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D9891

Sigma-Aldrich

Doxycycline hyclate

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Synonym(s):
6-Desoxy-5-hydroxytetracycline hydrochloride hemihydrate hemiethanolate, Doxycycline hydrochloride hemiethanolate hemihydrate
Empirical Formula (Hill Notation):
C22H24N2O8 · HCl · 0.5H2O · 0.5C2H6O
CAS Number:
Molecular Weight:
512.94
Beilstein/REAXYS Number:
5702728
MDL number:
PubChem Substance ID:
NACRES:
NA.85

biological source

synthetic

Quality Level

assay

≥93.5% (HPLC)
95.0-102.0% anhydrous basis (ethanol free based)

form

powder

storage condition

(Tightly closed. Dry. )

color

yellow to yellow-green

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycoplasma
parasites

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

Cl[H].Cl[H].[H]O[H].CCO.C[C@@H]1C2[C@H](O)C3[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C2C(=O)c4c(O)cccc14.C[C@@H]5C6[C@H](O)C7[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]7(O)C(O)=C6C(=O)c8c(O)cccc58

InChI

1S/2C22H24N2O8.C2H6O.2ClH.H2O/c2*1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29;1-2-3;;;/h2*4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);3H,2H2,1H3;2*1H;1H2/t2*7-,10?,14?,15-,17-,22-;;;;/m00..../s1

InChI key

HALQELOKLVRWRI-ZVACAFRPSA-N

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General description

Doxycycline Hyclate, a synthetic tetracycline antibiotic, demonstrates broad-spectrum antimicrobial activity against various bacteria by binding to the 30S and potentially the 50S ribosomal subunits. This binding disrupts the aminoacyl-tRNA binding to the mRNA-ribosome complex, effectively inhibiting bacterial protein synthesis, thereby halting growth and replication.

Beyond its antimicrobial effects, Doxycycline Hyclate serves as an inhibitor of matrix metalloproteinases (MMPs), enzymes crucial for collagen breakdown in connective tissues. Studies on corneal erosion and rheumatoid arthritis showcase its significant reduction in MMP-9 and MMP-8 levels, respectively. This MMP-inhibiting property helps preserve collagen integrity, preventing excessive tissue degradation and supporting tissue repair.

In cell biology, Doxycycline Hyclate impacts smooth muscle cells, enhancing adhesion and influencing the reorganization of fibrillar collagen matrices. Its influence on apicoplast gene expression in Plasmodium falciparum, the malaria-causing parasite, adds a dimension of significance in infectious disease research. Additionally, the inhibition of tissue formation in rat studies contributes to its relevance in understanding tissue development.

Moreover, Doxycycline Hyclate holds potential in metabolomics research, considering its multi-faceted effects on various cellular processes. In the broader context of biochemical research, its versatile actions make it a valuable tool for investigating molecular mechanisms and signaling pathways.

Application

Doxycycline hyclate has been used for the induction of glioma cells and human embryonic kidney 293T cells (HEK293T).
Doxycycline hyclate is a synthetic oxytetracycline derivative. It has been used to eliminate Borrelia burgdorferi and Anaplasma phagocytophilum in rodent reservoirs and to eliminate Ixodes scapularis ticks. It is a broad spectrum inhibitor used to inhibit matrix metalloproteinases (MMP), such as type 1 collagenase in studies on wound healing and tissue remodeling.

Biochem/physiol Actions

Mode of Action: Doxycycline hyclate inhibits the inflammatory response to the Lyme Disease Spirochete Borrelia burgdorferi.

Activity Spectrum: Effective against a broad spectrum inhibitor of matrix metalloproteinases in vivo.

Features and Benefits

  • High-quality antibiotic suitable for multiple research applications
  • Ideal for Cell Biology, Metabolomics, and Biochemical research.

Other Notes

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

pictograms

Exclamation markHealth hazard

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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