S/C31H37NO12/c1-13-38-11-22-29(42-13)27(34)25(32(2)3)31(43-22)44-28-16-9-19-18(40-12-41-19)8-15(16)23(24-17(28)10-39-30(24)35)14-6-20(36-4)26(33)21(7-14)37-5/h6-9,13,17,22-25,27-29,31,33-34H,10-12H2,1-5H3/t13?,17-,22+,23+,24-,25+,27+,28+,29+,31-/m0/s1

SMILES Code

O=C1OC[C@]2([H])[C@H](O[C@H]3[C@H](N(C)C)[C@H]([C@@H]([C@@H](CO4)O3)OC4C)O)C5=C(C=C6OCOC6=C5)[C@@H](C7=CC(OC)=C(O)C(OC)=C7)[C@]21[H]

Appearance

Solid powder

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 615.63 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: Hanauske AR, Wüster KC, Lehmer A, Rotter M, Schneider P, Kaeser-Fröhlich A, Rastetter J, Depenbrock H. Activity of NK 611, a new epipodophyllotoxin derivative, against colony forming units from freshly explanted human tumours in vitro. Eur J Cancer. 1995 Sep;31A(10):1677-81. PubMed PMID: 7488424. 2: Hüttmann A, Mross K, Hossfeld DK. Determination of the new podophyllotoxin derivative NK 611 in plasma by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 1993 Oct 29;620(2):233-8. PubMed PMID: 8300791. 3: Mross K, Hüttmann A, Herbst K, Hanauske AR, Schilling T, Manegold C, Burk K, Hossfeld DK. Pharmacokinetics and pharmacodynamics of the new podophyllotoxin derivative NK 611. A study by the AIO groups PHASE-I and APOH. Cancer Chemother Pharmacol. 1996;38(3):217-24. PubMed PMID: 8646795. 4: Daley L, Guminski Y, Demerseman P, Kruczynski A, Etiévant C, Imbert T, Hill BT, Monneret C. Synthesis and antitumor activity of new glycosides of epipodophyllotoxin, analogues of etoposide, and NK 611. J Med Chem. 1998 Nov 5;41(23):4475-85. PubMed PMID: 9804687. 5: Takigawa N, Ohnoshi T, Ueoka H, Kiura K, Moritaka T, Tabata M, Segawa Y, Shibayama T, Gemba K, Matsumura T, et al. [In vitro comparison of podophyllotoxin analogues; etoposide, teniposide and NK 611 using human lung cancer cell lines]. Gan To Kagaku Ryoho. 1993 Mar;20(4):473-7. Japanese. PubMed PMID: 8383949. 6: Capranico G, Giaccone G, Zunino F, Garattini S, D'Incalci M. DNA topoisomerase II poisons and inhibitors. Cancer Chemother Biol Response Modif. 1997;17:114-31. Review. PubMed PMID: 9551211. 7: Rassmann I, Thödtmann R, Mross M, Hüttmann A, Berdel WE, Manegold C, Fiebig HH, Kaeser-Fröhlich A, Burk K, Hanauske AR. Phase I clinical and pharmacokinetic trial of the podophyllotoxin derivative NK611 administered as intravenous short infusion. Invest New Drugs. 1998-1999;16(4):319-24. PubMed PMID: 10426664. 8: Pagani O, Zucchetti M, Sessa C, de Jong J, D'Incalci M, De Fusco M, Kaeser-Fröhlich A, Hanauske A, Cavalli F. Clinical and pharmacokinetic study of oral NK611, a new podophyllotoxin derivative. Cancer Chemother Pharmacol. 1996;38(6):541-7. PubMed PMID: 8823496. 9: De Fusco M, D'Incalci M, Gentili D, Reichert S, Zucchetti M. High-performance liquid chromatographic assay for the determination of the novel etoposide derivative dimethylaminoetoposide (NK611) and its metabolites in urine of cancer patients. J Chromatogr B Biomed Appl. 1995 Feb 17;664(2):409-14. PubMed PMID: 7780594. 10: Machida M, Tanaka S, Nakamori K. Simultaneous determination of NK611, a novel water-soluble derivative of etoposide, and its metabolite (DeNK611) in dog plasma by column-switching high performance liquid chromatography. Biomed Chromatogr. 1993 Mar-Apr;7(2):82-5. PubMed PMID: 8485379. 11: Rassmann I, Schrödel H, Schilling T, Zucchetti M, Kaeser-Fröhlich A, Rastetter J, Hanauske AR. Clinical and pharmacokinetic phase I trial of oral dimethylaminoetoposide (NK611) administered for 21 days every 35 days. Invest New Drugs. 1996;14(4):379-86. PubMed PMID: 9157073. 12: Zucchetti M, De Fusco M, Sessa C, Fröhlich A, Reichert S, D'Incalci M. High-performance liquid chromatographic assay for the determination of the novel podophyllotoxin derivative dimethylaminoetoposide (NK611) in human plasma. J Chromatogr B Biomed Appl. 1994 Mar 18;654(1):97-102. PubMed PMID: 8004249.