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K3394

Sigma-Aldrich

KH7

≥98% (HPLC)

Synonym(s):

(E)-2-(1H-Benzo[d]imidazol-2-ylthio)-N′-(5-bromo-2-hydroxybenzylidene)propanehydrazide

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About This Item

Empirical Formula (Hill Notation):
C17H15BrN4O2S
CAS Number:
330676-02-3
Molecular Weight:
419.30
MDL number:
MFCD01230899
UNSPSC Code:
41106305
PubChem Substance ID:
329817136
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

CC(Sc1nc2ccccc2[nH]1)C(=O)N\N=C\c3cc(Br)ccc3O

InChI

1S/C17H15BrN4O2S/c1-10(25-17-20-13-4-2-3-5-14(13)21-17)16(24)22-19-9-11-8-12(18)6-7-15(11)23/h2-10,23H,1H3,(H,20,21)(H,22,24)/b19-9+

InChI key

WILMXUAKQKGGCC-DJKKODMXSA-N

Application

KH7 has been used:
  • as a soluble adenyl cyclase (sAC) antagonist to study its effect on the signaling pathway mediated by the action of transient  receptor type 1 (TRPV1) in sperm cells.
  • as a selective sAC antagonist to study its effect on the signaling pathway of proton gated channels (HV1) induced action in sperm cells.
  • as a sAC inhibitor to study its effects on cAMP increase in monophosphorylated myosin light chain (pMLC).

Biochem/physiol Actions

KH7 is a selective inhibitor of soluble adenylyl cyclase. Soluble adenylyl cyclase (sAC) is an ubiquitously expressed, essential component of cAMP-signaling.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Suitability

KH7 is not active against sAC in the presence of detergents. When used in cellular experiments, KH7 exhibits non-specific membrane disruption effects at concentrations above 50 μM.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mandy Lo et al.
Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology, 191(1), 113-125 (2020-11-21)
We tested in six fish species [Pacific lamprey (Lampetra richardsoni), Pacific spiny dogfish (Squalus suckleyi), Asian swamp eel (Monopterus albus), white sturgeon (Acipenser transmontanus), zebrafish (Danio rerio), and starry flounder (Platichthys stellatus)] the hypothesis that elevated extracellular [HCO3-] protects spontaneous
Naveen Kumar et al.
Molecular and cellular biochemistry, 430(1-2), 115-125 (2017-02-18)
Despite the current progress in cancer research and therapy, breast cancer remains the leading cause of mortality among half a million women worldwide. Migration and invasion of cancer cells are associated with prevalent tumor metastasis as well as high mortality.
Nanshan Song et al.
Biochemical pharmacology, 150, 245-255 (2018-02-16)
β2-Aderenergic receptor (β2AR) agonist, Salmeterol exhibits anti-inflammatory activities. However, the inhibitory effects of Salmeterol on inflammasome activation are elusive and the underlying mechanisms need to be explored. In this study, we established inflammatory model in primary bone marrow-derived macrophages (BMDM)
Frances Evans et al.
Journal of cellular physiology, 235(3), 2947-2962 (2019-09-20)
In previous work, we reported that plasma membrane potential depolarization (PMPD) provokes cortical F-actin remodeling in bovine corneal endothelial (BCE) cells in culture, which eventually leads to the appearance of intercellular gaps. In kidney epithelial cells it has been shown
Carresse L Gerald et al.
Alcoholism, clinical and experimental research, 40(2), 273-283 (2016-02-05)
Farm workers in rural areas consume more alcohol than those who reside in urban areas. Occupational exposures such as agricultural work can pose hazards on the respiratory system. It is established that hog barn dust induces inflammation in the airway
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