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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:
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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This Item
D5207PHR114533429
Doxycycline hyclate

Sigma-Aldrich

D9891

Doxycycline hyclate

Doxycycline hyclate Suitable for Cell Culture

Sigma-Aldrich

D5207

Doxycycline hyclate

Doxycycline hyclate Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1145

Doxycycline hyclate

Doxycycline hyclate VETRANAL®, analytical standard

Supelco

33429

Doxycycline hyclate

assay

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

assay

-

assay

-

assay

-

form

powder

form

powder

form

-

form

-

color

yellow to yellow-green

color

-

color

-

color

-

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycoplasma, parasites

antibiotic activity spectrum

-

antibiotic activity spectrum

-

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycoplasma, parasites

mode of action

protein synthesis | interferes

mode of action

-

mode of action

-

mode of action

protein synthesis | interferes

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.

Pictograms

Exclamation markHealth hazard

Signal Word

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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