WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406519
CAS#: 321674-73-1
Description: BIBR1532 is a selective telomerase inhibitor. BIBR1132 is highly selective for inhibition of telomerase, resulting in delayed growth arrest of tumor cells. Treatment of cancer cells with BIBR1532 leads to progressive telomere shortening, consecutive telomere dysfunction, and finally growth arrest after a lag period that is largely dependent on initial telomere length.
MedKoo Cat#: 406519
Name: BIBR1532
CAS#: 321674-73-1
Chemical Formula: C21H17NO3
Exact Mass: 331.12084
Molecular Weight: 331.36
Elemental Analysis: C, 76.12; H, 5.17; N, 4.23; O, 14.49
Synonym: BIBR1532; BIBR-1532; BIBR 1532.
IUPAC/Chemical Name: (E)-2-(3-(naphthalen-2-yl)but-2-enamido)benzoic acid
InChi Key: PGFQXGLPJUCTOI-WYMLVPIESA-N
InChi Code: InChI=1S/C21H17NO3/c1-14(16-11-10-15-6-2-3-7-17(15)13-16)12-20(23)22-19-9-5-4-8-18(19)21(24)25/h2-13H,1H3,(H,22,23)(H,24,25)/b14-12+
SMILES Code: O=C(O)C1=CC=CC=C1NC(/C=C(C2=CC=C3C=CC=CC3=C2)\C)=O
Appearance: white 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, 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
| Biological target: | BIBR 1532 is a non-competitive telomerase inhibitor with IC50 of 100 nM in a cell-free assay. |
| In vitro activity: | In order to define the effects of BIBR1532 on TA in FOSCC, SCCF1, SCCF2, and SCCF3 were treated at 25, 50, and 100 μM for 48 h and subjected to TRAP assay. The results showed readily detectable TA (telomerase activity) at control conditions in SCCF1, SCCF2, and SCCF3 (Figure 1A), and importantly, gel scans and quantitative analysis demonstrated reduction of TA with a dose-dependent trend in BIBR1532-treated cells in all of the three cell lines (Figures 1A,B). However, SCCF3 appeared to be sensitive already at the lower dose (25 μM), whereas SCCF1 and SCCF2 showed significant telomerase inhibition from 50 μM onward (Figures 1A,B). Reference: Front Vet Sci. 2020; 7: 620776. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7855307/ |
| In vivo activity: | In order to find out whether the anti-proliferative and pro-apoptotic effects of short-term TERT inhibition observed in in vitro models were maintained in in vivo context, this study evaluated proliferation and viability of malignant human B cells xenografted in zebrafish. At 2 hpx the percentage of 4134/Late fluorescent tumor cells was similar between the embryos xenografted with DMSO- or BIBR-pretreated cells (1.49 ± 0.11% vs. 1.53 ± 0.07%, respectively; p = 0.623), confirming that an equal number of cells had been injected in the two groups. At 24 hpx the percentage of tumor cells remained stable in embryos injected with DMSO-pretreated cells, while significantly decreased in those injected with BIBR-pretreated cells (1.37 ± 0.001% vs. 1.03 ± 0.01%; p = 0.001). At 48 hpx the percentage of tumor cells in embryos xenografted with 4134/Late pretreated with DMSO was significantly higher than those in embryos xenografted with BIBR-pretreated cells (2.18 ± 0.8% vs. 0.60 ± 0.37%; p = 0.011). Similarly, at 72 hpx DMSO-pretreated cells proliferated up to 3.51%, whereas the percentage of cells pretreated with BIBR was significantly lower (0.52%; p = 0.004) (Figure 4a). Reference: Cancers (Basel). 2020 Aug; 12(8): 2052. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7463531/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 57.29 | 172.89 | |
| DMSO:PBS (pH 7.2) (1:1) | 0.5 | 1.51 | |
| DMF | 30.0 | 90.54 | |
| Ethanol | 4.09 | 12.34 |
The following data is based on the product molecular weight 331.36 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 |
| Formulation protocol: | 1. Altamura G, Degli Uberti B, Galiero G, De Luca G, Power K, Licenziato L, Maiolino P, Borzacchiello G. The Small Molecule BIBR1532 Exerts Potential Anti-cancer Activities in Preclinical Models of Feline Oral Squamous Cell Carcinoma Through Inhibition of Telomerase Activity and Down-Regulation of TERT. Front Vet Sci. 2021 Jan 20;7:620776. doi: 10.3389/fvets.2020.620776. PMID: 33553285; PMCID: PMC7855307. 2. Bikkul MU, Faragher RGA, Worthington G, Meinke P, Kerr ARW, Sammy A, Riyahi K, Horton D, Schirmer EC, Hubank M, Kill IR, Anderson RM, Slijepcevic P, Makarov E, Bridger JM. Telomere elongation through hTERT immortalization leads to chromosome repositioning in control cells and genomic instability in Hutchinson-Gilford progeria syndrome fibroblasts, expressing a novel SUN1 isoform. Genes Chromosomes Cancer. 2019 Jun;58(6):341-356. doi: 10.1002/gcc.22711. Epub 2019 Jan 7. PMID: 30474255; PMCID: PMC6590296. 3. Giunco S, Zangrossi M, Dal Pozzolo F, Celeghin A, Ballin G, Petrara MR, Amin A, Argenton F, Godinho Ferreira M, De Rossi A. Anti-Proliferative and Pro-Apoptotic Effects of Short-Term Inhibition of Telomerase In Vivo and in Human Malignant B Cells Xenografted in Zebrafish. Cancers (Basel). 2020 Jul 25;12(8):2052. doi: 10.3390/cancers12082052. PMID: 32722398; PMCID: PMC7463531. 4. Tahtouh R, Azzi AS, Alaaeddine N, Chamat S, Bouharoun-Tayoun H, Wardi L, Raad I, Sarkis R, Antoun NA, Hilal G. Telomerase inhibition decreases alpha-fetoprotein expression and secretion by hepatocellular carcinoma cell lines: in vitro and in vivo study. PLoS One. 2015 Mar 30;10(3):e0119512. doi: 10.1371/journal.pone.0119512. PMID: 25822740; PMCID: PMC4379025. |
| In vitro protocol: | 1. Altamura G, Degli Uberti B, Galiero G, De Luca G, Power K, Licenziato L, Maiolino P, Borzacchiello G. The Small Molecule BIBR1532 Exerts Potential Anti-cancer Activities in Preclinical Models of Feline Oral Squamous Cell Carcinoma Through Inhibition of Telomerase Activity and Down-Regulation of TERT. Front Vet Sci. 2021 Jan 20;7:620776. doi: 10.3389/fvets.2020.620776. PMID: 33553285; PMCID: PMC7855307. 2. Bikkul MU, Faragher RGA, Worthington G, Meinke P, Kerr ARW, Sammy A, Riyahi K, Horton D, Schirmer EC, Hubank M, Kill IR, Anderson RM, Slijepcevic P, Makarov E, Bridger JM. Telomere elongation through hTERT immortalization leads to chromosome repositioning in control cells and genomic instability in Hutchinson-Gilford progeria syndrome fibroblasts, expressing a novel SUN1 isoform. Genes Chromosomes Cancer. 2019 Jun;58(6):341-356. doi: 10.1002/gcc.22711. Epub 2019 Jan 7. PMID: 30474255; PMCID: PMC6590296. |
| In vivo protocol: | 1. Giunco S, Zangrossi M, Dal Pozzolo F, Celeghin A, Ballin G, Petrara MR, Amin A, Argenton F, Godinho Ferreira M, De Rossi A. Anti-Proliferative and Pro-Apoptotic Effects of Short-Term Inhibition of Telomerase In Vivo and in Human Malignant B Cells Xenografted in Zebrafish. Cancers (Basel). 2020 Jul 25;12(8):2052. doi: 10.3390/cancers12082052. PMID: 32722398; PMCID: PMC7463531. 2. Tahtouh R, Azzi AS, Alaaeddine N, Chamat S, Bouharoun-Tayoun H, Wardi L, Raad I, Sarkis R, Antoun NA, Hilal G. Telomerase inhibition decreases alpha-fetoprotein expression and secretion by hepatocellular carcinoma cell lines: in vitro and in vivo study. PLoS One. 2015 Mar 30;10(3):e0119512. doi: 10.1371/journal.pone.0119512. PMID: 25822740; PMCID: PMC4379025. |
1: Bashash D, Ghaffari SH, Mirzaee R, Alimoghaddam K, Ghavamzadeh A. Telomerase inhibition by non-nucleosidic compound BIBR1532 causes rapid cell death in pre-B acute lymphoblastic leukemia cells. Leuk Lymphoma. 2013 Mar;54(3):561-8. doi: 10.3109/10428194.2012.704034. Epub 2012 Sep 28. PubMed PMID: 22957790.
2: Parsch D, Brassat U, Brümmendorf TH, Fellenberg J. Consequences of telomerase inhibition by BIBR1532 on proliferation and chemosensitivity of chondrosarcoma cell lines. Cancer Invest. 2008 Jul;26(6):590-6. doi: 10.1080/07357900802072905. PubMed PMID: 18584350.
3: El Daly H, Martens UM. Telomerase inhibition and telomere targeting in hematopoietic cancer cell lines with small non-nucleosidic synthetic compounds (BIBR1532). Methods Mol Biol. 2007;405:47-60. doi: 10.1007/978-1-60327-070-0_6. PubMed PMID: 18369817.
4: Mueller S, Hartmann U, Mayer F, Balabanov S, Hartmann JT, Brummendorf TH, Bokemeyer C. Targeting telomerase activity by BIBR1532 as a therapeutic approach in germ cell tumors. Invest New Drugs. 2007 Dec;25(6):519-24. Epub 2007 May 30. PubMed PMID: 17534576.
5: El-Daly H, Kull M, Zimmermann S, Pantic M, Waller CF, Martens UM. Selective cytotoxicity and telomere damage in leukemia cells using the telomerase inhibitor BIBR1532. Blood. 2005 Feb 15;105(4):1742-9. Epub 2004 Oct 26. PubMed PMID: 15507522.
6: Pascolo E, Wenz C, Lingner J, Hauel N, Priepke H, Kauffmann I, Garin-Chesa P, Rettig WJ, Damm K, Schnapp A. Mechanism of human telomerase inhibition by BIBR1532, a synthetic, non-nucleosidic drug candidate. J Biol Chem. 2002 May 3;277(18):15566-72. Epub 2002 Feb 19. PubMed PMID: 11854300.
