1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane profile

This macrocyclic compound is a derivative of 1,4,7,10-tetraazacyclododecane (cyclam) with three carboxylmethyl substituents. It is commonly studied as a ligand for metal ions, particularly lanthanides, due to its ability to form stable and highly selective complexes. This compound has been investigated for its potential applications in various fields, including:
1. **Biomedical imaging:** The lanthanide complexes of 1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane exhibit strong luminescence properties, making them suitable for use as contrast agents in magnetic resonance imaging (MRI) and fluorescence imaging.
2. **Drug delivery:** The complexation with metal ions can enhance the pharmacokinetic properties of drugs, such as improving their bioavailability and targeted delivery.
3. **Catalysis:** The complexes have shown catalytic activity in various organic reactions, including oxidation, reduction, and hydrolytic reactions.
4. **Sensors:** The compound can be used to develop sensitive and selective sensors for various analytes, including metal ions and biological molecules.

The synthesis of 1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane involves several steps, typically starting with the reaction of cyclam with chloroacetic acid. The resulting compound is then purified and characterized using various analytical techniques, such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry.'

1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	107830
SCHEMBL ID	306395
MeSH ID	M0401906

Synonym
1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane
1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid ,
2-[4,7-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
114873-37-9
1,4,7,10-tetraazacyclododecane-1,4,7-triaceticacid
SCHEMBL306395
1,4,7,-triscarboxymethyl-1,4,7,10-tetraazacyclododecane
1,4,7-tris-(carboxymethyl)-1,4,7, 10-tetraazacyclododecane
do3a
1,4,7-tris-(carboxymethyl)-1,4,7,10-tetraazacyclododecane
1,4,7-tris-carboxymethyl-1,4,7,10-tetraazacyclododecane
1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane
1,4,7,10-teraazacyclododecane 1,4,7,-triacetic acid
HHLZCENAOIROSL-UHFFFAOYSA-N ,
DTXSID60276042
A900074
1,4,7,10-tetraazacyclododecane-1,4,7-triethanoic acid
do 3a
1,4,7,10-tetraazacyclododecaan-1,4,7-triyltriazijnzuur
AMY5806
BS-45007
FT-0776028
2,2',2''-(1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid
CS-0378047
2,2',2''-(1,4,7,10-tetraazacyclododecane-1,4,7-triyl) triacetate
mfcd30532453
E84011
A6DV6KJV7Z

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	6 (16.22)	29.6817
2010's	31 (83.78)	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	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	41 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.01	1	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	2.13	1	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	2.1	1	benzimidazole; polycyclic heteroarene
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.04	1	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
fluorene [no description available]	2.1	1	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon
benzothiazole benzothiazole: structure. benzothiazole : An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.	2.08	1	benzothiazoles	environmental contaminant; plant metabolite; xenobiotic
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	3.06	1	cyclohexanols; secondary alcohol	solvent
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	2.07	1	naphthylamine	human xenobiotic metabolite
thiazoles [no description available]	2.11	1	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
maleimide [no description available]	2.04	1	dicarboximide; maleimides	EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
pyridine n-oxide pyridine N-oxide: RN given refers to parent cpd. pyridine N-oxide : The pyridine N-oxide derived from the parent pyridine. It is a drug metabolite of the antihypertensive agent pinacidil.	2.48	2	pyridine N-oxides	drug metabolite
pentachloromethylthiobenzene [no description available]	2.08	1
dronabinol Dronabinol: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.. Delta(9)-tetrahydrocannabinol : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.	3.06	1	benzochromene; diterpenoid; phytocannabinoid; polyketide	cannabinoid receptor agonist; epitope; hallucinogen; metabolite; non-narcotic analgesic
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	2.08	1	carbon oxoanion
lutetium Lutetium: An element of the rare earth family of metals. It has the atomic symbol Lu, atomic number 71, and atomic weight 175.	2.49	2	d-block element atom; lanthanoid atom
technetium Technetium: The first artificially produced element and a radioactive fission product of URANIUM. Technetium has the atomic symbol Tc, and atomic number 43. All technetium isotopes are radioactive. Technetium 99m (m=metastable) which is the decay product of Molybdenum 99, has a half-life of about 6 hours and is used diagnostically as a radioactive imaging agent. Technetium 99 which is a decay product of technetium 99m, has a half-life of 210,000 years.	2.15	1	manganese group element atom
terbium Terbium: An element of the rare earth family of metals. It has the atomic symbol Tb, atomic number 65, and atomic weight 158.92.	2.49	2	f-block element atom; lanthanoid atom
europium Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.	3	4	f-block element atom; lanthanoid atom
gadolinium Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.	4.03	13	f-block element atom; lanthanoid atom
ytterbium Ytterbium: An element of the rare earth family of metals. It has the atomic symbol Yb, atomic number 70, and atomic weight 173. Ytterbium has been used in lasers and as a portable x-ray source.	2.1	1	f-block element atom; lanthanoid atom
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.41	2	benzenes; phenyl acetates
arginyl-glycyl-aspartic acid arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system	2.08	1	oligopeptide
1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid 1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid: structure given in first source. DOTA : An azamacrocyle in which four nitrogen atoms at positions 1, 4, 7 and 10 of a twelve-membered ring are each substituted with a carboxymethyl group.	3.15	5	azamacrocycle	chelator; copper chelator
1,4,7,10-tetraazacyclododecane-1,7-diacetic acid 1,4,7,10-tetraazacyclododecane-1,7-diacetic acid: structure in first source	2.07	1
alpha-aminobutyric acid alpha-aminobutyric acid: RN given refers to cpd without isomeric designation. alpha-aminobutyric acid : An alpha-amino acid that is butyric acid bearing a single amino substituent located at position 2.. D-alpha-aminobutyric acid : An optically active form of alpha-aminobutyric acid having D-configuration.	2.07	1	alpha-aminobutyric acid; D-alpha-amino acid
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.11	1	cyclodextrin
2-(4'-(methylamino)phenyl)-6-hydroxybenzothiazole 2-(4'-(methylamino)phenyl)-6-hydroxybenzothiazole: an amyloid imaging agent; structure in first source	2.11	1
3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol 3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol: (-)-CP-55,940 and (+)-CP-56,667 are enantiomers; RN refers to CP-55,940	3.06	1	alkylbenzene; ring assembly
anandamide anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.	3.06	1	endocannabinoid; N-acylethanolamine 20:4	human blood serum metabolite; neurotransmitter; vasodilator agent
glyceryl 2-arachidonate glyceryl 2-arachidonate: binds to cannabinoid receptors; structure in first source. 2-arachidonoylglycerol : An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.	3.06	1	2-acylglycerol 20:4; endocannabinoid	human metabolite
naltrexone Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.	2.03	1	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.04	1	cysteinium	fundamental metabolite
naltrindole naltrindole: delta opioid receptor antagonist	2.03	1	isoquinolines
jzl 184 JZL 184: inhibits monoacylglycerol lipase; structure in first source	3.06	1	benzodioxoles
pf 3845 PF 3845: inhibits fatty acid amide hydrolase	3.06	1	piperidines
piperidines Piperidines: A family of hexahydropyridines.	3.06	1
exenatide Exenatide: A synthetic form of exendin-4, a 39-amino acid peptide isolated from the venom of the Gila monster lizard (Heloderma suspectum). Exenatide increases CYCLIC AMP levels in pancreatic acinar cells and acts as a GLUCAGON-LIKE PEPTIDE-1 RECEPTOR (GLP-1) agonist and incretin mimetic, enhancing insulin secretion in response to increased glucose levels; it also suppresses inappropriate glucagon secretion and slows gastric emptying. It is used an anti-diabetic and anti-obesity agent.	2.08	1
amyloid beta-peptides amyloid beta-protein (1-40): although acutely neurotoxic in both rat & monkey cerebral cortex, neuronal degeneration in primates resembles more closely to that found in Alzheimer's disease; amino acid sequence has been determined	2.11	1

Condition	Relationship Strength	Studies
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.7	3
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	3.06	1
Experimental Hepatoma [description not available]	2.15	1
HIV Coinfection [description not available]	2.15	1
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	2.15	1
Benign Neoplasms [description not available]	2.76	3
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.76	3
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)	2.76	3
Breast Cancer [description not available]	2.48	2
Breast Neoplasms Tumors or cancer of the human BREAST.	2.48	2
Acute Confusional Senile Dementia [description not available]	2.11	1
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.11	1
Bone Cancer [description not available]	2.04	1
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.04	1
Atherogenesis [description not available]	2.47	2
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	2.47	2
Glial Cell Tumors [description not available]	2.07	1
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	2.07	1
Carcinoma, Squamous Cell of Head and Neck [description not available]	2.07	1
Carcinoma, Epidermoid [description not available]	2.07	1
Cancer of Head [description not available]	2.07	1
Squamous Cell Carcinoma of Head and Neck The most common type of head and neck carcinoma that originates from cells on the surface of the NASAL CAVITY; MOUTH; PARANASAL SINUSES, SALIVARY GLANDS, and LARYNX. Mutations in TNFRSF10B, PTEN, and ING1 genes are associated with this cancer.	2.07	1
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.07	1
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	2.07	1
Cancer of Pancreas [description not available]	2.03	1
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	2.03	1

1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Description

Cross-References

Synonyms (28)

Research

Studies (37)

Market Indicators

Research Demand Index: 11.28

Study Types