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MedKoo Cat#: 202834 | Name: TAS-103 HCl salt (BMS-247615)
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Description:

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

TAS-103, also known as BMS-247615, is a quinoline derivative that displays antitumor activity in murine and human tumor models. TAS-103 has been reported to be a potent topoisomerase II poison. TAS-103 showed the strongest antitumor activity among the conventional anticancer agents for colorectal cancer (p<0.05). The combination with CDDP augmented the antitumor activity of TAS-103 (p<0.05), indicating that CDDP is one of the most potent candidates to be used in combination with TAS-103 . TAS-103 may be useful in the chemotherapy of colorectal cancer.

Chemical Structure

TAS-103 HCl salt (BMS-247615)
TAS-103 HCl salt (BMS-247615)
CAS#174634-09-4

Theoretical Analysis

MedKoo Cat#: 202834

Name: TAS-103 HCl salt (BMS-247615)

CAS#: 174634-09-4

Chemical Formula: C20H21Cl2N3O2

Exact Mass: 0.0000

Molecular Weight: 406.31

Elemental Analysis: C, 59.12; H, 5.21; Cl, 17.45; N, 10.34; O, 7.88

Price and Availability

Size Price Availability Quantity
5mg USD 120.00 Ready to ship
10mg USD 190.00 Ready to ship
25mg USD 330.00 Ready to ship
50mg USD 550.00 Ready to ship
100mg USD 950.00 Ready to ship
200mg USD 1,450.00 Ready to ship
500mg USD 1,950.00 Ready to ship
1g USD 3,450.00 Ready to ship
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Related CAS #
174634-09-4 (HCl salt) 174634-08-3 (free base)
Synonym
TAS103; TAS-103; TAS 103 HCl; BMS247615; BMS 247615; BMS-247615 HCl,
IUPAC/Chemical Name
.6-((2-(dimethylamino)ethyl)amino)-3-hydroxy-7H-indeno[2,1-c]quinolin-7-one dihydrochloride
InChi Key
HAYAYGFVSIWSGQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H19N3O2.2ClH/c1-23(2)10-9-21-20-18-17(13-5-3-4-6-14(13)19(18)25)15-8-7-12(24)11-16(15)22-20;;/h3-8,11,24H,9-10H2,1-2H3,(H,21,22);2*1H
SMILES Code
O=C(C1=C2C3=CC=C(O)C=C3N=C1NCCN(C)C)C4=C2C=CC=C4.[H]Cl.[H]Cl
Appearance
Red 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
soluble in water, not soluble in DMSO, not soluble in chloroform.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in water.
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
Biological target:
TAS 103 is an inhibitor of DNA topoisomerase I and II with IC50s of 2 and 6.5 µM, respectively.
In vitro activity:
The in vitro antitumor effects of TAS-103 were evaluated. TAS-103 inhibited DNA synthesis more strongly than RNA and protein synthesis, and induced an increase of cell population in the S-G2/M phase. The cytotoxicity of TAS-103 was strongest against S-phase cells, but its cell cycle phase specificity was not clear, and depended on drug concentration and exposure time. Reference: Jpn J Cancer Res. 1999 May;90(5):578-87. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5926096/
In vivo activity:
To evaluate the anti-tumor efficacy of liposomal TAS-103, the therapeutic efficacy against solid tumor-bearing mice in vivo was examined. Liposomal TAS-103 effectively suppressed solid tumor growth accompanying longer survival time of tumor-bearing mice in comparison with the control. Reference: Biol Pharm Bull. 2002 Oct;25(10):1385-7. https://www.jstage.jst.go.jp/article/bpb/25/10/25_10_1385/_article
Solvent mg/mL mM
Solubility
PBS (pH 7.2) 1.0 2.46
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 406.31 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Tsunoda T, Tanimura H, Yamaue H, Ishimoto K, Kobunai T, Yamada Y. In vitro antitumor activity of TAS-103 against freshly-isolated human colorectal cancer. Anticancer Res. 2001 Nov-Dec;21(6A):3897-902. PMID: 11911266. 2. Aoyagi Y, Kobunai T, Utsugi T, Oh-hara T, Yamada Y. In vitro antitumor activity of TAS-103, a novel quinoline derivative that targets topoisomerases I and II. Jpn J Cancer Res. 1999 May;90(5):578-87. doi: 10.1111/j.1349-7006.1999.tb00786.x. PMID: 10391099; PMCID: PMC5926096. 3. Shimizu K, Takada M, Asai T, Kuromi K, Baba K, Oku N. Cancer chemotherapy by liposomal 6-[12-(dimethylamino)ethyl]aminol-3-hydroxy-7H-indeno[2,1-clquinolin-7-one dihydrochloride (TAS-103), a novel anti-cancer agent. Biol Pharm Bull. 2002 Oct;25(10):1385-7. doi: 10.1248/bpb.25.1385. PMID: 12392102.
In vitro protocol:
1. Tsunoda T, Tanimura H, Yamaue H, Ishimoto K, Kobunai T, Yamada Y. In vitro antitumor activity of TAS-103 against freshly-isolated human colorectal cancer. Anticancer Res. 2001 Nov-Dec;21(6A):3897-902. PMID: 11911266. 2. Aoyagi Y, Kobunai T, Utsugi T, Oh-hara T, Yamada Y. In vitro antitumor activity of TAS-103, a novel quinoline derivative that targets topoisomerases I and II. Jpn J Cancer Res. 1999 May;90(5):578-87. doi: 10.1111/j.1349-7006.1999.tb00786.x. PMID: 10391099; PMCID: PMC5926096.
In vivo protocol:
1. Shimizu K, Takada M, Asai T, Kuromi K, Baba K, Oku N. Cancer chemotherapy by liposomal 6-[12-(dimethylamino)ethyl]aminol-3-hydroxy-7H-indeno[2,1-clquinolin-7-one dihydrochloride (TAS-103), a novel anti-cancer agent. Biol Pharm Bull. 2002 Oct;25(10):1385-7. doi: 10.1248/bpb.25.1385. PMID: 12392102.
1: Massaro NP, Chatterji A, Sharma I. Three-Component Approach to Pyridine- Stabilized Ketenimines for the Synthesis of Diverse Heterocycles. J Org Chem. 2019 Nov 1;84(21):13676-13685. doi: 10.1021/acs.joc.9b01906. Epub 2019 Oct 7. PMID: 31550889. 2: Fukuda T, Nanjo Y, Fujimoto M, Yoshida K, Natsui Y, Ishibashi F, Okazaki F, To H, Iwao M. Lamellarin-inspired potent topoisomerase I inhibitors with the unprecedented benzo[g][1]benzopyrano[4,3-b]indol-6(13H)-one scaffold. Bioorg Med Chem. 2019 Jan 15;27(2):265-277. doi: 10.1016/j.bmc.2018.11.037. Epub 2018 Nov 28. PMID: 30553626. 3: Tomoda K, Ohkoshi T, Hirota K, Sonavane GS, Nakajima T, Terada H, Komuro M, Kitazato K, Makino K. Preparation and properties of inhalable nanocomposite particles for treatment of lung cancer. Colloids Surf B Biointerfaces. 2009 Jul 1;71(2):177-82. doi: 10.1016/j.colsurfb.2009.02.001. Epub 2009 Feb 11. PMID: 19264458. 4: Yoshida M, Kabe Y, Wada T, Asai A, Handa H. A new mechanism of 6-((2-(dimethylamino)ethyl)amino)-3-hydroxy-7H-indeno(2,1-c)quinolin-7-one dihydrochloride (TAS-103) action discovered by target screening with drug- immobilized affinity beads. Mol Pharmacol. 2008 Mar;73(3):987-94. doi: 10.1124/mol.107.043307. Epub 2007 Dec 18. PMID: 18089836. 5: Mizutani H. [Mechanism of DNA damage and apoptosis induced by anticancer drugs through generation of reactive oxygen species]. Yakugaku Zasshi. 2007 Nov;127(11):1837-42. Japanese. doi: 10.1248/yakushi.127.1837. PMID: 17978559. 6: Fujimoto S. Promising antitumor activity of a novel quinoline derivative, TAS-103, against fresh clinical specimens of eight types of tumors measured by flow cytometric DNA analysis. Biol Pharm Bull. 2007 Oct;30(10):1923-9. doi: 10.1248/bpb.30.1923. PMID: 17917263. 7: Mizutani H, Tada-Oikawa S, Hiraku Y, Kojima M, Kawanishi S. Mechanism of apoptosis induced by doxorubicin through the generation of hydrogen peroxide. Life Sci. 2005 Feb 11;76(13):1439-53. doi: 10.1016/j.lfs.2004.05.040. Epub 2005 Jan 20. PMID: 15680309. 8: Torigoe T, Izumi H, Wakasugi T, Niina I, Igarashi T, Yoshida T, Shibuya I, Chijiiwa K, Matsuo K, Itoh H, Kohno K. DNA topoisomerase II poison TAS-103 transactivates GC-box-dependent transcription via acetylation of Sp1. J Biol Chem. 2005 Jan 14;280(2):1179-85. doi: 10.1074/jbc.M410499200. Epub 2004 Nov 8. PMID: 15533934. 9: Denny WA, Baguley BC. Dual topoisomerase I/II inhibitors in cancer therapy. Curr Top Med Chem. 2003;3(3):339-53. doi: 10.2174/1568026033452555. PMID: 12570767. 10: Shimizu K, Takada M, Asai T, Kuromi K, Baba K, Oku N. Cancer chemotherapy by liposomal 6-[12-(dimethylamino)ethyl]aminol-3-hydroxy-7H-indeno[2,1-clquinolin-7-one dihydrochloride (TAS-103), a novel anti-cancer agent. Biol Pharm Bull. 2002 Oct;25(10):1385-7. doi: 10.1248/bpb.25.1385. PMID: 12392102. 11: Torigoe T, Izumi H, Ishiguchi H, Uramoto H, Murakami T, Ise T, Yoshida Y, Tanabe M, Nomoto M, Itoh H, Kohno K. Enhanced expression of the human vacuolar H+-ATPase c subunit gene (ATP6L) in response to anticancer agents. J Biol Chem. 2002 Sep 27;277(39):36534-43. doi: 10.1074/jbc.M202605200. Epub 2002 Jul 19. PMID: 12133827. 12: Ishida K, Asao T. Self-association and unique DNA binding properties of the anti-cancer agent TAS-103, a dual inhibitor of topoisomerases I and II. Biochim Biophys Acta. 2002 Jul 18;1587(2-3):155-63. doi: 10.1016/s0925-4439(02)00078-9. PMID: 12084457. 13: Mizutani H, Tada-Oikawa S, Hiraku Y, Oikawa S, Kojima M, Kawanishi S. Mechanism of apoptosis induced by a new topoisomerase inhibitor through the generation of hydrogen peroxide. J Biol Chem. 2002 Aug 23;277(34):30684-9. doi: 10.1074/jbc.M204353200. Epub 2002 Jun 14. PMID: 12068015. 14: Mistry P, Stewart AJ, Dangerfield W, Baker M, Liddle C, Bootle D, Kofler B, Laurie D, Denny WA, Baguley B, Charlton PA. In vitro and in vivo characterization of XR11576, a novel, orally active, dual inhibitor of topoisomerase I and II. Anticancer Drugs. 2002 Jan;13(1):15-28. doi: 10.1097/00001813-200201000-00002. PMID: 11914637. 15: Tsunoda T, Tanimura H, Yamaue H, Ishimoto K, Kobunai T, Yamada Y. In vitro antitumor activity of TAS-103 against freshly-isolated human colorectal cancer. Anticancer Res. 2001 Nov-Dec;21(6A):3897-902. PMID: 11911266. 16: Azuma R, Saeki M, Yamamoto Y, Hagiwara Y, Grochow LB, Donehower RC. Metabolism and urinary excretion of a new quinoline anticancer drug, TAS-103, in humans. Xenobiotica. 2002 Jan;32(1):63-72. doi: 10.1080/00498250110085818. PMID: 11820510. 17: Okamoto R, Takano H, Sekikawa T, Tanaka T, Toyada M, Ukon K, Tanimoto K, Kumazaki T, Nishiyama M. Unique action determinants of double acting topoisomerase inhibitor, TAS-103. Int J Oncol. 2001 Nov;19(5):921-7. doi: 10.3892/ijo.19.5.921. PMID: 11604989. 18: Stewart AJ, Mistry P, Dangerfield W, Bootle D, Baker M, Kofler B, Okiji S, Baguley BC, Denny WA, Charlton PA. Antitumor activity of XR5944, a novel and potent topoisomerase poison. Anticancer Drugs. 2001 Apr;12(4):359-67. doi: 10.1097/00001813-200104000-00009. PMID: 11335793. 19: Ewesuedo RB, Iyer L, Das S, Koenig A, Mani S, Vogelzang NJ, Schilsky RL, Brenckman W, Ratain MJ. Phase I clinical and pharmacogenetic study of weekly TAS-103 in patients with advanced cancer. J Clin Oncol. 2001 Apr 1;19(7):2084-90. doi: 10.1200/JCO.2001.19.7.2084. PMID: 11283142. 20: Etiévant C, Kruczynski A, Barret JM, Perrin D, van Hille B, Guminski Y, Hill BT. F 11782, a dual inhibitor of topoisomerases I and II with an original mechanism of action in vitro, and markedly superior in vivo antitumour activity, relative to three other dual topoisomerase inhibitors, intoplicin, aclarubicin and TAS-103. Cancer Chemother Pharmacol. 2000;46(2):101-13. doi: 10.1007/s002800000133. PMID: 10972479.