+ Resolve Article
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter

+ Translate
+ Subscribe to Site Feed
GeoScience Most Shared ContentMost Shared Content

Synthesis and binding affinity of bidentate phenothiazines with two different photoactive groups

, : Synthesis and binding affinity of bidentate phenothiazines with two different photoactive groups. Bioconjugate Chemistry 6(5): 567-572

The development of targeted, bidentate photoaffinity reagents for mapping the interacting domains of calmodulin (CaM) with the enzymes that it regulates required the synthesis and evaluation of the binding affinity of various phenothiazines. These photoaffinity reagents would possess a photoactive 3-azidophenothiazine group for cross-linking the hydrophobic binding domain of CaM, a second photoactive benzophenone group that would be activated at a different wavelength than the 3-azidophenothiazine group, and a suitable radiolabel. Difficulties were encountered in identifying those structural features that would be compatible with the introduction of a benzophenone group, with the solubility of these benzophenone-substituted phenothiazines, and with the ability of these phenothiazines to inhibit the calmodulin-mediated activation of phosphodiesterase. Solutions to this problem involved the preparation of phenothiazines possessing a quaternary ammonium salt, a zwitterionic amino acid, or a carbohydrate moiety. The phenothiazines that possessed photoactive 3-azido and benzophenone groups and in which one of the piperazine nitrogens in the side chain was converted to a quaternary, N-methylammonium iodide inhibited the calmodulin-mediated activation of phosphodiesterase at a level comparable to that of chlorpromazine.


PMID: 8974455

DOI: 10.1021/bc00035a010

Other references

Gowda, R.M.; Khan, I.A.; Mehta, N.J.; Gowda, M.R.; Sacchi, T.J.; Vasavada, B.C., 2003: Cardiac tamponade in patients with human immunodeficiency virus disease. The characteristics of cardiac tamponade in patients with human immunodeficiency virus (HIV) disease were examined by evaluating the cases, case series, and related articles, including autopsy series, identified through a comprehensive literature...

Petrova, A.N., 1962: Reactions involved in the transfer of glycosidic groups in the synthesis of oligo- and polysaccharides Carbohydrates and carbohydrate metabolism. At present these reactions can be divided into 3 types: that involving phosphorylase-catalyzed phosphorylation of the sugars; that involving uridine diphosphate glucose; and that in which phosphorus compounds do not participate and which are catal...

Reininger, A.J.; Reininger, C.B.; Wurzinger, L.J., 1993: The influence of fluid dynamics upon adhesion of ADP-stimulated human platelets to endothelial cells. Thrombosis Research 71(3): 245-249

Zgonis, T.; Jolly, G.Peter.; Garbalosa, J.C.; Cindric, T.; Godhania, V.; York, S., 2005: The value of radiographic parameters in the surgical treatment of hallux rigidus. The purpose of this study was to determine if metatarsal protrusion or the length of the first and second rays were associated with the incidence of hallux rigidus. For this retrospective study, anteroposterior radiographs from 51 patients diagnos...

Pakaln, A., 2004: The three critical issues I've learned in 23 years in clinical engineering. Department directors are often caught between cost and service. Help them, not by increasing expenditures, but by building into the institution fabric definitions they can use. Make risk assessment something everyone can see and understand. Make c...

Minoia, P.; Sciorsci, R.L., 2002: Metabolic control through L calcium channel, PKC and opioid receptors modulation by an association of naloxone and calcium salts. beta-endorphins (beta-ends) are released from the anterior pituitary and from lymphocytes directly into inflamed tissue in response to stress and pain. At the site of inflammation and trauma, the link of beta- ends to opioid receptors hyperpolariz...

Buchanan P.K., 1988: A new species of heterobasidion polyporaceae from australia. Heterobasidion araucariae sp. nov., previously considered to be a form of H. annosum (Fr.) Bref., is distinguished by larger pores, basidiospores and conidia, by homothallic sexuality, by a restricted host range and distribution, and by a reduced...

Miyamoto, K.; Fujita, M.; Shenton, M.R.; Akashi, S.; Sugawara, C.; Sakai, A.; Horie, K.; Hasegawa, M.; Kawaide, H.; Mitsuhashi, W.; Nojiri, H.; Yamane, H.; Kurata, N.; Okada, K.; Toyomasu, T., 2016: Evolutionary trajectory of phytoalexin biosynthetic gene clusters in rice. Plants frequently possess operon-like gene clusters for specialized metabolism. Cultivated rice, Oryza sativa, produces antimicrobial diterpene phytoalexins represented by phytocassanes and momilactones, and the majority of their biosynthetic gene...

Curry, J.; Qin, J.; Carrick, R.; Strande, J.; Robinson, J.; Nestle, F.; Nickoloff, B.J., 2002: Innate immune-related reactions intrinsic to symptomless psoriatic skin. Journal of Investigative Dermatology 119(1): 275, July

Wictorin, L.; Hillerström, K.; Sörensen, S., 1969: Biological and psycho-social factors in patients with malformation of the jaws. I. A study of 95 patients prior to treatment. Scandinavian Journal of Plastic and Reconstructive Surgery 3(2): 138-143