Biocytin | CAS#576-19-2 | adduct of lysine and biotin

MedKoo Cat#: 597568 | Name: Biocytin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Biocytin is an adduct of lysine and biotin. It is hydrolyzed by biotinidase, which acts on peptide-incorporated biotin or free biotin. Biocytin acts as a coenzyme. Biocytin is used as a substrate to study the specificity and kinetics of biotinidase(s), to measure biotinidase deficiency and as a model compound to study various uptake mechanisms of cells and tissues. Biocytin has been used to label neurons, medium spiny neurons and optic nerves.

Chemical Structure

Biocytin

CAS#576-19-2

Theoretical Analysis

MedKoo Cat#: 597568

Name: Biocytin

CAS#: 576-19-2

Chemical Formula: C16H28N4O4S

Exact Mass: 372.1831

Molecular Weight: 372.48

Elemental Analysis: C, 51.59; H, 7.58; N, 15.04; O, 17.18; S, 8.61

Price and Availability

Size	Price	Availability
100mg	USD 450.00	2 Weeks
250mg	USD 850.00	2 Weeks
1g	USD 1,650.00	2 Weeks

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Related CAS #

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Synonym

Biocytin; Biotinyl-L-lysine;

IUPAC/Chemical Name

N6-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl)-L-lysine

InChi Key

BAQMYDQNMFBZNA-MNXVOIDGSA-N

InChi Code

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

SMILES Code

N[C@@H](CCCCNC(CCCC[C@@H]1SC[C@]([C@]1([H])N2)([H])NC2=O)=O)C(O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 372.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Harsløf M, Müller FC, Rohrberg J, Rekling JC. Fast neuronal labeling in live tissue using a biocytin conjugated fluorescent probe. J Neurosci Methods. 2015 Sep 30;253:101-9. doi: 10.1016/j.jneumeth.2015.06.005. Epub 2015 Jun 12. PubMed PMID: 26079494. 2: Kang J. Biocytin staining of glia and neurons in brain slices. Cold Spring Harb Protoc. 2014 Sep 2;2014(9):948-50. doi: 10.1101/pdb.prot083527. PubMed PMID: 25183822. 3: Marx M, Günter RH, Hucko W, Radnikow G, Feldmeyer D. Improved biocytin labeling and neuronal 3D reconstruction. Nat Protoc. 2012 Feb 2;7(2):394-407. doi: 10.1038/nprot.2011.449. PubMed PMID: 22301777. 4: Swietek B, Gupta A, Proddutur A, Santhakumar V. Immunostaining of Biocytin-filled and Processed Sections for Neurochemical Markers. J Vis Exp. 2016 Dec 31;(118). doi: 10.3791/54880. PubMed PMID: 28117774; PubMed Central PMCID: PMC5264554. 5: Narayanan RT, Mohan H, Broersen R, de Haan R, Pieneman AW, de Kock CP. Juxtasomal biocytin labeling to study the structure-function relationship of individual cortical neurons. J Vis Exp. 2014 Feb 25;(84):e51359. doi: 10.3791/51359. PubMed PMID: 24638127; PubMed Central PMCID: PMC4132059. 6: Pinault D. A novel single-cell staining procedure performed in vivo under electrophysiological control: morpho-functional features of juxtacellularly labeled thalamic cells and other central neurons with biocytin or Neurobiotin. J Neurosci Methods. 1996 Apr;65(2):113-36. PubMed PMID: 8740589. 7: Asti M, Iori M, Erba PA, Atti G, Farioli D, Guidotti C, Versari A. Radiosynthesis of 68Ga-labelled DOTA-biocytin (68Ga-r-BHD) and assessment of its pharmaceutical quality for clinical use. Nucl Med Commun. 2012 Nov;33(11):1179-87. PubMed PMID: 22836735. 8: Eckert WA 3rd, Willcockson HH, Light AR. Interference of biocytin with opioid-evoked hyperpolarization and membrane properties of rat spinal substantia gelatinosa neurons. Neurosci Lett. 2001 Jan 12;297(2):117-20. PubMed PMID: 11121884. 9: Spiga S, Fattore L, Puddu MC, Cappai A, Picciau S, Brotzu G, Serra GP, Petruzzo P. Use of biocytin as neuroanatomic tracer in harvested human pancreas: a confocal laser scanning microscopy analysis. Pancreas. 2002 May;24(4):329-35. PubMed PMID: 11961484. 10: Ebrahim H, Dakshinamurti K. Determination of biocytin. Anal Biochem. 1987 May 1;162(2):319-24. PubMed PMID: 3111297. 11: Thomson AM, Armstrong WE. Biocytin-labelling and its impact on late 20th century studies of cortical circuitry. Brain Res Rev. 2011 Jan 7;66(1-2):43-53. doi: 10.1016/j.brainresrev.2010.04.004. Epub 2010 Apr 24. PubMed PMID: 20399808; PubMed Central PMCID: PMC2949688. 12: Baur B, Suormala T, Baumgartner ER. Biocytin and biotin uptake into NB2a neuroblastoma and C6 astrocytoma cells. Brain Res. 2002 Jan 25;925(2):111-21. PubMed PMID: 11792359. 13: McDonald AJ. Neuroanatomical labeling with biocytin: a review. Neuroreport. 1992 Oct;3(10):821-7. Review. PubMed PMID: 1384763. 14: Teranishi T, Negishi K. Double-staining of horizontal and amacrine cells by intracellular injection with lucifer yellow and biocytin in carp retina. Neuroscience. 1994 Mar;59(1):217-26. PubMed PMID: 7514770. 15: Chang SL, LoTurco JJ, Nisenbaum LK. In vitro biocytin injection into perinatal mouse brain: a method for tract tracing in developing tissue. J Neurosci Methods. 2000 Apr 1;97(1):1-6. PubMed PMID: 10771069. 16: Kenan-Vaknin G, Katz H, Malach R. Golgi-like staining of visual cortex cells obtained by extracellular biocytin application in vitro. Brain Res. 1992 Feb 7;571(2):338-41. PubMed PMID: 1611502. 17: Suormala TM, Baumgartner ER, Bausch J, Holick W, Wick H. Quantitative determination of biocytin in urine of patients with biotinidase deficiency using high-performance liquid chromatography (HPLC). Clin Chim Acta. 1988 Oct 31;177(3):253-69. PubMed PMID: 3148376. 18: Erişir A, Aoki C. A method of combining biocytin tract-tracing with avidin-biotin-peroxidase complex immunocytochemistry for pre-embedding electron microscopic labeling in neonatal tissue. J Neurosci Methods. 1998 Jun 1;81(1-2):189-97. PubMed PMID: 9696325. 19: Lapper SR, Bolam JP. The anterograde and retrograde transport of neurobiotin in the central nervous system of the rat: comparison with biocytin. J Neurosci Methods. 1991 Sep;39(2):163-74. PubMed PMID: 1724681. 20: Said HM, Thuy LP, Sweetman L, Schatzman B. Transport of the biotin dietary derivative biocytin (N-biotinyl-L-lysine) in rat small intestine. Gastroenterology. 1993 Jan;104(1):75-80. PubMed PMID: 8419264.