Compounds > 1,2-bis(3,5-dioxopiperazin-1-yl)ethane
Page last updated: 2024-12-06

1,2-bis(3,5-dioxopiperazin-1-yl)ethane

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

1,2-bis(3,5-dioxopiperazin-1-yl)ethane, often referred to as **BODIPY**, is not the correct name for the compound.

**BODIPY** refers to a class of **boron dipyrromethene dyes**, which are highly fluorescent organic compounds known for their:

* **High quantum yield:** They emit a large amount of light when excited.
* **Narrow emission bandwidth:** They emit light in a very specific range of wavelengths.
* **Excellent photostability:** They resist photobleaching (degradation due to light exposure).
* **Tunable properties:** Their fluorescence color can be adjusted by modifying their molecular structure.

**Importance in research:**

BODIPY dyes are widely used in various research fields, including:

* **Bioimaging:** They are excellent probes for fluorescent microscopy, enabling visualization of biological processes and structures within cells and tissues.
* **Sensing:** Their fluorescence can be sensitive to changes in their environment, making them useful as sensors for pH, temperature, metal ions, and other analytes.
* **Photodynamic therapy:** Some BODIPY derivatives can act as photosensitizers, generating reactive oxygen species upon light activation, which can be used for killing cancer cells.
* **Materials science:** Their unique photophysical properties make them promising components in organic light-emitting diodes (OLEDs), solar cells, and other optoelectronic devices.

**Note:** The compound you described, 1,2-bis(3,5-dioxopiperazin-1-yl)ethane, is a different molecule and does not have any fluorescence properties.

If you are interested in learning more about specific BODIPY dyes or their applications, I recommend searching for information using the specific name of the dye or the application area you are interested in.

Cross-References

ID SourceID
PubMed CID72760
CHEMBL ID2361164
SCHEMBL ID728996
MeSH IDM0040357

Synonyms (38)

Synonym
AC-15653
4,4'-ethane-1,2-diyldipiperazine-2,6-dione
1506-47-4
2, 4,4'-ethylenedi-
glycine,n'-1,2-ethanediylbis(n-carboxymethyl)-, n,n:n',n'-diimide
nsc129942
2, 4,4'-(1,2-ethanediyl)bis-
nsc-129942
4-[2-(3,5-dioxopiperazin-1-yl)ethyl]piperazine-2,6-dione
AKOS000646070
4,4'-(ethane-1,2-diyl)bis(piperazine-2,6-dione)
A809061
NCGC00184537-01
STK700954
ethyliminum
qml51s42cd ,
ai3-52846
unii-qml51s42cd
icrf-154
1,2-bis(3,5-dioxopiperazin-1-yl)ethane
2,6-piperazinedione, 4,4'-(1,2-ethanediyl)bis-
nsc 129942
2,6-piperazinedione, 4,4'-ethylenedi-
glycine, n,n'-1,2-ethanediylbis(n-(carboxymethyl)-, n,n:n',n'-diimide
antimet
SCHEMBL728996
GBLIGNUYGOFIKS-UHFFFAOYSA-N
1,2-bis(3,5-dioxopiperazin-1-yl)-ethane
CHEMBL2361164
DTXSID40164579
AS-66864
4,4'-(1,2-ethanediyl)bis(2,6-piperazinedione)
4,4'-(ethane-1,2-diyl)dipiperazine-2,6-dione
Q27287340
icrf-154;icrf 154;icrf154;nsc-129942;nsc 129942;nsc129942
BCP18398
D92901
CS-0328670

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" A comparative study (using the identical frequency of the dosing scheme and S alpha T segment as the decisive parameter) has revealed that antimet-as another original substance of the diketopiperazines group-also involves (though less significantly) protective effects against the toxic action of adriamycin."( Preclinical comparison of bis-diketopiperazine-propane (dexrazoxane) and bis-diketopiperazine-ethane (antimet) on the adriamycin-cardiotoxic effect.
Grossmann, V; Kvĕtina, J; Safárová, M; Svoboda, Z, 1997)		0.3
" A study published in 1984 by Camerman and colleagues proposed that the therapeutic effects of bimolane could be due to ICRF-154, an impurity present within the bimolane samples that may also be responsible for the toxic effects attributed to bimolane."( A comparative study of the cytotoxic and genotoxic effects of ICRF-154 and bimolane, two catalytic inhibitors of topoisomerase II.
Eastmond, DA; Hasegawa, LS; Vuong, MC, 2013)		0.39

Compound-Compound Interactions

ExcerptReferenceRelevance
"We studied the effects of ICRF-154 in combination with 11 anticancer agents on four human leukaemia cell lines."( The effects of ICRF-154 in combination with other anticancer agents in vitro.
Akutsu, M; Kano, Y; Miura, Y; Narita, T; Sakamoto, S; Suda, K; Suzuki, K, 1992)		0.28
" However, the drug administered in combination with an antimetastatic, 1,2-bis(3,5-dioxopiperazin-1-yl)ethane (ICRF-154), resulted in an increase in survival time."( Intratumor chemotherapy in combination with a systemic antimetastatic drug in the treatment of Lewis-lung carcinoma.
De-Oliveira, MM; Giannotti Filho, O; Joussef, AC; Nakamura, IT, 1985)		0.5

Dosage Studied

ExcerptRelevanceReference
" A comparative study (using the identical frequency of the dosing scheme and S alpha T segment as the decisive parameter) has revealed that antimet-as another original substance of the diketopiperazines group-also involves (though less significantly) protective effects against the toxic action of adriamycin."( Preclinical comparison of bis-diketopiperazine-propane (dexrazoxane) and bis-diketopiperazine-ethane (antimet) on the adriamycin-cardiotoxic effect.
Grossmann, V; Kvĕtina, J; Safárová, M; Svoboda, Z, 1997)		0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency7.51140.000811.382244.6684AID686978; AID686979
67.9K proteinVaccinia virusPotency28.18380.00018.4406100.0000AID720579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID1133125Induction of tumor growth in Syrian hamster LG1002 cells in allografted Syrian golden hamster at 15 mg/kg, ip for every 48 hrs for 4 weeks measured after 48 hrs of last treatment1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Stereoselective effects of cis- and trans-cyclopropylbis (dioxopiperazines) related to ICRF-159 on metastases of hamster lung adenocarcinoma.
AID1133126Antimetastatic activity against Syrian hamster LG1002 cells allografted to Syrian golden hamster LSH/LAK assessed as reduction of lung metastases at 15 mg/kg, ip for every 48 hrs for 4 weeks measured after 48 hrs of last treatment relative to carboxymethy1978Journal of medicinal chemistry, Dec, Volume: 21, Issue:12
Stereoselective effects of cis- and trans-cyclopropylbis (dioxopiperazines) related to ICRF-159 on metastases of hamster lung adenocarcinoma.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (18.18)18.7374
1990's10 (45.45)18.2507
2000's5 (22.73)29.6817
2010's3 (13.64)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.42

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.42 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index4.56 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.42)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.55%)6.00%
Case Studies1 (4.55%)4.05%
Observational0 (0.00%)0.25%
Other20 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
glycine
[no description available]		1.9910alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical
carmustine
Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.		1.9610N-nitrosoureas;
organochlorine compound		alkylating agent;
antineoplastic agent
sobuzoxane
sobuzoxane: used in treatment of leukemia L1210		4.3560organic molecular entity
edetic acid
Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.		2.2110ethylenediamine derivative;
polyamino carboxylic acid;
tetracarboxylic acid		anticoagulant;
antidote;
chelator;
copper chelator;
geroprotector
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		1.9810antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
cytarabine
[no description available]		2.0110beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
deoxycytidine
[no description available]		2.0110pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
daunorubicin
Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.		2.3920aminoglycoside antibiotic;
anthracycline;
p-quinones;
tetracenequinones		antineoplastic agent;
bacterial metabolite
razoxane
Razoxane: An antimitotic agent with immunosuppressive properties.		5.49210N-alkylpiperazine
etoposide
[no description available]		2.3920beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
vanadates
Vanadates: Oxyvanadium ions in various states of oxidation. They act primarily as ion transport inhibitors due to their inhibition of Na(+)-, K(+)-, and Ca(+)-ATPase transport systems. They also have insulin-like action, positive inotropic action on cardiac ventricular muscle, and other metabolic effects.. vanadate(3-) : A vanadium oxoanion that is a trianion with formula VO4 in which the vanadium is in the +5 oxidation state and is attached to four oxygen atoms.		2.0210trivalent inorganic anion;
vanadium oxoanion		EC 3.1.3.1 (alkaline phosphatase) inhibitor;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor;
EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
fibrinogen
Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.		3.1510iditolfungal metabolite
bimolane
bimolane: structure given in first source		4.1950
icrf 193
4,4'-(1,2-dimethyl-1,2-ethanediyl)bis-2,6-piperazinedione: structure given in first source; RN given refers to cpd without isomeric designation. ICRF-193 : An N-alkylpiperazine that is butane which is substituted by a 3,5-dioxopiperazin-1-yl group at positions 2 and 3. The meso isomer.		3.2560
at 2153
probimane: RN given refers to cpd without isomeric designation		3.1510
icrf 198
ICRF 198: hydrolysis product of dexrazoxane; ADR-925 is the (S)-enantiomer of ICRF-198; structure given in first source; ADR 925 is identical to N,N'-((1S)-1-methyl-1,2-ethanediyl)-bis(N-(2-amino-2-oxoethyl))glycine		1.9910
tretinoin
Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.		2.0110retinoic acid;
vitamin A		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
AP-1 antagonist;
human metabolite;
keratolytic drug;
retinoic acid receptor agonist;
retinoid X receptor agonist;
signalling molecule
dactinomycin
Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)		1.9810actinomycinmutagen
2'-deoxy-2'-methylenecytidine
[no description available]		2.0110
merbarone
merbarone: structure given in first source		2.0110
mitindomide
mitindomide: structure given in first source		2.0110
cardiovascular agents
Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.		2.6930
ConditionIndicatedRelationship StrengthStudiesTrials
Adenocarcinoma, Basal Cell
[description not available]		01.9510
Cancer of Lung
[description not available]		02.3620
Metastase
[description not available]		03.320
Experimental Neoplasms
[description not available]		02.3720
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		01.9510
Lung Neoplasms
Tumors or cancer of the LUNG.		02.3620
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		03.320
Abnormalities, Autosome
[description not available]		02.0810
Acute Promyelocytic Leukemia
[description not available]		02.0110
Leukemia, Promyelocytic, Acute
An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.		02.0110
Granulocytic Leukemia
[description not available]		01.9910
Palmoplantaris Pustulosis
[description not available]		01.9910
Chromosomal Translocation
[description not available]		01.9910
Cancer, Second Primary
[description not available]		01.9910
Acute Disease
Disease having a short and relatively severe course.		01.9910
Leukemia, Myeloid
Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.		01.9910
Psoriasis
A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.		01.9910
Germinoblastoma
[description not available]		01.9910
Lymphoma
A general term for various neoplastic diseases of the lymphoid tissue.		01.9910
African Lymphoma
[description not available]		01.9810
ATLL
[description not available]		01.9810
Burkitt Lymphoma
A form of undifferentiated malignant LYMPHOMA usually found in central Africa, but also reported in other parts of the world. It is commonly manifested as a large osteolytic lesion in the jaw or as an abdominal mass. B-cell antigens are expressed on the immature cells that make up the tumor in virtually all cases of Burkitt lymphoma. The Epstein-Barr virus (HERPESVIRUS 4, HUMAN) has been isolated from Burkitt lymphoma cases in Africa and it is implicated as the causative agent in these cases; however, most non-African cases are EBV-negative.		01.9810
Leukemia-Lymphoma, Adult T-Cell
Aggressive T-Cell malignancy with adult onset, caused by HUMAN T-LYMPHOTROPIC VIRUS 1. It is endemic in Japan, the Caribbean basin, Southeastern United States, Hawaii, and parts of Central and South America and sub-Saharan Africa.		01.9810
Acute Lymphoid Leukemia
[description not available]		01.9710
Precursor Cell Lymphoblastic Leukemia-Lymphoma
A neoplasm characterized by abnormalities of the lymphoid cell precursors leading to excessive lymphoblasts in the marrow and other organs. It is the most common cancer in children and accounts for the vast majority of all childhood leukemias.		01.9710
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		01.9710
Experimental Leukemia
[description not available]		01.9710
B16 Melanoma
[description not available]		01.9710
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		01.9610
Cardiac Diseases
[description not available]		01.9910
Heart Diseases
Pathological conditions involving the HEART including its structural and functional abnormalities.		01.9910