1,1'-ethylidene bis(tryptophan) profile

## 1,1'-Ethylidene bis(tryptophan) (EBT)

**What it is:**

1,1'-Ethylidene bis(tryptophan) (EBT) is a **synthetic dimer of tryptophan**, an amino acid found in proteins. It's formed by linking two tryptophan molecules together through a **single ethylidene bridge**, which connects the indole rings of the tryptophan residues.

**Why it's important for research:**

EBT has garnered attention in research due to its unique properties and potential applications in various fields, including:

* **Biomaterials and drug delivery:** EBT exhibits **self-assembly properties**, meaning it can spontaneously form organized structures in solution. This ability makes it attractive for the development of biomaterials like hydrogels, scaffolds, and drug delivery systems. The self-assembled structures can be further engineered to encapsulate therapeutic agents and release them in a controlled manner, improving drug efficacy and minimizing side effects.
* **Neurobiology:** EBT's structure mimics the **interaction between tryptophan residues** in proteins, which are crucial for **protein folding and function**, particularly in neurotransmitter receptors. Researchers are investigating EBT's potential to modulate these interactions and affect brain function.
* **Bioimaging:** EBT's intrinsic fluorescence makes it suitable for **fluorescence microscopy** and other imaging techniques. It can be used to track protein movement and interactions within living cells, providing insights into cellular processes and disease mechanisms.
* **Materials science:** EBT's self-assembly properties have also attracted interest in materials science. Its ability to form **complex structures** opens up possibilities for creating novel materials with unique optical, electrical, and mechanical properties.

**Further research is ongoing:**

While promising, research on EBT is still in its early stages. More research is needed to understand its full potential and address its potential limitations, such as its biocompatibility and stability.

**In summary:**

1,1'-Ethylidene bis(tryptophan) is a versatile molecule with a wide range of potential applications in biomaterials, neurobiology, bioimaging, and materials science. Its self-assembly properties, fluorescence, and structural similarity to tryptophan make it a valuable tool for researchers exploring various fields.

1,1'-ethylidene bis(tryptophan): may be associated with eosinophilla-myalgia syndrome; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	107700
CHEMBL ID	1433441
SCHEMBL ID	1339902
MeSH ID	M0191676

Synonym
peak e
NCGC00163331-01
SCHEMBL1339902
1,1'-ethylidene bis(tryptophan)
1,1'-ebt
xp857d0yl2 ,
1,1'-ethylidenebis(tryptophan)
132685-02-0
unii-xp857d0yl2
l-tryptophan, 1,1'-ethylidenebis-
1,1'-ethylidene bis[tryptophan]
CHEMBL1433441
J534.602I ,
tryptophan impurity a [ep impurity]
3,3-(ethane-1,1-diylbis(1h-indol-1,3-diyl))bis((2s)-2-aminopropanoic acid)
3,3'-ethylidenebis((1h-indole-1,3-diyl))bis((2s)-2-aminopropanoic acid)
(2s,2's)-3,3'-(ethane-1,1-diylbis(1h-indole-1,3-diyl))bis(2-aminopropanoic acid)
1,1'-ethylidenebis(l-tryptophan)
3,3'-[ethylidenebis(1h-indole-1,3-diyl)]bis[(2s)-2-aminopropanoic] acid (1,1'-ethylidenebistryptophan)
1,1'-ethylidenebis[l-tryptophan]
J-006207
1,1 inverted exclamation mark -ethylidenebis[l-tryptophan]
(2s)-2-amino-3-[1-[1-[3-[(2s)-2-amino-2-carboxyethyl]indol-1-yl]ethyl]indol-3-yl]propanoic acid
(2s,2's)-3,3'-(1,1'-(ethane-1,1-diyl)bis(1h-indole-3,1-diyl))bis(2-aminopropanoic acid)
Q27293947
DTXSID801301794
PD165962
(2s,2's)-3,3'-(1,1'-(ethane-1,1-diyl)bis(1h-indole-3,1-diyl))bis(2-aminopropanoicacid)

Excerpt	Relevance	Reference
" Previous experiments established that the dosing conditions produce several characteristics of EMS, including dermal inflammation and fibrosis, increased dermal mast cells, and increased levels of quinolinic acid."	( Cognitive deficits in a murine model of the eosinophilia-myalgia syndrome: a preliminary report. Bolster, MB; Ludwicka, A; Middaugh, LD; Nussbaum, R; Silver, RM, )	0.13

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE	Homo sapiens (human)	Potency	1.0000	0.0032	45.4673	12,589.2998	AID2517
Chain A, ATP-DEPENDENT DNA HELICASE Q1	Homo sapiens (human)	Potency	31.6228	0.1259	19.1169	125.8920	AID2549
phosphopantetheinyl transferase	Bacillus subtilis	Potency	28.1838	0.1413	37.9142	100.0000	AID1490
Microtubule-associated protein tau	Homo sapiens (human)	Potency	14.2191	0.1800	13.5574	39.8107	AID1460; AID1468
aldehyde dehydrogenase 1 family, member A1	Homo sapiens (human)	Potency	39.8107	0.0112	12.4002	100.0000	AID1030
glucocerebrosidase	Homo sapiens (human)	Potency	39.8107	0.0126	8.1569	44.6684	AID2101
vitamin D3 receptor isoform VDRA	Homo sapiens (human)	Potency	89.1251	0.3548	28.0659	89.1251	AID504847
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID1347154	Primary screen GU AMC qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630	Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay	2021	Cell reports, 04-27, Volume: 35, Issue:4	A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	30 (88.24)	18.2507
2000's	2 (5.88)	29.6817
2010's	0 (0.00)	24.3611
2020's	2 (5.88)	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	3 (8.57%)	6.00%
Case Studies	1 (2.86%)	4.05%
Observational	0 (0.00%)	0.25%
Other	31 (88.57%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
beta-alanine [no description available]	1.98	1	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
2,3-diaminopropionic acid 3-aminoalanine : A diamino acid that is alanine in which one of the hydrogens of the methyl group is replaced by an amino group.	1.98	1	alanine derivative; amino acid zwitterion; beta-amino acid; diamino acid; non-proteinogenic alpha-amino acid	Escherichia coli metabolite
quinolinic acid Quinolinic Acid: A metabolite of tryptophan with a possible role in neurodegenerative disorders. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS.. pyridinedicarboxylic acid : Any member of the class of pyridines carrying two carboxy groups.. quinolinic acid : A pyridinedicarboxylic acid that is pyridine substituted by carboxy groups at positions 2 and 3. It is a metabolite of tryptophan.	1.98	1	pyridinedicarboxylic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; NMDA receptor agonist
selenic acid Selenic Acid: A strong dibasic acid with the molecular formula H2SeO4. Included under this heading is the acid form, and inorganic salts of dihydrogen selenium tetraoxide.	1.99	1	selenium oxoacid
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	4.34	6	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	3.14	1	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	1.99	1	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	6.73	32	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
sodium selenite disodium selenite : An inorganic sodium salt composed of sodium and selenite ions in a 2:1 ratio.	1.99	1	inorganic sodium salt; selenite salt	nutraceutical
ethionine L-ethionine : An S-ethylhomocysteine that has S-configuration at the chiral centre.	3.14	1	S-ethylhomocysteine	antimetabolite; carcinogenic agent
1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid: precursor of mutagenic nitroso cpd in soy sauce; structure given in first source	3.08	5	harmala alkaloid
3-(phenylamino)alanine 3-(phenylamino)alanine: structure given in second source	4.34	6
canavanine L-canavanine : A non-proteinogenic L-alpha-amino acid that is L-homoserine substituted at oxygen with a guanidino (carbamimidamido) group. Although structurally related to L-arginine, it is non-proteinogenic.	3.14	1	amino acid zwitterion; non-proteinogenic L-alpha-amino acid	phytogenic insecticide; plant metabolite

Condition	Relationship Strength	Studies
Congenital Zika Syndrome [description not available]	2.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.84	4
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.25	1
Libman-Sacks Disease [description not available]	2.96	1
Idiopathic Parkinson Disease [description not available]	2.96	1
Lupus Erythematosus, Systemic A chronic, relapsing, inflammatory, and often febrile multisystemic disorder of connective tissue, characterized principally by involvement of the skin, joints, kidneys, and serosal membranes. It is of unknown etiology, but is thought to represent a failure of the regulatory mechanisms of the autoimmune system. The disease is marked by a wide range of system dysfunctions, an elevated erythrocyte sedimentation rate, and the formation of LE cells in the blood or bone marrow.	2.96	1
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	2.96	1
Eosinophilia-Myalgia Syndrome A complex systemic syndrome with inflammatory and autoimmune components that affect the skin, fascia, muscle, nerve, blood vessels, lung, and heart. Diagnostic features generally include EOSINOPHILIA, myalgia severe enough to limit usual activities of daily living, and the absence of coexisting infectious, autoimmune or other conditions that may induce eosinophilia. Biopsy of affected tissue reveals a microangiopathy associated with diffuse inflammation involving connective tissue. (From Spitzer et al., J Rheumatol Suppl 1996 Oct;46:73-9; Blackburn WD, Semin Arthritis Rheum 1997 Jun;26(6):788-93)	5.77	21
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	1.98	1
Innate Inflammatory Response [description not available]	1.98	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	1.98	1
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	1.98	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	1.98	1
Cirrhosis [description not available]	1.99	1
Hand Dermatosis [description not available]	1.99	1
Leg Dermatoses A nonspecific term used to denote any cutaneous lesion or group of lesions, or eruptions of any type on the leg. (From Stedman, 25th ed)	1.99	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	1.99	1
Hand Dermatoses Skin diseases involving the HANDS.	1.99	1
Muscle Disorders [description not available]	2.39	2
Dermatoses [description not available]	1.99	1
Muscular Diseases Acquired, familial, and congenital disorders of SKELETAL MUSCLE and SMOOTH MUSCLE.	2.39	2
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	1.99	1
Diffuse Myofascial Pain Syndrome [description not available]	2	1
Symptom Cluster [description not available]	2.67	3
Fibromyalgia A common nonarticular rheumatic syndrome characterized by myalgia and multiple points of focal muscle tenderness to palpation (trigger points). Muscle pain is typically aggravated by inactivity or exposure to cold. This condition is often associated with general symptoms, such as sleep disturbances, fatigue, stiffness, HEADACHES, and occasionally DEPRESSION. There is significant overlap between fibromyalgia and the chronic fatigue syndrome (FATIGUE SYNDROME, CHRONIC). Fibromyalgia may arise as a primary or secondary disease process. It is most frequent in females aged 20 to 50 years. (From Adams et al., Principles of Neurology, 6th ed, p1494-95)	2	1
Syndrome A characteristic symptom complex.	2.67	3
Anasarca [description not available]	1.97	1
Eosinophilia, Tropical [description not available]	2.38	2
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	1.97	1
Eosinophilia Abnormal increase of EOSINOPHILS in the blood, tissues or organs.	2.38	2
Ache [description not available]	1.97	1
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	1.97	1

1,1'-ethylidene bis(tryptophan)

Description

Cross-References

Synonyms (28)

Research Excerpts

Dosage Studied

Protein Targets (7)

Potency Measurements

Bioassays (2)

Research

Studies (34)

Market Indicators

Research Demand Index: 10.98

Study Types