BMVC
目录号 : GC68021BMVC 是一种有效的 G-四联体 (G4) 稳定剂和选择性的端粒酶 (Telomerase) 抑制剂，IC50 约为 0.2 μM。BMVC 抑制 Taq DNA 聚合酶，IC50 约为 2.5 μ M。BMVC 提高了端粒 G4 结构的熔化温度，并加速了端粒长度的缩短。抗癌活性。
Cas No.:627810-06-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
IC50: ~0.2 μM (Telomerase)[1]
G-quadruplex[1]
IC50: ~2.5 μM (Taq DNA polymerase)[1]
BMVC is a potent G-quadruplex (G4) stabilizer and a selective Telomerase inhibitor with an IC50 of ~0.2 μM. BMVC inhibits Taq DNA polymerase with an IC50 of ~2.5 μM. BMVC increases the melting temperature of G4 structure of telomere and accelerates telomere length shortening. Anticancer activities[1][2].
BMVC (0.5 μM; 0-18 days; H1299 cells) treatment markedly increases the percentage of sub-G1-phase cells after 18 days[1].
BMVC (0.5 μM; 0-18 days; H1299 cells) long-term treatment leads to ceasing of cell growth and eventually cell death through apoptosis. The long-term BMVC treatment induces senescence program in H1299 cells[1].
In BMVC-treated cancer cells, hallmarks of senescence, including morphologic changes, detection of senescence-associated β-galactosidase activity, and decreasesd bromodeoxyuridine incorporation, are detected. The BMVC-induced senescence phenotype is accompanied by progressive telomere shortening and detection of the DNA damage foci, indicating that BMVC caused telomere uncapping after long-term treatments[1].
BMVC also suppresses the tumor-related properties of cancer cells, including cell migration, colony-forming ability, and anchorage-independent growth[1].
Cell Cycle Analysis[1]
| Cell Line: | H1299 cells |
| Concentration: | 0.5 μM |
| Incubation Time: | 0 day, 6 days, 12 days, 18 days |
| Result: | The percentage of sub-G1-phase cells was markedly increased after 18 days. |
Apoptosis Analysis[1]
| Cell Line: | H1299 cells |
| Concentration: | 0.5 μM |
| Incubation Time: | 0 day, 6 days, 12 days, 18 days |
| Result: | Increased apoptotic cells. |
BMVC (1 mg/kg; intraperitoneal injection; every 3 day; BALB/cAnN.Cg-Foxn1nu/CrlNarl mice) treatment delays tumorigenic potential of cancer cells in vivo[1].
| Animal Model: | BALB/cAnN.Cg-Foxn1nu/CrlNarl mice injected with H1299 cells[1] |
| Dosage: | 1 mg/kg |
| Administration: | Intraperitoneal injection; every 3 day |
| Result: | The growth rates of tumors in animals were significantly slower than that of control animals. The tumor cells of the mice were indeed entering apoptosis. |
[1]. Huang FC, et al. G-quadruplex stabilizer 3,6-bis(1-methyl-4-vinylpyridinium)carbazole diiodide induces accelerated senescence and inhibits tumorigenic properties in cancer cells. Mol Cancer Res. 2008 Jun;6(6):955-64.
[2]. Jen-Fei Chu, et al. A Novel Method for Screening G-quadruplex Stabilizers to Human Telomeres. Journal of the Chinese Chemical Society, 2011, 58, 296-300.
| Cas No. | 627810-06-4 | SDF | Download SDF |
| 分子式 | C28H25I2N3 | 分子量 | 657.33 |
| 溶解度 | 储存条件 | Store at -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.5213 mL | 7.6065 mL | 15.2131 mL |
| 5 mM | 0.3043 mL | 1.5213 mL | 3.0426 mL |
| 10 mM | 0.1521 mL | 0.7607 mL | 1.5213 mL |
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动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
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The antifungal activities and biological consequences of BMVC-12C-P, a carbazole derivative against Candida species
Med Mycol 2020 Jun 1;58(4):521-529.PMID:31281934DOI:10.1093/mmy/myz071.
Fungal infections, particularly Candida species, have increased worldwide and caused high morbidity and mortality rates. The toxicity and development of resistance in present antifungal drugs justify the need of new drugs with different mechanism of action. BMVC-12C-P, a carbazole-type compound, has been found to dysfunction mitochondria. BMVC-12C-P displayed the strongest antifungal activities among all of the BMVC derivatives. The minimal inhibitory concentration (MIC) of BMVC-12C-P against Candida species ranged from 1 to 2 μg/ml. Fluconazole-resistant clinical isolates of Candida species were highly susceptible to BMVC-12C-P. The potent fungicidal activity of BMVC-12C-P relates to its impairing mitochondrial function. Furthermore, we found that the hyphae growth and biofilm formation were suppressed in C. albicans survived from BMVC-12C-P treatment. This study demonstrates the potential of BMVC-12C-P as an antifungal agent for treating Candida infections.
Emulsified BMVC derivative induced filtration for G-quadruplex DNA structural separation
Nucleic Acids Res 2011 Sep 1;39(17):e114.PMID:21715373DOI:10.1093/nar/gkr499.
A novel method based on emulsion/filtration is introduced for G-quadruplex DNA structural separation. We first synthesized a lipophilic analogue of BMVC, 3,6-Bis(1-methyl-4-vinylpyridinium)-9-(12'-bromododecyl) carbazole diiodide (BMVC-12C-Br), which can form an oil-in-water (o/w) phase emulsion. Due to the binding preferences of BMVC-12C-Br emulsion to some specific DNA structures, the large emulsion (∼2 µm) bound DNA was separated from the small free DNA in the filtrate by a 0.22 µm pore size MCE membrane. This method is able to isolate the non-parallel G-quadruplexes from the parallel G-quadruplexes and the linear duplexes from both G-quadruplexes. In addition, this method allows us not only to determine the absence of the parallel G-quadruplexes of d(T(2)AG(3))(4) and the presence of the parallel G-quadruplexes of d(T(2)AG(3))(2) in K(+) solution, but also to verify structural conversion from antiparallel to parallel G-quadruplexes of d[AG(3)(T(2)AG(3))(3)] in K(+) solution under molecular PEG condition. Moreover, this emulsion can separate the non-parallel G-quadruplexes of d(G(3)CGCG(3)AGGAAG(5)CG(3)) monomer from the parallel G-quadruplexes of its dimer in K(+) solution. Together with NMR spectra, one can simplify the spectra for both the free DNA and the bound DNA to establish a spectrum-structure correlation for further structural analysis.
BMVC test, an improved fluorescence assay for detection of malignant pleural effusions
Cancer Med 2014 Feb;3(1):162-73.PMID:24408009DOI:10.1002/cam4.179.
The diagnosis of malignant pleural effusions is an important issue in the management of malignancy patients. Generally, cytologic examination is a routine diagnostic technique. However, morphological interpretation of cytology is sometimes inconclusive. Here an ancillary method named BMVC test is developed for rapid detection of malignant pleural effusion to improve the diagnostic accuracy at low cost. A simple assay kit is designed to collect living cells from clinical pleural effusion and a fluorescence probe, 3,6-Bis(1-methyl-4-vinylpyridinium) carbazole diiodide (BMVC), is used to illuminate malignant cells. The fluorescence intensity is quantitatively analyzed by ImageJ program. This method yields digital numbers for the test results without any grey zone or ambiguities in the current cytology tests due to intra-observer and inter-observer variability. Comparing with results from double-blind cytologic examination, this simple test gives a good discrimination between malignant and benign specimens with sensitivity of 89.4% (42/47) and specificity of 93.3% (56/60) for diagnosis of malignant pleural effusion. BMVC test provides accurate results in a short time period, and the digital output could assist cytologic examination to become more objective and clear-cut. This is a convenient ancillary tool for detection of malignant pleural effusions.
Structures of 1:1 and 2:1 complexes of BMVC and MYC promoter G-quadruplex reveal a mechanism of ligand conformation adjustment for G4-recognition
Nucleic Acids Res 2019 Dec 16;47(22):11931-11942.PMID:31740959DOI:10.1093/nar/gkz1015.
BMVC is the first fluorescent probe designed to detect G-quadruplexes (G4s) in vivo. The MYC oncogene promoter forms a G4 (MycG4) which acts as a transcription silencer. Here, we report the high-affinity and specific binding of BMVC to MycG4 with unusual slow-exchange rates on the NMR timescale. We also show that BMVC represses MYC in cancer cells. We determined the solution structures of the 1:1 and 2:1 BMVC-MycG4 complexes. BMVC first binds the 5'-end of MycG4 to form a 1:1 complex with a well-defined structure. At higher ratio, BMVC also binds the 3'-end to form a second complex. In both complexes, the crescent-shaped BMVC recruits a flanking DNA residue to form a BMVC-base plane stacking over the external G-tetrad. Remarkably, BMVC adjusts its conformation to a contracted form to match the G-tetrad for an optimal stacking interaction. This is the first structural example showing the importance of ligand conformational adjustment in G4 recognition. BMVC binds the more accessible 5'-end with higher affinity, whereas sequence specificity is present at the weaker-binding 3'-site. Our structures provide insights into specific recognition of MycG4 by BMVC and useful information for design of G4-targeted anticancer drugs and fluorescent probes.
A novel carbazole derivative, BMVC: a potential antitumor agent and fluorescence marker of cancer cells
Chem Biodivers 2004 Sep;1(9):1377-84.PMID:17191915DOI:10.1002/cbdv.200490100.
We have investigated a novel compound, 3,6-bis[2-(1-methylpyridinium)vinyl]carbazole diiodide (BMVC), for inhibiting telomerase activity and distinguishing human lung H1299 and oral Ca9-22 cancer cells from lung IMR90 and skin Detroit-551 normal fibroblast cells. The telomeric repeat amplification protocol (TRAP) assay shows that the concentration of BMVC that inhibits 50% of the telomerase activity (IC50) is ca. 0.05 microM. On the other hand, the cell-viability assay indicates that the cytotoxicity was less than 15% to the H1299 and Ca9-22 cancer cells, and almost negligible to the MRC-5 and Detroit-551 normal cells after incubation with 0.5 microM BMVC for 72 h. The low concentration of 0.05 microM of BMVC can inhibit telomerase activity but does not have general toxic effects to normal cells, implying that BMVC is a promising telomerase inhibitor. Moreover, wide-field fluorescence images of 0.1 microM BMVC-treated cells show bright fluorescence spots in the nuclei of the most H1299 and Ca9-22 cancer cells. Interestingly, similar fluorescence spots are hardly observed in the nuclei of the IMR90 and Detroit-551 normal cells, implying that BMVC might be a useful marker to distinguish tumor cells and normal cells.