Identification of biotin sulfone, bisnorbiotin methyl ketone, and tetranorbiotin-/-sulfoxide in human urine

Janos Zempleni, Donald B. McCormick, Donald M. Mock

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

In previous studies using the HPLC and avidin-binding assay, five unidentified avidin-binding substances were observed in human urine. The present study investigated the identity of these substances. Urine was collected before and after intravenous administration of 18.5 μmol biotin to healthy adults. Unknown substances 1 and 3 were initially identified as biotin sulfone and bisnorbiotin methyl ketone, respectively, by coelution with authentic standards on HPLC. Identities were confirmed by thin-layer chromatography and by derivatization with p-dimethyl-aminocinnamaldehyde. As expected for biotin metabolites, the urinary excretion of biotin sulfone and bisnorbiotin methyl ketone increased with biotin administration. The urinary excretion of biotin sulfone increased 21-fold from 0.2 nmol/h before to 4.2 nmol/h after administration; the excretion of bisnorbiotin methyl ketone increased 130-fold from 0.4 to 51.8 nmol/h. At presumed steady state in free- living subjects (n = 6), biotin sulfone and bisnorbiotin methyl ketone accounted for 3.6% and 7.9% of total biotin excretion, respectively. Traces of tetranorbiotin-/-sulfoxide were also identified by using thin-layer chromatography and derivatization with p-dimethylaminocinnamaldehyde. However, tetranorbiotin-/-sulfoxide was not detectable in urine by the HPLC and avidin-binding assay because this metabolite has weak avidin-binding affinity. We conclude that biotin sulfone and bisnorbiotin methyl ketone are present in measurable quantities in human urine; their quantitation should allow more accurate studies on human biotin metabolism and turnover.

Original languageEnglish (US)
Pages (from-to)508-511
Number of pages4
JournalAmerican Journal of Clinical Nutrition
Volume65
Issue number2
DOIs
StatePublished - Jan 1 1997

Fingerprint

biotin
Biotin
ketones
Avidin
urine
Urine
avidin
High Pressure Liquid Chromatography
Thin Layer Chromatography
excretion
high performance liquid chromatography
derivatization
thin layer chromatography
Intravenous Administration
biotin sulfone
tetranorbiotin sulfoxide
bisnorbiotin methyl ketone
metabolites
assays
intravenous injection

Keywords

  • Biotin sulfone
  • biotin
  • bisnorbiotin methyl ketone
  • human
  • tetranorbiotin-/- sulfoxide
  • urine

ASJC Scopus subject areas

  • Medicine (miscellaneous)
  • Nutrition and Dietetics

Cite this

Identification of biotin sulfone, bisnorbiotin methyl ketone, and tetranorbiotin-/-sulfoxide in human urine. / Zempleni, Janos; McCormick, Donald B.; Mock, Donald M.

In: American Journal of Clinical Nutrition, Vol. 65, No. 2, 01.01.1997, p. 508-511.

Research output: Contribution to journalArticle

@article{42ea3cb544e240d6a8354ad92358a70b,
title = "Identification of biotin sulfone, bisnorbiotin methyl ketone, and tetranorbiotin-/-sulfoxide in human urine",
abstract = "In previous studies using the HPLC and avidin-binding assay, five unidentified avidin-binding substances were observed in human urine. The present study investigated the identity of these substances. Urine was collected before and after intravenous administration of 18.5 μmol biotin to healthy adults. Unknown substances 1 and 3 were initially identified as biotin sulfone and bisnorbiotin methyl ketone, respectively, by coelution with authentic standards on HPLC. Identities were confirmed by thin-layer chromatography and by derivatization with p-dimethyl-aminocinnamaldehyde. As expected for biotin metabolites, the urinary excretion of biotin sulfone and bisnorbiotin methyl ketone increased with biotin administration. The urinary excretion of biotin sulfone increased 21-fold from 0.2 nmol/h before to 4.2 nmol/h after administration; the excretion of bisnorbiotin methyl ketone increased 130-fold from 0.4 to 51.8 nmol/h. At presumed steady state in free- living subjects (n = 6), biotin sulfone and bisnorbiotin methyl ketone accounted for 3.6{\%} and 7.9{\%} of total biotin excretion, respectively. Traces of tetranorbiotin-/-sulfoxide were also identified by using thin-layer chromatography and derivatization with p-dimethylaminocinnamaldehyde. However, tetranorbiotin-/-sulfoxide was not detectable in urine by the HPLC and avidin-binding assay because this metabolite has weak avidin-binding affinity. We conclude that biotin sulfone and bisnorbiotin methyl ketone are present in measurable quantities in human urine; their quantitation should allow more accurate studies on human biotin metabolism and turnover.",
keywords = "Biotin sulfone, biotin, bisnorbiotin methyl ketone, human, tetranorbiotin-/- sulfoxide, urine",
author = "Janos Zempleni and McCormick, {Donald B.} and Mock, {Donald M.}",
year = "1997",
month = "1",
day = "1",
doi = "10.1093/ajcn/65.2.508",
language = "English (US)",
volume = "65",
pages = "508--511",
journal = "American Journal of Clinical Nutrition",
issn = "0002-9165",
publisher = "American Society for Nutrition",
number = "2",

}

TY - JOUR

T1 - Identification of biotin sulfone, bisnorbiotin methyl ketone, and tetranorbiotin-/-sulfoxide in human urine

AU - Zempleni, Janos

AU - McCormick, Donald B.

AU - Mock, Donald M.

PY - 1997/1/1

Y1 - 1997/1/1

N2 - In previous studies using the HPLC and avidin-binding assay, five unidentified avidin-binding substances were observed in human urine. The present study investigated the identity of these substances. Urine was collected before and after intravenous administration of 18.5 μmol biotin to healthy adults. Unknown substances 1 and 3 were initially identified as biotin sulfone and bisnorbiotin methyl ketone, respectively, by coelution with authentic standards on HPLC. Identities were confirmed by thin-layer chromatography and by derivatization with p-dimethyl-aminocinnamaldehyde. As expected for biotin metabolites, the urinary excretion of biotin sulfone and bisnorbiotin methyl ketone increased with biotin administration. The urinary excretion of biotin sulfone increased 21-fold from 0.2 nmol/h before to 4.2 nmol/h after administration; the excretion of bisnorbiotin methyl ketone increased 130-fold from 0.4 to 51.8 nmol/h. At presumed steady state in free- living subjects (n = 6), biotin sulfone and bisnorbiotin methyl ketone accounted for 3.6% and 7.9% of total biotin excretion, respectively. Traces of tetranorbiotin-/-sulfoxide were also identified by using thin-layer chromatography and derivatization with p-dimethylaminocinnamaldehyde. However, tetranorbiotin-/-sulfoxide was not detectable in urine by the HPLC and avidin-binding assay because this metabolite has weak avidin-binding affinity. We conclude that biotin sulfone and bisnorbiotin methyl ketone are present in measurable quantities in human urine; their quantitation should allow more accurate studies on human biotin metabolism and turnover.

AB - In previous studies using the HPLC and avidin-binding assay, five unidentified avidin-binding substances were observed in human urine. The present study investigated the identity of these substances. Urine was collected before and after intravenous administration of 18.5 μmol biotin to healthy adults. Unknown substances 1 and 3 were initially identified as biotin sulfone and bisnorbiotin methyl ketone, respectively, by coelution with authentic standards on HPLC. Identities were confirmed by thin-layer chromatography and by derivatization with p-dimethyl-aminocinnamaldehyde. As expected for biotin metabolites, the urinary excretion of biotin sulfone and bisnorbiotin methyl ketone increased with biotin administration. The urinary excretion of biotin sulfone increased 21-fold from 0.2 nmol/h before to 4.2 nmol/h after administration; the excretion of bisnorbiotin methyl ketone increased 130-fold from 0.4 to 51.8 nmol/h. At presumed steady state in free- living subjects (n = 6), biotin sulfone and bisnorbiotin methyl ketone accounted for 3.6% and 7.9% of total biotin excretion, respectively. Traces of tetranorbiotin-/-sulfoxide were also identified by using thin-layer chromatography and derivatization with p-dimethylaminocinnamaldehyde. However, tetranorbiotin-/-sulfoxide was not detectable in urine by the HPLC and avidin-binding assay because this metabolite has weak avidin-binding affinity. We conclude that biotin sulfone and bisnorbiotin methyl ketone are present in measurable quantities in human urine; their quantitation should allow more accurate studies on human biotin metabolism and turnover.

KW - Biotin sulfone

KW - biotin

KW - bisnorbiotin methyl ketone

KW - human

KW - tetranorbiotin-/- sulfoxide

KW - urine

UR - http://www.scopus.com/inward/record.url?scp=0030979108&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030979108&partnerID=8YFLogxK

U2 - 10.1093/ajcn/65.2.508

DO - 10.1093/ajcn/65.2.508

M3 - Article

C2 - 9022537

AN - SCOPUS:0030979108

VL - 65

SP - 508

EP - 511

JO - American Journal of Clinical Nutrition

JF - American Journal of Clinical Nutrition

SN - 0002-9165

IS - 2

ER -