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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H28N4O4S
Molecular Weight 372.483
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BIOCYTIN

SMILES

N[C@@H](CCCCNC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12)C(O)=O

InChI

InChIKey=BAQMYDQNMFBZNA-MNXVOIDGSA-N
InChI=1S/C16H28N4O4S/c17-10(15(22)23)5-3-4-8-18-13(21)7-2-1-6-12-14-11(9-25-12)19-16(24)20-14/h10-12,14H,1-9,17H2,(H,18,21)(H,22,23)(H2,19,20,24)/t10-,11-,12-,14-/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H28N4O4S
Molecular Weight 372.483
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Biocytin is a biotin-lysine complex of low molecular weight containing about 65% biotin, which retains a high affinity for avidin. Biocytin is also used in scientific research as a histological stain for nerve cells. Biocytin is a versatile marker used in anterograde, retrograde and intracellular neuroanatomical investigations and in biotinidase assays. Biocytin displays high solubility in aqueous solutions and has a low molecular weight facilitating injection using micropipettes. Biocytin can be incorporated with a variety of avidin and streptavidin conjugates for detection by light, fluorescence or electron microscope. In vitro injection of biocytin into explanted brain hemispheres provides a quick and easy method for tract tracing in developing brains. Biocytin can be used to measure the biotinidase activity and therefore diagnose biotinidase deficiency.

Originator

Curator's Comment: # Merck

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Use of biocytin as neuroanatomic tracer in harvested human pancreas: a confocal laser scanning microscopy analysis.
2002-05
NMDA receptor antagonists disinhibit rat posterior cingulate and retrosplenial cortices: a potential mechanism of neurotoxicity.
2002-04-15
Axon arbors and synaptic connections of a vulnerable population of interneurons in the dentate gyrus in vivo.
2002-04-15
Correlations between neuronal morphology and electrophysiological features in the rodent superficial dorsal horn.
2002-04-01
Morphology and projection pattern of medial and dorsal pallial neurons in the frog Discoglossus pictus and the salamander Plethodon jordani.
2002-04-01
Anatomical, physiological, molecular and circuit properties of nest basket cells in the developing somatosensory cortex.
2002-04
Connections of the ventral telencephalon and tyrosine hydroxylase distribution in the zebrafish brain (Danio rerio) lead to identification of an ascending dopaminergic system in a teleost.
2002-03-30
Cell types and response properties of neurons in the ventral division of the medial geniculate body of the rabbit.
2002-03-25
Colocalization of gamma-aminobutyric acid-like immunoreactivity and catecholamines in the feeding network of Aplysia californica.
2002-03-25
Firing properties of axotomized central nervous system neurons recover after graft reinnervation.
2002-03-18
A bisubstrate analog inhibitor of the carboxyltransferase component of acetyl-CoA carboxylase.
2002-03-15
Biotin decreases retinal apoptosis and induces eye malformations in the early chick embryo.
2002-03-04
Detailed passive cable models of layer 2/3 pyramidal cells in rat visual cortex at different temperatures.
2002-03-01
Slow excitatory synaptic potentials evoked by distension in myenteric descending interneurones of guinea-pig ileum.
2002-03-01
Interconnections of auditory areas in the guinea pig neocortex.
2002-03
Visual cortical organization at the single axon level: a beginning.
2002-03
Sexual dimorphisms in a copulatory neuromuscular system in the green anole lizard.
2002-02-11
Development of individual axon arbors in a thalamocortical circuit necessary for song learning in zebra finches.
2002-02-01
Repellent guidance of regenerating optic axons by chondroitin sulfate glycosaminoglycans in zebrafish.
2002-02-01
Recovery from spinal cord injury: a new transection model in the C57Bl/6 mouse.
2002-02-01
Biocytin and biotin uptake into NB2a neuroblastoma and C6 astrocytoma cells.
2002-01-25
Connections between the central posterior/prepacemaker nucleus and hypothalamic areas in the weakly electric fish Apteronotus leptorhynchus: evidence for an indirect, but not a direct, link.
2002-01-21
Dual cholinergic control of fast-spiking interneurons in the neostriatum.
2002-01-15
Neurons labeled from locomotor-related ventrolateral funiculus stimulus sites in the neonatal rat spinal cord.
2002-01-14
Firing patterns of inferior colliculus neurons-histology and mechanism to change firing patterns in rat brain slices.
2002-01-04
Serum biotinidase activity in children with chronic liver disease and its clinical significance.
2002-01
Somatostatin modulates Ca2+ currents in neostriatal neurons.
2002
In vitro formation of corticospinal synapses in an organotypic slice co-culture.
2002
Cholecystokinin-immunopositive basket and Schaffer collateral-associated interneurones target different domains of pyramidal cells in the CA1 area of the rat hippocampus.
2002
Early development of neuronal activity in the primate hippocampus in utero.
2001-12-15
Targeted PEG-based bioconjugates enhance the cellular uptake and transport of a HIV-1 TAT nonapeptide.
2001-12-13
Identification and characterization of an output neuron from the oscillatory molluscan olfactory network.
2001-12-07
Location of dye-coupled second order and of efferent vestibular neurons labeled from individual semicircular canal or otolith organs in the frog.
2001-12-07
Differential synaptic processing separates stationary from transient inputs to the auditory cortex.
2001-12
Synaptic targets of thalamic reticular nucleus terminals in the visual thalamus of the cat.
2001-11-26
P2X(7) receptors in the enteric nervous system of guinea-pig small intestine.
2001-11-19
Functionally independent columns of rat somatosensory barrel cortex revealed with voltage-sensitive dye imaging.
2001-11-01
NMDA receptor activation limits the number of synaptic connections during hippocampal development.
2001-11
Mutations in BTD causing biotinidase deficiency.
2001-11
Increased synaptic plasticity in the surround of visual cortex lesions in rats.
2001-10-29
AMPA receptor channels with long-lasting desensitization in bipolar interneurons contribute to synaptic depression in a novel feedback circuit in layer 2/3 of rat neocortex.
2001-10-15
A subpopulation of nervus terminalis neurons projects to the olfactory mucosa in Xenopus laevis.
2001-10-01
Electrophysiological analysis of suprachiasmatic nucleus projections to the ventrolateral preoptic area in the rat.
2001-10
Morphological changes in the neuronal substrate for the optokinetic reflex in albino ferrets.
2001-10
Recurrent CA1 collateral axons in developing rat hippocampus.
2001-09-21
Auditory and lateral line inputs to the midbrain of an aquatic anuran: neuroanatomic studies in Xenopus laevis.
2001-09-17
Compartmental models of rat cerebellar Purkinje cells based on simultaneous somatic and dendritic patch-clamp recordings.
2001-09-01
Physiology and morphology of intratelencephalically projecting corticostriatal-type neurons in pigeons as revealed by intracellular recording and cell filling.
2001
The fine organization of nigro-collicular channels with additional observations of their relationships with acetylcholinesterase in the rat.
2001
Regulation of the activity of hippocampal stratum oriens interneurons by alpha7 nicotinic acetylcholine receptors.
2001
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
The intracellular recording electrode contained 1% biocytin so the rat neurons could later be visualized with an avidin-biotin peroxidase method.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:22:24 GMT 2025
Edited
by admin
on Mon Mar 31 19:22:24 GMT 2025
Record UNII
G6D6147J22
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.EPSILON.-N-BIOTINYL-L-LYSINE
Preferred Name English
BIOCYTIN
MI  
Common Name English
N6-BIOTINYLLYSINE
Common Name English
BIOCYTIN [MI]
Common Name English
N(SUP 6)-(5-((3AS,4S,6AR)-HEXAHYDRO-2-OXO-1H-THIENO(3,4-D)IMIDAZOL-4-YL)-1-OXOPENTYL)-L-LYSINE
Common Name English
Code System Code Type Description
CAS
576-19-2
Created by admin on Mon Mar 31 19:22:24 GMT 2025 , Edited by admin on Mon Mar 31 19:22:24 GMT 2025
PRIMARY
MERCK INDEX
m2502
Created by admin on Mon Mar 31 19:22:24 GMT 2025 , Edited by admin on Mon Mar 31 19:22:24 GMT 2025
PRIMARY Merck Index
FDA UNII
G6D6147J22
Created by admin on Mon Mar 31 19:22:24 GMT 2025 , Edited by admin on Mon Mar 31 19:22:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID30973172
Created by admin on Mon Mar 31 19:22:24 GMT 2025 , Edited by admin on Mon Mar 31 19:22:24 GMT 2025
PRIMARY
CHEBI
27870
Created by admin on Mon Mar 31 19:22:24 GMT 2025 , Edited by admin on Mon Mar 31 19:22:24 GMT 2025
PRIMARY
MESH
C013411
Created by admin on Mon Mar 31 19:22:24 GMT 2025 , Edited by admin on Mon Mar 31 19:22:24 GMT 2025
PRIMARY
PUBCHEM
83814
Created by admin on Mon Mar 31 19:22:24 GMT 2025 , Edited by admin on Mon Mar 31 19:22:24 GMT 2025
PRIMARY
WIKIPEDIA
BIOCYTIN
Created by admin on Mon Mar 31 19:22:24 GMT 2025 , Edited by admin on Mon Mar 31 19:22:24 GMT 2025
PRIMARY