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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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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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