1,2-bis(5-amidino-2-benzimidazolyl)ethane profile

1,2-bis(5-amidino-2-benzimidazolyl)ethane, also known as **DBE**, is a synthetic compound with a distinctive structure. Here's a breakdown of its key features and importance in research:

**Structure:**

* **Benzimidazole core:** DBE contains two benzimidazole rings, which are nitrogen-containing heterocycles. These rings are known for their potential to interact with biological molecules.
* **Amidino groups:** Each benzimidazole ring is substituted with an amidino group (-C(=NH)NH₂). These groups are positively charged at physiological pH and can participate in electrostatic interactions.
* **Ethane linker:** The two benzimidazole moieties are connected by a simple ethane linker, providing flexibility and allowing the molecule to adopt different conformations.

**Research Importance:**

DBE has garnered significant attention in various research fields due to its:

* **Antimicrobial activity:** DBE exhibits potent antimicrobial properties against a wide range of bacteria, including drug-resistant strains. Its mechanism of action involves interfering with bacterial DNA replication and cell wall synthesis. This makes it a promising candidate for the development of new antibiotics.
* **Antiviral activity:** DBE has shown antiviral effects against certain viruses, including influenza and HIV. It's thought to inhibit viral entry into cells and disrupt viral replication processes.
* **Targeting DNA:** DBE's positively charged amidino groups readily bind to negatively charged DNA molecules. This property makes it a potential tool for studying DNA structure and function, as well as for developing new gene therapies.
* **Cancer research:** DBE has shown promising results in preliminary studies on cancer cells. It can induce cell death and inhibit tumor growth. Further research is needed to explore its potential as an anticancer agent.

**Current Research:**

Currently, research on DBE is actively pursuing:

* **Synthesis and optimization:** Researchers are working on improving the synthesis of DBE and developing analogues with enhanced activity and reduced toxicity.
* **Mechanism of action:** Elucidating the precise mechanisms by which DBE exerts its biological effects is crucial for understanding its therapeutic potential.
* **Preclinical studies:** Preclinical studies in animal models are ongoing to assess DBE's safety, efficacy, and pharmacokinetic properties.

**Overall, 1,2-bis(5-amidino-2-benzimidazolyl)ethane (DBE) is a promising compound with a broad range of potential applications in medicine and research. Its ability to interact with biological systems, particularly DNA, and its potent antimicrobial and antiviral activities make it a valuable tool for future drug development.**

1,2-bis(5-amidino-2-benzimidazolyl)ethane: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	135650
CHEMBL ID	356487
SCHEMBL ID	548419
MeSH ID	M0149877

Synonym
1h-benzimidazole-5-carboximidamide, 2,2'-(1,2-ethanediyl)bis-
babie
1,2-bis(5-amidino-2-benzimidazolyl)ethane
1,2-bis(5-amidino-2-benzimidazolyl)ethane tetrahydrochloride
2-[2-(5-carbamimidoyl-1h-benzimidazol-2-yl)ethyl]-1h-benzimidazole-5-carboxamidine
CHEMBL356487 ,
75846-15-0
SCHEMBL548419
DTXSID60226744
bdbm50009961

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Prothrombin	Bos taurus (cattle)	Ki	11.6000	0.0011	2.0694	8.3700	AID1132851
Glandular kallikrein	Sus scrofa (pig)	Ki	36.5000	2.7000	7.1033	9.5300	AID1132853
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
proteolysis	Prothrombin	Bos taurus (cattle)
acute-phase response	Prothrombin	Bos taurus (cattle)
positive regulation of blood coagulation	Prothrombin	Bos taurus (cattle)
protein polymerization	Prothrombin	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
serine-type endopeptidase activity	Prothrombin	Bos taurus (cattle)
calcium ion binding	Prothrombin	Bos taurus (cattle)
protein binding	Prothrombin	Bos taurus (cattle)
fibrinogen binding	Prothrombin	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay ID	Title	Year	Journal	Article
AID1132856	Anticoagulant activity in human plasma assessed as prolongation of partial thromboplastin time at 10'-4 M incubated for 30 secs (Rvb = 59 +/- 5.4 secs)	1978	Journal of medicinal chemistry, Jul, Volume: 21, Issue:7	Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases.
AID162094	Toxicity in Pneumocystis carinii no detectable toxicity	1995	Journal of medicinal chemistry, Nov-24, Volume: 38, Issue:24	New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.
AID54984	Thermal denaturation in sonicated calf thymus DNA (CT DNA)	1993	Journal of medicinal chemistry, Jun-11, Volume: 36, Issue:12	Structure, DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles).
AID233025	Thermal melting temperature determined for poly(dA).poly(dT) at a concentration of 5*10e-5) M base pairs at a ratio of 0.6 compound per base pair	1996	Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7	Synthesis and DNA interactions of benzimidazole dications which have activity against opportunistic infections.
AID1132853	Competitive reversible inhibition of porcine pancreatic kallikrein using alpha-N-benzoyl-DL-arginine-p-nitroanilide hydrochloride as substrate after 15 to 180 mins by Michaelis-Menten plot analysis	1978	Journal of medicinal chemistry, Jul, Volume: 21, Issue:7	Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases.
AID227749	Binding constant obtained in an ethidium displacement assay for the sequence d(CGGAATTCGCG)2	1996	Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7	Synthesis and DNA interactions of benzimidazole dications which have activity against opportunistic infections.
AID233023	Thermal melting temperature determined for (dG-C)4 at a concentration of 3*10e-6 M base pairs at a ratio of 0.6 compound per base pair	1996	Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7	Synthesis and DNA interactions of benzimidazole dications which have activity against opportunistic infections.
AID72882	Thermal denaturation in alternating poly(dG-dC)-poly(dG-dC) homopolymer (GC)	1993	Journal of medicinal chemistry, Jun-11, Volume: 36, Issue:12	Structure, DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles).
AID233022	Thermal melting temperature for (dCGCGAATTCGCG)2 at a concentration of 3*10e-6 M base pairs at a ratio of 0.6 compound per base pair	1996	Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7	Synthesis and DNA interactions of benzimidazole dications which have activity against opportunistic infections.
AID233024	Thermal melting temperature for poly(A).poly(U) at a concentration of 5*10e-5) M base pairs at a ratio of 0.6 compound per base pair	1996	Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7	Synthesis and DNA interactions of benzimidazole dications which have activity against opportunistic infections.
AID233938	Ratio between poly-dAdT and poly-dGdC binding	1993	Journal of medicinal chemistry, Jun-11, Volume: 36, Issue:12	Structure, DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles).
AID1132851	Competitive reversible inhibition of bovine thrombin using alpha-N-benzoyl-DL-arginine-p-nitroanilide hydrochloride as substrate after 15 to 40 mins by Michaelis-Menten plot analysis	1978	Journal of medicinal chemistry, Jul, Volume: 21, Issue:7	Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases.
AID1132852	Competitive reversible inhibition of bovine trypsin using alpha-N-benzoyl-DL-arginine-p-nitroanilide hydrochloride as substrate after 15 to 30 mins by Michaelis-Menten plot analysis	1978	Journal of medicinal chemistry, Jul, Volume: 21, Issue:7	Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases.
AID31893	Thermal denaturation in sonicated poly(dA)-poly(dT) homopolymer (AT)	1993	Journal of medicinal chemistry, Jun-11, Volume: 36, Issue:12	Structure, DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles).
AID1132857	Anticoagulant activity in human plasma assessed as prolongation of partial thromboplastin time at 10'-5 M incubated for 30 secs (Rvb = 59 +/- 5.4 secs)	1978	Journal of medicinal chemistry, Jul, Volume: 21, Issue:7	Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases.
AID31892	Thermal denaturation in alternating poly(dA-dT)poly(dA-dT) homopolymer (AT)	1993	Journal of medicinal chemistry, Jun-11, Volume: 36, Issue:12	Structure, DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles).
AID1132858	Anticoagulant activity in human plasma assessed as prolongation of partial thromboplastin time at 5 x 10'-6 M incubated for 30 secs (Rvb = 59 +/- 5.4 secs)	1978	Journal of medicinal chemistry, Jul, Volume: 21, Issue:7	Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases.
AID162085	Pneumocystis carinii cysts per gram of lung tissue was determined in Pneumocystis carinii expressed as perscent of saline treated- control	1995	Journal of medicinal chemistry, Nov-24, Volume: 38, Issue:24	New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (33.33)	18.7374
1990's	4 (66.67)	18.2507
2000's	0 (0.00)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (16.67%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	5 (83.33%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
bis(5-amidino-2-benzimidazolyl)methane bis(5-amidino-2-benzimidazolyl)methane: aromatic diamidine which has a significant suppressive effect on the cytopathology & yield of respiratory synctial (RS) virus; RN given refers to parent cpd	2.89	4
bisbenzimidazole Bisbenzimidazole: A benzimidazole antifilarial agent; it is fluorescent when it binds to certain nucleotides in DNA, thus providing a tool for the study of DNA replication; it also interferes with mitosis.	1.98	1	bibenzimidazole; N-methylpiperazine	anthelminthic drug; fluorochrome
dapi DAPI: RN given refers to parent cpd.	2.66	3	indoles	fluorochrome
dapsone [no description available]	3.08	1	substituted aniline; sulfone	anti-inflammatory drug; antiinfective agent; antimalarial; leprostatic drug
netropsin Netropsin: A basic polypeptide isolated from Streptomyces netropsis. It is cytotoxic and its strong, specific binding to A-T areas of DNA is useful to genetics research.	1.98	1
pentamidine Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.	3.78	3	aromatic ether; carboxamidine; diether	anti-inflammatory agent; antifungal agent; calmodulin antagonist; chemokine receptor 5 antagonist; EC 2.3.1.48 (histone acetyltransferase) inhibitor; NMDA receptor antagonist; S100 calcium-binding protein B inhibitor; trypanocidal drug; xenobiotic
primaquine Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.	3.08	1	aminoquinoline; aromatic ether; N-substituted diamine	antimalarial
pyrimethamine Maloprim: contains above 2 cpds	3.08	1	aminopyrimidine; monochlorobenzenes	antimalarial; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
sulfamethoxazole Sulfamethoxazole: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208). sulfamethoxazole : An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.	3.08	1	isoxazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; antiinfective agent; antimicrobial agent; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; epitope; P450 inhibitor; xenobiotic
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	3.08	1	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
trimetrexate Trimetrexate: A nonclassical folic acid inhibitor through its inhibition of the enzyme dihydrofolate reductase. It is being tested for efficacy as an antineoplastic agent and as an antiparasitic agent against PNEUMOCYSTIS PNEUMONIA in AIDS patients. Myelosuppression is its dose-limiting toxic effect.	3.08	1
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	1.98	1	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
cycloguanil cycloguanil: the active metabolite of proguanil; antifolate drug; structure in first source. cycloguanil : A triazine in which a 1,6-dihydro-1,3,5-triazine ring is substituted at N-1 by a 4-chlorophenyl group, at C-2 and -4 by amino groups and at C-6 by gem-dimethyl groups. A dihydrofolate reductase inhibitor, it is a metabolite of the antimalarial drug proguanil.	3.08	1	triazines	antifolate; antiinfective agent; antimalarial; antiparasitic agent; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
ethidium bromide [no description available]	1.98	1	organic bromide salt	geroprotector; intercalator; trypanocidal drug
sitamaquine [no description available]	3.08	1
1,2-di(5-amidino-2-benzofuranyl)ethane 1,2-di(5-amidino-2-benzofuranyl)ethane: preferential inhibitor of bovine factor Xa; structure given in first source	1.95	1
piritrexim piritrexim: RN given refers to parent cpd; structure given in first source	3.08	1
propamidine propamidine: structure given in first source. propamidine : A polyether that is the bis(4-guanidinophenyl) ether of propane-1,3-diol. Used (as its isethionate salt) for the treatment of minor eye or eyelid infections, such as conjunctivitis and blepharitis.	3.08	1	aromatic ether; guanidines; polyether	antimicrobial agent; antiseptic drug
tetroxoprim tetroxoprim: structure given in Negwer 5th ed, #6419	3.08	1	dimethoxybenzene
epiroprim epiroprim: an analog of trimethoprim with improved antimicrobial and pharmacokinetic properties; structure given in first source	3.08	1
tafenoquine tafenoquine : A racemate comprising equimolar amounts of (R)- and (S)-tafenoquine.. N(4)-{2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl}pentane-1,4-diamine : An aminoquinoline that is 8-aminoquinoline which is substituted by methoxy groups at positions 2 and 6, a methyl group at position 4, and a m-(trifluoromethyl)phenoxy group at position 5, and in which the amino substituent at position 8 is itself substituted by a 5-aminopentan-2-yl group.	3.08	1	(trifluoromethyl)benzenes; aminoquinoline; aromatic ether; primary amino compound; secondary amino compound
methotrexate [no description available]	3.08	1	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
butamidine butamidine: RN refers to HCl; structure in first source	3.08	1
wr 242511 WR 242511: RN given refers to parent cpd	3.08	1
2-(4-amidinophenyl)-1-benzofuran-5-carboxamidine 2-(4-amidinophenyl)-1-benzofuran-5-carboxamidine: structure given in first source	1.95	1
2-methyl-3-(4-phenylpiperidino)propionohydroxamic acid hydrochloride 2-methyl-3-(4-phenylpiperidino)propionohydroxamic acid hydrochloride: RN given refers to HCl; do not confuse with either the fungal metabolite K-76 terpene or K 76 carboxylic acid	1.97	1
wr 225448 WR 225448: used as prophylaxis for Plasmodium yoelii infections; structure given in first source	3.08	1

Condition	Relationship Strength	Studies
Opportunistic Infections An infection caused by an organism which becomes pathogenic under certain conditions, e.g., during immunosuppression.	2.9	1
P carinii Pneumonia [description not available]	3.31	2
Pneumonia, Pneumocystis A pulmonary disease in humans occurring in immunodeficient or malnourished patients or infants, characterized by DYSPNEA, tachypnea, and HYPOXEMIA. Pneumocystis pneumonia is a frequently seen opportunistic infection in AIDS. It is caused by the fungus PNEUMOCYSTIS JIROVECII. The disease is also found in other MAMMALS where it is caused by related species of Pneumocystis.	3.31	2
AIDS-Related Opportunistic Infections Opportunistic infections found in patients who test positive for human immunodeficiency virus (HIV). The most common include PNEUMOCYSTIS PNEUMONIA, Kaposi's sarcoma, cryptosporidiosis, herpes simplex, toxoplasmosis, cryptococcosis, and infections with Mycobacterium avium complex, Microsporidium, and Cytomegalovirus.	1.99	1
Bright Disease A historical classification which is no longer used. It described acute glomerulonephritis, acute nephritic syndrome, or acute nephritis. Named for Richard Bright.	1.97	1
Hypersensitivity, Type III [description not available]	1.97	1
Glomerulonephritis Inflammation of the renal glomeruli (KIDNEY GLOMERULUS) that can be classified by the type of glomerular injuries including antibody deposition, complement activation, cellular proliferation, and glomerulosclerosis. These structural and functional abnormalities usually lead to HEMATURIA; PROTEINURIA; HYPERTENSION; and RENAL INSUFFICIENCY.	1.97	1

1,2-bis(5-amidino-2-benzimidazolyl)ethane

Description

Cross-References

Synonyms (10)

Protein Targets (2)

Inhibition Measurements

Biological Processes (4)

Molecular Functions (4)

Bioassays (18)

Research

Studies (6)

Market Indicators

Research Demand Index: 12.67

Study Types

1,2-bis(5-amidino-2-benzimidazolyl)ethane

Description

Cross-References

Synonyms (10)

Protein Targets (2)

Inhibition Measurements

Biological Processes (4)

Molecular Functions (4)

Bioassays (18)

Research

Studies (6)

Market Indicators

Research Demand Index: 12.67

Study Types

Related Drugs (27)

Related Conditions (7)