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\def\RunningAuthor{Mohammed Sabah kadhi al zwaed et al.}
\firstPage{4402}
\articleType{Original Article}
\receivedDate{18 Mar 2020}
\acceptedDate{23 Apr 2020}
\revisedDate{12 Apr 2020}
\journalVolume{2020, 11}
\journalIssue{3}
\journalDoi{ijrps.v11i3.2659}
\copyrightYear{2020}
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\title{Design, synthesis, and biological evaluation of some new charge transfer complexes as a combination model}
\author{Mohammed~Sabah~kadhi~al~zwaed\textsuperscript{*},  
            Raheem~Jameel~Mohaisen, 
            Khawla~Salman~Abd~al~rasool~\\[5pt]{Department of Pharmaceutical Chemistry, Pharmacy College, Basrah University, Iraq }}

\begin{abstract}
The present work includes design and synthesis a new model of charge transfer complexes from simvastatine which is antihyperlipidemic drug as acceptor with angiotensin receptor blockers(candesartan, losartan, valsartan, telmisartan, irbesartan) as donors and characterization the models by UV, FT-IR, HNMR spectrophotometry, it shows change in spectral peaks which refer to formation of charge transfer complexes. And study the effect of interaction on availability of drugs with the time, different PH and different concentrations. Which shows the variability in availability of drugs in combination (charge transfer complexes) due to PH, concentration, and time changing, this variability in availability mostly effect on simvastatine which mean decrease or absence the availability of simvastatine and increase the availability of angiotensin receptor blockers (mostly not absolutly). Beside this we study the evaluation of biological activity of combinations and compare with the biological activity of simvastatine alone on the lipid profile of rabbits , by induced hypercholesterolemia in rabbits for two weeks (except the positive control group) and gave the drugs for four weeks and measuring the lipid profile changing in order to improve the change in the efficacy of simvastaine alone and simvastatine in combinations and this variability due to donor-acceptor interaction (charge transfer interaction) 
\end{abstract}\def\keywordstitle{Keywords}

\begin{keywords}charge transfer complex,\newline simvastatine,\newline angiotensin receptor blockers,\newline UV spectroscopy,\newline lipid profile
\end{keywords}
\twocolumn[ \maketitle {\printKwdAbsBox}]
\makeatletter{\raggedright\textsuperscript{*}Corresponding Author\par Name:\ Mohammed~Sabah~kadhi~al~zwaed~\\ Phone:\ 009647812246698~\\  Email:\ mohammedsabah18@gmail.com
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\section{Introduction}
The term charge transfer complex (CTC) was first used by Mulliken. He describes a new type of adduct to describe the behavior of certain molecular groups, which do not adhere to the traditional patterns of ionic, covalent, and hydrogen bonding components. While these adducts generally retain some of the component properties, some changes are obvious. For example, its solubility, its diamagnetic and paramagnetic susceptibility. Charging interactions within a molecular complex consisting of an electron donor D and an electron acceptor A include resonance with charging transfer from D to A \unskip~\citep{831330:19822130}.

It is important phenomenon in the process of biochemical and bioelectrochemical energy. The term charge transfer gives kind of complex resulting from donor and acceptor interactions with the formation of weak bonds and widely discussed by Foster. In molecular interactions between electron donors and receivers are correlated with formation of strongly colored charge Transfer complexes (CTCs) which absorb radiation in  visible region. Important processes in biological systems are molecular complexation and structural recognition. Drug action, catalysis of enzymes and movement of ions via lipophilic membranes all require complexation.


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\caption{\boldmath {Chemical structures of (a) simvastatine (b) candesartn (c)valsartan (d) irbesartan (e) telmisartan (f) losartan}}
\label{f-5981eb2e7d7f}
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\egroup

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\caption{\boldmath {Synthesis of complexes}}
\label{f-cf56d3a53ac8}
\end{figure*}
\egroup
The key directors of the specificity, rate regulation and reversibility are the characteristics in many biochemical reactions \unskip~\citep{831330:19822131}. Many drugs are easily identifiable by spectrophotometry on the basis of complex color transfer charges formed between electron acceptors and electron donors. Methods of analyzing many drugs are recorded mainly by direct UV spectrophotometry, fluorometry, polarography, colorimetry and HPLC \unskip~\citep{831330:19822136}. The charging-transfer (CT) reaction between electron-donating and electron-accepting molecules is of considerable importance in various fields of chemistry due to their existence in biological systems, widespread applications as organic electrical conductors, the study of drug-receptor interaction mechanisms, the storage of solar energy and the study of thermodynamics and pharmacodynamics In medical molecules. CT reactions are generally associated with the development of strongly colored CT complexes, which normally absorb radiation; however, a new light-absorbing band exists at much longer wavelengths than in the CT complex component spectrum. The rapid creation of these complexes results in their comprehensive usefulness in the production of spectrophotometric methods for analyzing many organic and/or pharmaceutical molecules\unskip~\citep{831330:19822135}, spectrophotometric assays offer significant economic advantages over gas chromatography and high-performance liquid chromatographic techniques \unskip~\citep{831330:19822140}. Obtain quantitative estimates of drugs in pure form or in cheaper, faster, quicker and more precise pharmaceutical preparations. Plays important roles in many biological fields such as DNA-binding, antibacterial, antifungal and insecticidal Some CT drug complexes exhibit antimicrobial activity against gram-positive and gram-negative bacteria and fungi\unskip~\citep{831330:19822338}


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\caption{\boldmath {Asorbance of complex 1 spectra versus time}}
\label{f-ccc1126761a9}
\end{figure}
\egroup

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\caption{\boldmath {absorbance of complex 2 spectra versus time}}
\label{f-1bb44ccade6b}
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\egroup
Chemistry of CT or H-bonding interactions between either drugs or biological compounds and small organic or inorganic solid-state molecular acceptors In recent years, the solution has attracted growing attention, considerable interest and increasing significance and has become a common research area. There are many examples for charge transfer complex such as cloxacillin sodium with riboflavin\unskip~\citep{831330:19822137}, vitamin K with quinine and quinidine \unskip~\citep{831330:19822128}, losartan with iodine\unskip~\citep{831330:19822133}, losartan with antidiabetic \unskip~\citep{831330:19822125}, determination of dapson by charge transfer complex formation with chloranil\unskip~\citep{831330:19822141}, complex formation with metals \unskip~\citep{831330:19822138}\textbf{.}

\textbf{Objective of the work}


  
  \begin{enumerate}
  \item \relax Synthesis a complex model from combination of two drugs by a charge transfer complex formation.
  \item \relax Study the effect of solvents on complex.
  \item \relax Study the effect of time on complex.
  \item \relax Study the effect of temperature and PH on complex.
  \item \relax Evaluation the bioavailability of each drug in complex.
  \end{enumerate}
  
\bgroup
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\centering \makeatletter\IfFileExists{images/3e2ea2b1-2d19-4b4c-8644-7358115c47ee-upicture5.png}{\includegraphics{images/3e2ea2b1-2d19-4b4c-8644-7358115c47ee-upicture5.png}}{}
\makeatother 
\caption{\boldmath {Absorbance of complex 3 spectra versus time}}
\label{f-0cab29522508}
\end{figure}
\egroup

\bgroup
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\centering \makeatletter\IfFileExists{images/c05a5543-0dda-4391-9381-3f2217a105bc-upicture6.png}{\includegraphics{images/c05a5543-0dda-4391-9381-3f2217a105bc-upicture6.png}}{}
\makeatother 
\caption{\boldmath {Absorbance of complex 4 spectra versus time}}
\label{f-6454c5feeb98}
\end{figure}
\egroup

\bgroup
\fixFloatSize{images/3bed7a98-49c3-4a28-9062-4c7bc9fefbdf-upicture7.png}
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\centering \makeatletter\IfFileExists{images/3bed7a98-49c3-4a28-9062-4c7bc9fefbdf-upicture7.png}{\includegraphics{images/3bed7a98-49c3-4a28-9062-4c7bc9fefbdf-upicture7.png}}{}
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\caption{\boldmath {Absorbance of complex 5 spectra versus time}}
\label{f-a7ed4c01cd32}
\end{figure}
\egroup

\bgroup
\fixFloatSize{images/9277067b-fd3b-4398-a960-6f89dcd529e0-upicture8.png}
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\centering \makeatletter\IfFileExists{images/9277067b-fd3b-4398-a960-6f89dcd529e0-upicture8.png}{\includegraphics{images/9277067b-fd3b-4398-a960-6f89dcd529e0-upicture8.png}}{}
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\caption{\boldmath {Absorbance of complex 1 spectra versus conc}}
\label{f-0ee1db87ceed}
\end{figure}
\egroup

\bgroup
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\centering \makeatletter\IfFileExists{images/fbf68730-4a8a-415e-96a3-c5ff056be194-upicture9.png}{\includegraphics{images/fbf68730-4a8a-415e-96a3-c5ff056be194-upicture9.png}}{}
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\caption{\boldmath {Absorbance of complex 2 spectra versus conc}}
\label{f-1b356519a0c4}
\end{figure}
\egroup

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\caption{\boldmath {Absorbance of complex 3 spectra versus conc}}
\label{f-5797ad455934}
\end{figure}
\egroup

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\caption{\boldmath {Absorbance of complex 4 spectra versus conc}}
\label{f-c0322658e763}
\end{figure}
\egroup

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\fixFloatSize{images/be85b6a4-08b6-4f26-87fb-e7c1bde5e3b0-upicture12.png}
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\centering \makeatletter\IfFileExists{images/be85b6a4-08b6-4f26-87fb-e7c1bde5e3b0-upicture12.png}{\includegraphics{images/be85b6a4-08b6-4f26-87fb-e7c1bde5e3b0-upicture12.png}}{}
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\caption{\boldmath {Absorbance of complex 5 spectra versus conc}}
\label{f-202a876743f5}
\end{figure}
\egroup

\bgroup
\fixFloatSize{images/0a6fb1c1-d33b-4d7a-9b2d-e203e60de838-upicture13.png}
\begin{figure}[!htbp]
\centering \makeatletter\IfFileExists{images/0a6fb1c1-d33b-4d7a-9b2d-e203e60de838-upicture13.png}{\includegraphics{images/0a6fb1c1-d33b-4d7a-9b2d-e203e60de838-upicture13.png}}{}
\makeatother 
\caption{\boldmath {Effect of PH on simvastatine in complex 1}}
\label{f-488ba96324ef}
\end{figure}
\egroup

\bgroup
\fixFloatSize{images/5c83197c-7605-40f1-a0ac-ced4ca5745ee-upicture14.png}
\begin{figure}[!htbp]
\centering \makeatletter\IfFileExists{images/5c83197c-7605-40f1-a0ac-ced4ca5745ee-upicture14.png}{\includegraphics{images/5c83197c-7605-40f1-a0ac-ced4ca5745ee-upicture14.png}}{}
\makeatother 
\caption{\boldmath {Effect of PH on simvastatine in complex 2}}
\label{f-4844dc909f30}
\end{figure}
\egroup

\bgroup
\fixFloatSize{images/4e04010e-9b34-47e1-8f4a-3b2f269314e7-upicture15.png}
\begin{figure}[!htbp]
\centering \makeatletter\IfFileExists{images/4e04010e-9b34-47e1-8f4a-3b2f269314e7-upicture15.png}{\includegraphics{images/4e04010e-9b34-47e1-8f4a-3b2f269314e7-upicture15.png}}{}
\makeatother 
\caption{\boldmath {Effect of PH on simvastatine in complex 3}}
\label{f-630f628d6867}
\end{figure}
\egroup

\bgroup
\fixFloatSize{images/b6f795f0-a49a-42fc-b1d4-971cbbd82978-upicture16.png}
\begin{figure}[!htbp]
\centering \makeatletter\IfFileExists{images/b6f795f0-a49a-42fc-b1d4-971cbbd82978-upicture16.png}{\includegraphics{images/b6f795f0-a49a-42fc-b1d4-971cbbd82978-upicture16.png}}{}
\makeatother 
\caption{\boldmath {Effectof PH on simvastatine in complex 5}}
\label{f-8908cca7cec4}
\end{figure}
\egroup

\bgroup
\fixFloatSize{images/0fd8367c-bc5f-4801-b16b-94d704314690-upicture17.png}
\begin{figure}[!htbp]
\centering \makeatletter\IfFileExists{images/0fd8367c-bc5f-4801-b16b-94d704314690-upicture17.png}{\includegraphics{images/0fd8367c-bc5f-4801-b16b-94d704314690-upicture17.png}}{}
\makeatother 
\caption{\boldmath {Effectof PH on candesartan in complex 1}}
\label{f-0e0520ddadb8}
\end{figure}
\egroup

\bgroup
\fixFloatSize{images/7e929f9b-6108-4a63-b859-4eb6dc301b5f-upicture18.png}
\begin{figure}[!htbp]
\centering \makeatletter\IfFileExists{images/7e929f9b-6108-4a63-b859-4eb6dc301b5f-upicture18.png}{\includegraphics{images/7e929f9b-6108-4a63-b859-4eb6dc301b5f-upicture18.png}}{}
\makeatother 
\caption{\boldmath {Effect of PH on valsartan in complex 2}}
\label{f-b66d41fd6422}
\end{figure}
\egroup

\bgroup
\fixFloatSize{images/10e17b7a-f3b5-434c-bed5-3e7973cd9be6-upicture19.png}
\begin{figure}[!htbp]
\centering \makeatletter\IfFileExists{images/10e17b7a-f3b5-434c-bed5-3e7973cd9be6-upicture19.png}{\includegraphics{images/10e17b7a-f3b5-434c-bed5-3e7973cd9be6-upicture19.png}}{}
\makeatother 
\caption{\boldmath {Effect of PH on irbesartan in complex 3}}
\label{f-95d7f9d356e5}
\end{figure}
\egroup

\bgroup
\fixFloatSize{images/c412fc6c-ca85-418c-86a6-280ce0469244-upicture20.png}
\begin{figure}[!htbp]
\centering \makeatletter\IfFileExists{images/c412fc6c-ca85-418c-86a6-280ce0469244-upicture20.png}{\includegraphics{images/c412fc6c-ca85-418c-86a6-280ce0469244-upicture20.png}}{}
\makeatother 
\caption{\boldmath {Effect of PH on telmisartan in complex 4}}
\label{f-3b59157f717a}
\end{figure}
\egroup

\bgroup
\fixFloatSize{images/430d2ad8-a50f-4ce0-b7ce-91e347936c73-upicture21.png}
\begin{figure}[!htbp]
\centering \makeatletter\IfFileExists{images/430d2ad8-a50f-4ce0-b7ce-91e347936c73-upicture21.png}{\includegraphics{images/430d2ad8-a50f-4ce0-b7ce-91e347936c73-upicture21.png}}{}
\makeatother 
\caption{\boldmath {Effect of PH on losartan in complex 5}}
\label{f-452d2bae9ea8}
\end{figure}
\egroup

    
\section{Materials and Methods}
\textbf{Chemicals}


  
  \begin{enumerate}
  \item \relax Candesartan, sigma {\textendash}aldrich Germany.
  \item \relax valsartan, sigma {\textendash}aldrich Germany.
  \item \relax irbesartan, sigma {\textendash}aldrich Germany.
  \item \relax telmisartan, sigma {\textendash}aldrich Germany.
  \item \relax Losartan potassium, sigma {\textendash}aldrich Germany.
  \item \relax simvastatine, sigma {\textendash}aldrich Germany.
  \item \relax Acetone,
  \item \relax Sodium hydroxide, Merck Germany.
  \item \relax Ethanol,
  \item \relax Methanol, sigma {\textendash}aldrich Germany.
  \item \relax Ethyl acetate,
  \item \relax Dmso India
  \item \relax Dichloromethane, Ajax chemical Australia
  \item \relax Chloroform India
  \item \relax Hexane, Merck Germany.
  \item \relax Hydrochloric acid, Merck Germany.
  \item \relax Sodium carbonate.
  \end{enumerate}
  \textbf{Synthesis}

Dissolve (1mmole) (0,41857 gm) of Simvastatin (acceptor) in 40ml of methanol. Dissolve (1mmole) of sartans (donors): 0,44045 gm candesartan/0,43552 gm valsartan/0,4285 gm irbesartan/0,5146 gm telmisartan/0,42291 gm losartan (as seen in Figure~\ref{f-5981eb2e7d7f}) each of these sartans in 40 ml of methanol separately. The solutions have been mixed (each donor has an acceptor) with regular stirring and reflux in a round bottom flask. TLC had monitored and tracked the progress of the reaction. Solvent was evaporated after the reaction was completed. Re-crystallization of the compounds in methanol purified the products: chloroform (8:2) \unskip~\citep{831330:19822127}. The products of reaction seen in Table~\ref{tw-87990396f8a6}, Figures~\ref{f-cf56d3a53ac8} and~\ref{f-430afd705c9b}.
    
\section{Results and Discussion}
\textbf{Ultraviolet spectra}

Use Cecil 7200 spectrophotometer at the department of pharmaceutical /collage of pharmacy /university of Basrah. from UV analysis lambda max of drugs 230.5, 237.5, 246 nm for simvastatin. and for sartan from (1 to 5), and 251, 252, 246, 293 and 246.5 nm respectively. For candesartan, valsartan, irbesartan, telmisartan and losartan.

\textbf{FT.IR spectrum}

Infrared spectra of the synthesized compounds were recorded by FT-IR. 8400S Shimadzu. spectrophotometer (Japan) using KBrdisk in range 4000-400 cm\ensuremath{^{-1}} at Department of pharmaceutical chemistry /collage of pharmacy /university of Basra. 


\bgroup
\fixFloatSize{images/e8f06241-1a4a-476a-868e-5a4714432b58-upicture22.png}
\begin{figure*}[!htbp]
\centering \makeatletter\IfFileExists{images/e8f06241-1a4a-476a-868e-5a4714432b58-upicture22.png}{\includegraphics{images/e8f06241-1a4a-476a-868e-5a4714432b58-upicture22.png}}{}
\makeatother 
\caption{\boldmath {(a)complex1 (b) complex 2 (c) complex 3 (d) complex 4 (e) complex 5}}
\label{f-430afd705c9b}
\end{figure*}
\egroup

\begin{table*}[!htbp]
\caption{\boldmath {Features of Complexes} }
\label{tw-87990396f8a6}
\def\arraystretch{1.1}
\ignorespaces 
\centering 
\begin{tabulary}{\linewidth}{p{\dimexpr.16\linewidth-2\tabcolsep}p{\dimexpr.16\linewidth-2\tabcolsep}p{\dimexpr.1718\linewidth-2\tabcolsep}p{\dimexpr.18340000000000003\linewidth-2\tabcolsep}p{\dimexpr.1659\linewidth-2\tabcolsep}p{\dimexpr.1589\linewidth-2\tabcolsep}}
\tbltoprule \rowcolor{kwdboxcolor}Compound & Combination & Molecular formula  & Molecular \mbox{}\protect\newline weight & Colour & Melting point \ensuremath{^\circ}C. \\
\tblmidrule 
Complex1 &
  candesartan &
  C49H58N6O8 &
   859.02 &
  White powder &
  174-176\\
Complex2  &
  valsartan &
  C49H67N5O8 &
  854.09 &
  White powder &
  100-102\\
Complex3 &
  irbesartan &
  C50H66N6O6 &
   847.07 &
  White powder &
  157-159\\
Complex4 &
  telmisartan &
  C58H68N4O7 &
   933.17 &
  White powder &
  150-152\\
Complex5 &
  losartan &
  C47H61N6O6 &
  841.47 &
  White powder &
  160-167\\
\tblbottomrule 
\end{tabulary}\par 
\end{table*}

\begin{table*}[!htbp]
\caption{\boldmath {Lipid Profile Results } }
\label{tw-3a3776a60992}
\def\arraystretch{1.1}
\ignorespaces 
\centering 
\begin{tabulary}{\linewidth}{LLLLLLLLLLLLL}
\tbltoprule \rowcolor{kwdboxcolor}Group & Cholestrol 0 & Cholestrol 2 & Cholestrol 4 & TG 0 & TG 2 & TG 4 & LDL 0 & LDL 2 & LDL 4 & HDL 0 & HDL 2 & HDL 4\\
\tblmidrule 
s &
  58 &
  106 &
  30 &
  80 &
  110 &
  70 &
  31 &
  46 &
  39 &
  29 &
  25 &
  25\\
s &
  69 &
  110 &
  19 &
  140 &
  167 &
  115 &
  32 &
  40 &
  40 &
  27 &
  30 &
  20\\
s &
  61 &
  98 &
  15 &
  90 &
  146 &
  80 &
  40 &
  42 &
  35 &
  29 &
  30 &
  20\\
c+s &
  82 &
  95 &
  36 &
  92 &
  105 &
  95 &
  37 &
  42 &
  38 &
  29 &
  31 &
  29\\
c+s &
  65 &
  67 &
  30 &
  105 &
  100 &
  90 &
  34 &
  35 &
  29 &
  26 &
  24 &
  22\\
c+s &
  77 &
  100 &
  52 &
  80 &
  110 &
  75 &
  31 &
  35 &
  30 &
  23 &
  22 &
  24\\
v+s &
  80 &
  90 &
  25 &
  62 &
  90 &
  80 &
  34 &
  39 &
  40 &
  25 &
  20 &
  19\\
v+s &
  72 &
  85 &
  40 &
  94 &
  98 &
  80 &
  38 &
  43 &
  33 &
  22 &
  25 &
  23\\
v+s &
  35 &
  76 &
  32 &
  66 &
  114 &
  86 &
  30 &
  42 &
  39 &
  25 &
  21 &
  25\\
l+s &
  36 &
  60 &
  45 &
  60 &
  100 &
  100 &
  31 &
  41 &
  39 &
  26 &
  25 &
  19\\
l+s &
  47 &
  85 &
  30 &
  75 &
  118 &
  95 &
  39 &
  43 &
  40 &
  30 &
  31 &
  23\\
l+s &
  52 &
  112 &
  70 &
  56 &
  122 &
  105 &
  30 &
  31 &
  33 &
  25 &
  23 &
  24\\
i+s &
  43 &
  80 &
  32 &
  50 &
  95 &
  80 &
  36 &
  42 &
  37 &
  29 &
  26 &
  20\\
i+s &
  36 &
  60 &
  30 &
  140 &
  162 &
  140 &
  32 &
  34 &
  36 &
  26 &
  26 &
  22\\
i+s &
  22 &
  63 &
  39 &
  75 &
  120 &
  95 &
  29 &
  31 &
  32 &
  28 &
  24 &
  23\\
t+s &
  47 &
  78 &
  40 &
  95 &
  109 &
  109 &
  28 &
  36 &
  42 &
  29 &
  25 &
  27\\
t+s &
  43 &
  69 &
  20 &
  80 &
  97 &
  97 &
  27 &
  35 &
  36 &
  28 &
  24 &
  20\\
t+s &
  80 &
  105 &
  70 &
  90 &
  110 &
  90 &
  25 &
  30 &
  25 &
  27 &
  26 &
  25\\
c+ &
  34 &
  35 &
  38 &
  73 &
  85 &
  110 &
  42 &
  40 &
  40 &
  27 &
  30 &
  32\\
c+ &
  29 &
  25 &
  15 &
  65 &
  68 &
  70 &
  37 &
  34 &
  37 &
  25 &
  22 &
  25\\
c+ &
  18 &
  25 &
  15 &
  60 &
  70 &
  90 &
  32 &
  33 &
  37 &
  23 &
  25 &
  22\\
c- &
  32 &
  90 &
  75 &
  115 &
  123 &
  120 &
  31 &
  40 &
  43 &
  23 &
  30 &
  35\\
c- &
  32 &
  27 &
  80 &
  80 &
  110 &
  170 &
  36 &
  49 &
  65 &
  26 &
  23 &
  25\\
c- &
  100 &
  104 &
  115 &
  125 &
  155 &
  155 &
  41 &
  45 &
  50 &
  32 &
  27 &
  25\\
\tblbottomrule 
\end{tabulary}\par 
\end{table*}
\textbf{Complex 1 }

Show strong broad at 3475 cm\ensuremath{^{-1}} refer to O-H, at 3444 cm\ensuremath{^{-1}} attributed N-H, strong band at 3059 refer to C-H aromatic, C-H aliphatic at 2966,2931,2873 cm\ensuremath{^{-1}}, strong band at 1716 cm\ensuremath{^{-1}} refer to C=O, and C=N, C=C, C-O, C-N at 1624, 1473, 1261, 1056 cm\ensuremath{^{-1}} respectively.

\textbf{Complex 2 }

Show strong broad at 3444 cm\ensuremath{^{-1}} refer to O-H, at 3066 cm\ensuremath{^{-1}} attributed N-H, C-H aromatic overlap by O-H, C-H aliphatic at 2970, 2935, 2877 cm\ensuremath{^{-1}}, strong band at 1705 cm\ensuremath{^{-1}} refer to C=O, and C=N, C=C, C-O, C-N at 1612, 1480, 1242, 1037 cm\ensuremath{^{-1}} respectively.

\textbf{Complex 3 }

Show strong broad at 3383 cm\ensuremath{^{-1}} refer to O-H, C-H aromatic overlap by O-H, C-H aliphatic at 2931, 2877 cm\ensuremath{^{-1}}, strong band at 1728 cm\ensuremath{^{-1}} refer to C=O, and C=N, C=C, C-O, C-N at 1620, 1462, 1253, 1060 cm\ensuremath{^{-1}} respectively.

\textbf{Complex 4 }

Show strong broad at 3383cm\ensuremath{^{-1}} refer to O-H, C-H aromatic overlap by O-H, C-H aliphatic at 2928cm\ensuremath{^{-1}}, strong band at 1712 cm\ensuremath{^{-1}} refer to C=O, and C=N, C=C, C-O, C-N at 1658, 1454, 1084, 1045cm\ensuremath{^{-1}} respectively.

\textbf{Complex5 }

Show strong broad at 3378 cm\ensuremath{^{-1}} refer to O-H, C-H aromatic overlap by O-H, C-H aliphatic at 2928, 2877 cm\ensuremath{^{-1}}, strong band at 1716 cm\ensuremath{^{-1}} refer to C=O, and C=C, C-O, C-N at 1462, 1257, 1026cm\ensuremath{^{-1}} respectively.

As a result of all complexes peaks ; there is a broad OH band, shift C=O band of carbonyl to the right, decrease the intensity of C=C, C-O, and C-N bands\textbf{. }

\ensuremath{^{\textbf{1}}} \textbf{H-NMR Spectra}

The compounds were studied for \ensuremath{^{1}}H-NMR Spectra at the analytical Laboratory of Tehran University, College of Sciences, Chemistry Department, using 500MHz NMR (INOVA Switzerland). DMSO-d\ensuremath{_{6}} was used as a solvent and TMS as an internal standard. As a consequence of all HNMR complex peaks Most peaks are moved to the right (shielding).

\textbf{Study the effect of solvents on charge transfer complexes}

Dissolve 1* 10-5 molar concentrations of each complex (1 to 5) in 10 ml of each solvent (acetone, dichloromethane, chloroform, methanol, ethanol, dmso) and watch the effect by UV spectroscopy. The Study shows that the use of ethanol and methanol as solvents is ideally suited to stability of complexes.

\textbf{Study the effect of time on charge transfer complexes}

Dissolve 1* 10\ensuremath{^{-5}} molar concentration of each complex (1 to 5) and determine the effect by UV-spectroscopy within 5 to 30 min, with 5 min as interval. 

As seen in Figures~\ref{f-ccc1126761a9}, \ref{f-1bb44ccade6b}, \ref{f-0cab29522508}, \ref{f-6454c5feeb98} and~\ref{f-a7ed4c01cd32} and this is mostly referred to raise the concentration of complexes after 5 min of addition or mixing.

\textbf{Study the effect of concentration on charge transfer complexes}

Various concentrations of complexes versus absorbance. As in Figures~\ref{f-0ee1db87ceed}, \ref{f-1b356519a0c4}, \ref{f-5797ad455934}, \ref{f-c0322658e763} and~\ref{f-202a876743f5}  and this to improve the concentration is located with the linearity which is 1* 10\ensuremath{^{-5}} according to beer\ensuremath{^{'}}s law \unskip~\citep{831330:19822126}.

\textbf{Study of interaction }

Using Caleva dissolution tester at Department of pharmaceutical /collage of pharmacy /university of Basrah. simvastatin interaction with sartan was performed in vitro in the same set of dissolution media. Simvastatin was added to the dissolution medium already established at 37 \ensuremath{^\circ} C at zero time in each set of experiments, while sartan was added after 15 minutes of time interval. aliquots were removed and assayed. Absorbance of each drug versus time In each experiment set was determined\unskip~\citep{831330:19822134}. As in Figures~\ref{f-488ba96324ef}, \ref{f-4844dc909f30}, \ref{f-630f628d6867}, \ref{f-8908cca7cec4}, \ref{f-0e0520ddadb8}, \ref{f-b66d41fd6422}, \ref{f-95d7f9d356e5}, \ref{f-3b59157f717a} and~\ref{f-452d2bae9ea8} and from this study we see the availability of sartan increase mostly while availability of simvastatine decrease or absent at PH 1,4, 7.4 and 9. (availability of simvastatine in complex 4 is zero). So the effect of PH on complexes is various due to acidity and basicity

\textbf{Biological activity }

Using 24 white rabbits (male) (weight 1.5 to 2 kg) divided into 8 groups each one includes 3 rabbits five group for five complexes and one negative control and one for positive control and one for simvastatine alone ,induce hypercholesterolemia for two week to all groups (except the positive control group). After this period the drug model was given to each category as a classification for four weeks, then the lipid profile (cholesterol, triglyceride, LDL, HDL) was calculated and the difference in availability was found between the complex and simvastatin alone\unskip~\citep{831330:19822139,831330:19822132,831330:19822129}as seen in Table~\ref{tw-3a3776a60992}.

Abbreviations For Table~\ref{tw-3a3776a60992} is given below,
  
  \begin{enumerate}
  \item \relax TG= triglyceride 
  \item \relax LDL = low density lipoprotein
  \item \relax HDL=high density lipoprotein
  \item \relax 0 = zero time
  \item \relax 2 = after 2 weeks
  \item \relax 4 = after 4 weeks 
  \item \relax S = simvastatine
  \item \relax C+S = complex 1
  \item \relax V+S = complex 2
  \item \relax i+s= complex 3
  \item \relax t+s= complex 4
  \item \relax l+s= complex 5
  \item \relax c+ = positive control
  \item \relax c- = negative control
  \end{enumerate}
  
    
\section{Conclusions}
Charge transfer complexes (1,2,3,4 and 5) characterized by the UV, IR, HNMR spectrophotometry studies. The effect of CT interactions that decrease or increase the availability of acceptor or donor and this depends mostly on temperature and PH. In this study, the availability of simvastatin (acceptor) is shown to be decreased or absent and increased for donors (1,2,3,4 and 5). Dose adjustment for both drugs (acceptor and donor) is required if both drugs are given at the same time or in conjunction with two drugs. The biological activity of the combinations is not clear because the sample is small (three rabbits in each group) and a large sample (at least 10 rabbits in each group) is required for further studies. To get a good picture of the difference between combinations and simvastatin alone for the effect on the lipid profile.
    
\section{Acknowledgement}
I would like to thank collage of pharmacy /university of Basrah /pharmaceutical chemistry department, pharmaceutics department for providing laboratory facility for this work and veterinary Dr. Khaled Mezhir and clinical chemist Mohsen Enad for helping me in biological activity test (in rabbits) and lipid profile measuring.

\textbf{Funding Support}

Nil.

\textbf{Conflict of Interest}

Nil.
    

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