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bisBenzimide H 33258 - 98%, high purity , CAS No.23491-45-4

18 Citations
  • ≥98%
Item Number
B113844
Grouped product items
SKUSizeAvailabilityPrice Qty
B113844-25mg
25mg
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$39.90
B113844-100mg
100mg
In stock
$105.90
B113844-500mg
500mg
In stock
$499.90
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Cell-permeable, adenine-thymine selective DNA fluorescent stain. DNA minor groove-directed agent

View related series
Benzimidazoles Five-Membered Heterocyclic Compounds Fluorescent Dye

Basic Description

SynonymsBBIH | NSC334072 | BXI-72 | (2'-(4-Hydroxyphenyl)-5-(4-Methyl-1-Piperazinyl)-2,5'-Bi(1H-Benzimidazole) Trihydrochloride | Bisbenzimidazole trihydrochloride | p-(5-(5-(4-methyl-1-piperazinyl)-1h-2-benzo[d]imidazolyl)-1h-2-benzo[d]imidazolyl)phenol trihydro
Specifications & Purity≥98%
Biochemical and Physiological MechanismsDescription:IC50 Value: N/AHoechst stains are part of a family of blue fluorescent dyes used to stain DNA. These Bis-benzimides were originally developed by Hoechst AG, which numbered all their compounds so that the dye Hoechst 33342 is the 33342nd compou
Storage TempStore at -20°C
Shipped InIce chest + Ice pads
NoteWherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Associated Targets(Human)

TOP1 Tclin DNA topoisomerase I (7553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KG-1 (867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterobacter cloacae (7976 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella pneumoniae (43867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Shigella flexneri (1836 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus epidermidis (22802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Acinetobacter baumannii (41033 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Citrobacter freundii (1864 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecium (13803 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecalis (29875 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Calf thymus DNA (4845 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

IUPAC Name 4-[6-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-benzimidazol-2-yl]phenol;trihydrochloride
INCHI InChI=1S/C25H24N6O.3ClH/c1-30-10-12-31(13-11-30)18-5-9-21-23(15-18)29-25(27-21)17-4-8-20-22(14-17)28-24(26-20)16-2-6-19(32)7-3-16;;;/h2-9,14-15,32H,10-13H2,1H3,(H,26,28)(H,27,29);3*1H
InChi Key SMNPLAKEGAEPJD-UHFFFAOYSA-N
Canonical SMILES CN1CCN(CC1)C2=CC3=C(C=C2)N=C(N3)C4=CC5=C(C=C4)N=C(N5)C6=CC=C(C=C6)O.Cl.Cl.Cl
Isomeric SMILES CN1CCN(CC1)C2=CC3=C(C=C2)N=C(N3)C4=CC5=C(C=C4)N=C(N5)C6=CC=C(C=C6)O.Cl.Cl.Cl
WGK Germany 3
RTECS SM1140500
PubChem CID 31953
Molecular Weight 533.90
Beilstein 4088183

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Find and download the COA for your product by matching the lot number on the packaging.

5 results found

Lot NumberCertificate TypeDateItem
B2216110Certificate of AnalysisJan 14, 2022 B113844
B2216113Certificate of AnalysisJan 14, 2022 B113844
B2216128Certificate of AnalysisJan 14, 2022 B113844
D2403030Certificate of AnalysisJan 14, 2022 B113844
E2431003Certificate of AnalysisJan 14, 2022 B113844

Chemical and Physical Properties

Sensitivitylight sensitive，heat sensitive
Melt Point(°C)314°C

Safety and Hazards(GHS)

Pictogram(s) GHS07
Signal Warning
Hazard Statements

H315:Causes skin irritation

H319:Causes serious eye irritation

H302:Harmful if swallowed

Precautionary Statements

P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing.

P280:Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352:IF ON SKIN: wash with plenty of water.

P321:Specific treatment (see ... on this label).

P501:Dispose of contents/container to ...

P264:Wash hands [and …] thoroughly after handling.

P270:Do not eat, drink or smoke when using this product.

P362+P364:Take off contaminated clothing and wash it before reuse.

P330:Rinse mouth.

P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes.

P301+P317:IF SWALLOWED: Get medical help.

P337+P317:If eye irritation persists: Get medical help.

P332+P317:If skin irritation occurs: Get medical help.

WGK Germany 3
RTECS SM1140500

Related Documents

 SDS

 Specification Sheet

FAQs and Articles

FAQ
Fluorescent Probes - Absorption and Fluorescence
Categories: Technical articles
Tags:
Fluorescence Fuorescent Probe Fluorescent dyes
Flow cytometry cell cycle analysis using propidium iodide DNA staining
Categories: Protocols
Tags:
Propidium Iodide Flow Cytometry Antibody Cell Cycle

Citations of This Product

How to Cite Aladdin Scientific Products?
1. Weiyuan Ma, Xiuwen Zhang, Le Zhuang.  (2023)  Exogenous Hydrogen Sulfide Induces A375 Melanoma Cell Apoptosis Through Overactivation of the Unfolded Protein Response.  Clinical Cosmetic and Investigational Dermatology,      [PMID:37396710] [10.2147/CCID.S412588]
2. Yingying Zhang, Tiange Wang, Yinping Zhuang, Tiandi He, Xiaoli Wu, Lin Su, Jun Kang, Jin Chang, Hanjie Wang.  (2021)  Sodium Alginate Hydrogel-Mediated Cancer Immunotherapy for Postoperative In Situ Recurrence and Metastasis.  ACS Biomaterials Science & Engineering,  7  (12): (5717–5726).  [PMID:34757733] [10.1021/acsbiomaterials.1c01216]
3. Yunran Zhang, Haiping Zhou, Zhe Zhang, Yijun Zhu, Tao Wang, Liguo Yu, Hongrui Song.  (2021)  Redox/NIR dual-responsive PEG-betulinic acid/pluronic-cypate prodrug micelles for chemophotothermal therapy.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,  609  (125662).  [PMID:] [10.1016/j.colsurfa.2020.125662]
4. Chenglong Ma, Wei Sun, Waqas Qamar Zaman, Zhenhua Zhou, Hao Zhang, Qicheng Shen, Limei Cao, Ji Yang.  (2020)  Lanthanides Regulated the Amorphization–Crystallization of IrO2 for Outstanding OER Performance.  ACS Applied Materials & Interfaces,  12  (31): (34980–34989).  [PMID:32658446] [10.1021/acsami.0c08969]
5. Zhang Tao, Jiang Zhenqi, Chen Libin, Pan Chunshu, Sun Shan, Liu Chuang, Li Zihou, Ren Wenzhi, Wu Aiguo, Huang Pintong.  (2020)  PCN-Fe(III)-PTX nanoparticles for MRI guided high efficiency chemo-photodynamic therapy in pancreatic cancer through alleviating tumor hypoxia.  Nano Research,  13  (1): (273-281).  [PMID:] [10.1007/s12274-019-2610-6]
6. Jun Dai, Yinghao Li, Zi Long, Ruming Jiang, Zeyan Zhuang, Zhiming Wang, Zujin Zhao, Xiaoding Lou, Fan Xia, Ben Zhong Tang.  (2020)  Efficient Near-Infrared Photosensitizer with Aggregation-Induced Emission for Imaging-Guided Photodynamic Therapy in Multiple Xenograft Tumor Models.  ACS Nano,  14  (1): (854–866).  [PMID:31820925] [10.1021/acsnano.9b07972]
7. Tao Zhang, Zhenqi Jiang, Ting Xve, Shan Sun, Juan Li, Wenzhi Ren, Aiguo Wu, Pintong Huang.  (2019)  One-pot synthesis of hollow PDA@DOX nanoparticles for ultrasound imaging and chemo-thermal therapy in breast cancer.  Nanoscale,  11  (45): (21759-21766).  [PMID:31482919] [10.1039/C9NR05671H]
8. Hailing Yang, Zhenjie Liu, Yonglong Song, Changjiang Hu.  (2019)  Hyaluronic acid-functionalized bilosomes for targeted delivery of tripterine to inflamed area with enhancive therapy on arthritis.  DRUG DELIVERY,  26  (1): (820-830).  [PMID:31389248] [10.1080/10717544.2019.1636423]
9. Zigui Wang, Gaizhen Kuang, Zhiqiang Yu, Aimin Li, Dongfang Zhou, Yubin Huang.  (2019)  Light-activatable dual prodrug polymer nanoparticle for precise synergistic chemotherapy guided by drug-mediated computed tomography imaging.  Acta Biomaterialia,  94  (459).  [PMID:31128323] [10.1016/j.actbio.2019.05.047]
10. Zhao Shuai, Sun Shan, Jiang Kai, Wang Yuhui, Liu Yu, Wu Song, Li Zhongjun, Shu Qinghai, Lin Hengwei.  (2019)  In Situ Synthesis of Fluorescent Mesoporous Silica–Carbon Dot Nanohybrids Featuring Folate Receptor-Overexpressing Cancer Cell Targeting and Drug Delivery.  Nano-Micro Letters,  11  (1): (1-13).  [PMID:34137970] [10.1007/s40820-019-0263-3]
11. Rui Wang, Xing Hu, Junhui Pan, Guowen Zhang, Deming Gong.  (2019)  Interaction of isoeugenol with calf thymus DNA and its protective effect on DNA oxidative damage.  JOURNAL OF MOLECULAR LIQUIDS,  282  (356).  [PMID:] [10.1016/j.molliq.2019.03.018]
12. Jie Li, Suqin Shen, Fei Kong, Ting Jiang, Cui Tang, Chunhua Yin.  (2018)  Effects of pore size on in vitro and in vivo anticancer efficacies of mesoporous silica nanoparticles.  RSC Advances,  8  (43): (24633-24640).  [PMID:35539161] [10.1039/C8RA03914C]
13. Jie-Hua Shi, Yan-Yue Lou, Kai-Li Zhou, Dong-Qi Pan.  (2018)  Exploration of intermolecular interaction of calf thymus DNA with sulfosulfuron using multi-spectroscopic and molecular docking techniques.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,  204  (209).  [PMID:29935392] [10.1016/j.saa.2018.06.054]
14. Ying Wang, Yating Zhao, Yu Cui, Qinfu Zhao, Qiang Zhang, Sara Musetti, Karina A Kinghorn, Siling Wang.  (2018)  Overcoming multiple gastrointestinal barriers by bilayer modified hollow mesoporous silica nanocarriers.  Acta Biomaterialia,  65  (405).  [PMID:29037897] [10.1016/j.actbio.2017.10.025]
15. Huanan Wang, Wenqing Xu.  (2017)  Mito-methyl coumarin, a novel mitochondria-targeted drug with great antitumor potential was synthesized.  BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS,  489  (1).  [PMID:28546001] [10.1016/j.bbrc.2017.05.116]
16. Hongxia Liu, Shuqin Wu, Jingmou Yu, Dun Fan, Jin Ren, Lei Zhang, Jianguo Zhao.  (2017)  Reduction-sensitive micelles self-assembled from amphiphilic chondroitin sulfate A-deoxycholic acid conjugate for triggered release of doxorubicin.  Materials Science & Engineering C-Materials for Biological Applications,  75  (55).  [PMID:28415498] [10.1016/j.msec.2017.02.030]
17. Huanan Wang, Ming Yao, Wenqing Xu.  (2016)  The antitumor effects of mitochondria-targeted 6-(nicotinamide) methyl coumarin.  Open Life Sciences,  11  (1): (542-551).  [PMID:] [10.1515/biol-2016-0070]
18. Haibo Mu, Qianjin Liu, Hong Niu, Dongdong Wang, Jiangjiang Tang, Jinyou Duan.  (2016)  Autophagy promotes DNA–protein crosslink clearance.  MUTATION RESEARCH-GENETIC TOXICOLOGY AND ENVIRONMENTAL MUTAGENESIS,  797  (21).  [PMID:26921017] [10.1016/j.mrgentox.2015.12.001]

References

1. Zhang F et al..  (2022)  Inhibition of major histocompatibility complex-I antigen presentation by sarbecovirus ORF7a proteins..  Proc Natl Acad Sci U S A,  119  (41): (e2209042119).  [PMID:36136978]
2. Sirota R et al..  (2015)  The role of the catecholic and the electrophilic moieties of caffeic acid in Nrf2/Keap1 pathway activation in ovarian carcinoma cell lines..  Redox Biol,  4  (48-59).  [PMID:25498967]
3. Weiyuan Ma, Xiuwen Zhang, Le Zhuang.  (2023)  Exogenous Hydrogen Sulfide Induces A375 Melanoma Cell Apoptosis Through Overactivation of the Unfolded Protein Response.  Clinical Cosmetic and Investigational Dermatology,      [PMID:37396710] [10.2147/CCID.S412588]
4. Yingying Zhang, Tiange Wang, Yinping Zhuang, Tiandi He, Xiaoli Wu, Lin Su, Jun Kang, Jin Chang, Hanjie Wang.  (2021)  Sodium Alginate Hydrogel-Mediated Cancer Immunotherapy for Postoperative In Situ Recurrence and Metastasis.  ACS Biomaterials Science & Engineering,  7  (12): (5717–5726).  [PMID:34757733] [10.1021/acsbiomaterials.1c01216]
5. Yunran Zhang, Haiping Zhou, Zhe Zhang, Yijun Zhu, Tao Wang, Liguo Yu, Hongrui Song.  (2021)  Redox/NIR dual-responsive PEG-betulinic acid/pluronic-cypate prodrug micelles for chemophotothermal therapy.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,  609  (125662).  [PMID:] [10.1016/j.colsurfa.2020.125662]
6. Chenglong Ma, Wei Sun, Waqas Qamar Zaman, Zhenhua Zhou, Hao Zhang, Qicheng Shen, Limei Cao, Ji Yang.  (2020)  Lanthanides Regulated the Amorphization–Crystallization of IrO2 for Outstanding OER Performance.  ACS Applied Materials & Interfaces,  12  (31): (34980–34989).  [PMID:32658446] [10.1021/acsami.0c08969]
7. Zhang Tao, Jiang Zhenqi, Chen Libin, Pan Chunshu, Sun Shan, Liu Chuang, Li Zihou, Ren Wenzhi, Wu Aiguo, Huang Pintong.  (2020)  PCN-Fe(III)-PTX nanoparticles for MRI guided high efficiency chemo-photodynamic therapy in pancreatic cancer through alleviating tumor hypoxia.  Nano Research,  13  (1): (273-281).  [PMID:] [10.1007/s12274-019-2610-6]
8. Jun Dai, Yinghao Li, Zi Long, Ruming Jiang, Zeyan Zhuang, Zhiming Wang, Zujin Zhao, Xiaoding Lou, Fan Xia, Ben Zhong Tang.  (2020)  Efficient Near-Infrared Photosensitizer with Aggregation-Induced Emission for Imaging-Guided Photodynamic Therapy in Multiple Xenograft Tumor Models.  ACS Nano,  14  (1): (854–866).  [PMID:31820925] [10.1021/acsnano.9b07972]
9. Tao Zhang, Zhenqi Jiang, Ting Xve, Shan Sun, Juan Li, Wenzhi Ren, Aiguo Wu, Pintong Huang.  (2019)  One-pot synthesis of hollow PDA@DOX nanoparticles for ultrasound imaging and chemo-thermal therapy in breast cancer.  Nanoscale,  11  (45): (21759-21766).  [PMID:31482919] [10.1039/C9NR05671H]
10. Hailing Yang, Zhenjie Liu, Yonglong Song, Changjiang Hu.  (2019)  Hyaluronic acid-functionalized bilosomes for targeted delivery of tripterine to inflamed area with enhancive therapy on arthritis.  DRUG DELIVERY,  26  (1): (820-830).  [PMID:31389248] [10.1080/10717544.2019.1636423]
11. Zigui Wang, Gaizhen Kuang, Zhiqiang Yu, Aimin Li, Dongfang Zhou, Yubin Huang.  (2019)  Light-activatable dual prodrug polymer nanoparticle for precise synergistic chemotherapy guided by drug-mediated computed tomography imaging.  Acta Biomaterialia,  94  (459).  [PMID:31128323] [10.1016/j.actbio.2019.05.047]
12. Zhao Shuai, Sun Shan, Jiang Kai, Wang Yuhui, Liu Yu, Wu Song, Li Zhongjun, Shu Qinghai, Lin Hengwei.  (2019)  In Situ Synthesis of Fluorescent Mesoporous Silica–Carbon Dot Nanohybrids Featuring Folate Receptor-Overexpressing Cancer Cell Targeting and Drug Delivery.  Nano-Micro Letters,  11  (1): (1-13).  [PMID:34137970] [10.1007/s40820-019-0263-3]
13. Rui Wang, Xing Hu, Junhui Pan, Guowen Zhang, Deming Gong.  (2019)  Interaction of isoeugenol with calf thymus DNA and its protective effect on DNA oxidative damage.  JOURNAL OF MOLECULAR LIQUIDS,  282  (356).  [PMID:] [10.1016/j.molliq.2019.03.018]
14. Jie Li, Suqin Shen, Fei Kong, Ting Jiang, Cui Tang, Chunhua Yin.  (2018)  Effects of pore size on in vitro and in vivo anticancer efficacies of mesoporous silica nanoparticles.  RSC Advances,  8  (43): (24633-24640).  [PMID:35539161] [10.1039/C8RA03914C]
15. Jie-Hua Shi, Yan-Yue Lou, Kai-Li Zhou, Dong-Qi Pan.  (2018)  Exploration of intermolecular interaction of calf thymus DNA with sulfosulfuron using multi-spectroscopic and molecular docking techniques.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,  204  (209).  [PMID:29935392] [10.1016/j.saa.2018.06.054]
16. Ying Wang, Yating Zhao, Yu Cui, Qinfu Zhao, Qiang Zhang, Sara Musetti, Karina A Kinghorn, Siling Wang.  (2018)  Overcoming multiple gastrointestinal barriers by bilayer modified hollow mesoporous silica nanocarriers.  Acta Biomaterialia,  65  (405).  [PMID:29037897] [10.1016/j.actbio.2017.10.025]
17. Huanan Wang, Wenqing Xu.  (2017)  Mito-methyl coumarin, a novel mitochondria-targeted drug with great antitumor potential was synthesized.  BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS,  489  (1).  [PMID:28546001] [10.1016/j.bbrc.2017.05.116]
18. Hongxia Liu, Shuqin Wu, Jingmou Yu, Dun Fan, Jin Ren, Lei Zhang, Jianguo Zhao.  (2017)  Reduction-sensitive micelles self-assembled from amphiphilic chondroitin sulfate A-deoxycholic acid conjugate for triggered release of doxorubicin.  Materials Science & Engineering C-Materials for Biological Applications,  75  (55).  [PMID:28415498] [10.1016/j.msec.2017.02.030]
19. Huanan Wang, Ming Yao, Wenqing Xu.  (2016)  The antitumor effects of mitochondria-targeted 6-(nicotinamide) methyl coumarin.  Open Life Sciences,  11  (1): (542-551).  [PMID:] [10.1515/biol-2016-0070]
20. Haibo Mu, Qianjin Liu, Hong Niu, Dongdong Wang, Jiangjiang Tang, Jinyou Duan.  (2016)  Autophagy promotes DNA–protein crosslink clearance.  MUTATION RESEARCH-GENETIC TOXICOLOGY AND ENVIRONMENTAL MUTAGENESIS,  797  (21).  [PMID:26921017] [10.1016/j.mrgentox.2015.12.001]

Solution Calculators

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