Nitric Oxide Donors: Chemical Activities and Biological Applications

S-nitrosohemoglobin: a mechanism for its formation in conjunction with nitrite reduction by deoxyhemoglobin.

The tumor microenvironment maintains a sufficient immunosuppressive state owing to the existence of the immunosuppressive factors. The most prominent such factor is transforming growth factor β (TGF-β), which is mainly provided by platelets. Moreover, platelets have been shown to be the main accomplice in assisting tumor metastasis. Therefore, blocking tumor-associated platelets is endowed with functions of enhancing immunity and reducing metastasis. Herein, we designed a tumor microenvironment-responsive nitric oxide (NO) release nanoparticle, Ptx@AlbSNO, which was able to specifically and safely co-deliver the antiplatelet agent NO and the chemotherapeutic agent paclitaxel (Ptx) into tumor tissues and inhibit platelet-tumor cell interactions. We discovered that Ptx@AlbSNO could successfully block tumor-specific platelet functions, thereby suppressing the process of tumor epithelial-mesenchymal transition (EMT), preventing platelet adhesion around circulating tumor cells (CTCs) and reducing distant metastasis. In vivo studies demonstrate that the co-delivery of NO and Ptx can suppress primary tumor growth. With the ability to effectively inhibit activated platelets and TGF-β secretion in tumors, Ptx@AlbSNO can enhance intratumoral immune cell infiltration to reverse the immunosuppressive tumor microenvironment.

Blockade of Platelets Using Tumor-Specific NO-Releasing Nanoparticles Prevents Tumor Metastasis and Reverses Tumor Immunosuppression

Bearing the public image of a deadly "gas of rotten eggs," hydrogen sulfide (H2S) can be generated in many types of mammalian cells. Functionally, H 2S has been implicated in the induction of hippocampal long-term potentiation, brain development, and blood pressure regulation. By acting specifically on KATP channels, H 2S can hyperpolarize cell membranes, relax smooth muscle cells, or decrease neuronal excitability. The endogenous metabolism and physiological functions of H 2S position this gas well in the novel family of endogenous gaseous transmitters, termed "gasotransmitters." It is hypothesized that H 2S is the third endogenous signaling gasotransmitter, besides nitric oxide and carbon monoxide. This positioning of H 2S will open an exciting field-H2S physiology-encompassing realization of the interaction of H 2S and other gasotransmitters, sulfurating modification of proteins, and the functional role of H 2S in multiple systems. It may shed light on the pathogenesis of many diseases related to the abnormal metabolism of H 2S.-Wang, R. Two's company, three's a crowd: can H 2S be the third endogenous gaseous transmitter? FASEBJ. 16, 1792-1798 (2002)

/pdf/signal-transduction-and-the-gasotransmitters-59ddymix3k.pdf

Signal Transduction and the Gasotransmitters

High-level theoretical methods (UB3LYP/6-311++g(2df,p), RMP2/6-311++g(d,p), CBS-4M, CBS-Q, and G3) were used to study the structures and bond dissociation energies (BDE) of the X-Y-NO molecules. The data were used to evaluate the previous experimental and theoretical results. It was found that the syn conformation is favored by CH 3 -Y-NO, C 2 H 5 -Y-NO, and CH 3 O-Y-NO (Y = C, N, O, S), whereas the anti conformation is favored by CH 3 CO-Y-NO and Ph-Y-NO (Y = C, N, O). For Ph-S-NO, the syn conformation is preferred because of the long S-N bond. When X is an alkyl substituent, the Y-NO BDEs increase in the order X-S-NO (∼30 kcal/mol) < X-CH 2 -NO (∼40 kcal/mol) < X-O-NO (∼43 kcal/ mol) < X-NH-NO (48 kcal/mol). When X is an aromatic substituent, the Y-NO BDEs increase in the order X-O-NO (∼21 kcal/mol) < X-S-NO (26 kcal/mol) < X-CH 2 -NO (∼30 kcal/mol) < X-NH-NO (∼35 kcal/mol). The solvent effects of acetonitrile on the free energy change of C-NO and N-NO homolysis are significant, which are about 3-5 kcal/mol. The solvent effects of acetonitrile on the free energy change of O-NO and S-NO homolysis are relatively small, which are about 1-2 kcal/mol. Finally, we found that the remote substituent effects on C-NO, N-NO, O-NO, and S-NO BDEs have ρ + values of -0.4∼-0.9, 1.7-1.8, 3.2-3.9, and 1.2-1.7 kcal/mol. These values are significantly different from those on the C-H (0.4-0.6 kcal/mol), N-H (3.4-4.6 kcal/mol), O-H (4.1-5.7 kcal/mol), and S-H (2.0-3.8 kcal/ mol) BDEs. Therefore, the ground effects are important for the net substituent effects on BDEs.

Structures of the X-Y-NO molecules and homolytic dissociation energies of the Y-NO bonds (Y = C, N, O, S)

Nitric oxide (NO) possesses many physiological effects and S-nitrosothiols have been identified in a variety of tissues exhibiting many NO-like activities. This review focuses on the latest discoveries pertaining to the biological functions of S-nitrosothiols and the recent research progress in the chemical properties and biomedical applications of RSNOs.

New chemical and biological aspects of S-nitrosothiols.

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New chemical and biological aspects of S-nitrosothiols.