FITC-Trehalose

FITC-Trehalose

FITC-trehalose selectively labels live mycobacteria in vitro and in vivo, allowing for downstream fluorescent imaging of Mycobacterium tuberculosis in culture and in infected macrophages.

Highlights:

  • Trehalose moiety - selectively incorporates into M. tuberculosis via the extracellular Ag85 enzymes
  • FITC moiety - allows for simple downstream fluorescent imaging
  • Shows no significant inhibition of M. tuberculosis growth - allows for imaging of healthy, viable bacteria

Tuberculosis is an infection that has plagued mankind for millennia, and remains a leading cause of death worldwide. A substantial obstacle to the development of new diagnostics, drugs and vaccines is the lack of tuberculosis-specific probes that can be used to rapidly assess infection and monitor response to treatment.

From the laboratory of Benjamin G. Davis, PhD, University of Oxford.

Catalog Number Product DataSheet Size AVAILABILITY Price Qty
EOX101
FITC-Trehalose
1mg Currently unavailable
Regular Price:$985.00
On Sale:
Specifications

Product Type: Small Molecule
Name: FITC-Trehalose
Alternative Name(s): 1-Deoxy-α-D-gluco-hept-2-ulopyranosyl-(2→1)-2-deoxy-2-(N'-(fluorescein-5-yl)-thioureido)-α-D-glucopyranoside
Chemical Formula: C34H36N2O15S
Molecular Weight: 744.72
Format: yellow solid
Purity: 95+% (NMR, HPLC)
Solubility: Soluble in MeOH and water
Spectral Information: [α]D = 72.2 (c = 0.18, MeOH); 1H NMR (500 MHz, D2O): δ 1.48 (3 H, s, C-1’), 3.26 (1 H, d, J3,4 = 9.8 Hz, H-3’), 3.49 (3 H, m, H4’, H-5’, H-4), 3.74 (6 H, m, H5, H-6’, H-6a, H-6b, H-7a’, H-7b’), 4.00 (1 H, at, J2,3 = J3,4 = 9.8 Hz, H-3), 4.41 (1 H, dd, J2,3 = 10.9 Hz, 1,2 = 2.9 Hz, H-2), 5.59 (1 H, d, J1,2 = 3.6 Hz, H-1), 6.84 (4 H, t, J = 0.9 Hz), 7.12 - 7.18 (3 H, m), 7.68 (1 H, dt, J = 7.7, J = 0.9 Hz), 8.00 (1 H, d, J = 1.0 Hz); 13C NMR (126 MHz, D2O) δ 22.79 (C-1’), 58.8 (C-2), 60.0 (C-7’), 60.56 (C-6), 68.9 (C-4), 70.4 (C-3, C-4’), 71.9 (C-6'), 72.8 (C-5), 72.8 (C-5’), 76.3 (C-3’), 89.6 (C-1), 101.5 (C-2’), 102.5, 113.9, 115.1, 117.1, 117.4, 128.3, 130.2, 131.4, 140.4, 156.2, 162.8, 163.1, 166.0, 170.2, 181.6; HRMS (m/z): [M-H]- calcd. for C34H35N2O15S-,743.1764; found: 743.1754; analysis (calcd., found for C34H36N2O15S): C(54.83, 54.77), H (4.87,4.80), N (3.76,3.69), S(4.31, 4.26).
Storage: -20C, protect from light
Shipped: Room temperature

Data

Labeling of individual bacilli in vitro and within infected macrophages

(a) H37Rv M. tuberculosis are labeled with FITC-trehalose and show signification accumulation of probe at the bacterial poles and membrane. (b) FITC-trehalose labeling of the RFP-expressing strain of H37Rv. (c) A merge of the FITC-trehalose and the RFP channels. (d) The mean fluorescence of poles and midsections of H37Rv M. tuberculosis, labeled with FITC-trehalose, are quantified and show statistically significant differential labeling. RFU, relative fluorescence units.

Adapted from: Backus, KM et al. Nat. Chem. Biol. 7, 228–235 (2011).

Provider
From the laboratory of Benjamin G. Davis, PhD, University of Oxford.
References
  1. Backus KM, Boshoff HI, Barry CS, Boutureira O, Patel MK, D'Hooge F, Lee SS, Via LE, Tahlan K, Barry CE 3rd, Davis BG. Uptake of unnatural trehalose analogs as a reporter for Mycobacterium tuberculosis. Nat Chem Biol. 2011 Apr;7(4):228-35.

If you publish research with this product, please let us know so we can cite your paper.