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87128

Sigma-Aldrich

Tetracycline

98.0-102.0% (HPLC)

Synonym(s):

Tetracycline HCL, Tetracycline Monohydrochloride

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About This Item

Empirical Formula (Hill Notation):
C22H24N2O8 · xH2O
CAS Number:
60-54-8
Molecular Weight:
444.43 (anhydrous basis)
Beilstein:
2230417
EC Number:
200-481-9
MDL number:
MFCD00151232
UNSPSC Code:
51284017
PubChem Substance ID:
57653229
NACRES:
NA.85
Pricing and availability is not currently available.

biological source

synthetic

Quality Level

200

Assay

98.0-102.0% (HPLC)

form

powder or crystals

color

faint yellow to dark yellow

mp

172-174 °C (dec.)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c4c(O)cccc4[C@@]3(C)O

InChI

1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1

InChI key

OFVLGDICTFRJMM-WESIUVDSSA-N

Gene Information

human ... CYP1A2(1544) , TERT(7015)

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General description

Chemical structure: tetracycline

Biochem/physiol Actions

Mode of Action: Tetracycline passively diffuses through proin channels in the cell membrane, binding to 30S ribosomes and inhibits protein synthesis by preventing access of aminoacyl tRNA to the acceptor site on the mRNA-ribosome complex. It also binds to the bacterial 50S ribosomal subunit, altering the membrane and causing intracellular components to leak from bacterial cells. The inhibitory effects can be reversed by washing, suggesting that it is the reversibly bound antibiotic, and not the irreversibly bound drug, that is responsible for antibacterial action.

Mode of Resistance: The effects are inactivated via a loss of cell wall permeability.

Antimicrobial spectrum: Includes a wide range of antimicrobial activity against gram-positive and gram-negative bacteria.

Packaging

25g, 100g

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Hygroscopic. Light sensitive. Keep in a dry place.

related product

Product No.
Description
Pricing

Signal Word

Warning

Hazard Statements

H302,H361fd,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Repr. 2

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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Certificates of Analysis (COA)

Lot/Batch Number
0000395313
0000384412
0000384412
0000395313
0000223580

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Zsófia Pénzváltó et al.
BMC cancer, 14, 837-837 (2014-11-20)
Primary systemic treatment for ovarian cancer is surgery, followed by platinum based chemotherapy. Platinum resistant cancers progress/recur in approximately 25% of cases within six months. We aimed to identify clinically useful biomarkers of platinum resistance. A database of ovarian cancer
Parveen Kumar et al.
PloS one, 10(5), e0123725-e0123725 (2015-05-15)
The myeloid translocation gene 16 (MTG16) co-repressor down regulates expression of multiple glycolytic genes, which are targets of the hypoxia-inducible factor 1 (HIF1) heterodimer transcription factor that is composed of oxygen-regulated labile HIF1α and stable HIF1β subunits. For this reason
Tadayuki Akagi et al.
The Journal of biological chemistry, 290(37), 22460-22473 (2015-08-01)
The pluripotency and self-renewal capacity of embryonic stem (ES) cells is regulated by several transcription factors. Here, we show that the ETS-related transcription factors Etv4 and Etv5 (Etv4/5) are specifically expressed in undifferentiated ES cells, and suppression of Oct3/4 results
Zhijie Li et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(13), 5004-5009 (2013-03-12)
Reported here is a piggyBac transposon-based expression system for the generation of doxycycline-inducible, stably transfected mammalian cell cultures for large-scale protein production. The system works with commonly used adherent and suspension-adapted mammalian cell lines and requires only a single transfection
Bizhan Romani et al.
The Journal of biological chemistry, 290(28), 17380-17389 (2015-06-03)
Human immunodeficiency virus type 1 Vpr is an accessory protein that induces G2/M cell cycle arrest. It is well documented that interaction of Vpr with the Cul4-DDB1[VprBP] E3 ubiquitin ligase is essential for the induction of G2/M arrest. In this
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Questions

1–4 of 4 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. How to prepare stock solutions for item 87128-25G, Tetracycline?

    1 answer

    1. Tetracycline is soluble in methanol, giving a clear solution at up to 30 mg/ml. It is practically insoluble in chloroform and ether, very slightly soluble in water, slightly soluble in alcohol, very soluble in dilute hydrochloric acid and alkali hydroxide solutions.

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  4. devo fare lo stock della tetraciclina. come e in cosa la devo diluire?

    1 answer

    1. This product is soluble in methanol or ethanol, giving a completely clear solution at up to 30 mg/ml. The stability of this material in solution is pH-dependent. Stock solutions prepared in ethanol are estimated to be stable for 1-3 months when aliquoted and stored at -20°C. Please see the link below to review the product datasheet for T3258, an identical tetracycline product of another brand. The information provided applies to both products.
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/406/734/t3258dat.pdf

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