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SBR00028

Sigma-Aldrich

FITC labeled vancomycin

for fluorescent microbial imaging

Synonym(s):

Vancomycin -FITC, Vancomycin FITC conjugate

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About This Item

Empirical Formula (Hill Notation):
C87H88Cl2N10O29S
Molecular Weight:
1840.65
UNSPSC Code:
51102829
NACRES:
NA.76

Quality Level

100

Assay

≥85% (HPLC)

form

solid

mol wt

Mw 1840.66 g/mol

availability

not available in China

storage condition

protect from light

color

yellow to dark orange

suitability

suitable for (Fluorescent detection of gram-positive bacteria)
suitable for (Microbiome)
suitable for microbiology

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

DNA synthesis

shipped in

dry ice

storage temp.

−20°C

General description

FITC labeled Vancomycin (Vancomycin-FITC), is a Fluorescein conjugated Vancomycin, with a similar mode of action as Vancomycin. Vancomycin -FITC can be used to detect Gram-positive bacteria by common fluorescent instruments. Vancomycin is a glycopeptide antibiotic, used to treat gram-positive infections. Fluorescent antibiotics are obtained by synthetic conjugation of an antibiotic to a fluorophore.

Application

Fluorescent antibiotics can be used for many applications including:

  • Antimicrobial resistance research.
  • Bacterial visualization and imaging.
  • Parent antibiotic mode of action research and new antibiotic discovery.
  • Toxicity studies.
  • Research of bacterial infections and tracking its uptake in vivo.

Biochem/physiol Actions

Vancomycin inhibits cell wall synthesis at the level of peptidoglycan biosynthesis. Vancomycin binds with high affinity and specificity to the terminal D-Ala-D-Ala of the growing peptide chain during cell wall synthesis. The binding inhibits transpeptidase activity, which prevents further elongation and cross-linking of the peptidoglycan matrix. Vancomycin-FITC has fluorescein attached to the amine group on the disaccharide moiety of the vancomycin molecule. This disaccharide moiety does not play any role in D-Ala-D-Ala binding site, affording a comparable binding affinity of Vancomycin-FITC to Gram-positive bacteria as the parent drug. However, a minimum inhibitory concentration (MIC) decrease of about two orders of magnitude in comparison to Vancomycin was observed. This activity decrease can be linked to repulsive interactions between the negatively charged Fluorescein moiety and the anionic environment of the peptidoglycan.

Features and Benefits

  • High-quality antibiotic suitable for multiple research applications
  • Ideal for immunological, biochemical, and cell biology applications
  • Suitable for fluorescent microscopy imaging

Analysis Note

  • Aliquots of the DMSO solution can be stored at -20°C, protected from light for at least 1 month.
  • Fluorescent microscopy application: Vancomycin -FITC has excitation/emission wavelength at 495 nm/515 nm.
  • It is recommended to dissolve Vancomycin-FITC in DMSO (Dimethyl Sulfoxide) to a concentration of 1mg/mL.
  • Recommended working concentration for Bacillus cereus in fluorescent microscopy imaging application is 25μg/mL.

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Storage Class Code

12 - Non Combustible Liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SBR00028-VAR:
SBR00028-1.5MG-PW:
SBR00028-BULK:
SBR00028-1.5MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000350707
0000350707
0000265667
0000103879
0000100310

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Analytical techniques for vancomycin−A review.
Sattur A P, et al.
Biotechnology and Bioprocess Engineering: BBE, 5, 153-158 (2000)
Pedro M Pereira et al.
Antimicrobial agents and chemotherapy, 51(10), 3627-3633 (2007-07-25)
A new method of fluorescence ratio imaging microscopy was used to compare the in vivo binding capacity and the access of a fluorescent derivative of vancomycin to the cell wall synthetic sites in isogenic pairs of vancomycin-susceptible and -resistant laboratory
Richard A Daniel et al.
Cell, 113(6), 767-776 (2003-06-18)
Cell shape in most eubacteria is maintained by a tough external peptidoglycan cell wall. Recently, cell shape determining proteins of the MreB family were shown to form helical, actin-like cables in the cell. We used a fluorescent derivative of the
P J Loll et al.
Annual review of biophysics and biomolecular structure, 29, 265-289 (2000-08-15)
Vancomycin is the archetype among naturally occurring compounds known as glycopeptide antibiotics. Because it is a vital therapeutic agent used world-wide for the treatment of infections with gram-positive bacteria, emerging bacterial resistance to vancomycin is a major public health threat.
Kittichoat Tiyanont et al.
Proceedings of the National Academy of Sciences of the United States of America, 103(29), 11033-11038 (2006-07-13)
The peptidoglycan (PG) layers surrounding bacterial cells play an important role in determining cell shape. The machinery controlling when and where new PG is made is not understood, but is proposed to involve interactions between bacterial actin homologs such as
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