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MedKoo Cat#: 528824 | Name: GL-331

Description:

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

GL-331, also known as W-68, is a DNA topoisomerase II inhibitor potentially for the treatment of small cell lung cancer and gastric cancer.

Chemical Structure

GL-331
GL-331
CAS#127882-73-9

Theoretical Analysis

MedKoo Cat#: 528824

Name: GL-331

CAS#: 127882-73-9

Chemical Formula: C27H24N2O9

Exact Mass: 520.1482

Molecular Weight: 520.49

Elemental Analysis: C, 62.31; H, 4.65; N, 5.38; O, 27.66

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 #
No Data
Synonym
GL-331; W-68; GL331; W68; GL 331; W 68
IUPAC/Chemical Name
(5R,5aR,8aS,9S)-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4-nitrophenyl)amino)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
InChi Key
DLROLUIVVKTFPW-LVEBQJTPSA-N
InChi Code
InChI=1S/C27H24N2O9/c1-34-21-7-13(8-22(35-2)26(21)30)23-16-9-19-20(38-12-37-19)10-17(16)25(18-11-36-27(31)24(18)23)28-14-3-5-15(6-4-14)29(32)33/h3-10,18,23-25,28,30H,11-12H2,1-2H3/t18-,23+,24-,25+/m0/s1
SMILES Code
O=C1OC[C@]2([H])[C@H](NC3=CC=C([N+]([O-])=O)C=C3)C4=C(C=C5OCOC5=C4)[C@@H](C6=CC(OC)=C(O)C(OC)=C6)[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
Soluble in DMSO
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 520.49 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
1: Wang YJ, Chen XG, Xiao ZY, Liu GT, Sun H. Induction of cell cycle arrest by GL331 via triggering an ATM-dependent DNA damage response in HepG2 cells. J Asian Nat Prod Res. 2012;14(7):657-64. doi: 10.1080/10286020.2012.684683. Epub 2012 May 15. PubMed PMID: 22583615. 2: Lee CC, Huang TS. A novel topoisomerase II poison GL331 preferentially induces DNA cleavage at (C/G)T sites and can cause telomere DNA damage. Pharm Res. 2001 Jun;18(6):846-51. PubMed PMID: 11474790. 3: Huang TS, Lee CC, Chao Y, Shu CH, Chen LT, Chen LL, Chen MH, Yuan CC, Whang-Peng J. A novel podophyllotoxin-derived compound GL331 is more potent than its congener VP-16 in killing refractory cancer cells. Pharm Res. 1999 Jul;16(7):997-1002. PubMed PMID: 10450922. 4: Chen Y, Su YH, Wang CH, Wu JM, Chen JC, Tseng SH. Induction of apoptosis and cell cycle arrest in glioma cells by GL331 (a topoisomerase II inhibitor). Anticancer Res. 2005 Nov-Dec;25(6B):4203-8. PubMed PMID: 16309217. 5: Huang TS, Lee CC, Chang AC, Lin S, Chao CC, Jou YS, Chu YW, Wu CW, Whang-Peng J. Shortening of microsatellite deoxy(CA) repeats involved in GL331-induced down-regulation of matrix metalloproteinase-9 gene expression. Biochem Biophys Res Commun. 2003 Jan 24;300(4):901-7. PubMed PMID: 12559958. 6: Huang TS, Shu CH, Lee CC, Chen LT, Whang-Peng J. In vitro evaluation of GL331's cancer cell killing and apoptosis-inducing activity in combination with other chemotherapeutic agents. Apoptosis. 2000 Feb;5(1):79-85. PubMed PMID: 11227495. 7: Chang H, Shyu KG, Lee CC, Tsai SC, Wang BW, Hsien Lee Y, Lin S. GL331 inhibits HIF-1alpha expression in a lung cancer model. Biochem Biophys Res Commun. 2003 Feb 28;302(1):95-100. PubMed PMID: 12593853. 8: Huang TS, Shu CH, Yang WK, Whang-Peng J. Activation of CDC 25 phosphatase and CDC 2 kinase involved in GL331-induced apoptosis. Cancer Res. 1997 Jul 15;57(14):2974-8. PubMed PMID: 9230211. 9: Kuo ML, Shen SC, Yang CH, Chuang SE, Cheng AL, Huang TS. Bcl-2 prevents topoisomerase II inhibitor GL331-induced apoptosis is mediated by down-regulation of poly(ADP-ribose)polymerase activity. Oncogene. 1998 Oct 29;17(17):2225-34. PubMed PMID: 9811453. 10: Liu JM, Chen LT, Chao Y, Li AF, Wu CW, Liu TS, Shiah HS, Chang JY, Chen JD, Wu HW, Lin WC, Lan C, Whang-Peng J. Phase II and pharmacokinetic study of GL331 in previously treated Chinese gastric cancer patients. Cancer Chemother Pharmacol. 2002 May;49(5):425-8. Epub 2002 Mar 8. PubMed PMID: 11976838. 11: Huang TS, Shu CH, Chao Y, Chen LT. Evaluation of GL331 in combination with paclitaxel: GL331's interference with paclitaxel-induced cell cycle perturbation and apoptosis. Anticancer Drugs. 2001 Mar;12(3):259-66. PubMed PMID: 11290873. 12: Huang TS, Shu CH, Shih YL, Huang HC, Su YC, Chao Y, Yang WK, Whang-Peng J. Protein tyrosine phosphatase activities are involved in apoptotic cancer cell death induced by GL331, a new homolog of etoposide. Cancer Lett. 1996 Dec 20;110(1-2):77-85. PubMed PMID: 9018084. 13: Liu YQ, Tian J, Qian K, Zhao XB, Morris-Natschke SL, Yang L, Nan X, Tian X, Lee KH. Recent progress on C-4-modified podophyllotoxin analogs as potent antitumor agents. Med Res Rev. 2015 Jan;35(1):1-62. doi: 10.1002/med.21319. Epub 2014 May 14. Review. PubMed PMID: 24827545; PubMed Central PMCID: PMC4337794. 14: Kamal A, Ali Hussaini SM, Rahim A, Riyaz S. Podophyllotoxin derivatives: a patent review (2012 - 2014). Expert Opin Ther Pat. 2015;25(9):1025-34. doi: 10.1517/13543776.2015.1051727. Epub 2015 Jun 2. Review. PubMed PMID: 26027947. 15: Lin S, Huang HC, Chen LL, Lee CC, Huang TS. GL331 induces down-regulation of cyclin D1 expression via enhanced proteolysis and repressed transcription. Mol Pharmacol. 2001 Oct;60(4):768-75. PubMed PMID: 11562439. 16: Chen Y, Lin TY, Chen JC, Yang HZ, Tseng SH. GL331, a topoisomerase II inhibitor, induces radiosensitization of human glioma cells. Anticancer Res. 2006 May-Jun;26(3A):2149-56. PubMed PMID: 16827158. 17: van Hille B, Perrin D, Hill BT. Differential in vitro interactions of a series of clinically useful topoisomerase-interacting compounds with the cleavage/religation activity of the human topoisomerase IIalpha and IIbeta isoforms. Anticancer Drugs. 1999 Jul;10(6):551-60. PubMed PMID: 10885903. 18: Shiah SG, Chuang SE, Chau YP, Shen SC, Kuo ML. Activation of c-Jun NH2-terminal kinase and subsequent CPP32/Yama during topoisomerase inhibitor beta-lapachone-induced apoptosis through an oxidation-dependent pathway. Cancer Res. 1999 Jan 15;59(2):391-8. PubMed PMID: 9927052. 19: Zhang YB, Fang M, He FL, Hua TF, Hu BD, Zhao H, Liu RY. [Mechanism of regulation of leptin expression in human lung adenocarcinoma cells by hypoxia inducible factor-1alpha: a preliminary study]. Zhonghua Yi Xue Za Zhi. 2008 Nov 4;88(40):2848-53. Chinese. PubMed PMID: 19080496. 20: Lee KH. Novel antitumor agents from higher plants. Med Res Rev. 1999 Nov;19(6):569-96. Review. PubMed PMID: 10557371.

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