1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylenephosphonic acid) profile

1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylenephosphonic acid), often abbreviated as **DOTP**, is a polyaminopolyphosphonic acid with a unique structure and several important applications in research.

**Structure:**

DOTP consists of a 12-membered ring containing four nitrogen atoms (tetraazacyclododecane) with four methylenephosphonic acid groups attached to each nitrogen atom. This creates a molecule with:

* **High affinity for metal ions:** The phosphonic acid groups are excellent chelators for metal ions, especially lanthanides, due to their strong binding affinity.
* **High stability:** The cyclic structure and multiple chelating groups contribute to DOTP's high thermodynamic and kinetic stability, even in challenging environments.
* **Water solubility:** The phosphonic acid groups also impart excellent water solubility, making DOTP suitable for applications in aqueous solutions.

**Importance in Research:**

DOTP plays a crucial role in various fields of research, including:

* **Medical imaging:**
* **Magnetic Resonance Imaging (MRI):** DOTP can be used to develop contrast agents for MRI, which enhance image contrast and help visualize specific tissues or organs. The ability of DOTP to bind to paramagnetic metal ions like gadolinium creates strong MRI signals.
* **Positron Emission Tomography (PET):** DOTP can be modified to chelate radioactive metals like gallium-68, used in PET imaging for diagnosing various conditions like cancer and Alzheimer's disease.
* **Biotechnology:**
* **Drug delivery:** DOTP can be used as a carrier for targeted drug delivery. Its ability to bind to specific receptors on cells or tissues allows for selective delivery of therapeutic agents.
* **Bioseparation:** DOTP's metal-binding properties make it suitable for metal-affinity chromatography, a technique used to purify proteins and other biomolecules.
* **Materials science:**
* **Nanomaterials:** DOTP can be used to synthesize metal-organic frameworks (MOFs) with specific properties for applications like catalysis, gas storage, and sensing.
* **Surfaces:** DOTP can be used to modify surfaces and create coatings with specific functionalities, such as antimicrobial properties or enhanced adhesion.

**Overall:**

1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylenephosphonic acid) (DOTP) is a versatile molecule with unique properties that make it valuable in diverse research areas, including medical imaging, biotechnology, and materials science. Its ability to bind metal ions with high affinity, its stability, and its water solubility have made it a crucial tool for developing advanced technologies and applications.

1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylenephosphonic acid): a bone-seeking radiopharmaceutical; has been complexed with gadolinium (see Gd-DOTP) and holmium [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	124761
CHEMBL ID	1977086
SCHEMBL ID	336769
MeSH ID	M0218825

Synonym
[4,7,10-tris(phosphonomethyl)-1,4,7,10-tetrazacyclododec-1-yl]methylphosphonic acid
(4,7,10-tris(phosphonomethyl)-1,4,7,10-tetraazacyclododecan-1-yl)methylphosphonic acid
91987-74-5
NCI60_028932
dotmp
nsc681106
nsc-681106
AKOS005068310
((1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetrakis(methylene))tetraphosphonic acid
nsc 681106
1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylenephosphonic acid)
1,4,7,10-tetraazacyclododecanetrayl-1,4,7,10-tetrakis(methylene)tetrakisphosphonic acid
(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayltetrakis(methylene))tetrakisphosphonic acid
1,4,7,10-tetraazacyclododecane-1,4,7,10-tetra(methylene phosphonic acid)
65f5kpt4jk ,
unii-65f5kpt4jk
phosphonic acid, (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayltetrakis(methylene))tetrakis-
1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl-tetrakis(methylphosphonic acid)
1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylenephosphonic acid
BP-21002
cyclen phosphonic acid
SCHEMBL336769
CHEMBL1977086
mfcd01863112
((1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetrakis(methylene))tetrakis(phosphonic acid)
{[4,7,10-tris(phosphonomethyl)-1,4,7,10-tetraazacyclododecan-1-yl]methyl}phosphonic acid
1,4,7,10-tetrakis(dihydroxyphosphorylmethyl)-1,4,7,10-tetraazacyclododecane
DTXSID50919416
[1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayltetrakis(methylene)]tetrakis(phosphonic acid)
((1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetrakis(methylene))tetraphosphonicacid
FT-0776037
Q27263874
A854445
[4,7,10-tris(phosphonomethyl)-1,4,7,10-tetrazacyclododec-1-yl]methylphosphonic acid;
((1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)-tetrakis(methylene))tetraphosphonic acid
CS-0155232
PD059155

Excerpt	Reference	Relevance
"166Ho-DOTMP has physical and pharmacokinetic characteristics compatible with high-dose myeloablative treatment of multiple myeloma."	( High-dose 166Ho-DOTMP in myeloablative treatment of multiple myeloma: pharmacokinetics, biodistribution, and absorbed dose estimation. Bensinger, W; Durack, LD; Eary, JF; Fritzberg, A; Rajendran, JG; Vernon, C, 2002)	0.31

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	3 (12.50)	18.2507
2000's	13 (54.17)	29.6817
2010's	7 (29.17)	24.3611
2020's	1 (4.17)	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	4 (16.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	21 (84.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2	1	0	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
etidronate Etidronic Acid: A diphosphonate which affects calcium metabolism. It inhibits ectopic calcification and slows down bone resorption and bone turnover.. etidronic acid : A 1,1-bis(phosphonic acid) that is (ethane-1,1-diyl)bis(phosphonic acid) having a hydroxy substituent at the 1-position. It inhibits the formation, growth, and dissolution of hydroxyapatite crystals by chemisorption to calcium phosphate surfaces.	2.11	1	0	1,1-bis(phosphonic acid)	antineoplastic agent; bone density conservation agent; chelator
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	2.49	2	0
lanthanum [no description available]	2.21	1	0	f-block element atom; lanthanoid atom; scandium group element atom
lutetium Lutetium: An element of the rare earth family of metals. It has the atomic symbol Lu, atomic number 71, and atomic weight 175.	2.77	3	0	d-block element atom; lanthanoid atom
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	2.1	1	0	elemental mercury; zinc group element atom	neurotoxin
samarium Samarium: An element of the rare earth family of metals. It has the atomic symbol Sm, atomic number 62, and atomic weight 150.36. The oxide is used in the control rods of some nuclear reactors.	2.85	3	0	f-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.	2.05	1	0	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.	2.05	1	0	f-block element atom; lanthanoid atom
thulium Thulium: An element of the rare earth family of metals. It has the atomic symbol Tm, atomic number 69, and atomic weight 168.93.	2	1	0	f-block element atom; lanthanoid atom
actinium Actinium: A trivalent radioactive element and the prototypical member of the actinide family. It has the atomic symbol Ac, and atomic number 89. Its principal isotope is 227 and it decays primarily by beta-emission.	2.21	1	0	actinoid atom; f-block element atom; scandium group element atom
americium Americium: A completely man-made radioactive actinide with atomic symbol Am, and atomic number 95. Its valence can range from +3 to +6. Because of its nonmagnetic ground state, it is an excellent superconductor. It is also used in bone mineral analysis and as a radiation source for radiotherapy.	2.21	1	0	actinoid atom; f-block element atom
curium Curium: A radioactive actinide with atomic symbol Cm, and atomic number 96. Thirteen curium isotopes have been produced with mass numbers ranging from 238-250. Its valence can be +3 or +4. It is intensely radioactive and decays by alpha-emission.	2.21	1	0	actinoid atom; f-block element atom
erbium Erbium: Erbium. An element of the rare earth family of metals. It has the atomic symbol Er, atomic number 68, and atomic weight 167.26.	2.1	1	0	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.	2	1	0	f-block element atom; lanthanoid atom
holmium Holmium: An element of the rare earth family of metals. It has the atomic symbol Ho, atomic number 67, and atomic weight 164.93.	8	8	5	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.	2.44	2	0	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.	2.04	1	0	benzenes; phenyl acetates
yttrium radioisotopes Yttrium Radioisotopes: Unstable isotopes of yttrium that decay or disintegrate emitting radiation. Y atoms with atomic weights 82-88 and 90-96 are radioactive yttrium isotopes.	2.17	1	0
dansylsarcosine [no description available]	2	1	0
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	3.11	5	0	divalent inorganic anion; phosphite ion
melphalan Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.	4.36	2	2	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	2.4	2	0	metal atom; pnictogen
lead radioisotopes Lead Radioisotopes: Unstable isotopes of lead that decay or disintegrate emitting radiation. Pb atoms with atomic weights 194-203, 205, and 209-214 are radioactive lead isotopes.	1.99	1	0

Condition	Relationship Strength	Studies	Trials
Cancer-Associated Pain [description not available]	2.15	1	0
Bone Cancer [description not available]	4.69	6	1
Cancer Pain Pain that may be caused by or related to cellular, tissue, and systemic changes that occur during NEOPLASM growth, tissue invasion, and METASTASIS.	2.15	1	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	4.69	6	1
Kahler Disease [description not available]	8.86	9	7
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	8.86	9	7
Metastase [description not available]	2.05	1	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.05	1	0
Breast Cancer [description not available]	2.05	1	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.05	1	0
Ache [description not available]	2.01	1	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.01	1	0
Bleeding [description not available]	7.44	4	4
Dysmyelopoietic Syndromes [description not available]	7.44	4	4
Blood Clot [description not available]	7.44	4	4
Cystitis Inflammation of the URINARY BLADDER, either from bacterial or non-bacterial causes. Cystitis is usually associated with painful urination (dysuria), increased frequency, urgency, and suprapubic pain.	7.44	4	4
Hemorrhage Bleeding or escape of blood from a vessel.	7.44	4	4
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	7.44	4	4
Myelodysplastic Syndromes Clonal hematopoietic stem cell disorders characterized by dysplasia in one or more hematopoietic cell lineages. They predominantly affect patients over 60, are considered preleukemic conditions, and have high probability of transformation into ACUTE MYELOID LEUKEMIA.	7.44	4	4
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	7.44	4	4
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)	3.41	1	1

1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylenephosphonic acid)

Description

Cross-References

Synonyms (37)

Research Excerpts

Pharmacokinetics

Research

Studies (24)

Market Indicators

Research Demand Index: 11.51

Study Types